NP-MRD: Showing NP-Card for Calocoumarin A (NP0079825)

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Record Information

Version

2.0

Created at

2022-04-29 00:53:05 UTC

Updated at

2022-04-29 00:53:05 UTC

NP-MRD ID

NP0079825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calocoumarin A

Description

(8S,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H,8H,9H,10H-pyrano[2,3-h]chromene-2,10-dione 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. Calocoumarin A is found in Calophyllum brasiliense and Calophyllum inophyllum L. . Based on a literature review very few articles have been published on (8S,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H,8H,9H,10H-pyrano[2,3-h]chromene-2,10-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202532D          

 30 33  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   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
    3.6020   -0.3020    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
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   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 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
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   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
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  1  0  0  0
 19 24  1  1  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    2.9706   -2.9428    1.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.9905    0.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -1.6855    0.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015   -1.4050   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652   -1.7139   -0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783   -0.5738   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9002    0.6657   -0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231    1.7191    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3471    1.5175    0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0961    2.5602    0.4572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3883    2.4797    0.4695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1340    3.4932    0.6917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9663    1.2576    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2242    0.0986   -0.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8805   -1.1765   -0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6885   -1.4531   -1.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3551   -2.6582   -1.4043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2050   -3.6098   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4059   -3.3661    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7509   -2.1466    0.7701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8567    0.2512   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9914   -0.7905   -0.2570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4938   -2.0468   -0.5086 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5574    3.0497    0.4963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    4.0247    0.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    3.1764    0.7814 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4181    4.6208    0.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    2.2659   -0.1640 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5525    2.6973   -1.5904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448    0.9620    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -3.1026    2.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -2.4883    1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127   -3.8907    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -2.5126    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.4653   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1871   -0.8003    0.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1428   -0.7188   -1.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0184   -2.1144   -1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0568   -2.5602    0.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0397    1.1605    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7879   -0.6858   -2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9883   -2.8898   -2.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249   -4.5777   -0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3194   -4.1436    1.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1317   -2.0158    1.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8891   -2.8329   -0.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    2.8085    1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783    5.1814    1.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5036    4.7300    0.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9604    4.9830   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8238    2.2669    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1124    2.0030   -2.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120    3.6975   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4616    2.6871   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 30  1  0
 30  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6 22  1  0
 22 23  1  0
 22 21  2  0
 21  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 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
  9  8  2  0
  8 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
  8  7  1  0
 14 21  1  0
 20 15  1  0
 29 52  1  0
 29 53  1  0
 29 54  1  0
 28 51  1  1
  5 38  1  0
  5 39  1  0
  4 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 23 46  1  0
 13 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 26 47  1  1
 27 48  1  0
 27 49  1  0
 27 50  1  0
M  END


  Mrv1652304292202532D          

 30 33  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   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
    3.6020   -0.3020    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
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   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 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
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 O   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
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  1  1  0  0  0
 19 24  1  1  0  0  0
  4 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC2=C(CC=C(C)C)C(O)=C3C(OC(=O)C=C3C3=CC=CC=C3)=C2C(=O)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O5/c1-13(2)10-11-17-23(28)20-18(16-8-6-5-7-9-16)12-19(26)30-25(20)21-22(27)14(3)15(4)29-24(17)21/h5-10,12,14-15,28H,11H2,1-4H3/t14-,15+/m1/s1

> <INCHI_KEY>
ZJXOEBUGDGYYOO-CABCVRRESA-N

> <FORMULA>
C25H24O5

> <MOLECULAR_WEIGHT>
404.462

> <EXACT_MASS>
404.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.634658674829645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8S,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H,8H,9H,10H-pyrano[2,3-h]chromene-2,10-dione

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.939439185666667

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.138752611953723

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.693910099992714

> <JCHEM_PKA_STRONGEST_BASIC>
-4.933138591397548

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
125.3246

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-8H,9H-pyrano[2,3-h]chromene-2,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.104  -3.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -5.898   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.804  -3.231   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   25                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   21                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20    8   22                                                  
CONECT   22   21                                                            
CONECT   23   20                                                            
CONECT   24   19                                                            
CONECT   25    4   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₄O₅

Average Mass

404.4620 Da

Monoisotopic Mass

404.16237 Da

IUPAC Name

(8S,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-2H,8H,9H,10H-pyrano[2,3-h]chromene-2,10-dione

Traditional Name

(8S,9R)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-8H,9H-pyrano[2,3-h]chromene-2,10-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC2=C(CC=C(C)C)C(O)=C3C(OC(=O)C=C3C3=CC=CC=C3)=C2C(=O)[C@@H]1C

InChI Identifier

InChI=1S/C25H24O5/c1-13(2)10-11-17-23(28)20-18(16-8-6-5-7-9-16)12-19(26)30-25(20)21-22(27)14(3)15(4)29-24(17)21/h5-10,12,14-15,28H,11H2,1-4H3/t14-,15+/m1/s1

InChI Key

ZJXOEBUGDGYYOO-CABCVRRESA-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 brasiliense	Plant	KNApSAcK
Calophyllum inophyllum L.	Plant	KNApSAcK

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
Angular pyranocoumarin
Pyranocoumarin
Pyranochromene
Coumarin
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	5.18	ALOGPS
logP	4.94	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	5.69	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	125.32 m³·mol⁻¹	ChemAxon
Polarizability	43.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162936716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Calocoumarin A (NP0079825)

MOL for NP0079825 (Calocoumarin A)

3D MOL for NP0079825 (Calocoumarin A)

3D SDF for NP0079825 (Calocoumarin A)

3D-SDF for NP0079825 (Calocoumarin A)

PDB for NP0079825 (Calocoumarin A)

3D PDB for NP0079825 (Calocoumarin A)

SMILES for NP0079825 (Calocoumarin A)

INCHI for NP0079825 (Calocoumarin A)

Structure for NP0079825 (Calocoumarin A)

3D Structure for NP0079825 (Calocoumarin A)