11beta,13-dihydrodesacylcynaropicrin

ID: ALA5172465

PubChem CID: 12047617

Max Phase: Preclinical

Molecular Formula: C15H20O4

Molecular Weight: 264.32

Names and Identifiers

Canonical SMILES:  C=C1[C@@H]2[C@H]3OC(=O)[C@@H](C)[C@@H]3[C@@H](O)CC(=C)[C@@H]2C[C@@H]1O

Standard InChI:  InChI=1S/C15H20O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h8-14,16-17H,1-2,4-5H2,3H3/t8-,9-,10-,11-,12-,13+,14+/m0/s1

Standard InChI Key:  AEWOONBLAKEKSC-CLSQCYNNSA-N

Molfile:  

 
     RDKit          2D

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   -2.4008    0.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    0.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0810    1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939    0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428    1.8014    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2939    0.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -0.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160   -0.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457   -0.6506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518   -0.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5346    0.4514    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1539   -0.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5109    0.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1534    1.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3518    1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1382    2.2956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3360    0.5774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783   -0.1365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5758   -0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0450   -1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2867   -1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2585   -2.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4008   -0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  3  2  1  0
  4  3  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  2  1  0
  7  8  2  0
  6  9  1  6
  6 10  1  0
 10 11  1  1
 12 10  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
  4 15  1  0
 15 16  2  0
 13 17  1  6
 12 18  1  6
 12 19  1  0
 19 20  1  0
 21 20  1  0
 10 21  1  0
 20 22  2  0
 19 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA5172465

   (3S,3aR,4S,6aR,8S,9aR,9bR)-4,8-dihydroxy-3-methyl-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 264.32

Molecular Weight (Monoisotopic): 264.1362

AlogP: 1.04

#Rotatable Bonds: ┄

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.36

CX LogD: 0.36

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.51

Np Likeness Score: 3.57

References

1. Tanaka N, Yoshino Y, Nakano F, Kurimoto SI, Kawazoe K, Tsuji D, Itoh K, Li SL, Sun HD, Takaishi Y, Kashiwada Y..  (2022)  Lanicepines A and B, Sesquiterpenes with Amino Acid-Derived Substituents from the Flowering Aerial Parts of Saussurea laniceps.,  85  (4.0): [PMID:35179378] [10.1021/acs.jnatprod.1c01069]

Source

Source(1):

• Scientific Literature