1beta-hydroxymaprounic acid 3-p-hydroxybenzoate - Compound Card

1beta-hydroxymaprounic acid 3-p-hydroxybenzoate

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1beta-hydroxymaprounic acid 3-p-hydroxybenzoate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpene
Canonical Smiles Oc1ccc(cc1)C(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)C[C@@H]([C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@@H](C(=O)O)[C@H](C)CC1)C)C)O)C
InChI InChI=1S/C37H52O6/c1-21-14-16-34(4)18-19-36(6)24(30(34)29(21)31(40)41)12-13-25-35(5)17-15-28(43-32(42)22-8-10-23(38)11-9-22)33(2,3)26(35)20-27(39)37(25,36)7/h8-12,21,25-30,38-39H,13-20H2,1-7H3,(H,40,41)/t21-,25-,26+,27+,28-,29+,30-,34-,35-,36-,37+/m1/s1
InChIKey ZUSBKFQCLQZULB-QRIOGHQNSA-N
Formula C37H52O6
HBA 5
HBD 3
MW 592.82
Rotatable Bonds 3
TPSA 104.06
LogP 7.63
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 592.38
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: 328712

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(CC2)CC(CC3)C2C(CC4)C3C(C=45)CCC6C5CCCC6

Level: 1

Mol. Weight: 592.82 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 592.82 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 592.82 g/mol

Hiv-1 reverse transcriptase

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.030
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
4.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.840
Plasma Protein Binding
110.53
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.150
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.100
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.650
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
2.760
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
-11895.180
Rat (Acute)
2.420
Rat (Chronic Oral)
2.000
Fathead Minnow
29.570
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
387.110
Hydration Free Energy
-2.850
Log(D) at pH=7.4
5.390
Log(P)
8.44
Log S
-6.32
Log(Vapor Pressure)
-15.4
Melting Point
258.51
pKa Acid
6.42
pKa Basic
6.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8866
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8866
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8319
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8319
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8198
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8198
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7799
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7799
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7740
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7740
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7256
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7256
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7198
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7198
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7182
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7182
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7094
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7094
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7021
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7021
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7020
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7020

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