Grandifotane A - Compound Card

Grandifotane A

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Grandifotane A

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles COC(=O)[C@H]([C@H]1C(C)(C)[C@@H]([C@@]23[C@]1(C)[C@H]1CC[C@@]4([C@@]([C@]1(C2)OC3=O)(O)CC(=O)O[C@H]4c1ccoc1)C)OC(=O)C)O
InChI InChI=1S/C29H36O11/c1-14(30)38-22-24(2,3)19(18(32)21(33)36-6)26(5)16-7-9-25(4)20(15-8-10-37-12-15)39-17(31)11-29(25,35)28(16)13-27(22,26)23(34)40-28/h8,10,12,16,18-20,22,32,35H,7,9,11,13H2,1-6H3/t16-,18+,19+,20+,22+,25+,26-,27+,28-,29+/m1/s1
InChIKey VDCDOIQPTDMABK-QLFMBACMSA-N
Formula C29H36O11
HBA 11
HBD 2
MW 560.6
Rotatable Bonds 4
TPSA 158.8
LogP 2.23
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.72
Exact Mass 560.23
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]
Pubchem: 102171884

No compound-protein relationship available.

Structure

SMILES: C1CCC(C123)C4C(C3)(OC2=O)C5C(CC4)C(OC(=O)C5)c6ccoc6

Level: 1

Mol. Weight: 560.6 g/mol

Structure

SMILES: C1CCC(C123)C4C(C3)(OC2=O)C5C(CC4)COC(=O)C5

Level: 0

Mol. Weight: 560.6 g/mol

Structure

SMILES: c1ccoc1

Level: 0

Mol. Weight: 560.6 g/mol

Anti-plasmodial
Antibacterial

Absorption

Caco-2 (logPapp)
-5.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
80.65
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.710
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.030
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.040
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3729.100
Rat (Acute)
5.180
Rat (Chronic Oral)
2.650
Fathead Minnow
11.820
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
411.340
Hydration Free Energy
-2.890
Log(D) at pH=7.4
2.060
Log(P)
1.36
Log S
-4.14
Log(Vapor Pressure)
-9.61
Melting Point
264.82
pKa Acid
6.19
pKa Basic
3.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7954
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7881
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7857
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7739
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7670
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7308
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7261
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7132
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7132
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7125
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7008
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7006

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