Prototiamin B - Compound Card

Prototiamin B

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Prototiamin B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=C1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@H]1[C@@]2(C)[C@H](O)C[C@@H]2[C@]1(C)C=CC(=O)C2(C)C)[C@H](C(O)(C)C)O
InChI InChI=1S/C30H44O6/c1-26(2)21-15-23(32)30(7)19-9-8-17(16-14-18(36-25(16)34)24(33)27(3,4)35)28(19,5)12-10-20(30)29(21,6)13-11-22(26)31/h9,11,13,16-18,20-21,23-24,32-33,35H,8,10,12,14-15H2,1-7H3/t16-,17-,18+,20+,21-,23+,24+,28-,29+,30-/m0/s1
InChIKey PBMIHQFKVOCZOV-RPXOSLCWSA-N
Formula C30H44O6
HBA 6
HBD 3
MW 500.68
Rotatable Bonds 3
TPSA 104.06
LogP 3.97
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 500.31
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]
Pubchem: 122178978

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 500.68 g/mol

Structure

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

Level: 0

Mol. Weight: 500.68 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 500.68 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.32
Plasma Protein Binding
83.24
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
5.97
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.96
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.11
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.63
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
-373.62
Rat (Acute)
3.99
Rat (Chronic Oral)
2.0
Fathead Minnow
3.95
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
498.0
Hydration Free Energy
-3.03
Log(D) at pH=7.4
3.5
Log(P)
3.51
Log S
-5.12
Log(Vapor Pressure)
-9.74
Melting Point
255.38
pKa Acid
7.61
pKa Basic
5.12
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7890
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7865
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7385
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7345
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7205
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7183

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