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Isorhamnetin 3-rutinoside

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

Canonical Smiles	COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1OC(CO[C@@H]2OC(C)[C@@H](C([C@@H]2O)O)O)[C@H]([C@@H](C1O)O)O)O
InChI	InChI=1S/C28H32O16/c1-9-18(32)21(35)23(37)27(41-9)40-8-16-19(33)22(36)24(38)28(43-16)44-26-20(34)17-13(31)6-11(29)7-15(17)42-25(26)10-3-4-12(30)14(5-10)39-2/h3-7,9,16,18-19,21-24,27-33,35-38H,8H2,1-2H3/t9?,16?,18-,19+,21?,22-,23-,24?,27+,28-/m0/s1
InChIKey	UIDGLYUNOUKLBM-RQEWDDNZSA-N
Formula	C₂₈H₃₂O₁₆
HBA	16
HBD	9
MW	624.55
Rotatable Bonds	7
TPSA	258.43
LogP	-1.38
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	624.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ammi majus	Apiaceae	Plantae	48026
2	Bupleurum plantagineum	Apiaceae	Plantae	198849

Showing of synonyms

Singab AN (1998). Acetylated flavonol triglycosides from Ammi majus L.. Phytochemistry,1998,49(7),2177-2180. [View] [PubMed]
Bencheraiet R, Kabouche A, et al. (2012). Flavonol 3-O-glycosides from three Algerian Bupleurum species. Records of Natural Products,2012,6(2),171-174. [View]

Pubchem: 162995386

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 624.55 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 624.55 g/mol

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

Level: 2

Mol. Weight: 624.55 g/mol

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

Level: 1

Mol. Weight: 624.55 g/mol

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

Level: 1

Mol. Weight: 624.55 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 624.55 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 624.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 624.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 624.55 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: -5.200
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 13.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.820
Plasma Protein Binding: 47.79
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: 12.370
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.050
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.900
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.660
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: -22490.660
Rat (Acute): 2.270
Rat (Chronic Oral): 4.430
Fathead Minnow: 45.590
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 361.530
Hydration Free Energy: -2.930
Log(D) at pH=7.4: -0.250
Log(P): -0.05
Log S: -4.88
Log(Vapor Pressure): -16.73
Melting Point: 212.3
pKa Acid: 4.21
pKa Basic: 5.99

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9065
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9065
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8864
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8864
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8860
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8860
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8724
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8724
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8658
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8658
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8447
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8447
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8391
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8391
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8377
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8377
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8367
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8367
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8336
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.8336
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8252
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8252
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8104
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8104
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7998
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7998
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7986
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7986
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7922
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7922
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7903
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7903
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7883
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7883
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7872
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7872
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7866
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7866
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7862
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.7862
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7824
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7824
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7739
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7739
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7726
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7726
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7720
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7720
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7611
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7611
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7589
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7589
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7567
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7567
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7554
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7554
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7519
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7519
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7517
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7517
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7502
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7502
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7473
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7473
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7448
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7448
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7441
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7441
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7432
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7432
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7410
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7410
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7375
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7375
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7332
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7332
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7320
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7320
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7297
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7297
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7294
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7294
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7244
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7244
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7230
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7230
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7211
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7211
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7146
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7146
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7095
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7095
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7064
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7064
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7037
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7037
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7018
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7018

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