Vilmorrianone

ID: ALA516691

PubChem CID: 44566629

Max Phase: Preclinical

Molecular Formula: C23H27NO5

Molecular Weight: 397.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Vilmorrianone | Vilmorrianone|CHEBI:66358|CHEMBL516691|Q27134905

Canonical SMILES:  C=C1C[C@@]23C(=O)C(=O)[C@@H]4[C@@]5(C)C[C@H](OC(C)=O)C[C@@]46[C@@H]2C[C@@H]1C(=O)[C@@H]3[C@H]6N(C)C5

Standard InChI:  InChI=1S/C23H27NO5/c1-10-6-22-14-5-13(10)16(26)15(22)19-23(14)8-12(29-11(2)25)7-21(3,9-24(19)4)18(23)17(27)20(22)28/h12-15,18-19H,1,5-9H2,2-4H3/t12-,13-,14+,15+,18+,19+,21-,22+,23+/m0/s1

Standard InChI Key:  MCKIOPXSFPCTTR-NGELOBKFSA-N

Molfile:  

     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
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    4.8844  -14.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3043  -14.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0148  -13.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7313  -14.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4477  -13.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7456  -12.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7565  -11.2050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3314  -11.9272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0048  -16.2176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4357  -15.4020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781  -14.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1686  -13.7494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647  -12.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4532  -12.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766  -12.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3058  -13.1539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2903  -12.4465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  2  5  1  0
  3  4  1  0
  4  7  1  0
  6  5  1  1
  6  7  1  0
  6 10  1  0
  7  8  1  0
  8  9  1  0
  9 11  1  0
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 10 15  1  0
 11 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10 16  1  1
  7 17  1  1
  4 18  1  1
  6 19  1  0
  4 20  1  0
 11 21  1  0
 19 21  1  0
 14 22  1  0
 22 21  1  0
 22 23  2  0
 14 24  1  1
 13 25  2  0
  8 26  2  0
  9 27  2  0
  1 20  1  0
 19  1  1  0
  1 28  1  0
  2 29  1  6
 29 30  1  0
 30 31  1  0
 30 32  2  0
 21 33  1  6
 19 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA516691

   VILMORRIANONE

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: 397.47

Molecular Weight (Monoisotopic): 397.1889

AlogP: 1.57

#Rotatable Bonds: 1

Polar Surface Area: 80.75

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.95

CX LogP: 1.69

CX LogD: 1.03

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.38

Np Likeness Score: 3.09

References

1. Atta-ur-Rahman, Nasreen A, Akhtar F, Shekhani MS, Clardy J, Parvez M, Choudhary MI..  (1997)  Antifungal diterpenoid alkaloids from Delphinium denudatum.,  60  (5): [PMID:9170290] [10.1021/np960663n]

Source

Source(1):

• Scientific Literature