pseudoirroratin A

ID: ALA517614

PubChem CID: 637422

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)[C@]23[C@H](O)C[C@@H]4C(C)(C)CCC[C@]45CO[C@](O)(C[C@@H]1[C@H]2O)[C@@H]53

Standard InChI:  InChI=1S/C20H28O5/c1-10-11-8-19(24)16-18(9-25-19)6-4-5-17(2,3)12(18)7-13(21)20(16,14(10)22)15(11)23/h11-13,15-16,21,23-24H,1,4-9H2,2-3H3/t11-,12+,13+,15+,16+,18-,19+,20+/m0/s1

Standard InChI Key:  NDYPVJHBSKUXPP-VWIBHASISA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   -4.5305   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5305   -1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205    0.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1058   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1046   -1.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3893   -1.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6751   -1.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914    0.2155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6758   -0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610    0.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554    1.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6711    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3924    1.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353   -1.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8295   -2.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1141   -1.8456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988   -0.6009    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3988    1.8694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739    0.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729   -0.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2480    0.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6834   -1.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7625   -1.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5433    0.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1141    0.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8248    1.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9634    1.8647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  2  3  1  0
  3 15  1  0
  5  9  1  0
  3 16  1  0
  6  7  1  0
  6 17  1  1
  7  8  1  0
  9 18  1  1
  8 10  1  0
 14 19  1  1
  9 10  1  0
 11 20  1  1
  3  6  1  0
 10 21  1  1
  5  4  1  0
 12 22  1  0
 21 22  1  0
  5  6  1  0
  8 23  1  6
 21 24  2  0
  1  2  1  0
 22 25  2  0
  1  4  1  0
  5 26  1  6
  9 14  1  0
 26 27  1  0
 27 14  1  0
 10 11  1  0
 12 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA517614

   PSEUDOIRRORATIN A

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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 1.40

#Rotatable Bonds: ┄

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.76

CX Basic pKa: ┄

CX LogP: 1.12

CX LogD: 1.12

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: 3.75

References

1. Zhang H, Fan Z, Tan GT, Chai HB, Pezzuto JM, Sun H, Fong HH..  (2002)  Pseudoirroratin A, a new cytotoxic ent-kaurene diterpene from Isodon pseudo-irrorata.,  65  (2): [PMID:11858760] [10.1021/np010420h]

2. Guo L, Tsang SW, Zhang TX, Liu KL, Guan YF, Wang B, Sun HD, Zhang HJ, Wong MS..  (2017)  Efficient Semisynthesis of (-)-Pseudoirroratin A from (-)-Flexicaulin A and Assessment of Their Antitumor Activities.,  8  (3): [PMID:28337333] [10.1021/acsmedchemlett.7b00033]

Source

Source(1):

• Scientific Literature