ANPDB

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Tingitanol B

Family: Plantae - Iridaceae
Kingdom: Plantae
Class: Stilbene
- Subclass: Stilbene Glycoside

Canonical Smiles	OC[C@H]1OC(Oc2cc(O)cc(c2)[C@@H]2[C@H](Oc3c2c2ccc4c(c2c(c3)OC2O[C@@H](CO)[C@@H]([C@H]([C@@H]2O)O)O)cc(cc4)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C40H40O16/c41-14-27-32(46)34(48)36(50)39(55-27)52-22-10-18(9-21(45)11-22)29-31-23-8-4-16-1-7-20(44)12-24(16)30(23)25(54-40-37(51)35(49)33(47)28(15-42)56-40)13-26(31)53-38(29)17-2-5-19(43)6-3-17/h1-13,27-29,32-51H,14-15H2/t27-,28+,29+,32-,33+,34+,35-,36-,37+,38-,39?,40?/m1/s1
InChIKey	RXVROCWTMVACDR-SOUOMJQJSA-N
Formula	C₄₀H₄₀O₁₆
HBA	16
HBD	11
MW	776.74
Rotatable Bonds	8
TPSA	268.68
LogP	0.73
Number Rings	8
Number Aromatic Rings	5
Heavy Atom Count	56
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	776.23
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Iris tingitana	Iridaceae	Plantae	292520

Showing of synonyms

Farag SF, Takaya Y, et al. (2009). Stilbene glucosides from the bulbs of Iris tingitana. Phytochemistry Letters,2009,2(4),148-151. [View]

Pubchem: 163070407

Nmrshiftdb2: 70109472

No compound-protein relationship available.

SMILES: c1cccc2c1ccc3c2c(OC4CCCCO4)cc(c35)OC(c6ccccc6)C5c7cc(ccc7)OC8CCCCO8

Level: 4

Mol. Weight: 776.74 g/mol

SMILES: c1cccc2c1ccc3c2c(OC4CCCCO4)cc(c35)OCC5c6cc(ccc6)OC7CCCCO7

Level: 3

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1C2C(c3ccccc3)Oc(c24)cc(OC5CCCCO5)c6c4ccc7c6cccc7

Level: 3

Mol. Weight: 776.74 g/mol

SMILES: c1cccc2c1ccc3c2ccc(c34)OC(c5ccccc5)C4c6cc(ccc6)OC7CCCCO7

Level: 3

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1C2COc(c23)cc(OC4CCCCO4)c5c3ccc6c5cccc6

Level: 2

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1C(C2)Oc(c23)cc(OC4CCCCO4)c5c3ccc6c5cccc6

Level: 2

Mol. Weight: 776.74 g/mol

SMILES: c1cccc2c1ccc3c2ccc(c34)OCC4c5cc(ccc5)OC6CCCCO6

Level: 2

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1C2C(c3ccccc3)Oc(c24)ccc5c4ccc6c5cccc6

Level: 2

Mol. Weight: 776.74 g/mol

SMILES: O1CCCCC1Oc(cc(c23)OCC2)c4c3ccc5c4cccc5

Level: 1

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1C2COc(c23)ccc4c3ccc5c4cccc5

Level: 1

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1C(C2)Oc(c23)ccc4c3ccc5c4cccc5

Level: 1

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 776.74 g/mol

SMILES: C1COc(c12)ccc3c2ccc4c3cccc4

Level: 0

Mol. Weight: 776.74 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 776.74 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 776.74 g/mol

Free radical scavenging

Absorption

Caco-2 (logPapp): -6.34
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 79.55
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 11176.23

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.23
Plasma Protein Binding: 79.06
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Inhibitor

Excretion

Clearance: 4.53
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -260.66
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.01
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.92
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
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: -20281526.92
Rat (Acute): 2.64
Rat (Chronic Oral): 5.09
Fathead Minnow: 25609.53
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: 2274974.35
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.28
Log(P): 0.15
Log S: -4.84
Log(Vapor Pressure): -74825.62
Melting Point: 266.74
pKa Acid: -492.97
pKa Basic: 7.34

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8851
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8851
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8477
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8477
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8475
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8475
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8394
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8394
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8209
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8209
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8124
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8124
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8072
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8072
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8056
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8056
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7911
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7911
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7886
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7886
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7844
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7844
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7827
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7827
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7696
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7696
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7600
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7600
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7598
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7598
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7420
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7420
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7364
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7364
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7287
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7287
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7215
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7215
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7208
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7208
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7133
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.7133
Cysteine synthase	P45040	CYSK_HAEIN	Haemophilus influenzae	3	0.7027
Cysteine synthase	P45040	CYSK_HAEIN	Haemophilus influenzae	3	0.7027

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