Dimethylamino micheliolide

ID: ALA4207458

Cas Number: 1582289-91-5

PubChem CID: 71812122

Max Phase: Preclinical

Molecular Formula: C21H31NO7

Molecular Weight: 293.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2CC[C@@](C)(O)[C@@H]2[C@H]2OC(=O)[C@@H](CN(C)C)[C@@H]2CC1.O=C(O)/C=C/C(=O)O

Standard InChI:  InChI=1S/C17H27NO3.C4H4O4/c1-10-5-6-12-13(9-18(3)4)16(19)21-15(12)14-11(10)7-8-17(14,2)20;5-3(6)1-2-4(7)8/h12-15,20H,5-9H2,1-4H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t12-,13-,14-,15-,17+;/m0./s1

Standard InChI Key:  PDWGVXJIDIRQME-DCNFBYMVSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   10.2025   -4.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9102   -4.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6179   -4.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9102   -3.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2025   -5.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4948   -5.8937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4948   -6.7109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7871   -5.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843   -6.5849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6060   -6.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3928   -6.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7543   -3.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4920   -3.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -3.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678   -5.3249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5579   -4.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7859   -4.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -5.7853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4040   -4.7007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8864   -5.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3247   -6.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1133   -5.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1629   -5.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433   -6.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8517   -4.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5748   -4.9341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2636   -4.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6133   -5.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1237   -3.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -6.1031    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9811   -4.1211    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -6.1425    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
 10  9  1  0
 10 11  1  1
 12 13  1  0
 13 14  1  0
 12 16  2  0
 14 19  1  0
 15 20  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 10  1  0
 10 15  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 22 24  2  0
 23 25  1  6
 25 26  1  0
 26 27  1  0
 26 28  1  0
 12 29  1  0
 15 30  1  6
 19 31  1  6
 20 32  1  1
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 293.41

Molecular Weight (Monoisotopic): 293.1991

AlogP: 1.98

#Rotatable Bonds: 2

Polar Surface Area: 49.77

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.26

CX LogP: 1.26

CX LogD: -0.60

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.62

Np Likeness Score: 2.36

References

1. Li J, Li S, Guo J, Li Q, Long J, Ma C, Ding Y, Yan C, Li L, Wu Z, Zhu H, Li KK, Wen L, Zhang Q, Xue Q, Zhao C, Liu N, Ivanov I, Luo M, Xi R, Long H, Wang PG, Chen Y..  (2018)  Natural Product Micheliolide (MCL) Irreversibly Activates Pyruvate Kinase M2 and Suppresses Leukemia.,  61  (9): [PMID:29641204] [10.1021/acs.jmedchem.8b00241]

Source

Source(1):

• Scientific Literature