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

3-beta-phenylcarbamoyl-18-beta-glycyrrhetinic acid

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3-beta-phenylcarbamoyl-18-beta-glycyrrhetinic acid

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=C(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)Nc1ccccc1
InChI InChI=1S/C37H51NO5/c1-32(2)27-13-16-37(7)29(35(27,5)15-14-28(32)43-31(42)38-23-11-9-8-10-12-23)26(39)21-24-25-22-34(4,30(40)41)18-17-33(25,3)19-20-36(24,37)6/h8-12,21,25,27-29H,13-20,22H2,1-7H3,(H,38,42)(H,40,41)/t25-,27?,28-,29+,33+,34-,35-,36+,37+/m0/s1
InChIKey UFYTZDOIQONUBL-SWUUHUQKSA-N
Formula C37H51NO5
HBA 4
HBD 2
MW 589.82
Rotatable Bonds 3
TPSA 92.7
LogP 8.67
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 589.38
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: c1ccccc1NC(=O)OC(CC2)CC(CC3)C2C(C(=O)C4)C3C(C=45)CCC6C5CCCC6

Level: 1

Mol. Weight: 589.82 g/mol

Structure

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

Level: 0

Mol. Weight: 589.82 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 589.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.25
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
3.73

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.49
Plasma Protein Binding
113.15
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
3.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.79
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.23
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.78
Micronucleos
Toxic
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
-11734.06
Rat (Acute)
2.55
Rat (Chronic Oral)
2.34
Fathead Minnow
30.69
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
368.44
Hydration Free Energy
-2.86
Log(D) at pH=7.4
4.73
Log(P)
7.18
Log S
-6.57
Log(Vapor Pressure)
-16.11
Melting Point
280.46
pKa Acid
5.9
pKa Basic
6.28
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 0.8540
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7986
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7947
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7800
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 2 0.7387
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7313
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7181
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7141
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7133
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7110
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7102
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7038
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 2 0.7033

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