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Isorhamnetin 3-xylosylrobinobioside

Family: Plantae - Nitrariaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	COc1cc(ccc1O)c1oc2cc(O)cc(c2c(=O)c1OC1OC[C@H](C(C1O)O)OC1OC(CO[C@@H]2OC(C)[C@@H]([C@@H](C2O)O)O)[C@@H](C(C1O)O)O)O
InChI	InChI=1S/C33H40O20/c1-10-20(37)24(41)27(44)31(49-10)47-8-17-21(38)25(42)28(45)33(51-17)52-18-9-48-32(26(43)22(18)39)53-30-23(40)19-14(36)6-12(34)7-16(19)50-29(30)11-3-4-13(35)15(5-11)46-2/h3-7,10,17-18,20-22,24-28,31-39,41-45H,8-9H2,1-2H3/t10?,17?,18-,20+,21+,22?,24+,25?,26?,27?,28?,31-,32?,33?/m1/s1
InChIKey	BMLFZGYQGSVVGU-CTFMKGLLSA-N
Formula	C₃₃H₄₀O₂₀
HBA	20
HBD	11
MW	756.66
Rotatable Bonds	9
TPSA	317.35
LogP	-2.92
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	53
Formal Charge	0
Fraction CSP3	0.55
Exact Mass	756.21
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Nitraria retusa	Nitrariaceae	Plantae	43875

Showing of synonyms

Halim AF, Saad HE, et al. (1995). Flavonol glycosides from Nitraria retusa. Phytochemistry,1995,40(1),349-351. [View] [PubMed]

Pubchem: 162817147

Nmrshiftdb2: 60059128

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCC(OC3)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCC(OC3)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 756.66 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC(OC4)CCC4OC5CCCCO5

Level: 3

Mol. Weight: 756.66 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC(OC3)CCC3OC4CCCCO4

Level: 2

Mol. Weight: 756.66 g/mol

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

Level: 2

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 756.66 g/mol

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

Level: 1

Mol. Weight: 756.66 g/mol

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

Level: 1

Mol. Weight: 756.66 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 756.66 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 756.66 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 756.66 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 756.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 756.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1.590
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1034.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 10.45
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: 9.300
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -23.610
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.720
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.240
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: -1872970.140
Rat (Acute): 2.340
Rat (Chronic Oral): 4.700
Fathead Minnow: 2372.630
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: 203874.950
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -1.140
Log(P): -0.88
Log S: -4.82
Log(Vapor Pressure): -6701.0
Melting Point: 229.41
pKa Acid: -16.76
pKa Basic: 5.67

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	0.9125
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9125
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9078
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9078
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8966
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8966
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8836
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8836
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8763
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8763
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8722
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8722
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8630
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8630
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8575
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8575
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8545
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8545
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8451
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8451
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8411
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8411
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8375
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8375
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8349
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8349
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8311
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8311
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8235
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8235
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8190
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8190
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8083
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8083
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8082
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8082
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8062
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8062
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7974
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7974
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7941
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7941
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7921
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7921
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7888
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7888
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7841
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7841
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7798
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7798
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7793
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7793
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7788
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7788
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7781
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7781
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7776
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7776
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7702
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7702
Baculoviral IAP repeat-containing protein 8	Q96P09	BIRC8_HUMAN	Homo sapiens	5	0.7568
Baculoviral IAP repeat-containing protein 8	Q96P09	BIRC8_HUMAN	Homo sapiens	5	0.7568
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7550
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7550
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7550
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7550
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7530
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7530
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7489
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7489
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7478
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7478
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7459
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7459
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7450
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7450
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7430
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7430
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7380
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7380
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7379
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7379
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7273
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7273
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7263
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7263
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7211
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7211
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7208
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7208
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7192
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7192
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7174
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	3	0.7174
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7165
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7165
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7162
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7162
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7156
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7156
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7135
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.7135
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7112
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7112
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7102
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7102
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7083
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7083
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7073
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7073
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7046
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7046
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7038
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7038

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