3-oxo-18-beta-glycyrrhetinic acid - Compound Card

3-oxo-18-beta-glycyrrhetinic acid

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3-oxo-18-beta-glycyrrhetinic acid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)O[C@H]1CC[C@]2(C(C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C
InChI InChI=1S/C32H48O5/c1-19(33)37-24-10-11-30(6)23(27(24,2)3)9-12-32(8)25(30)22(34)17-20-21-18-29(5,26(35)36)14-13-28(21,4)15-16-31(20,32)7/h17,21,23-25H,9-16,18H2,1-8H3,(H,35,36)/t21-,23?,24-,25+,28+,29-,30-,31+,32+/m0/s1
InChIKey FTQDJVZNPJRVPG-MFVSDTKSSA-N
Formula C32H48O5
HBA 4
HBD 1
MW 512.73
Rotatable Bonds 2
TPSA 80.67
LogP 6.98
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.84
Exact Mass 512.35
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Glycyrrhiza glabra Leguminosae/Fabaceae Plantae 49827

Showing of synonyms

  • Abdel Bar .FM, Elimam D.M, et al. (2019). Derivatization, molecular docking and in vitro acetylcholinesterase inhibitory activity of glycyrrhizin as a selective anti-Alzheimer agent. Natural product research, 2019, 33(18), 2591-2599. [View] [PubMed]
Pubchem: 11060315

No compound-protein relationship available.

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(C(=O)C3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 512.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.34
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.01

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.29
Plasma Protein Binding
97.3
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.85
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
Safe
T. Pyriformis
-432.82
Rat (Acute)
2.23
Rat (Chronic Oral)
2.14
Fathead Minnow
4.04
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
513.43
Hydration Free Energy
-2.87
Log(D) at pH=7.4
3.94
Log(P)
5.92
Log S
-6.36
Log(Vapor Pressure)
-9.61
Melting Point
288.74
pKa Acid
6.28
pKa Basic
6.8
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8666
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8199
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8199
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7773
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7326
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7270
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7183
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7173
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7119

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