3-beta-acetyl-18-beta-glycyrrhetinic-30-anilinamide - Compound Card

3-beta-acetyl-18-beta-glycyrrhetinic-30-anilinamide

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3-beta-acetyl-18-beta-glycyrrhetinic-30-anilinamide

Structure
Zoomed Structure
  • Family: 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)ONc1ccccc1)C)C)C
InChI InChI=1S/C38H53NO5/c1-24(40)43-30-15-16-36(6)29(33(30,2)3)14-17-38(8)31(36)28(41)22-26-27-23-35(5,19-18-34(27,4)20-21-37(26,38)7)32(42)44-39-25-12-10-9-11-13-25/h9-13,22,27,29-31,39H,14-21,23H2,1-8H3/t27-,29?,30-,31+,34+,35-,36-,37+,38+/m0/s1
InChIKey PCOVFZLIJYCNSP-ZBYDWTGVSA-N
Formula C38H53NO5
HBA 6
HBD 1
MW 603.84
Rotatable Bonds 4
TPSA 81.7
LogP 8.47
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 603.39
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: c1ccccc1NOC(=O)C(CC2)CC3C2CCC(C3=4)C5C(C(=O)C4)C6C(CC5)CCCC6

Level: 1

Mol. Weight: 447.62 g/mol

Structure

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

Level: 0

Mol. Weight: 312.5 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.76
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
7.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.44
Plasma Protein Binding
104.24
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
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
Inhibitor

Excretion

Clearance
6.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.07
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.8
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
-19244.81
Rat (Acute)
2.43
Rat (Chronic Oral)
2.3
Fathead Minnow
43.47
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
339.55
Hydration Free Energy
-2.92
Log(D) at pH=7.4
6.06
Log(P)
7.06
Log S
-6.94
Log(Vapor Pressure)
-10.84
Melting Point
243.37
pKa Acid
9.15
pKa Basic
5.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8406
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.8264
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8012
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7753
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7660
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7647
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7604
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7567
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 2 0.7493
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7471
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7465
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7460
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7279
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 3 0.7277
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7264
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7225
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7202
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7180
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7150
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7125
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7122
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7093
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7076
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7044
Class B acid phosphatase P0AE22 APHA_ECOLI Escherichia coli 2 0.7042
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7022
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7015
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7012
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7010
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7004

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