4-(11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-(2-methyl-cyclopropyl)-4,5-dihydro-thiazole

ID: ALA89138

Chembl Id: CHEMBL89138

Cas Number: 155233-30-0

PubChem CID: 5281967

Max Phase: Preclinical

Molecular Formula: C23H35NOS

Molecular Weight: 373.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Curacin A | Curacin A|CHEMBL89138|Curacin B|CHEBI:3961|155233-30-0|(+)-curacin A|AC1NQZCP|S9C9YBJ48Q|Euracin A|SCHEMBL61304|CHEBI:244483|DTXSID001032406|Thiazole, 4,5-dihydro-4-(11-methoxy-8-methyl-1,5,7,13-tetradecatetraenyl)-2-(2-methylcyclopropyl)-, [1R-[1alpha[R*(1Z,5E,7E,11R*)],2alpha]]-|BDBM50290537|(4R)-4-[(1Z,5E,7E,11R)-11-methoxy-8-methyltetradeca-1,5,7,13-tetraenyl]-2-[(1R,2S)-2-methylcyclopropyl]-4,5-dihydro-1,3-thiazole|Q25323731|(4R)-4,5-Dihydro-4-[(1Z,5E,7E,11R)-11-methoxy-8-methylShow More⌵

Canonical SMILES:  C=CC[C@@H](CC/C(C)=C/C=C/CC/C=C\[C@@H]1CSC([C@@H]2C[C@@H]2C)=N1)OC

Standard InChI:  InChI=1S/C23H35NOS/c1-5-11-21(25-4)15-14-18(2)12-9-7-6-8-10-13-20-17-26-23(24-20)22-16-19(22)3/h5,7,9-10,12-13,19-22H,1,6,8,11,14-17H2,2-4H3/b9-7+,13-10-,18-12+/t19-,20+,21-,22+/m0/s1

Standard InChI Key:  LUEYTMPPCOCKBX-KWYHTCOPSA-N

Alternative Forms

1. Parent:

   

   ALA89138

   CURACIN A

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

Calculated Properties

Molecular Weight: 373.61

Molecular Weight (Monoisotopic): 373.2439

AlogP: 6.37

#Rotatable Bonds: 12

Polar Surface Area: 21.59

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.35

CX LogP: 6.09

CX LogD: 6.09

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.23

Np Likeness Score: 2.57

References

1. Wipf P, Reeves JT, Balachandran R, Day BW..  (2002)  Synthesis and biological evaluation of structurally highly modified analogues of the antimitotic natural product curacin A.,  45  (9): [PMID:11960501] [10.1021/jm0105171]

2. Nishikawa A, Shirai R, Koiso Y, Hashimoto Y, Iwasaki S.  (1997)  Design and synthesis of curacin a analogs with varied side chain structures,  7  (20): [10.1016/S0960-894X(97)10055-5]

3. Nishikawa A, Shirai R, Koiso Y, Hashimoto Y, Iwasaki S.  (1997)  Design and synthesis of curacin a analogs with varied side chain structures,  7  (20): [10.1016/S0960-894X(97)10055-5]

4. Yoo H, Gerwick WH.  (1995)  Curacins B and C, New Antimitotic Natural Products from the Marine Cyanobacterium Lyngbya majuscula,  58  (12): [10.1021/np50126a029]

5. Orjala J, Gerwick WH..  (1996)  Barbamide, a chlorinated metabolite with molluscicidal activity from the Caribbean cyanobacterium Lyngbya majuscula.,  59  (4): [PMID:8699186] [10.1021/np960085a]

6. Kokoshka JM, Ireland CM, Barrows LR..  (1996)  Cell-based screen for identification of inhibitors of tubulin polymerization.,  59  (12): [PMID:8988604] [10.1021/np960144k]

7.  (2002)  Synthesis and biological evaluation of analogs of the antimitotic marine natural product curacin A, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data