Prototiamin D - Compound Card

Prototiamin D

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Prototiamin D

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=O)O[C@@H]1C[C@H]2C(C)(C)[C@H](O)CC[C@@]2([C@@H]2[C@]1(C)C1=CC[C@H]([C@]1(C)CC2)[C@@H]1C[C@@H](OC1=O)[C@@H](C(O)(C)C)O)C
InChI InChI=1S/C32H50O7/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/h10,18-20,22-26,34-35,37H,9,11-16H2,1-8H3/t18-,19-,20+,22+,23-,24+,25+,26-,30-,31+,32-/m0/s1
InChIKey JTBQVVWNWDFTSZ-MKUWHFERSA-N
Formula C32H50O7
HBA 7
HBD 3
MW 546.75
Rotatable Bonds 4
TPSA 113.29
LogP 4.56
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 546.36
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: 122178980

No compound-protein relationship available.

Structure

SMILES: O1CCC(C1=O)C(CC2)C(C=23)CCC4C3CCC5C4CCCC5

Level: 1

Mol. Weight: 546.75 g/mol

Structure

SMILES: C1CCC(C=12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 546.75 g/mol

Structure

SMILES: O=C1CCCO1

Level: 0

Mol. Weight: 546.75 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
82.36
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
3.74
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.86
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.53
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.0
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
-1385.21
Rat (Acute)
3.28
Rat (Chronic Oral)
2.17
Fathead Minnow
5.76
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
495.75
Hydration Free Energy
-2.85
Log(D) at pH=7.4
3.83
Log(P)
3.75
Log S
-5.65
Log(Vapor Pressure)
-9.73
Melting Point
241.51
pKa Acid
9.0
pKa Basic
6.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7958

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