Chrotacumine J

ID: ALA3262779

PubChem CID: 86294756

Max Phase: Preclinical

Molecular Formula: C24H25NO8

Molecular Weight: 455.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(=O)O[C@@H]2CN(C)CC[C@@H]2c2c(O)cc(O)c3c(=O)cc(C)oc23)ccc1O

Standard InChI:  InChI=1S/C24H25NO8/c1-12-8-16(27)22-18(29)10-17(28)21(23(22)32-12)14-6-7-25(2)11-20(14)33-24(30)13-4-5-15(26)19(9-13)31-3/h4-5,8-10,14,20,26,28-29H,6-7,11H2,1-3H3/t14-,20+/m0/s1

Standard InChI Key:  KAVOSXPIAAZLGG-VBKZILBWSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   14.5347  -14.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5383  -13.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2576  -12.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2617  -12.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5472  -11.6252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8279  -12.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8235  -12.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1136  -11.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1128  -10.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5490  -10.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6792  -13.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6792  -14.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3902  -14.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1054  -14.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1054  -13.2731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3902  -12.8549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3896  -15.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6765  -15.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6760  -16.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3915  -16.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1050  -15.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1092  -16.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8213  -16.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5340  -16.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5279  -15.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8108  -15.3266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3902  -12.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8191  -14.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8164  -17.7988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3825  -17.8072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2372  -15.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9583  -15.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2528  -14.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  8  9  1  0
  5 10  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 22  1  0
 21 17  1  0
 13 17  1  1
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 21  1  0
 16 27  1  0
 14 28  1  1
 28  1  1  0
 23 29  2  0
 20 30  1  0
 25 31  1  0
 18 32  1  0
  1 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3262779

   [(3S,4R)-4-(5,7-dihydroxy-2-methyl-4-oxochromen-8-yl)-1-methylpiperidin-3-yl] 4-hydroxy-3-methoxybenzoate

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: 455.46

Molecular Weight (Monoisotopic): 455.1580

AlogP: 2.87

#Rotatable Bonds: 4

Polar Surface Area: 129.67

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.73

CX Basic pKa: 6.13

CX LogP: 2.73

CX LogD: 2.34

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: 1.25

References

1. Morita H, Nugroho AE, Nagakura Y, Hirasawa Y, Yoshida H, Kaneda T, Shirota O, Ismail IS..  (2014)  Chrotacumines G-J, chromone alkaloids from Dysoxylum acutangulum with osteoclast differentiation inhibitory activity.,  24  (11): [PMID:24767841] [10.1016/j.bmcl.2014.04.020]

Source

Source(1):

• Scientific Literature