Cyclocurcumin

ID: ALA4098368

Cas Number: 153127-42-5

PubChem CID: 69879809

Product Number: C650574, Order Now?

Max Phase: Preclinical

Molecular Formula: C21H20O6

Molecular Weight: 368.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C2=CC(=O)CC(c3ccc(O)c(OC)c3)O2)ccc1O

Standard InChI:  InChI=1S/C21H20O6/c1-25-20-9-13(4-7-17(20)23)3-6-16-11-15(22)12-19(27-16)14-5-8-18(24)21(10-14)26-2/h3-11,19,23-24H,12H2,1-2H3/b6-3+

Standard InChI Key:  IZLBLUIBVMGMIY-ZZXKWVIFSA-N

Molfile:  

     RDKit          2D

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    6.1331   -6.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561   -6.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2503   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1331   -5.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6618   -6.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8388   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446   -6.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8388   -5.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5446   -5.6749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4232   -6.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4149   -5.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7092   -6.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6589   -7.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3606   -8.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0697   -7.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0727   -6.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3665   -6.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3565   -8.9552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7822   -6.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4880   -6.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1971   -6.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2013   -5.7040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4905   -5.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7843   -5.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9104   -5.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9003   -6.9350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6101   -6.5300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  7  1  0
  4  1  2  0
  5  2  1  0
  6  1  1  0
  7  6  2  0
  8  4  1  0
  9  7  1  0
 10  1  1  0
 11  4  1  0
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  8  9  2  0
  5 13  2  0
  5 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 14 18  2  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 26 27  1  0
 21 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098368

   Cyclocurcumin

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: 368.39

Molecular Weight (Monoisotopic): 368.1260

AlogP: 3.74

#Rotatable Bonds: 5

Polar Surface Area: 85.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.38

CX Basic pKa: ┄

CX LogP: 3.24

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.84

Np Likeness Score: 1.16

References

1. Kim K, Kim JJ, Jung Y, Noh JY, Syed AS, Kim CY, Lee MY, Lim KM, Bae ON, Chung JH..  (2017)  Cyclocurcumin, an Antivasoconstrictive Constituent of Curcuma longa (Turmeric).,  80  (1): [PMID:28068085] [10.1021/acs.jnatprod.6b00331]

Source

Source(1):

• Scientific Literature