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

3-methoxy-18-beta-glycyrrhetinic acid

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3-methoxy-18-beta-glycyrrhetinic acid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C(C1CC2)(C)C)OC(C)(C)C)C)C)C(=O)O
InChI InChI=1S/C34H54O4/c1-28(2,3)38-25-12-13-32(8)24(29(25,4)5)11-14-34(10)26(32)23(35)19-21-22-20-31(7,27(36)37)16-15-30(22,6)17-18-33(21,34)9/h19,22,24-26H,11-18,20H2,1-10H3,(H,36,37)/t22-,24?,25-,26+,30+,31-,32-,33+,34+/m0/s1
InChIKey YOORXFVWRWHVKX-VAKSMUNFSA-N
Formula C34H54O4
HBA 3
HBD 1
MW 526.8
Rotatable Bonds 2
TPSA 63.6
LogP 8.24
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 526.4
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]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 526.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.37
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.500
Plasma Protein Binding
103.24
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
1.820
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.160
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.180
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.160
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
-548.960
Rat (Acute)
2.340
Rat (Chronic Oral)
1.960
Fathead Minnow
4.100
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
495.460
Hydration Free Energy
-2.860
Log(D) at pH=7.4
5.040
Log(P)
7.4
Log S
-6.73
Log(Vapor Pressure)
-9.1
Melting Point
293.34
pKa Acid
6.21
pKa Basic
7.42
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 0.8692
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8349
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7563
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7475

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