Nimbolidin A

ID: ALA4764171

PubChem CID: 21123503

Max Phase: Preclinical

Molecular Formula: C40H48O12

Molecular Weight: 720.81

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C[C@H]1[C@](C)(C2=C(C)[C@H](c3ccoc3)C[C@@H]2OC(C)=O)[C@H](OC(=O)c2ccccc2)[C@@H]2OC[C@]3(C)[C@H](OC(C)=O)C[C@H](OC(C)=O)[C@@]1(C)[C@@H]23

Standard InChI:  InChI=1S/C40H48O12/c1-21-27(26-14-15-47-19-26)16-28(49-22(2)41)33(21)40(7)29(17-32(44)46-8)39(6)31(51-24(4)43)18-30(50-23(3)42)38(5)20-48-34(35(38)39)36(40)52-37(45)25-12-10-9-11-13-25/h9-15,19,27-31,34-36H,16-18,20H2,1-8H3/t27-,28+,29-,30-,31+,34-,35+,36-,38-,39+,40-/m1/s1

Standard InChI Key:  NOANSNPNWFTAEY-WNNCTZNVSA-N

Molfile:  

 
     RDKit          2D

 54 59  0  0  0  0  0  0  0  0999 V2000
   42.7041  -25.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4089  -25.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1537  -25.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6996  -25.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2988  -24.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5564  -24.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5088  -25.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.9178  -25.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.7180  -25.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.8077  -24.9677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.0629  -24.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.3194  -26.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6962  -25.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9864  -27.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2693  -26.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6279  -27.0153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.8684  -27.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7084  -27.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8649  -25.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8649  -26.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5743  -25.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2837  -25.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7006  -26.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9934  -25.4038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2764  -24.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9957  -24.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4101  -27.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1701  -27.0672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5743  -24.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.0424  -27.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4460  -26.6805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7471  -27.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4210  -25.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8625  -24.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8625  -23.3436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1506  -24.5776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5583  -26.1584    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.9822  -26.2285    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   41.2892  -24.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2915  -23.3547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4964  -24.1278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.4076  -27.8729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1140  -28.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6986  -28.2793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.1066  -29.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8122  -29.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5221  -29.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5220  -28.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8158  -27.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9671  -24.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.1628  -23.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9477  -23.0189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5734  -22.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.5849  -22.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  1  2  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11  7  2  0
  4  7  1  1
  3 12  1  0
  1 13  1  1
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 19 20  1  0
 19 21  1  0
 20 16  1  0
 22 21  1  0
 22 15  1  0
 22 24  1  0
 14 23  1  0
 23  1  1  0
  1 24  1  0
 22 25  1  1
 24 26  1  1
 23 27  1  6
 20 28  1  6
 21 29  1  6
 16 30  1  1
 28 31  1  0
 31 32  1  0
 31 33  2  0
 29 34  1  0
 34 35  2  0
 34 36  1  0
 15 37  1  6
 14 38  1  1
 26 39  1  0
 39 40  1  0
 39 41  2  0
 27 42  1  0
 42 43  1  0
 42 44  2  0
 43 45  2  0
 45 46  1  0
 46 47  2  0
 47 48  1  0
 48 49  2  0
 49 43  1  0
  6 50  1  1
 50 51  1  0
 51 52  1  0
 51 53  2  0
 40 54  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4764171

   [(1R,4R,5R,7S,8R,9R,10R,11S,12R)-5,7-diacetyloxy-10-[(3R,5S)-5-acetyloxy-3-(furan-3-yl)-2-methylcyclopenten-1-yl]-9-(2-methoxy-2-oxoethyl)-4,8,10-trimethyl-2-oxatricyclo[6.3.1.04,12]dodecan-11-yl] benzoate

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: 720.81

Molecular Weight (Monoisotopic): 720.3146

AlogP: 5.73

#Rotatable Bonds: 9

Polar Surface Area: 153.87

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.96

CX LogD: 3.96

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.18

Np Likeness Score: 2.33

References

1. Song M,Zhang J,Chan G,Hou Y,Chen XP,Zhang XQ,Ye WC,Zhang QW.  (2020)  Bioactive Limonoids and Triterpenoids from the Fruits of Melia azedarach.,  83  (12): [PMID:33253570] [10.1021/acs.jnatprod.9b01151]

Source

Source(1):

• Scientific Literature