ANPDB

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Hirtellin B

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Tannin

Canonical Smiles	O=C1O[C@H]2[C@@H](O[C@H]3[C@H]([C@@H]2OC(=O)c2cc(O)c(c(c2)O)O)OC(=O)c2cc(O)c(c(c2c2c(C(=O)OC3)cc(c(c2O)O)O)O)O)OC(=O)c2cc(Oc3c1cc(Oc1c(cc(c(c1O)O)O)C(=O)O[C@H]1[C@@H](O[C@H]4[C@H]([C@@H]1OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1c1c(C(=O)OC4)cc(c(c1O)O)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O)c(c3O)O)c(O)c(c2)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)21-9-34(90)51(99)57(105)43(21)45-23(77(117)127-65)11-36(92)53(101)59(45)107)125-81(133-73(113)19-5-31(87)49(97)32(88)6-19)69(67)131-79(119)25-13-38(94)55(103)61(109)63(25)124-40-14-26-64(62(110)56(40)104)123-39-8-20(7-33(89)50(39)98)74(114)134-82-70(132-80(26)120)68(130-72(112)18-3-29(85)48(96)30(86)4-18)66-42(126-82)16-122-76(116)22-10-35(91)52(100)58(106)44(22)46-24(78(118)128-66)12-37(93)54(102)60(46)108/h1-14,41-42,65-70,81-110H,15-16H2/t41-,42-,65-,66-,67+,68+,69-,70-,81+,82+/m1/s1
InChIKey	UOUAIWRZGXIRCC-QHNYOMBNSA-N
Formula	C₈₂H₅₆O₅₂
HBA	52
HBD	28
MW	1873.3
Rotatable Bonds	10
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: 16133926

Cas: 135404-48-7

Nmrshiftdb2: 60033594

Chembl: CHEMBL1077254

Comptox: DTXSID70159332

No compound-protein relationship available.

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C(C(O4)OC(=O)c6ccccc6)OC(=O)c7c(cccc7)Oc(cc8)cc(C(=O)O9)c8Oc(ccc1)cc1C(=O)OC(O1)C9C(OC(=O)c2ccccc2)C(OC(=O)c2cccc3)C1COC(=O)c(c1c23)cccc1

Level: 5

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC(C(O4)OC(=O)c5ccccc5)OC(=O)c6c(cccc6)Oc(cc7)cc(C(=O)O8)c7Oc(ccc9)cc9C(=O)OC(O1)C8C(OC(=O)c2ccccc2)C(OC(=O)c2cccc3)C1COC(=O)c(c1c23)cccc1

Level: 4

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C(CO4)OC(=O)c6c(cccc6)Oc(cc7)cc(C(=O)O8)c7Oc(ccc9)cc9C(=O)OC(O1)C8C(OC(=O)c2ccccc2)C(OC(=O)c2cccc3)C1COC(=O)c(c1c23)cccc1

Level: 4

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C(C(O4)OC(=O)c6ccccc6)OC(=O)c7c(cccc7)Oc(cc8)cc(C(=O)O9)c8Oc(ccc1)cc1C(=O)OC(O1)C9CC(OC(=O)c2cccc3)C1COC(=O)c(c1c23)cccc1

Level: 4

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC(CO4)OC(=O)c5c(cccc5)Oc(cc6)cc(C(=O)O7)c6Oc(ccc8)cc8C(=O)OC(O9)C7C(OC(=O)c1ccccc1)C(OC(=O)c1cccc2)C9COC(=O)c(c3c12)cccc3

Level: 3

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC(C(O4)OC(=O)c5ccccc5)OC(=O)c6c(cccc6)Oc(cc7)cc(C(=O)O8)c7Oc(ccc9)cc9C(=O)OC(O1)C8CC(OC(=O)c2cccc3)C1COC(=O)c(c1c23)cccc1

Level: 3

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C(CO4)OC(=O)c6c(cccc6)Oc(cc7)cc(C(=O)O8)c7Oc(ccc9)cc9C(=O)OC(O1)C8CC(OC(=O)c2cccc3)C1COC(=O)c(c1c23)cccc1

Level: 3

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)C(OC(=O)c5ccccc5)C(OC(=O)c6ccccc6)C(O4)OC(=O)c7ccccc7

Level: 3

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC(CO4)OC(=O)c5c(cccc5)Oc(cc6)cc(C(=O)O7)c6Oc(ccc8)cc8C(=O)OC(O9)C7CC(OC(=O)c1cccc2)C9COC(=O)c(c3c12)cccc3

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(C(=O)O6)cc(cc8)Oc9ccccc9

Level: 2

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1C(=O)OC(O2)CC(OC(=O)c3ccccc3)C(OC(=O)c4cccc5)C2COC(=O)c(c6c45)cccc6

Level: 2

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1C(=O)OC(O2)C(OC(=O)c3ccccc3)CC(OC(=O)c4cccc5)C2COC(=O)c(c6c45)cccc6

Level: 2

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1C(=O)OC(CO2)C(OC(=O)c3ccccc3)C(OC(=O)c4cccc5)C2COC(=O)c(c6c45)cccc6

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(C(=O)O6)cccc8

Level: 1

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC5C(O4)OC(=O)c6cc(ccc6)Oc7c(C(=O)O5)cc(cc7)Oc8ccccc8

Level: 1

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1C(=O)OC(O2)CCC(OC(=O)c3cccc4)C2COC(=O)c(c5c34)cccc5

Level: 1

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1C(=O)OC(CO2)CC(OC(=O)c3cccc4)C2COC(=O)c(c5c34)cccc5

Level: 1

Mol. Weight: 1873.3 g/mol

SMILES: c1ccccc1C(=O)OC(CCO2)C(OC(=O)c3cccc4)C2COC(=O)c(c5c34)cccc5

Level: 1

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(OC(=O)c2cccc3)CC5C(O4)OC(=O)c6cc(ccc6)Oc7c(C(=O)O5)cccc7

Level: 0

Mol. Weight: 1873.3 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC4C(CCCO4)OC(=O)c2cccc3

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: 131639560264885240000000000000000
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 17203756164215940000000000000000000

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): -0.25
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: 9.98
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -400120388785594240000000000000000
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -163373972801048160000000000
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.05
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: -Infinity
Rat (Acute): 25180854679070734000000
Rat (Chronic Oral): 66972742014959950000000000000
Fathead Minnow: 39413640373796790000000000000000000
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: 3511832790683306500000000000000000000
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -1952228831038805200000000000000
Log(P): -227262468551668250000000000
Log S: -12.0
Log(Vapor Pressure): -115642858752317020000000000000000000
Melting Point: -35139725285100560000000000000
pKa Acid: -842641097450021000000000000000000
pKa Basic: -6779021139291599000000000000000

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8122
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8122
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8066
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8066
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7730
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7730
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7479
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7479
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7309
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7309
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7138
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7138
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7034
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7034

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