ID: ALA48257

Max Phase: Preclinical

Molecular Formula: C23H45NO4

Molecular Weight: 399.62

Molecule Type: Small molecule

Representations

Synonyms (1): Rac-Hemipalmitoylcarnitinium
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCCCCCCCCCCCC[C@@]1(O)C[N+](C)(C)C[C@@H](CC(=O)[O-])O1

Standard InChI:  InChI=1S/C23H45NO4/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(27)20-24(2,3)19-21(28-23)18-22(25)26/h21,27H,4-20H2,1-3H3/t21-,23+/m1/s1

Standard InChI Key:  SPDGRWIGMIHIAC-GGAORHGYSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 399.62

Molecular Weight (Monoisotopic): 399.3349

AlogP: 3.77

#Rotatable Bonds: 16

Polar Surface Area: 69.59

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.20

CX Basic pKa:

CX LogP: 1.88

CX LogD: 2.65

Aromatic Rings: 0

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 0.70

References

1. Kumaravel G, Ashendel CL, Gandour RD..  (1993)  Hemicholinium and related lipids: inhibitors of protein kinase C.,  36  (1): [PMID:8421285] [10.1021/jm00053a024]

2. Gandour RD, Leung OT, Greway AT, Ramsay RR, Nic a'Bháird N, Fronczek FR, Bellard BM, Kumaravel G..  (1993)  (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransferase-I in intact mitochondria.,  36  (2): [PMID:8423595] [10.1021/jm00054a007]

3. Savle PS, Doncel GF, Bryant SD, Hubieki MP, Robinette RG, Gandour RD..  (1999)  Acylcarnitine analogues as topical, microbicidal spermicides.,  9  (17): [PMID:10498205] [10.1016/s0960-894x(99)00423-0]

4. Ceccarelli SM, Chomienne O, Gubler M, Arduini A..  (2011)  Carnitine palmitoyltransferase (CPT) modulators: a medicinal chemistry perspective on 35 years of research.,  54  (9): [PMID:21504156] [10.1021/jm100809g]

Source

Source(1):

• Scientific Literature