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Vicenin-2

Family: Plantae - Apiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

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-VQVVXJKKSA-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	Pistacia atlantica	Anacardiaceae	Plantae	434234
2	Pistacia chinensis	Anacardiaceae	Plantae	289741
3	Pistacia lentiscus	Anacardiaceae	Plantae	371726
4	Bombax malabaricum	Bombacaceae	Plantae	45325
5	Cleome species	Capparaceae	Plantae	25782
6	Artemisia monosperma	Asteraceae	Plantae	72348
7	Artemisia herba-alba	Asteraceae	Plantae	72329
8	Artemisia judaica	Asteraceae	Plantae	205369
9	Artemisia monosperma	Asteraceae	Plantae	72348
10	Artemisia herba-alba	Asteraceae	Plantae	72329
11	Ephedra alata	Ephedraceae	Plantae	302006
12	Ephedra aphylla	Ephedraceae	Plantae	191304
13	Jatropha multifida	Euphorbiaceae	Plantae	3996
14	Hyparrhenia hirta	Poaceae	Plantae	42079
15	Thymelaea hirsuta	Thymelaeaceae	Plantae	69845
16	Pituranthos scoparius	Apiaceae	Plantae	489362

Showing of synonyms

Dahia M, Siracusa L, et al. (2009). Constituents of the polar extracts from Algerian Pituranthos scoparius. Natural Product Communications,2009,4(12),1691-1692. [View] [PubMed]
Nawwar MAM, El-Sissi HI, et al. (1984). Flavonoid constituents of Ephedra alata. Phytochemistry,1984,23(12),2937-2939. [View]
Saleh NAM, El-Newumy SI, et al. (1985). Flavonoid glycosides of Artemisia monosperma and A. herba-alba.. Phytochemistry,1985,24(1),201-203. [View]
Hussein SAM, Barakat HH, et al. (1997). Flavonoids from Ephedra aphylla. Phytochemistry,1997,45(7),1529-1532. [View]
Bouaziz M, Simmonds MS, et al. (2001). Flavonoids from Hyparrhenia hirta Stapf (Poaceae) growing in Tunisia. Biochemical Systematics and Ecology,2001,29(8),849-851. [View] [PubMed]
Saleh NAM, El-Negoumy SI, et al. (1987). Flavonoids of Artemisia judaica, A. monosperma and A. Herba-alba.. Phytochemistry,1987,26(11),3059-3064. [View]
Sharaf M, El-Ansari MA, et al. (1997). Flavonoids of four Cleome and three Capparis species.. Biochemical Systematics and Ecology,1997,25(2),161-166. [View]
Nawwar MAM, Ishak MS, et al. (1977). Flavonoids of Reaumuria mucronata and Thymelaea hirsuta. Phytochemistry,1977,16(8),1319-1320. [View]
Marzouk MS, Moharram FA, et al. (2012). Novel biflavone diglycosides and biological activity of Jatropha multifida leaves. Chemistry of Natural Compounds,2012,48(5),765-770. [View]
El-Hagrassi AM, Ali MM, et al. (2011). Phytochemical investigation and biological studies of Bombax malabaricum flowers. Natural Product Research,2011,25(2),141-151. [View] [PubMed]
Kawashty SA, Mosharrafa SAM, et al. (2000). The flavonoids of four Pistacia species in Egypt. Biochemical Systematics and Ecology,2000,28(9),915-917. [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: 64.02
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: 6.940
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.230
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: 5.390
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: -9477.310
Rat (Acute): 2.480
Rat (Chronic Oral): 5.020
Fathead Minnow: 17.110
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: 614.710
Hydration Free Energy: -3.140
Log(D) at pH=7.4: -1.600
Log(P): -0.47
Log S: -3.24
Log(Vapor Pressure): -13.34
Melting Point: 207.9
pKa Acid: 1.05
pKa Basic: 11.41

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	0.8327
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8327
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7949
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7949
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7821
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7821
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7618
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7618
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7556
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7556
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7544
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7544
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7418
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7418
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7344
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7344
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7318
Neopullulanase 2	Q08751	NEPU2_THEVU	Thermoactinomyces vulgaris	3	0.7318
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7214
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7214
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7191
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7191
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7120
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7120
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7037
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7037

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