Penicilindole A

ID: ALA4292080

PubChem CID: 139589953

Max Phase: Preclinical

Molecular Formula: C28H41NO2

Molecular Weight: 423.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC[C@@]12[C@@H](O)CC[C@@H](C)[C@]1(C)CC[C@@](C)(O)[C@H]2Cc1c[nH]c2ccccc12

Standard InChI:  InChI=1S/C28H41NO2/c1-19(2)9-8-14-28-24(17-21-18-29-23-11-7-6-10-22(21)23)27(5,31)16-15-26(28,4)20(3)12-13-25(28)30/h6-7,9-11,18,20,24-25,29-31H,8,12-17H2,1-5H3/t20-,24-,25+,26+,27-,28-/m1/s1

Standard InChI Key:  GFSPEIJDKJGERO-FSTPOKOHSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    7.0906  -10.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0947   -9.5215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3849   -9.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0037  -10.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0026  -11.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7106  -12.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7088  -10.5778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4174  -10.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4222  -11.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2023  -12.0501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6796  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1945  -10.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4425   -9.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8921   -9.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7960   -8.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5459   -8.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5956   -7.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1372   -8.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9253   -8.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1783   -7.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6367   -7.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8422   -7.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0122   -7.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2951   -6.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4708   -9.0086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126   -9.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5009   -9.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7131  -10.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5026  -10.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7148  -11.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0799   -9.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 12 13  1  0
 14 13  1  6
 14 18  1  0
 14  2  1  0
 17 15  1  0
 15 16  1  0
 16  2  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 17 23  1  6
 22 24  1  6
 19 25  1  6
 18 26  1  6
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4292080

   ---

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: 423.64

Molecular Weight (Monoisotopic): 423.3137

AlogP: 6.40

#Rotatable Bonds: 5

Polar Surface Area: 56.25

Molecular Species: NEUTRAL

HBA: 2

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.92

CX LogD: 5.92

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.49

Np Likeness Score: 2.11

References

1. Zheng CJ, Bai M, Zhou XM, Huang GL, Shao TM, Luo YP, Niu ZG, Niu YY, Chen GY, Han CR..  (2018)  Penicilindoles A-C, Cytotoxic Indole Diterpenes from the Mangrove-Derived Fungus Eupenicillium sp. HJ002.,  81  (4): [PMID:29489361] [10.1021/acs.jnatprod.7b00673]

Source

Source(1):

• Scientific Literature