Prototiamin A - Compound Card

Prototiamin A

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Prototiamin A

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC[C@H]([C@]1(C)CC3)[C@@H]1C[C@@H](OC1=O)[C@@H](C(O)(C)C)O)(C)C=CC(=O)C2(C)C
InChI InChI=1S/C32H46O7/c1-17(33)38-25-16-23-28(2,3)24(34)12-14-31(23,7)22-11-13-30(6)19(9-10-21(30)32(22,25)8)18-15-20(39-27(18)36)26(35)29(4,5)37/h10,12,14,18-20,22-23,25-26,35,37H,9,11,13,15-16H2,1-8H3/t18-,19-,20+,22+,23-,25+,26-,30-,31+,32-/m0/s1
InChIKey INWMCYHICBYRCK-QAPXOFNMSA-N
Formula C32H46O7
HBA 7
HBD 2
MW 542.71
Rotatable Bonds 4
TPSA 110.13
LogP 4.54
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 542.32
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma congoënse Meliaceae Plantae 2590899
2 Entandrophragma congoense Meliaceae Plantae 2590899

Showing of synonyms

  • Happi GM, Kouam SF, et al. (2015). Antiplasmodial and Cytotoxic Triterpenoids from the Bark of the Cameroonian Medicinal Plant Entandrophragma congoënse.. Journal of natural products,2015, 78(4), 604-614. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCC(C1=O)C(CC2)C(C=23)CCC4C3CCC5C4C=CC(=O)C5

Level: 1

Mol. Weight: 542.71 g/mol

Structure

SMILES: C1CCC(C=12)CCC3C2CCC4C3C=CC(=O)C4

Level: 0

Mol. Weight: 542.71 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 542.71 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.19

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.45
Plasma Protein Binding
89.26
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
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.41
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.69
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1382.93
Rat (Acute)
3.28
Rat (Chronic Oral)
1.94
Fathead Minnow
6.6
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
495.67
Hydration Free Energy
-2.83
Log(D) at pH=7.4
3.82
Log(P)
3.61
Log S
-5.84
Log(Vapor Pressure)
-9.33
Melting Point
252.07
pKa Acid
9.16
pKa Basic
5.01
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7946
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7216
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7159
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7066

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