ID: ALA28898

Max Phase: Preclinical

Molecular Formula: C37H66O7

Molecular Weight: 622.93

Molecule Type: Small molecule

Representations

Synonyms (2): (2,4-Cis/Trans)-Squamolinone | Bullatacinone
Synonyms from Alternative Forms(2):

Canonical SMILES:  CCCCCCCCCC[C@H](O)[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H](O)CCCCCCCCCC[C@@H]3CC(CC(C)=O)C(=O)O3)O2)O1

Standard InChI:  InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3/t29?,30-,31+,32-,33-,34-,35-,36-/m1/s1

Standard InChI Key:  KGGVWMAPBXIMEM-UHABWWFJSA-N

Molecule Features

Natural Product: Yes

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: 622.93

Molecular Weight (Monoisotopic): 622.4809

AlogP: 8.15

#Rotatable Bonds: 25

Polar Surface Area: 102.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.90

CX Basic pKa:

CX LogP: 8.47

CX LogD: 8.47

Aromatic Rings: 0

Heavy Atoms: 44

QED Weighted: 0.08

Np Likeness Score: 1.53

References

1. Rodier S, Le Huérou Y, Renoux B, Doyon J, Renard P, Pierré A, Gesson JP, Grée R..  (2000)  Synthesis and cytotoxic activity of acetogenin analogues.,  10  (12): [PMID:10890167] [10.1016/s0960-894x(00)00236-5]

2. Alali FQ, Liu XX, McLaughlin JL..  (1999)  Annonaceous acetogenins: recent progress.,  62  (3): [PMID:10096871] [10.1021/np980406d]

3. Li XH, Hui YH, Rupprecht JK, Liu YM, Wood KV, Smith DL, Chang CJ, McLaughlin JL..  (1990)  Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa.,  53  (1): [PMID:2348205] [10.1021/np50067a010]

4. Rupprecht JK, Hui YH, McLaughlin JL..  (1990)  Annonaceous acetogenins: a review.,  53  (2): [PMID:2199608] [10.1021/np50068a001]

5. McLaughlin JL..  (2008)  Paw paw and cancer: annonaceous acetogenins from discovery to commercial products.,  71  (7): [PMID:18598079] [10.1021/np800191t]

6. Hui YH, Rupprecht JK, Liu YM, Anderson JE, Smith DL, Chang CJ, McLaughlin JL..  (1989)  Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata.,  52  (3): [PMID:2778448] [10.1021/np50063a002]

Source

Source(1):

• Scientific Literature