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Tingitanol A

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

Canonical Smiles	OC[C@@H]1OC(Oc2cc(/C=C/c3ccc(cc3)O)c3c(c2)O[C@@H]([C@H]3c2cc(O)cc(c2)OC2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C40H42O16/c41-16-28-32(46)34(48)36(50)39(55-28)52-25-13-21(11-24(45)14-25)31-30-20(4-1-18-2-7-22(43)8-3-18)12-26(53-40-37(51)35(49)33(47)29(17-42)56-40)15-27(30)54-38(31)19-5-9-23(44)10-6-19/h1-15,28-29,31-51H,16-17H2/b4-1+/t28-,29+,31+,32-,33+,34+,35-,36-,37+,38-,39?,40?/m1/s1
InChIKey	LZDBTSVRCPFSKK-JRHPLFMDSA-N
Formula	C₄₀H₄₂O₁₆
HBA	16
HBD	11
MW	778.76
Rotatable Bonds	10
TPSA	268.68
LogP	0.6
Number Rings	7
Number Aromatic Rings	4
Heavy Atom Count	56
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	778.25
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: 163070503

Nmrshiftdb2: 70109471

No compound-protein relationship available.

SMILES: c1ccccc1C=Cc2cc(OC3CCCCO3)cc(c24)OC(c5ccccc5)C4c6cc(ccc6)OC7CCCCO7

Level: 5

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cc(OC3CCCCO3)cc(c24)OCC4c5cc(ccc5)OC6CCCCO6

Level: 4

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OC(c4ccccc4)C3c5cc(ccc5)OC6CCCCO6

Level: 4

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cc(OC3CCCCO3)cc(c24)OC(c5ccccc5)C4c6ccccc6

Level: 4

Mol. Weight: 778.76 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)OC(c4ccccc4)C3c5cc(ccc5)OC6CCCCO6

Level: 4

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3c4cc(ccc4)OC5CCCCO5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cc(OC3CCCCO3)cc(c24)OCC4c5ccccc5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cc(OC3CCCCO3)cc(c24)OC(C4)c5ccccc5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)OCC3c4cc(ccc4)OC5CCCCO5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OC(c4ccccc4)C3c5ccccc5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C2c4cc(ccc4)OC5CCCCO5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)OC(c4ccccc4)C3c5ccccc5

Level: 3

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cc(cc(c23)OCC3)OC4CCCCO4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3c4ccccc4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OC(C3)c4ccccc4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C(C2)Oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: c1cccc(c12)OCC2c3cc(ccc3)OC4CCCCO4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: O1CCCCC1Oc(cc2)cc(c23)OCC3c4ccccc4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C2c4ccccc4

Level: 2

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)OCC3

Level: 1

Mol. Weight: 778.76 g/mol

SMILES: C1COc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 778.76 g/mol

SMILES: c1cccc(c12)OCC2c3ccccc3

Level: 1

Mol. Weight: 778.76 g/mol

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 778.76 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 778.76 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 778.76 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 778.76 g/mol

Free radical scavenging

Absorption

Caco-2 (logPapp): -6.54
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 60.97
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 8737.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.99
Plasma Protein Binding: 81.52
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: 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: 4.12
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -203.83
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.82
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.42
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: -15857489.32
Rat (Acute): 2.46
Rat (Chronic Oral): 5.13
Fathead Minnow: 20025.05
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 1777479.5
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.25
Log(P): 0.34
Log S: -5.17
Log(Vapor Pressure): -58443.12
Melting Point: 271.37
pKa Acid: -372.76
pKa Basic: 6.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8413
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8413
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8235
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8235
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8209
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8209
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8054
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8054
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7880
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7880
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7847
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7847
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7527
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.7527
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7359
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7359
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7354
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7354
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7221
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7221
Bromodomain-containing protein 9	Q9H8M2	BRD9_HUMAN	Homo sapiens	3	0.7176
Bromodomain-containing protein 9	Q9H8M2	BRD9_HUMAN	Homo sapiens	3	0.7176
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7104
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7104
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7022
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7022
Beta-glucosidase A	Q08638	BGLA_THEMA	Thermotoga maritima	3	0.7016
Beta-glucosidase A	Q08638	BGLA_THEMA	Thermotoga maritima	3	0.7016
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7011
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7011

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