Tigloylcumambrin B

ID: ALA4583549

PubChem CID: 101133894

Max Phase: Preclinical

Molecular Formula: C20H26O5

Molecular Weight: 346.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2[C@H]3C(C)=CC[C@H]3[C@](C)(O)C[C@H](OC(=O)C=C(C)C)[C@@H]12

Standard InChI:  InChI=1S/C20H26O5/c1-10(2)8-15(21)24-14-9-20(5,23)13-7-6-11(3)16(13)18-17(14)12(4)19(22)25-18/h6,8,13-14,16-18,23H,4,7,9H2,1-3,5H3/t13-,14+,16+,17-,18-,20-/m1/s1

Standard InChI Key:  MOUVSDLSLQNVBE-CNBYDDNMSA-N

Molfile:  

 
     RDKit          2D

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   19.0637  -25.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0678  -26.3441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7734  -25.9319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7282  -28.9154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0719  -29.3900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4090  -28.9162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4814  -28.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6633  -28.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9909  -27.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8070  -26.6953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1526  -27.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3281  -26.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6244  -26.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0071  -26.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3337  -27.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0730  -30.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9369  -28.2756    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.3208  -25.8819    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.9217  -28.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2936  -28.1353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0678  -27.4254    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8384  -27.4956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5377  -29.1781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2452  -26.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0624  -26.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8349  -26.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4693  -26.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2865  -26.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0590  -25.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  8  6  1  0
  4  7  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  8 11  1  0
  7  9  1  0
  9 10  1  0
 12  2  1  0
 10  2  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
  5 16  2  0
 11 17  1  6
 12 18  1  6
 15 19  1  0
  7 20  1  6
  8 21  1  1
  9 22  1  6
  4 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  2  0
 27 28  1  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4583549

   [(3aR,4S,6R,6aR,9aR,9bR)-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] 3-methylbut-2-enoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 346.42

Molecular Weight (Monoisotopic): 346.1780

AlogP: 2.70

#Rotatable Bonds: 2

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: 3.26

References

1. Luo P, Cheng Y, Yin Z, Li C, Xu J, Gu Q..  (2019)  Monomeric and Dimeric Cytotoxic Guaianolide-Type Sesquiterpenoids from the Aerial Parts of Chrysanthemum indicum.,  82  (2): [PMID:30726671] [10.1021/acs.jnatprod.8b00863]

Source

Source(1):

• Scientific Literature