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Isohirtellin C

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Tannin
- Subclass: Macrocyclic-Type Ellagitannin

Canonical Smiles	Oc1cc2cc(c1O)Oc1c(cc(c(c1O)O)O)C(=O)OC1C(OC3C(C1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1c1c(C(=O)OC3)cc(c(c1O)O)O)O)O)OC(=O)c1cc(Oc3c(C(=O)OC4C(OC2=O)OC2COC(=O)c5cc(O)c(c(c5c5c(C(=O)OC2C4OC(=O)c2cc(O)c(c(c2)O)O)cc(O)c(c5O)O)O)O)cc(O)c(c3O)O)c(O)c(c1)O
InChI	InChI=1S/C82H56O52/c83-27-1-17(2-28(84)47(27)95)71(111)129-67-65-41(15-121-75(115)21-9-33(89)51(99)57(105)43(21)45-23(77(117)127-65)11-35(91)53(101)59(45)107)125-81-69(67)131-79(119)25-13-37(93)55(103)61(109)63(25)123-40-8-20(6-32(88)50(40)98)74(114)134-82-70(132-80(120)26-14-38(94)56(104)62(110)64(26)124-39-7-19(73(113)133-81)5-31(87)49(39)97)68(130-72(112)18-3-29(85)48(96)30(86)4-18)66-42(126-82)16-122-76(116)22-10-34(90)52(100)58(106)44(22)46-24(78(118)128-66)12-36(92)54(102)60(46)108/h1-14,41-42,65-70,81-110H,15-16H2
InChIKey	VLGWWDSHLSYKKP-UHFFFAOYSA-N
Formula	C₈₂H₅₆O₅₂
HBA	52
HBD	28
MW	1873.3
Rotatable Bonds	4
TPSA	866.36
LogP	4.13
Number Rings	15
Number Aromatic Rings	10
Heavy Atom Count	134
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	1872.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tamarix nilotica	Tamaricaceae	Plantae	189799

Showing of synonyms

Orabi MA, Taniguchi S, et al. (2010). Hydrolyzable tannins of tamaricaceous plants. III. Hellinoyl- and macrocyclic-type ellagitannins from Tamarix nilotica. Journal of Natural Products,2010,73(5),870-879. [View] [PubMed]

Pubchem: 16130420

Cas: 143201-46-1

Nmrshiftdb2: 70121411

No compound-protein relationship available.

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C6C(O4)OC(=O)c7cc(ccc7)Oc8c(cccc8)C(=O)OC9C(OC(=O)c1cc(ccc1)Oc1c(C(=O)O6)cccc1)OC1C(C9OC(=O)c2ccccc2)OC(=O)c2c(cccc2)c2c(C(=O)OC1)cccc2

Level: 2

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C6C(O4)OC(=O)c7cc(ccc7)Oc8c(cccc8)C(=O)OC9C(OC(=O)c1cc(ccc1)Oc1c(C(=O)O6)cccc1)OC1C(C9)OC(=O)c2c(cccc2)c2c(C(=O)OC1)cccc2

Level: 1

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC5C(O4)OC(=O)c6cc(ccc6)Oc7c(cccc7)C(=O)OC8C(OC(=O)c9cc(ccc9)Oc1c(C(=O)O5)cccc1)OC1C(C8)OC(=O)c2c(cccc2)c2c(C(=O)OC1)cccc2

Level: 0

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1873.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 185723484170856529778042338279424.000
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 24271873015641254000000000000000000

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): -0.260
Plasma Protein Binding: 89.29
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: 9.920
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -564508787018036945042731618533376.000
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -230495690368984208294019072.000
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Toxic
NR-TR: Toxic
T. Pyriformis: -inf
Rat (Acute): 35526330269191140016128.000
Rat (Chronic Oral): 94488255585488759331036856320.000
Fathead Minnow: 55606636849748186308932277781921792.000
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 4954660343899088254211781552399974400.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -2754296473437456986448544661504.000
Log(P): -320632636147764900000000000
Log S: -13.65
Log(Vapor Pressure): -163154468367519450000000000000000000
Melting Point: -49576783289834990000000000000
pKa Acid: -1188837629127555300000000000000000
pKa Basic: -9564161162943922000000000000000

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8135
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8135
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7372
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7372
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7365
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7365

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