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Isorhamnetin 3-O-sophoroside

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

Canonical Smiles	OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)C(C([C@@H]1O)O)O[C@@H]1OC(CO)[C@H](C([C@H]1O)O)O
InChI	InChI=1S/C28H32O17/c1-40-13-4-9(2-3-11(13)32)24-25(20(36)17-12(33)5-10(31)6-14(17)41-24)44-28-26(22(38)19(35)16(8-30)43-28)45-27-23(39)21(37)18(34)15(7-29)42-27/h2-6,15-16,18-19,21-23,26-35,37-39H,7-8H2,1H3/t15?,16?,18-,19-,21?,22?,23-,26?,27+,28+/m1/s1
InChIKey	JWCIGPTUZBZFDW-MMJUEZNNSA-N
Formula	C₂₈H₃₂O₁₇
HBA	17
HBD	10
MW	640.55
Rotatable Bonds	8
TPSA	278.66
LogP	-2.41
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	640.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	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]

Pubchem: 44258015

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OCCC4)C4OC5CCCCO5

Level: 3

Mol. Weight: 640.55 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 640.55 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 640.55 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 640.55 g/mol

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

Level: 1

Mol. Weight: 640.55 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 640.55 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 640.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 640.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 640.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.3
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 23.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.74
Plasma Protein Binding: 27.77
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: 11.09
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.61
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.84
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.18
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: -38999.88
Rat (Acute): 2.25
Rat (Chronic Oral): 4.56
Fathead Minnow: 66.02
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 380.96
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.78
Log(P): -0.99
Log S: -4.57
Log(Vapor Pressure): -21.78
Melting Point: 194.0
pKa Acid: 3.37
pKa Basic: 6.1

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	0.8952
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8952
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8905
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8905
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8831
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8831
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8829
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8829
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8799
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8799
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8562
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8562
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8555
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8555
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8381
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8381
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8298
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8298
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8226
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8226
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8157
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8157
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8092
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8092
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8091
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8091
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8040
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8040
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8015
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8015
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7998
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7998
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7914
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7914
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7909
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7909
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7847
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7847
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7833
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7833
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7737
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7737
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7704
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7704
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7670
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7670
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7647
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7647
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7541
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7541
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7490
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7490
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7391
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7391
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7372
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7372
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7251
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7251
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7245
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7245
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7218
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7218
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7175
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7175
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7130
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7130
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7119
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7119
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7110
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7110
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7099
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7099
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7071
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7071
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7058
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7058
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7051
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7051
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7046
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7046
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7032
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	4	0.7032
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7021
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7021
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7014
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7014

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