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6,8-di-C-glucosylapigenin

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

Canonical Smiles	OC[C@H]1OC([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)c(C2O[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-DAMJSERUSA-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	Centaurea incana	Asteraceae	Plantae	405077
2	Cotula cinerea	Asteraceae	Plantae	—

Showing of synonyms

Akkal S, Benayache F, et al. (1997). Flavonoids from Centaurea incana (Asteraceae). Biochemical Systematics and Ecology,1997,25(4),361-362. [View]
Ahmed AA, Meek FR, et al. (1987). Sulfated and non-sulfated flavonoids from Pluchea dioscoridis. Journal of Natural Products,1987,50(2),311. [View]

Pubchem: 69542256

No compound-protein relationship available.

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: 9.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.590
Plasma Protein Binding: 51.65
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: 6.890
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -4.190
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: -9476.870
Rat (Acute): 2.480
Rat (Chronic Oral): 5.030
Fathead Minnow: 17.190
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: 613.280
Hydration Free Energy: -3.140
Log(D) at pH=7.4: -1.670
Log(P): -0.54
Log S: -3.22
Log(Vapor Pressure): -13.01
Melting Point: 205.86
pKa Acid: 1.04
pKa Basic: 11.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.8781
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.8781
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8596
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8596
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8568
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8568
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8504
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8504
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8355
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8355
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8248
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8248
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7987
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7987
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7778
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7778
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7777
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7777
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7758
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7758
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7745
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7745
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7594
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7594
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7526
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7526
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	4	0.7453
Nuclear receptor subfamily 5 group A member 2	O00482	NR5A2_HUMAN	Homo sapiens	4	0.7453
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7424
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7424
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7399
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7399
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7232
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7232
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7141
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7141
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7129
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7129
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7107
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7107
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7075
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7075
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7041
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7041
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7041

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