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Vicenin-2

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	OC[C@H]1O[C@H]([C@@H]([C@@H]([C@@H]1O)O)O)c1c(O)c([C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c(c2c1oc(cc2=O)c1ccc(cc1)O)O
InChI	InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17-,18-,21+,22-,23-,24-,26+,27+/m1/s1
InChIKey	FIAAVMJLAGNUKW-JDGZUBLHSA-N
Formula	C₂₇H₃₀O₁₅
HBA	15
HBD	11
MW	594.52
Rotatable Bonds	5
TPSA	271.2
LogP	-2.39
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	594.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ficus variifolia	Moraceae	Plantae	425835
2	Ficus polita	Moraceae	Plantae	378027
3	Ficus sansibarica	Moraceae	Plantae	309319
4	Ficus saussureana	Moraceae	Plantae	309296

Showing of synonyms

Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]

Pubchem: 442664

Cas: 23666-13-9

Gnps: CCMSLIB00000077238

Zinc: ZINC000004098604

Kegg Ligand: C10195

Chebi: 69814

Nmrshiftdb2: 60022756

Metabolights: MTBLC69814

Chembl: CHEMBL1442950

CPRiL: 79656

SMILES: c1ccccc1-c(cc2=O)oc(c23)c(C4CCCCO4)cc(c3)C5CCCCO5

Level: 3

Mol. Weight: 594.52 g/mol

SMILES: O=c1ccoc(c12)c(C3CCCCO3)cc(c2)C4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 594.52 g/mol

SMILES: O1CCCCC1c(ccc2)c(c23)oc(cc3=O)-c4ccccc4

Level: 2

Mol. Weight: 594.52 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: O=c1ccoc(c12)c(ccc2)C3CCCCO3

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.41
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -6.270
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 9.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.590
Plasma Protein Binding: 64.09
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: 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: Non-Inhibitor

Excretion

Clearance: 6.930
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.270
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.400
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: -9477.270
Rat (Acute): 2.480
Rat (Chronic Oral): 5.020
Fathead Minnow: 17.100
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 615.590
Hydration Free Energy: -3.140
Log(D) at pH=7.4: -1.640
Log(P): -0.42
Log S: -3.25
Log(Vapor Pressure): -13.33
Melting Point: 207.26
pKa Acid: 1.06
pKa Basic: 11.43

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8726
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8726
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8495
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8495
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8431
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8431
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.8106
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.8106
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8101
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8101
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7984
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7984
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7978
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7978
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7911
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7911
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7907
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7907
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7726
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7726
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7665
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7665
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7551
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7551
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7498
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7498
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7405
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7405
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7389
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7389
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7366
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7366
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7261
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7261
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7238
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.7238
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7234
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7234
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7159
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7159
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7035
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7035
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7025
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7025

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