ANPDB

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Acutissimin B

Family: Plantae - Fagaceae
Kingdom: Plantae
Class: Tannin

Canonical Smiles	O[C@@H]1Cc2c(O[C@@H]1c1ccc(c(c1)O)O)cc(c(c2O)[C@@H]1[C@@H]2OC(=O)c3c1c(O)c(O)c(c3c1c3C(=O)O[C@@H]2[C@H]2OC(=O)c4cc(O)c(c(c4c4c(C(=O)OC[C@@H]2OC(=O)c2c(c3c(c(c1O)O)O)c(O)c(c(c2)O)O)cc(c(c4O)O)O)O)O)O)O
InChI	InChI=1S/C56H38O31/c57-15-2-1-10(3-16(15)58)48-21(63)4-11-22(83-48)8-17(59)27(35(11)64)32-31-34-30(44(73)47(76)45(31)74)29-33-28(42(71)46(75)43(29)72)26-14(7-20(62)38(67)41(26)70)53(78)84-23-9-82-52(77)12-5-18(60)36(65)39(68)24(12)25-13(6-19(61)37(66)40(25)69)54(79)85-49(23)51(87-56(33)81)50(32)86-55(34)80/h1-3,5-8,21,23,32,48-51,57-76H,4,9H2/t21-,23+,32+,48-,49+,50+,51-/m1/s1
InChIKey	IGVSILAHFPDUTO-BBKCZMQOSA-N
Formula	C₅₆H₃₈O₃₁
HBA	31
HBD	20
MW	1206.89
Rotatable Bonds	2
TPSA	545.33
LogP	3.28
Number Rings	13
Number Aromatic Rings	7
Heavy Atom Count	87
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	1206.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Quercus suber	Fagaceae	Plantae	58331

Showing of synonyms

Ito H, Yamaguchi K, et al. (2002). Dimeric and trimeric hydrolyzable tannins from Quercus coccifera and Quercus suber. Journal of Natural Products,2002,65(3),339-345. [View] [PubMed]

Pubchem: 101676953

No compound-protein relationship available.

SMILES: c12c3c4c5c(ccc4)c6c(cccc6)C(=O)OC7C(OC(=O)c8c(cccc8)c9c(C(=O)OC7)cccc9)C(OC5=O)C(OC2=O)C(c1ccc3)c(c1)ccc(c12)OC(CC2)c1ccccc1

Level: 2

Mol. Weight: 1206.89 g/mol

SMILES: c12c3c4c5c(ccc4)c6c(cccc6)C(=O)OC7C(OC(=O)c8c(cccc8)c9c(C(=O)OC7)cccc9)C(OC5=O)C(OC2=O)C(c1ccc3)c(c1)ccc(c12)OCCC2

Level: 1

Mol. Weight: 1206.89 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 1206.89 g/mol

SMILES: c12c3c4c5c(ccc4)c6c(cccc6)C(=O)OC7C(C(OC5=O)C(OC2=O)Cc1ccc3)OC(=O)c8c(cccc8)c9c(C(=O)OC7)cccc9

Level: 0

Mol. Weight: 1206.89 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 1206.89 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1206.89 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.12
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 56807057838.58
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 7424020344164.29

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.02
Plasma Protein Binding: 18.97
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: 10.44
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -172665932159.12
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -70503.04
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.05
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -13474239348554022
Rat (Acute): 2.58
Rat (Chronic Oral): 28901061.2
Fathead Minnow: 17008366290885.2
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 1515478435587507.5
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -842454804.91
Log(P): -98069.91
Log S: -10.39
Log(Vapor Pressure): -49903935665161.09
Melting Point: -15159012.92
pKa Acid: -363628922815.1
pKa Basic: -2925383885.61

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8641
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8641
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8602
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8602
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8562
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8562
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8393
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8393
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8332
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8332
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8322
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8322
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8307
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8307
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8300
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8300
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7974
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7974
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7963
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7963
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7903
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7903
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	4	0.7876
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	4	0.7876
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7793
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7793
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.7262
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	4	0.7262
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7169
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	5	0.7169
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7165
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7165
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7108
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7108
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	5	0.7063
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	5	0.7063
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7058
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7058
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7051
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7051

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