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Cocciferin D2

Family: Plantae - Fagaceae
Kingdom: Plantae
Class: Tannin

Canonical Smiles	CC1OC(COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1Oc1cc2C(=O)OCC3OC(C)[C@H]([C@H]([C@@H]3OC(=O)c3c(c2c(c1O)O)c(O)c(c(c3)O)O)C)C)O)O
InChI	InChI=1S/C58H52O32/c1-16-17(2)48-35(84-18(16)3)14-83-56(79)24-13-34(44(72)46(74)38(24)37-23(57(80)87-48)11-32(65)42(70)45(37)73)86-50-25(12-33(66)43(71)47(50)75)58(81)89-51-36(15-82-53(76)20-5-26(59)39(67)27(60)6-20)85-19(4)49(88-54(77)21-7-28(61)40(68)29(62)8-21)52(51)90-55(78)22-9-30(63)41(69)31(64)10-22/h5-13,16-19,35-36,48-49,51-52,59-75H,14-15H2,1-4H3/t16-,17+,18?,19?,35?,36?,48-,49+,51+,52+/m0/s1
InChIKey	XNTMFHCBZXYPAS-PROGSAJMSA-N
Formula	C₅₈H₅₂O₃₂
HBA	32
HBD	17
MW	1261.02
Rotatable Bonds	11
TPSA	529.4
LogP	4.52
Number Rings	9
Number Aromatic Rings	6
Heavy Atom Count	90
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	1260.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Quercus suber	Fagaceae	Plantae	58331

Showing of synonyms

Ito H, Yamaguchi K, et al. (2002). Dimeric and trimeric hydrolyzable tannins from Quercus coccifera and Quercus suber. Journal of Natural Products,2002,65(3),339-345. [View] [PubMed]

Pubchem: 162870658

Nmrshiftdb2: 60067337

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2C(C(OC(=O)c3ccccc3)C(CO2)OC(=O)c4ccccc4)OC(=O)c5c(cccc5)Oc(cc6)cc7C(=O)OCC(OCCC8)C8OC(=O)c(c9c67)cccc9

Level: 5

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(CC(CO2)OC(=O)c3ccccc3)OC(=O)c4c(cccc4)Oc(cc5)cc6C(=O)OCC(OCCC7)C7OC(=O)c(c8c56)cccc8

Level: 4

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(C(CCO2)OC(=O)c3ccccc3)OC(=O)c4c(cccc4)Oc(cc5)cc6C(=O)OCC(OCCC7)C7OC(=O)c(c8c56)cccc8

Level: 4

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2COCC(C2OC(=O)c3ccccc3)OC(=O)c4c(cccc4)Oc(cc5)cc6C(=O)OCC(OCCC7)C7OC(=O)c(c8c56)cccc8

Level: 4

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(OC(=O)c4ccccc4)C(CO2)OC(=O)c5ccccc5

Level: 4

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(CCCO2)OC(=O)c3c(cccc3)Oc(cc4)cc5C(=O)OCC(OCCC6)C6OC(=O)c(c7c45)cccc7

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2C(COCC2)OC(=O)c3c(cccc3)Oc(cc4)cc5C(=O)OCC(OCCC6)C6OC(=O)c(c7c45)cccc7

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC(COC2)CC2OC(=O)c3c(cccc3)Oc(cc4)cc5C(=O)OCC(OCCC6)C6OC(=O)c(c7c45)cccc7

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2CC(OC(=O)c3ccccc3)C(CO2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)CC(CO2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(OC(=O)c3ccccc3)C(CCO2)OC(=O)c4ccccc4

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2C(OC(=O)c3ccccc3)COCC2OC(=O)c4ccccc4

Level: 3

Mol. Weight: 1261.02 g/mol

SMILES: C1OCCCC1OC(=O)c2c(cccc2)Oc(cc3)cc4C(=O)OCC(OCCC5)C5OC(=O)c(c6c34)cccc6

Level: 2

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2CCC(CO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2CC(CCO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2C(CCCO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2CC(COC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2C(COCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 1261.02 g/mol

SMILES: c1cccc(c1c23)C(=O)OC4C(OCCC4)COC(=O)c2cc(cc3)Oc5ccccc5

Level: 1

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 1261.02 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(CCCO4)OC(=O)c2cccc3

Level: 0

Mol. Weight: 1261.02 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 1261.02 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1261.02 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.44
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 54968285642.49
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7183713497494.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.24
Plasma Protein Binding: 9.46
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 10.25
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -167076933639.07
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -68220.69
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -13038093852974034
Rat (Acute): 2.77
Rat (Chronic Oral): 27965567.5
Fathead Minnow: 16457819978280.76
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 1466424094822939.0
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -815185455.84
Log(P): -94893.25
Log S: -9.64
Log(Vapor Pressure): -48288603577406.17
Melting Point: -14668401.2
pKa Acid: -351858664948.27
pKa Basic: -2830692175.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8276
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8276
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8212
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8212
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7148
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7148
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7058
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7058

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