sodium;(6aS,6bS,8aS,11R,12aR,14aR)-2,3-diacetoxy-11-carboxy-4,6a,6b,8a,11,14a-hexamethyl-7,8,9,10,12,12a,13,14-octahydro-5H-picene-5-sulfonate

ID: ALA5285489

Max Phase: Preclinical

Molecular Formula: C33H43NaO9S

Molecular Weight: 616.77

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1cc2c(c(C)c1OC(C)=O)C(S(=O)(=O)[O-])C=C1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]12C.[Na+]

Standard InChI:  InChI=1S/C33H44O9S.Na/c1-18-26-21(15-22(41-19(2)34)27(18)42-20(3)35)31(6)12-14-33(8)25-17-30(5,28(36)37)10-9-29(25,4)11-13-32(33,7)24(31)16-23(26)43(38,39)40;/h15-16,23,25H,9-14,17H2,1-8H3,(H,36,37)(H,38,39,40);/q;+1/p-1/t23?,25-,29-,30-,31+,32-,33+;/m1./s1

Standard InChI Key:  CCMYJMBLZJWFME-DBTCIOILSA-M

Molfile:  

     RDKit          2D

 45 48  0  0  0  0  0  0  0  0999 V2000
    1.5132   -3.0362    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    2.2395    1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    2.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    1.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    0.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    0.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539   -0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2394   -0.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5248   -0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    0.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104   -0.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0958   -0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959    0.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104    0.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103   -1.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0477   -0.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3331   -0.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5413    2.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3666    2.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6687    0.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624   -0.3156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7625   -1.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3332   -2.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6188    0.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5248   -1.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    0.0962    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1919    2.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9539    3.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4771   -0.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1919   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4771   -1.5536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7625   -2.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4772   -3.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0477   -3.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0957   -2.7913    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8104   -3.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013   -3.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1178   -3.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  2  7  1  0
  7  6  1  0
  6  8  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
  7 11  1  0
 10 12  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 11 15  1  0
 12 16  2  0
 17 16  1  0
 18 17  1  0
 19 18  2  0
 13 19  1  0
 18 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 19 23  1  0
  3 24  1  1
  3 25  1  0
  6 26  1  1
 22 27  1  0
 21 28  1  0
 20 29  1  0
 13 30  1  1
 10 31  1  1
 11 32  1  6
  7 33  1  1
 25 34  1  0
 25 35  2  0
 27 36  1  0
 36 37  1  0
 36 38  2  0
 28 39  1  0
 39 40  1  0
 39 41  2  0
 17 42  1  0
 42 43  1  0
 42 44  2  0
 42 45  2  0
M  CHG  2   1   1  43  -1
M  END

Molecule Features

Natural Product: No

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: 616.77

Molecular Weight (Monoisotopic): 616.2706

AlogP: 6.47

#Rotatable Bonds: 4

Polar Surface Area: 144.27

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.85

CX Basic pKa: ┄

CX LogP: 5.51

CX LogD: 0.26

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.17

Np Likeness Score: 1.97

References

1. Hou W, Liu B, Xu H..  (2020)  Celastrol: Progresses in structure-modifications, structure-activity relationships, pharmacology and toxicology.,  189  [PMID:31991334] [10.1016/j.ejmech.2020.112081]

Source

Source(1):

• Scientific Literature