3-beta-hydroxy-18-beta-glycyrrhetinic prenyl ester - Compound Card

3-beta-hydroxy-18-beta-glycyrrhetinic prenyl ester

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3-beta-hydroxy-18-beta-glycyrrhetinic prenyl ester

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=CCOC(=O)[C@@]1(C)CC[C@]2([C@@H](C1)C1=CC(=O)[C@H]3[C@@]([C@@]1(CC2)C)(C)CCC1[C@]3(C)CC[C@@H](C1(C)C)O)C)C
InChI InChI=1S/C35H54O4/c1-22(2)12-19-39-29(38)32(6)16-15-31(5)17-18-34(8)23(24(31)21-32)20-25(36)28-33(7)13-11-27(37)30(3,4)26(33)10-14-35(28,34)9/h12,20,24,26-28,37H,10-11,13-19,21H2,1-9H3/t24-,26?,27-,28+,31+,32-,33-,34+,35+/m0/s1
InChIKey XJWFEWRRAFLFSE-VXOAYBHBSA-N
Formula C35H54O4
HBA 4
HBD 1
MW 538.81
Rotatable Bonds 3
TPSA 63.6
LogP 7.84
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 538.4
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: 538.81 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
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)
1.96
Plasma Protein Binding
98.81
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.0
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.43
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
-1180.67
Rat (Acute)
2.26
Rat (Chronic Oral)
1.96
Fathead Minnow
6.92
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
490.29
Hydration Free Energy
-2.95
Log(D) at pH=7.4
6.81
Log(P)
8.24
Log S
-6.94
Log(Vapor Pressure)
-8.45
Melting Point
238.75
pKa Acid
10.66
pKa Basic
5.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8972
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8287
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8064
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7641
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7529
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7392
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7361
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7175
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7075
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7058
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7018
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7007

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