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Vicenin 3

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Flavone Glycoside

Canonical Smiles	OCC1O[C@H](C([C@H]([C@@H]1O)O)O)c1c(O)c([C@@H]2OC[C@H]([C@@H](C2O)O)O)c2c(c1O)c(=O)cc(o2)c1ccc(cc1)O
InChI	InChI=1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)15-19(33)14-10(29)5-12(8-1-3-9(28)4-2-8)39-24(14)16(20(15)34)25-22(36)17(31)11(30)7-38-25/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13?,17+,18-,21+,22?,23?,25+,26+/m1/s1
InChIKey	MMDUKUSNQNWVET-ISRRCNJUSA-N
Formula	C₂₆H₂₈O₁₄
HBA	14
HBD	10
MW	564.5
Rotatable Bonds	4
TPSA	250.97
LogP	-1.75
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.42
Exact Mass	564.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Atractylis flava	Asteraceae	Plantae	41483

Showing of synonyms

Chabani S, Haba H, et al. (2013). Flavonoid glycosides and triterpenoids from Atractylis flava.. Phytochemistry Letters,2013,6,9-13. [View]

Pubchem: 44257698

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 564.5 g/mol

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

Level: 2

Mol. Weight: 564.5 g/mol

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

Level: 2

Mol. Weight: 564.5 g/mol

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

Level: 2

Mol. Weight: 564.5 g/mol

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

Level: 1

Mol. Weight: 564.5 g/mol

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

Level: 1

Mol. Weight: 564.5 g/mol

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

Level: 1

Mol. Weight: 564.5 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 564.5 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 564.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 564.5 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: -6.2
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 5.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.65
Plasma Protein Binding: 54.82
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: 8.26
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.57
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.74
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.37
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: -3786.03
Rat (Acute): 2.47
Rat (Chronic Oral): 4.9
Fathead Minnow: 8.03
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: 678.91
Hydration Free Energy: -3.16
Log(D) at pH=7.4: -1.14
Log(P): -0.42
Log S: -3.39
Log(Vapor Pressure): -13.59
Melting Point: 213.48
pKa Acid: 2.06
pKa Basic: 10.47

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	0.8695
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8695
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8661
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8661
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	0.8008
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8008
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7882
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7882
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7753
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7753
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7638
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7638
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7624
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7624
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7527
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7527
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7497
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7497
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7496
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7496
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7348
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7348
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7227
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7227
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7163
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7163
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7043
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7043

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