ID: ALA145449

Max Phase: Preclinical

Molecular Formula: C37H66O6

Molecular Weight: 606.93

Molecule Type: Small molecule

Representations

Synonyms (2): Bullanin | Desacetyluvaricin
Synonyms from Alternative Forms(2):

Canonical SMILES:  CCCCCCCCCC[C@H](O)[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H](O)CCCCCCCCCCCCC3=C[C@H](C)OC3=O)O2)O1

Standard InChI:  InChI=1S/C37H66O6/c1-3-4-5-6-7-13-16-19-22-31(38)33-24-26-35(42-33)36-27-25-34(43-36)32(39)23-20-17-14-11-9-8-10-12-15-18-21-30-28-29(2)41-37(30)40/h28-29,31-36,38-39H,3-27H2,1-2H3/t29-,31-,32+,33+,34+,35+,36+/m0/s1

Standard InChI Key:  URLVCROWVOSNPT-HJPPHTJLSA-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: 606.93

Molecular Weight (Monoisotopic): 606.4859

AlogP: 8.89

#Rotatable Bonds: 25

Polar Surface Area: 85.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.39

CX Basic pKa:

CX LogP: 10.07

CX LogD: 10.07

Aromatic Rings: 0

Heavy Atoms: 43

QED Weighted: 0.08

Np Likeness Score: 1.69

References

1. Gallardo T, Zafra-Polo MC, Tormo JR, González MC, Franck X, Estornell E, Cortes D..  (2000)  Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I.,  43  (25): [PMID:11123988] [10.1021/jm000911j]

2. Chávez D, Acevedo LA, Mata R..  (1999)  Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.,  62  (8): [PMID:10479316] [10.1021/np990118x]

3. He K, Shi G, Zhao GX, Zeng L, Ye Q, Schwedler JT, Wood KV, McLaughlin JL..  (1996)  Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.,  59  (11): [PMID:8946743] [10.1021/np9605145]

4. Gallardo T, Saez J, Granados H, Tormo JR, Velez ID, Brun N, Torres B, Cortes D..  (1998)  10-Oximeguanacone, the first nitrogenated acetogenin derivative found to be a potent inhibitor of mitochondrial complex I.,  61  (8): [PMID:9722484] [10.1021/np980079+]

5. Chen Y, Chen JW, Xu SS, Wang Y, Li X, Cai BC, Fan NB..  (2012)  Antitumor activity of annonaceous acetogenins in HepS and S180 xenografts bearing mice.,  22  (8): [PMID:22446092] [10.1016/j.bmcl.2012.02.109]

6. Dang QL, Kim WK, Nguyen CM, Choi YH, Choi GJ, Jang KS, Park MS, Lim CH, Luu NH, Kim JC..  (2011)  Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens.,  59  (20): [PMID:21910504] [10.1021/jf203017f]

7. OHSAWA K, ATSUZAWA S, MITSUI T, YAMAMOTO I.  (1991)  Isolation and Insecticidal Activity of Three Acetogenins from Seeds of Pond Apple, Annona glabra L.,  16  (1): [10.1584/jpestics.16.93]

Source

Source(1):

• Scientific Literature