24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one - Compound Card

24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one

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24-acetoxy-21,25-dihydroxy-21,23-epoxytirucall-7-en-3-one

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Limonoid
Canonical Smiles OC(=O)OC(C(O)(C)C)C1OC(C(C1)C1CC[C@]2([C@@]1(C)CCC1C2=CCC2[C@]1(C)CCC(=O)C2(C)C)C)O
InChI InChI=1S/C31H48O7/c1-27(2)22-9-8-20-19(29(22,5)13-12-23(27)32)11-15-30(6)18(10-14-31(20,30)7)17-16-21(37-25(17)33)24(28(3,4)36)38-26(34)35/h8,17-19,21-22,24-25,33,36H,9-16H2,1-7H3,(H,34,35)/t17?,18?,19?,21?,22?,24?,25?,29-,30+,31-/m1/s1
InChIKey QIWDPUKDUZITBS-DVLDLCPTSA-N
Formula C31H48O7
HBA 6
HBD 3
MW 532.72
Rotatable Bonds 4
TPSA 113.29
LogP 5.72
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 532.34
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Trichilia monadelpha Meliaceae Plantae 1640473

Showing of synonyms

  • Djoumessi AK, Nono RN, et al. (2023). Constituents of the Stem Bark of Trichilia monadelpha (Thonn.) J. J. De Wilde (Meliaceae) and Their Antibacterial and Antiplasmodial Activities. Metabolites 2023, 13, 298. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1OCCC1C2CCC(C23)C=4C(CC3)C5C(CC4)CC(=O)CC5

Level: 1

Mol. Weight: 532.72 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(=O)C4

Level: 0

Mol. Weight: 532.72 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 532.72 g/mol

Anti-plasmodial
Antibacterial

Absorption

Caco-2 (logPapp)
-5.39
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.930
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.310
Plasma Protein Binding
74.61
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
Non-Inhibitor

Excretion

Clearance
2.580
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.180
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.080
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.420
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
Toxic
T. Pyriformis
-910.550
Rat (Acute)
1.970
Rat (Chronic Oral)
2.310
Fathead Minnow
4.440
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
465.590
Hydration Free Energy
-3.130
Log(D) at pH=7.4
3.990
Log(P)
4.09
Log S
-5.09
Log(Vapor Pressure)
-9.43
Melting Point
231.72
pKa Acid
3.18
pKa Basic
6.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9137
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8919
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8435
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8014
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7749
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7393
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7282

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