Penicilindole B

ID: ALA4280765

PubChem CID: 139589954

Max Phase: Preclinical

Molecular Formula: C28H39NO2

Molecular Weight: 421.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H39NO2/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/h6-7,9-11,18,20,24,29,31H,8,12-17H2,1-5H3/t20-,24-,26+,27-,28-/m1/s1

Standard InChI Key:  KPIWQVIPQWGFNG-VFRRUXMTSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   16.7318  -10.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7359   -9.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0261   -9.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6449  -10.8587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6438  -11.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3518  -12.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3500  -10.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0586  -10.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0634  -11.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8435  -11.9222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3208  -11.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8357  -10.5976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0837   -9.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5333   -9.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4373   -8.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1871   -8.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2368   -7.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7784   -8.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5666   -8.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8195   -7.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2779   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4834   -7.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6534   -7.2515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9363   -6.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1120   -8.8807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3538   -9.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1421   -9.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3543  -10.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1438  -10.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3560  -11.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7211   -9.6460    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  2  0
 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:

   

   ALA4280765

   ---

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: 421.63

Molecular Weight (Monoisotopic): 421.2981

AlogP: 6.61

#Rotatable Bonds: 5

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.48

CX LogD: 6.48

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: 2.01

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