(1'R,3R,3'S,7'S,12'R)-12'-hydroxy-4',4',7,7,12',14'-hexamethyl-2,7-dihydro-1H-9',14'-diazaspiro[[1,4]dioxepino[2,3-g]indole-3,5'-tetracyclo[5.5.2.0^{1,9}.0^{3,7}]tetradecane]-2,10',13'-trione

ID: ALA2252927

PubChem CID: 14337025

Max Phase: Preclinical

Molecular Formula: C28H33N3O6

Molecular Weight: 507.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)[C@]23C[C@H]4C(C)(C)[C@@]5(C[C@@]41CN2C(=O)C[C@@]3(C)O)C(=O)Nc1c5ccc2c1OC=CC(C)(C)O2

Standard InChI:  InChI=1S/C28H33N3O6/c1-23(2)9-10-36-20-16(37-23)8-7-15-19(20)29-21(33)27(15)13-26-14-31-18(32)12-25(5,35)28(31,22(34)30(26)6)11-17(26)24(27,3)4/h7-10,17,35H,11-14H2,1-6H3,(H,29,33)/t17-,25+,26+,27+,28-/m0/s1

Standard InChI Key:  HHMKOJPJOSZYET-MGUBYGHDSA-N

Molfile:  

     RDKit          2D

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 21 22  1  1
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M  END

Alternative Forms

1. Parent:

   

   ALA2252927

   (1'S,6'R,7'R,8R,9'S)-6'-Hydroxy-4,4,6',10',10',13'-hexamethylspiro[10H-[1,4]dioxepino[2,3-g]indole-8,11'-3,13-diazatetracyclo[5.5.2.01,9.03,7]tetradecane]-4',9,14'-trione

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: 507.59

Molecular Weight (Monoisotopic): 507.2369

AlogP: 2.32

#Rotatable Bonds: ┄

Polar Surface Area: 108.41

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.59

CX Basic pKa: ┄

CX LogP: 0.88

CX LogD: 0.88

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.56

Np Likeness Score: 1.83

References

1. López-Gresa MP, González MC, Ciavatta L, Ayala I, Moya P, Primo J..  (2006)  Insecticidal activity of Paraherquamides, including paraherquamide H and paraherquamide I, two new alkaloids isolated from Penicillium cluniae.,  54  (8): [PMID:16608209] [10.1021/jf0530998]

Source

Source(1):

• Scientific Literature