ID: ALA1099355

Max Phase: Preclinical

Molecular Formula: C28H36O7

Molecular Weight: 484.59

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1=C(C)[C@H]([C@H]2O[C@@]3(O)C[C@H]4[C@@H](C[C@H]5O[C@]56CC=CC(=O)[C@]46C)[C@@H]4CC[C@@](O)([C@@H]2C)[C@]43C)OC1=O

Standard InChI:  InChI=1S/C28H36O7/c1-13-14(2)23(30)33-21(13)22-15(3)26(31)10-8-17-16-11-20-27(34-20)9-6-7-19(29)24(27,4)18(16)12-28(32,35-22)25(17,26)5/h6-7,15-18,20-22,31-32H,8-12H2,1-5H3/t15-,16+,17+,18+,20-,21-,22+,24+,25+,26-,27-,28+/m1/s1

Standard InChI Key:  MFPJMEIBOYFMKC-GQYGZUCJSA-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: 484.59

Molecular Weight (Monoisotopic): 484.2461

AlogP: 2.83

#Rotatable Bonds: 1

Polar Surface Area: 105.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.54

CX Basic pKa:

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 0

Heavy Atoms: 35

QED Weighted: 0.44

Np Likeness Score: 3.67

References

1. Nicotra VE, Gil RR, Oberti JC, Burton G..  (2007)  Withanolides with phytotoxic activity from Jaborosa caulescens var. caulescens and J. caulescens var. bipinnatifida 1.,  70  (5): [PMID:17428092] [10.1021/np070030g]

2. Misico RI, Song LL, Veleiro AS, Cirigliano AM, Tettamanzi MC, Burton G, Bonetto GM, Nicotra VE, Silva GL, Gil RR, Oberti JC, Kinghorn AD, Pezzuto JM..  (2002)  Induction of quinone reductase by withanolides.,  65  (5): [PMID:12027740] [10.1021/np0106337]

3. Machin RP, Veleiro AS, Nicotra VE, Oberti JC, M Padrón J..  (2010)  Antiproliferative activity of withanolides against human breast cancer cell lines.,  73  (5): [PMID:20438092] [10.1021/np9006734]

4. Enriz RD, Baldoni HA, Zamora MA, Jáuregui EA, Sosa ME, Tonn CE, Luco JM, Gordaliza M..  (2000)  Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin.,  48  (4): [PMID:10775402] [10.1021/jf990006b]

Source

Source(1):

• Scientific Literature