Curcumolide

ID: ALA3357931

PubChem CID: 118722530

Max Phase: Preclinical

Molecular Formula: C15H22O3

Molecular Weight: 250.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C[C@]2(C(C)(C)O)C[C@]3(OC2=O)[C@@H](C)CC[C@@H]13

Standard InChI:  InChI=1S/C15H22O3/c1-9-7-14(13(3,4)17)8-15(18-12(14)16)10(2)5-6-11(9)15/h7,10-11,17H,5-6,8H2,1-4H3/t10-,11-,14-,15-/m0/s1

Standard InChI Key:  UHWGHSHQYHMIOP-GVARAGBVSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   27.1943  -10.4171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9838  -11.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7753  -10.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4934  -11.4035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1987  -10.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1987  -10.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4934   -9.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7881  -10.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7836  -10.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0051   -9.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5284  -10.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0124  -11.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7840  -11.8163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1914  -11.8163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7666  -12.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1952  -11.9989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4945   -8.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5653   -9.3894    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.7642  -12.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  9  7  1  0
  8  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  8 13  1  1
  5 14  1  0
 13 14  1  0
 14 15  2  0
  5  2  1  6
  2 16  1  0
  7 17  1  0
  9 18  1  6
 12 19  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3357931

   ---

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: 250.34

Molecular Weight (Monoisotopic): 250.1569

AlogP: 2.44

#Rotatable Bonds: 1

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: 2.09

Aromatic Rings: ┄

Heavy Atoms: 18

QED Weighted: 0.57

Np Likeness Score: 2.29

References

1. Dong J, Shao W, Yan P, Cai X, Fang L, Zhao X, Lin W, Cai Y..  (2015)  Curcumolide, a unique sesquiterpenoid with anti-inflammatory properties from Curcuma wenyujin.,  25  (2): [PMID:25515561] [10.1016/j.bmcl.2014.11.075]

2. Cai Y, Li W, Tu H, Chen N, Zhong Z, Yan P, Dong J..  (2017)  Curcumolide reduces diabetic retinal vascular leukostasis and leakage partly via inhibition of the p38MAPK/NF-κ B signaling.,  27  (8): [PMID:28274631] [10.1016/j.bmcl.2017.02.045]

Source

Source(1):

• Scientific Literature