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Procyanidin dimer monogallate

Family: Plantae - Ximeniaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol

Canonical Smiles	C1([C@H](C(c2c(cc(cc2O1)O)O)O)OC(=O)c1cc(O)c(O)c(O)c1)(O[C@@H]1C(Oc2c(C1)c(cc(c2)O)O)c1cc(c(cc1)O)O)c1cc(c(cc1)O)O
InChI	InChI=1S/C37H30O17/c38-17-9-22(42)19-13-30(34(51-28(19)11-17)14-1-3-20(40)23(43)5-14)54-37(16-2-4-21(41)24(44)8-16)35(33(49)31-25(45)10-18(39)12-29(31)53-37)52-36(50)15-6-26(46)32(48)27(47)7-15/h1-12,30,33-35,38-49H,13H2/t30-,33?,34?,35-,37?/m0/s1
InChIKey	GBVJWAHIWSSVKA-YQQOODEESA-N
Formula	C₃₇H₃₀O₁₇
HBA	17
HBD	12
MW	746.63
Rotatable Bonds	6
TPSA	296.75
LogP	3.71
Number Rings	7
Number Aromatic Rings	5
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	746.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ximenia americana	Ximeniaceae	Plantae	50174

Showing of synonyms

Sobeh M, Mahmoud MF, et al. (2017). Hepatoprotective and hypoglycemic effects of a tannin rich extract from Ximenia americana var. caffra root. Phytomedicine : international journal of phytotherapy and phytopharmacology,2017, 33(), 36-42. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(C2)C(c3ccccc3)(Oc(c24)cccc4)OC(C5)C(c6ccccc6)Oc(c57)cccc7

Level: 4

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(=O)OC(C2)C(c3ccccc3)(Oc(c24)cccc4)OC(C5)COc(c56)cccc6

Level: 3

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(=O)OC(C2)C(Oc(c23)cccc3)OC(C4)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(CC2)(Oc(c23)cccc3)OC(C4)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(=O)OC(C2)C(Oc(c23)cccc3)OC(C4)COc(c45)cccc5

Level: 2

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(CC2)(Oc(c23)cccc3)OC(C4)COc(c45)cccc5

Level: 2

Mol. Weight: 746.63 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2)OC(CC4)Oc(c45)cccc5

Level: 2

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(=O)OC(C2)C(c3ccccc3)Oc(c24)cccc4

Level: 2

Mol. Weight: 746.63 g/mol

SMILES: c1cccc(c12)OCC(C2)OC(CC3)Oc(c34)cccc4

Level: 1

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1C(=O)OC(C2)COc(c23)cccc3

Level: 1

Mol. Weight: 746.63 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 746.63 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 746.63 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 746.63 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.35
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 7.96
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1888.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 46.74
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: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: 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: 10.96
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -41.17
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.19
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.34
Micronucleos: Toxic
NR-AhR: Safe
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: -3422946.15
Rat (Acute): 2.39
Rat (Chronic Oral): 4.67
Fathead Minnow: 4330.79
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 376677.71
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.53
Log(P): 2.56
Log S: -6.08
Log(Vapor Pressure): -12396.88
Melting Point: 284.65
pKa Acid: -59.78
pKa Basic: 4.29

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8351
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8173
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8082
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8020
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7933
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7793
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7691
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7638
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7588
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7418
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7415
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7299
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7211
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7165
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7057
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7014

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