latrunculeic acid

ID: ALA512338

PubChem CID: 11426344

Max Phase: Preclinical

Molecular Formula: C17H24O4

Molecular Weight: 292.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Latrunculeic Acid | Latrunculeic Acid|CHEMBL512338|SCHEMBL3235127|(2Z,6Z,8S)-3,8-dimethyl-10-[(2R)-6-oxo-2,3-dihydropyran-2-yl]deca-2,6-dienoic Acid

Canonical SMILES:  C/C(=C/C(=O)O)CC/C=C\[C@@H](C)CC[C@@H]1CC=CC(=O)O1

Standard InChI:  InChI=1S/C17H24O4/c1-13(6-3-4-7-14(2)12-16(18)19)10-11-15-8-5-9-17(20)21-15/h3,5-6,9,12-13,15H,4,7-8,10-11H2,1-2H3,(H,18,19)/b6-3-,14-12-/t13-,15+/m1/s1

Standard InChI Key:  OHWFPMKLBOHSHY-WKTSBRCASA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -4.0010  -11.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866  -10.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676  -11.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1377  -12.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1341  -11.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514  -10.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0010  -12.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7114  -12.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7137  -13.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9964  -13.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9951  -14.6919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818  -15.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5680  -14.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676  -13.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2823  -13.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2817  -15.9300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538  -12.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8573  -13.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665  -12.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175  -10.9908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866  -12.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  5  6  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
  1  7  1  0
 10 15  1  0
 15 14  1  0
  1  2  2  0
 12 16  2  0
  7  8  1  0
  4 17  1  0
  8  9  1  0
 17 18  2  0
 10  9  1  6
 17 19  1  0
  3  2  1  0
  5 20  1  0
  3  6  1  0
  7 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA512338

   LATRUNCULEIC ACID

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: 292.38

Molecular Weight (Monoisotopic): 292.1675

AlogP: 3.64

#Rotatable Bonds: 8

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.86

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 1.67

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.42

Np Likeness Score: 2.98

References

1. Vilozny B, Amagata T, Mooberry SL, Crews P..  (2004)  A new dimension to the biosynthetic products isolated from the sponge Negombata magnifica.,  67  (6): [PMID:15217296] [10.1021/np0340753]

2. Amagata T, Johnson TA, Cichewicz RH, Tenney K, Mooberry SL, Media J, Edelstein M, Valeriote FA, Crews P..  (2008)  Interrogating the bioactive pharmacophore of the latrunculin chemotype by investigating the metabolites of two taxonomically unrelated sponges.,  51  (22): [PMID:18942825] [10.1021/jm8008585]

Source

Source(1):

• Scientific Literature