12-Deacetoxy-23-hydroxyheteronemin

ID: ALA574521

PubChem CID: 11248811

Max Phase: Preclinical

Molecular Formula: C29H44O6

Molecular Weight: 488.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@H]1OC=C2[C@@H](OC(C)=O)C[C@@H]3[C@](C)(CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)CCC[C@@]34CO)[C@H]21

Standard InChI:  InChI=1S/C29H44O6/c1-17(31)34-20-14-23-27(5)12-8-21-26(3,4)10-7-11-29(21,16-30)22(27)9-13-28(23,6)24-19(20)15-33-25(24)35-18(2)32/h15,20-25,30H,7-14,16H2,1-6H3/t20-,21-,22-,23-,24+,25-,27+,28-,29+/m0/s1

Standard InChI Key:  WJXDNRYRYAGILU-GJTCYCQFSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA574521

   [(1S,4S,5aS,5bS,7aS,11aR,11bS,13aS,13bR)-1-acetyloxy-11a-(hydroxymethyl)-5b,8,8,13a-tetramethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate

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

Calculated Properties

Molecular Weight: 488.67

Molecular Weight (Monoisotopic): 488.3138

AlogP: 5.38

#Rotatable Bonds: 3

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: ┄

Heavy Atoms: 35

QED Weighted: 0.54

Np Likeness Score: 2.92

References

1. Rho JR, Lee HS, Shin HJ, Ahn JW, Kim JY, Sim CJ, Shin J..  (2004)  New sesterterpenes from the sponge Smenospongia sp.,  67  (10): [PMID:15497955] [10.1021/np040103l]

2. Song J, Jeong W, Wang N, Lee HS, Sim CJ, Oh KB, Shin J..  (2008)  Scalarane sesterterpenes from the sponge Smenospongia sp.,  71  (11): [PMID:18973387] [10.1021/np8003694]

3. Hahn D, Won DH, Mun B, Kim H, Han C, Wang W, Chun T, Park S, Yoon D, Choi H, Nam SJ, Ekins M, Chin J, Kang H..  (2013)  Cytotoxic scalarane sesterterpenes from a Korean marine sponge Psammocinia sp.,  23  (8): [PMID:23489626] [10.1016/j.bmcl.2013.02.061]

Source

Source(1):

• Scientific Literature