T3DB: Octyl gallate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (16)XML

Targets (16)

Record Information

Version

2.0

Creation Date

2014-09-11 05:18:20 UTC

Update Date

2014-12-24 20:26:57 UTC

Accession Number

T3D4831

Identification

Common Name

Octyl gallate

Class

Small Molecule

Description

Octyl gallate is an antioxidant used in margarine Octyl gallate has been shown to exhibit anti-viral function (1).

Compound Type

Ester
Ether
Food Toxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
Benzoic acid, 3,4,5-trihydroxy-, octyl ester
E311
GA 8
Gallic acid octyl ester
Gallic acid, octyl ester
N-Octyl ester of 3,4,5-trihydroxybenzoic acid
N-Octyl gallate
N-Octylgallate
Octyl 3,4,5-trihydroxybenzoate
Octyl gallic acid
Octylgallate
Oktylester kyseliny gallove
Progallin O
Stabilizer GA 8

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Mass

282.332 g/mol

Monoisotopic Mass

282.147 g/mol

CAS Registry Number

1034-01-1

IUPAC Name

octyl 3,4,5-trihydroxybenzoate

Traditional Name

octyl gallate

SMILES

CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H22O5/c1-2-3-4-5-6-7-8-20-15(19)11-9-12(16)14(18)13(17)10-11/h9-10,16-18H,2-8H2,1H3

InChI Key

InChIKey=NRPKURNSADTHLJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

gallate ester (CHEBI:83631 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	94 - 95 °C
Boiling Point	Not Available
Solubility	0.036 mg/mL at 20 °C
LogP	3.66

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	4.1	ALOGPS
logP	4.17	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	76.3 m³·mol⁻¹	ChemAxon
Polarizability	31.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4900000000-878a0a7a4a67ed06c0ff	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-01c0-5209400000-3d5229f775270bdd8868	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-019r-0920000000-dd0646e49d169d2d39a4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-020c-2900000000-2dfd6a3290e77879474e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-017i-0920000000-b750c5426d2367f6bfda	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-0190000000-eb4afbede645135b7663	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-004i-1900000000-34fdedc0e3ae08ef6c4c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-004u-1900000000-41eaaa406b8a3f84606b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-001i-0090000000-6eb2ef731eb900efa48a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9500000000-25e3c2fbd78d072d820b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1900000000-f97f06cdbe5ca99b4bae	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pdi-3900000000-169a117fdd40fbb3f66b	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0790000000-1a568cbe925ce46780bc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-2910000000-32a6f3e83cb258626b0a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kbf-9600000000-c74166cded4e492c3e24	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0590000000-150fabd6eb0d5e81d0b9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016r-0910000000-652ef7ed882c584e3879	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fvi-1900000000-0a04645a38fadbbab692	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0290000000-c333499f784512ab5549	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fw9-0930000000-d3463202c650e369f74d	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00vi-5900000000-e9a5b02eb650d4f7a67c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0590000000-18e43656b88b6abb544e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-3950000000-cb1f00495f16a31abcb0	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-8900000000-38f3d1a994ec952bab6a	2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Octyl_gallate

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Yamasaki H, Uozaki M, Katsuyama Y, Utsunomiya H, Arakawa T, Higuchi M, Higuti T, Koyama AH: Antiviral effect of octyl gallate against influenza and other RNA viruses. Int J Mol Med. 2007 Apr;19(4):685-8. [17334645 ]
Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Translocator protein

General Function:: Cholesterol binding
Specific Function:: Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
Gene Name:: TSPO
Uniprot ID:: P30536
Molecular Weight:: 18827.81 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.37 uM	NVS_MP_hPBR	Novascreen

References

Target Details

2. Matrix metalloproteinase-9

General Function:: Zinc ion binding
Specific Function:: May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments. Degrades fibronectin but not laminin or Pz-peptide.
Gene Name:: MMP9
Uniprot ID:: P14780
Molecular Weight:: 78457.51 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	0.819 uM	NVS_ENZ_hMMP9	Novascreen

References

Target Details

3. Glucocorticoid receptor

General Function:: Zinc ion binding
Specific Function:: Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
Gene Name:: NR3C1
Uniprot ID:: P04150
Molecular Weight:: 85658.57 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.11 uM	NVS_NR_hGR	Novascreen

References

Target Details

4. 72 kDa type IV collagenase

General Function:: Zinc ion binding
Specific Function:: Ubiquitinous metalloproteinase that is involved in diverse functions such as remodeling of the vasculature, angiogenesis, tissue repair, tumor invasion, inflammation, and atherosclerotic plaque rupture. As well as degrading extracellular matrix proteins, can also act on several nonmatrix proteins such as big endothelial 1 and beta-type CGRP promoting vasoconstriction. Also cleaves KISS at a Gly-|-Leu bond. Appears to have a role in myocardial cell death pathways. Contributes to myocardial oxidative stress by regulating the activity of GSK3beta. Cleaves GSK3beta in vitro. Involved in the formation of the fibrovascular tissues in association with MMP14.PEX, the C-terminal non-catalytic fragment of MMP2, posseses anti-angiogenic and anti-tumor properties and inhibits cell migration and cell adhesion to FGF2 and vitronectin. Ligand for integrinv/beta3 on the surface of blood vessels.Isoform 2: Mediates the proteolysis of CHUK/IKKA and initiates a primary innate immune response by inducing mitochondrial-nuclear stress signaling with activation of the pro-inflammatory NF-kappaB, NFAT and IRF transcriptional pathways.
Gene Name:: MMP2
Uniprot ID:: P08253
Molecular Weight:: 73881.695 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.61 uM	NVS_ENZ_hMMP2	Novascreen

References

Target Details

5. Tyrosine-protein phosphatase non-receptor type 6

General Function:: Transmembrane receptor protein tyrosine phosphatase activity
Specific Function:: Modulates signaling by tyrosine phosphorylated cell surface receptors such as KIT and the EGF receptor/EGFR. The SH2 regions may interact with other cellular components to modulate its own phosphatase activity against interacting substrates. Together with MTUS1, induces UBE2V2 expression upon angiotensin II stimulation. Plays a key role in hematopoiesis.
Gene Name:: PTPN6
Uniprot ID:: P29350
Molecular Weight:: 67560.79 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.66 uM	NVS_ENZ_hPTPN6_Activator	Novascreen

References

Target Details

6. Collagenase 3

General Function:: Zinc ion binding
Specific Function:: Plays a role in the degradation of extracellular matrix proteins including fibrillar collagen, fibronectin, TNC and ACAN. Cleaves triple helical collagens, including type I, type II and type III collagen, but has the highest activity with soluble type II collagen. Can also degrade collagen type IV, type XIV and type X. May also function by activating or degrading key regulatory proteins, such as TGFB1 and CTGF. Plays a role in wound healing, tissue remodeling, cartilage degradation, bone development, bone mineralization and ossification. Required for normal embryonic bone development and ossification. Plays a role in the healing of bone fractures via endochondral ossification. Plays a role in wound healing, probably by a mechanism that involves proteolytic activation of TGFB1 and degradation of CTGF. Plays a role in keratinocyte migration during wound healing. May play a role in cell migration and in tumor cell invasion.
Gene Name:: MMP13
Uniprot ID:: P45452
Molecular Weight:: 53819.32 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	2.71 uM	NVS_ENZ_hMMP13	Novascreen

References

Target Details

7. Estrogen receptor

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular Weight:: 66215.45 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	3.38 uM	OT_ERa_EREGFP_0120	Odyssey Thera

References

Target Details

8. Sodium-dependent noradrenaline transporter

General Function:: Norepinephrine:sodium symporter activity
Specific Function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular Weight:: 69331.42 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	4.97 uM	NVS_TR_hNET	Novascreen

References

Target Details

9. Cytochrome P450 2C19

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular Weight:: 55930.545 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	5.58 uM	NVS_ADME_hCYP2C19	Novascreen

References

Target Details

10. Estrogen receptor beta

General Function:: Zinc ion binding
Specific Function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular Weight:: 59215.765 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	6.67 uM	OT_ER_ERaERb_0480	Odyssey Thera

References

Target Details

11. Substance-K receptor

General Function:: Tachykinin receptor activity
Specific Function:: This is a receptor for the tachykinin neuropeptide substance K (neurokinin A). It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: substance K > neuromedin-K > substance P.
Gene Name:: TACR2
Uniprot ID:: P21452
Molecular Weight:: 44441.705 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.21 uM	NVS_GPCR_hNK2	Novascreen

References

Target Details

12. Cytochrome P450 2C9

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular Weight:: 55627.365 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.23 uM	NVS_ADME_hCYP2C9	Novascreen

References

Target Details

13. Nuclear factor erythroid 2-related factor 2

General Function:: Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
Specific Function:: Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
Gene Name:: NFE2L2
Uniprot ID:: Q16236
Molecular Weight:: 67825.9 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.66 uM	ATG_NRF2_ARE_CIS	Attagene

References

Target Details

14. Cytochrome P450 2B6

General Function:: Steroid hydroxylase activity
Specific Function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular Weight:: 56277.81 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.89 uM	NVS_ADME_hCYP2B6	Novascreen

References

Target Details

15. Adenosine receptor A2a

General Function:: Identical protein binding
Specific Function:: Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name:: ADORA2A
Uniprot ID:: P29274
Molecular Weight:: 44706.925 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	7.91 uM	NVS_GPCR_hAdoRA2a	Novascreen

References

Target Details

16. Cytochrome P450 2D6

General Function:: Steroid hydroxylase activity
Specific Function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular Weight:: 55768.94 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	8.83 uM	NVS_ADME_hCYP2D6	Novascreen

References

Octyl gallate (T3D4831)

Structure for T3D4831: Octyl gallate

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