NP-MRD: Showing NP-Card for Calophyllolide (NP0051436)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:10 UTC

Updated at

2022-04-27 22:48:10 UTC

NP-MRD ID

NP0051436

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calophyllolide

Description

Calophyllolide belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Thus, calophyllolide is considered to be a flavonoid. Calophyllolide is found in Calophyllum bracteatum, Calophyllum brasiliense , Calophyllum inophyllum and Lissachatina fulica. Calophyllolide was first documented in 2010 (PMID: 21344845). Based on a literature review a small amount of articles have been published on Calophyllolide (PMID: 33759279) (PMID: 29020015) (PMID: 26198219) (PMID: 21579166).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200482D          

 31 34  0  0  0  0            999 V2000
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    6.7163   -0.0047    0.7079 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6984    0.0729   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4214    0.0127   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0480   -0.1266    1.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3657    0.0838   -1.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7039    0.2024   -2.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9664    0.0228   -0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621   -1.2149   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0789   -2.3826   -0.9868 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -2.8066   -2.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0215   -1.3662   -0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -0.2497   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1357    0.9846   -0.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8779    2.1077    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3032    2.1296    0.3547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2214    1.8049   -0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5863    1.8153   -0.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0686    2.1608    0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1855    2.4889    1.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8264    2.4754    1.6015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2151    3.3365    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1216    3.3642   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7173    4.4748   -0.2936 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    2.2854   -0.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2072    1.1361   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0930   -0.3641    0.1673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7602   -1.5919    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9085   -1.6203   -0.7954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135   -1.8075    1.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8991   -2.7483   -0.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6209   -2.6637   -0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5931    0.6572    0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3321    0.3783    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0953   -1.0460    0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9656    0.1743   -1.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580   -0.9486    1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932   -0.4474    1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2240    0.8155    1.9438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249   -2.4608   -2.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0368   -2.4642   -2.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902   -3.9297   -2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9190    1.5233   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3163    1.5615   -1.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1531    2.1691    1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6106    2.7572    2.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579    2.7428    2.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7972    4.2182    0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8443   -1.2468   -0.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6612   -0.9767   -1.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804   -2.6389   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4955   -2.8875    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4419   -1.3960    1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8477   -1.2816    2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3773   -3.7436   -0.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0044   -3.5416   -0.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 31  1  0
 31 30  2  0
 30 27  1  0
 27 28  1  0
 27 29  1  0
 27 26  1  0
 26 12  1  0
 12 13  2  0
 13 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 25  7  2  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
  7  8  1  0
 12 11  1  0
 14 13  1  0
 20 15  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
 31 55  1  0
 30 54  1  0
 28 48  1  0
 28 49  1  0
 28 50  1  0
 29 51  1  0
 29 52  1  0
 29 53  1  0
 21 47  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  2 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
M  END


  Mrv1652304282200482D          

 31 34  0  0  0  0            999 V2000
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -1.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  1 10  1  0  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051436

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C=CC(C)(C)OC2=C2C(OC(=O)C=C2C2=CC=CC=C2)=C1C(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C26H24O5/c1-6-15(2)22(28)21-23(29-5)17-12-13-26(3,4)31-24(17)20-18(14-19(27)30-25(20)21)16-10-8-7-9-11-16/h6-14H,1-5H3/b15-6+

> <INCHI_KEY>
PMBLOLOJQZPEND-GIDUJCDVSA-N

> <FORMULA>
C26H24O5

> <MOLECULAR_WEIGHT>
416.473

> <EXACT_MASS>
416.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.813584987978786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
5.055636339

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.629986863813287

> <JCHEM_POLAR_SURFACE_AREA>
61.83

> <JCHEM_REFRACTIVITY>
131.039

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.77e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calophyllolide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.104  -0.564   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.724   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.724   4.771   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.414   6.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.874   6.105   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.104   7.438   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.184   7.438   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3   30                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11   12                                             
CONECT    9    8   10                                                       
CONECT   10    9    1                                                       
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    5   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    4                                                       
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24    3   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26                                                            
CONECT   30    2   31                                                       
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₄O₅

Average Mass

416.4730 Da

Monoisotopic Mass

416.16237 Da

IUPAC Name

5-methoxy-2,2-dimethyl-6-[(2E)-2-methylbut-2-enoyl]-10-phenyl-2H,8H-pyrano[2,3-f]chromen-8-one

Traditional Name

calophyllolide

CAS Registry Number

Not Available

SMILES

COC1=C2C=CC(C)(C)OC2=C2C(OC(=O)C=C2C2=CC=CC=C2)=C1C(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C26H24O5/c1-6-15(2)22(28)21-23(29-5)17-12-13-26(3,4)31-24(17)20-18(14-19(27)30-25(20)21)16-10-8-7-9-11-16/h6-14H,1-5H3/b15-6+

InChI Key

PMBLOLOJQZPEND-GIDUJCDVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calophyllum bracteatum	Plant	KNApSAcK
Calophyllum brasiliense	Plant	KNApSAcK
Calophyllum inophyllum	Plant	KNApSAcK
Lissachatina fulica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Prenylated neoflavonoids

Direct Parent

Prenylated neoflavonoids

Alternative Parents

Substituents

Prenylated neoflavonoid
Pyranoneoflavonoid
4-phenylcoumarin
Pyranocoumarin
Angular pyranocoumarin
2,2-dimethyl-1-benzopyran
Coumarin
Benzopyran
1-benzopyran
Anisole
Aryl ketone
Alkyl aryl ether
Pyranone
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Pyran
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Heteroaromatic compound
Acryloyl-group
Enone
Lactone
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

neoflavonoid (CHEBI:3328 )
coumarins (C09158 )
Neoflavonoids (C09158 )
Neoflavonoids (LMPK12100001 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.3	ALOGPS
logP	5.06	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.04 m³·mol⁻¹	ChemAxon
Polarizability	44.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002455

Chemspider ID

4444746

KEGG Compound ID

C09158

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281392

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sisakht M, Mahmoodzadeh A, Darabian M: Plant-derived chemicals as potential inhibitors of SARS-CoV-2 main protease (6LU7), a virtual screening study. Phytother Res. 2021 Jun;35(6):3262-3274. doi: 10.1002/ptr.7041. Epub 2021 Mar 23. [PubMed:33759279 ]
Nguyen VL, Truong CT, Nguyen BCQ, Vo TV, Dao TT, Nguyen VD, Trinh DT, Huynh HK, Bui CB: Anti-inflammatory and wound healing activities of calophyllolide isolated from Calophyllum inophyllum Linn. PLoS One. 2017 Oct 11;12(10):e0185674. doi: 10.1371/journal.pone.0185674. eCollection 2017. [PubMed:29020015 ]
Liu WH, Liu YW, Chen ZF, Chiou WF, Tsai YC, Chen CC: Calophyllolide content in Calophyllum inophyllum at different stages of maturity and its osteogenic activity. Molecules. 2015 Jul 7;20(7):12314-27. doi: 10.3390/molecules200712314. [PubMed:26198219 ]
Ma T, Wang L, Cheng GF, Liu G: Synthesis of calophyllolide analogue and its preliminary anti-inflammatory activity. Yao Xue Xue Bao. 2010 Oct;45(10):1265-9. [PubMed:21344845 ]
Kalyanaraman L, Mohan Kumar R, Vishweshwar P, Pichai R, Narasimhan S: 5-Meth-oxy-2,2-dimethyl-6-[(2E)-2-methyl-but-2-eno-yl]-10-phenyl-2H,8H-pyrano[2,3 -f]chromen-8-one (calophyllolide). Acta Crystallogr Sect E Struct Rep Online. 2010 Apr 17;66(Pt 5):o1115. doi: 10.1107/S1600536810013577. [PubMed:21579166 ]

Showing NP-Card for Calophyllolide (NP0051436)

MOL for NP0051436 (Calophyllolide)

3D MOL for NP0051436 (Calophyllolide)

3D SDF for NP0051436 (Calophyllolide)

3D-SDF for NP0051436 (Calophyllolide)

PDB for NP0051436 (Calophyllolide)

3D PDB for NP0051436 (Calophyllolide)

SMILES for NP0051436 (Calophyllolide)

INCHI for NP0051436 (Calophyllolide)

Structure for NP0051436 (Calophyllolide)

3D Structure for NP0051436 (Calophyllolide)