Methylpendolmycin

ID: ALA484452

PubChem CID: 44576031

Max Phase: Preclinical

Molecular Formula: C23H33N3O2

Molecular Weight: 383.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Methylpendolmycin | Methylpendolmycin|CHEBI:69599|CHEMBL484452|BDBM50478561|Q27137941

Canonical SMILES:  C=CC(C)(C)c1ccc2c3c(c[nH]c13)C[C@@H](CO)NC(=O)[C@H]([C@@H](C)CC)N2C

Standard InChI:  InChI=1S/C23H33N3O2/c1-7-14(3)21-22(28)25-16(13-27)11-15-12-24-20-17(23(4,5)8-2)9-10-18(19(15)20)26(21)6/h8-10,12,14,16,21,24,27H,2,7,11,13H2,1,3-6H3,(H,25,28)/t14-,16-,21-/m0/s1

Standard InChI Key:  DALRIICDQKRRFF-HTZUNMPGSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -1.2986   -1.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3004   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5846   -3.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1220   -0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930   -0.6204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373   -0.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -1.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -1.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2563   -0.6209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5442   -0.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279   -1.8476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1326   -2.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220   -2.9247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4003   -2.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1194    0.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8334    1.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5997    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5829   -3.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906   -4.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2391   -3.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4093   -3.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3055   -5.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111   -0.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9711   -0.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -0.6293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -1.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8318    0.2134    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 13  2  0
  4  1  1  0
  4 12  2  0
  4  6  1  0
  7  5  1  0
  5  6  1  0
  7 11  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15  8  2  0
  8 12  1  0
  5 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
  3 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 21 24  2  0
  6 25  1  0
 10 26  1  6
 26 27  1  0
  7 28  2  0
  5 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA484452

   METHYLPENDOLMYCIN

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: 383.54

Molecular Weight (Monoisotopic): 383.2573

AlogP: 3.52

#Rotatable Bonds: 5

Polar Surface Area: 68.36

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.21

CX Basic pKa: ┄

CX LogP: 4.07

CX LogD: 4.07

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: 2.05

References

1. Sun HH, White CB, Dedinas J, Cooper R, Sedlock DM..  (1991)  Methylpendolmycin, an indolactam from a Nocardiopsis sp.,  54  (5): [PMID:1800642] [10.1021/np50077a040]

2. Huang H, Yao Y, He Z, Yang T, Ma J, Tian X, Li Y, Huang C, Chen X, Li W, Zhang S, Zhang C, Ju J..  (2011)  Antimalarial β-carboline and indolactam alkaloids from Marinactinospora thermotolerans, a deep sea isolate.,  74  (10): [PMID:21977916] [10.1021/np200399t]

Source

Source(1):

• Scientific Literature