Cryptotanshinone

ID: ALA4573182

PubChem CID: 25181389

Max Phase: Preclinical

Molecular Formula: C19H22O3

Molecular Weight: 298.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1COC2c3ccc4c(c3C(=O)C(=O)C21)CCCC4(C)C

Standard InChI:  InChI=1S/C19H22O3/c1-10-9-22-18-12-6-7-13-11(5-4-8-19(13,2)3)15(12)17(21)16(20)14(10)18/h6-7,10,14,18H,4-5,8-9H2,1-3H3/t10-,14?,18?/m0/s1

Standard InChI Key:  IJSBKZLSTIFYIE-FPKDZHNTSA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    4.1561  -13.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7517  -12.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3427  -13.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629  -12.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8726  -12.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4548  -12.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4544  -11.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7523  -10.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0460  -11.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464  -12.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1611  -10.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8688  -11.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8622   -9.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1547  -10.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5700  -10.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5721  -10.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3441  -11.1628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8192  -10.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3407   -9.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4452   -9.7014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8606   -8.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5911   -9.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  6  4  1  0
  4  5  2  0
  5 12  1  0
 11  7  1  0
  6  7  2  0
  6  2  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  2  1  0
 11 12  2  0
 11 14  1  0
 12 16  1  0
 15 13  1  0
 13 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 14 20  2  0
 13 21  2  0
 19 22  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4573182

   (1R)-1,6,6-trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11(3aH,11aH)-dione

Molecule Features

Natural Product: Yes

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: 298.38

Molecular Weight (Monoisotopic): 298.1569

AlogP: 3.39

#Rotatable Bonds: ┄

Polar Surface Area: 43.37

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.33

CX Basic pKa: ┄

CX LogP: 4.17

CX LogD: 4.17

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.69

Np Likeness Score: 1.87

References

1. Stevens M, Abdeen S, Salim N, Ray AM, Washburn A, Chitre S, Sivinski J, Park Y, Hoang QQ, Chapman E, Johnson SM..  (2019)  HSP60/10 chaperonin systems are inhibited by a variety of approved drugs, natural products, and known bioactive molecules.,  29  (9): [PMID:30852084] [10.1016/j.bmcl.2019.02.028]

Source

Source(1):

• Scientific Literature