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5-hydroxysesamin 5-O-beta-D-glucopyranosyl-(1→2)-[beta-D-gluco-pyranosyl-(1→6)]-beta-D-glucopyranoside

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Glycosylated Lignan

Canonical Smiles	OCC1O[C@@H](O[C@@H]2[C@@H](OC([C@H](C2O)O)CO[C@@H]2OC(CO)[C@H](C([C@@H]2O)O)O)Oc2cc(cc3c2OCO3)[C@H]2OC[C@]3([C@]2(C)CO[C@@H]3c2ccc3c(c2)OCO3)C)[C@H](C([C@@H]1O)O)O
InChI	InChI=1S/C40H52O22/c1-39-11-53-35(40(39,2)12-52-34(39)15-3-4-17-18(5-15)55-13-54-17)16-6-19-32(57-14-56-19)20(7-16)58-38-33(62-37-31(50)28(47)25(44)22(9-42)60-37)29(48)26(45)23(61-38)10-51-36-30(49)27(46)24(43)21(8-41)59-36/h3-7,21-31,33-38,41-50H,8-14H2,1-2H3/t21?,22?,23?,24-,25-,26-,27?,28?,29?,30+,31+,33+,34-,35-,36-,37+,38-,39-,40-/m1/s1
InChIKey	ODDCWCGSSVTPIY-OLSJFBFNSA-N
Formula	C₄₀H₅₂O₂₂
HBA	22
HBD	10
MW	884.83
Rotatable Bonds	11
TPSA	313.06
LogP	-3.17
Number Rings	9
Number Aromatic Rings	2
Heavy Atom Count	62
Formal Charge	0
Fraction CSP3	0.7
Exact Mass	884.3
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tabebuia argentea	Bignoniaceae	Plantae	3350745

Showing of synonyms

De Abreu B, Temraz A, et al. (2014). Phenolic glycosides from Tabebuia argentea and Catalpa bignonioides. Phytochemistry Letters,2014,7,85-88. [View]

Pubchem: 162817423

Nmrshiftdb2: 70002393

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc4cc(cc(c45)OCO5)C6OCC(C67)C(OC7)c(c8)ccc(c89)OCO9

Level: 5

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3cc(cc(c34)OCO4)C5OCC(C56)C(OC6)c(c7)ccc(c78)OCO8

Level: 4

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OC2C(OCCC2)Oc3cc(cc(c34)OCO4)C5OCC(C56)C(OC6)c(c7)ccc(c78)OCO8

Level: 4

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc4cc(cc(c45)OCO5)C6OCC(C67)COC7

Level: 4

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1Oc2cc(cc(c23)OCO3)C4OCC(C45)C(OC5)c(c6)ccc(c67)OCO7

Level: 3

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3cc(cc(c34)OCO4)C5OCC(C56)COC6

Level: 3

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OCC2CCC(OC3CCCCO3)C(O2)Oc4cccc(c45)OCO5

Level: 3

Mol. Weight: 884.83 g/mol

SMILES: C1OCC(C12)COC2c(cc(c34)OCO4)cc3OC(OCCC5)C5OC6CCCCO6

Level: 3

Mol. Weight: 884.83 g/mol

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)C(OC4)c(c5)ccc(c56)OCO6

Level: 2

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc3cccc(c34)OCO4

Level: 2

Mol. Weight: 884.83 g/mol

SMILES: C1OCC(C12)COC2c(cc(c34)OCO4)cc3OC5CCCCO5

Level: 2

Mol. Weight: 884.83 g/mol

SMILES: O1COc(c12)cccc2OC(OCCC3)C3OC4CCCCO4

Level: 2

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1OCC2CCC(CO2)OC3CCCCO3

Level: 2

Mol. Weight: 884.83 g/mol

SMILES: O1COc(c12)ccc(c2)C3OCC(C34)COC4

Level: 1

Mol. Weight: 884.83 g/mol

SMILES: O1COc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 884.83 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 884.83 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 884.83 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 884.83 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 884.83 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 884.83 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.48
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 1956.98
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 256579.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 64.87
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.04
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -5961.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.22
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.05
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: -465676929.03
Rat (Acute): 3.03
Rat (Chronic Oral): 5.28
Fathead Minnow: 587825.94
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 52370362.82
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -16.38
Log(P): -0.91
Log S: -3.1
Log(Vapor Pressure): -1724412.13
Melting Point: 209.57
pKa Acid: -12495.65
pKa Basic: -73.8

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9790
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9790
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9051
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9051
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9027
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9027
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8303
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8303
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7899
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7899
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7470
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7470
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7461
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7461
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7452
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7452
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7363
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7363
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7349
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7349
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7276
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7276
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7263
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7263
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7258
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7258
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7108
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7108
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7092
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7092
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7051
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7051

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