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2alpha-hydroxymaprounic acid 2,3-bis-p-hydroxybenzoate

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Pentacyclic Triterpene

Canonical Smiles	Oc1ccc(cc1)C(=O)O[C@@H]1C[C@@]2(C)C(C([C@H]1OC(=O)c1ccc(cc1)O)(C)C)CC[C@@]1(C2CC[C@@]2(C1=CC[C@@]1(C2CC(C)(C)CC1)C(=O)O)C)C
InChI	InChI=1S/C44H56O8/c1-39(2)22-23-44(38(49)50)21-18-32-41(5)19-16-31-40(3,4)35(52-37(48)27-10-14-29(46)15-11-27)30(51-36(47)26-8-12-28(45)13-9-26)24-43(31,7)33(41)17-20-42(32,6)34(44)25-39/h8-15,18,30-31,33-35,45-46H,16-17,19-25H2,1-7H3,(H,49,50)/t30-,31?,33?,34?,35+,41+,42-,43+,44-/m1/s1
InChIKey	XPEVLOSUULAUFH-QOAKHUDCSA-N
Formula	C₄₄H₅₆O₈
HBA	7
HBD	3
MW	712.92
Rotatable Bonds	5
TPSA	130.36
LogP	9.35
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.61
Exact Mass	712.4
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Maprounea africana	Euphorbiaceae	Plantae	316848

Showing of synonyms

Pengsuparp T, Cai L, et al. (1994). Pentacyclic triterpenes derived from Maprounea africana are potent inhibitors of HIV-1 reverse transcriptase.. Journal of natural products,1994,57(3),415-418. [View] [PubMed]

Pubchem: 455330

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(C2)C(OC(=O)c3ccccc3)CC(CC4)C2C(C4C=56)CCC6C7C(CC5)CCCC7

Level: 2

Mol. Weight: 712.92 g/mol

SMILES: c1ccccc1C(=O)OC(CC2)CC(CC3)C2C(C3C=45)CCC5C6C(CC4)CCCC6

Level: 1

Mol. Weight: 712.92 g/mol

SMILES: c1ccccc1C(=O)OC(C2)CCC(CC3)C2C(C3C=45)CCC5C6C(CC4)CCCC6

Level: 1

Mol. Weight: 712.92 g/mol

SMILES: C1CCCC(CC2)C1C(C2C=34)CCC4C5C(CC3)CCCC5

Level: 0

Mol. Weight: 712.92 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 712.92 g/mol

Hiv-1 reverse transcriptase

Absorption

Caco-2 (logPapp): -5.48
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -1.400
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 512.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.680
Plasma Protein Binding: 93.55
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: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 6.930
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -9.950
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.690
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.050
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -933940.250
Rat (Acute): 2.010
Rat (Chronic Oral): 3.070
Fathead Minnow: 1188.290
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 100781.690
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 6.270
Log(P): 10.0
Log S: -7.4
Log(Vapor Pressure): -3300.84
Melting Point: 318.57
pKa Acid: 1.5
pKa Basic: 6.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9230
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9230
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9011
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9011
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8848
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8848
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8739
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8739
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8707
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8707
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8498
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8498
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8366
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8366
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8148
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8148
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8118
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8118
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8072
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8072
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8044
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8044
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7892
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7892
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7890
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7890
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7874
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7874
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7789
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7789
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7727
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7727
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7714
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7714
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7713
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.7713
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7606
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7606
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7578
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7578
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7462
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7462
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7451
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7451
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7441
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7441
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7419
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7419
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7397
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7397
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7317
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7317
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7257
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7257
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7208
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7208
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7196
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7196
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7191
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7191
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7185
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7185
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7093
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7093
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7053
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7053
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7040
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7040
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7040
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7040
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7028
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7028
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7014
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7014
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7001
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7001

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