(4S,5S,7R,8S,9S,10S,11S,12S,13S,14R)-Kumulactone B

ID: ALA4536253

PubChem CID: 155548332

Max Phase: Preclinical

Molecular Formula: C22H32O7

Molecular Weight: 408.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC1=C[C@@H](C)[C@@H]2C[C@H]3OC(=O)C[C@@]4(O)[C@@H](C)[C@H](OC)[C@@H](O)[C@H]([C@@]2(C)C1=O)[C@@]34C

Standard InChI:  InChI=1S/C22H32O7/c1-10-7-13(27-5)19(25)20(3)12(10)8-14-21(4)18(20)16(24)17(28-6)11(2)22(21,26)9-15(23)29-14/h7,10-12,14,16-18,24,26H,8-9H2,1-6H3/t10-,11+,12+,14-,16-,17+,18-,20+,21-,22-/m1/s1

Standard InChI Key:  OWEIWANWIOORGM-XKDCPSQWSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    4.3584  -13.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3584  -14.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678  -14.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678  -13.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772  -13.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7737  -14.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4799  -14.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1937  -14.4905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8980  -14.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6106  -14.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6143  -13.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4868  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1937  -13.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9058  -13.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9172  -12.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2104  -12.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4921  -12.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2204  -11.2136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9372  -10.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6342  -12.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7843  -12.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0678  -12.4312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495  -13.2587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471  -12.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7657  -15.3038    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855  -15.3120    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0686  -15.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7699  -12.8439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1855  -12.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4797  -14.0780    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995  -14.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3158  -14.9140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 12  1  0
  6  7  1  0
  7  8  1  0
 13  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 14  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  1
 18 19  1  0
 15 20  1  6
 17 21  1  6
  4 22  2  0
  1 23  1  0
 23 24  1  0
  6 25  1  6
  8 26  1  1
  3 27  1  6
  5 28  1  1
 13 29  1  1
 12 30  1  6
 14 31  1  1
 10 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536253

   ---

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: 408.49

Molecular Weight (Monoisotopic): 408.2148

AlogP: 1.46

#Rotatable Bonds: 2

Polar Surface Area: 102.29

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.50

CX Basic pKa: ┄

CX LogP: 0.99

CX LogD: 0.99

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: 3.37

References

1. Zhao WY, Song XY, Zhao L, Zou CX, Zhou WY, Lin B, Yao GD, Huang XX, Song SJ..  (2019)  Quassinoids from Picrasma quassioides and Their Neuroprotective Effects.,  82  (4): [PMID:30917277] [10.1021/acs.jnatprod.8b00470]

Source

Source(1):

• Scientific Literature