NP-MRD: Showing NP-Card for (+)-Cordianol H (NP0079856)

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Record Information

Version

2.0

Created at

2022-04-29 00:56:05 UTC

Updated at

2022-04-29 00:56:05 UTC

NP-MRD ID

NP0079856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Cordianol H

Description

(1R,2S,7R,10R,11R,14S,15R,17R)-14-[(2E,4S,5S)-4,5-dihydroxy-6-methylhepta-2,6-dien-2-yl]-17-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Cordianol H is found in Cordia multispicata and Varronia multispicata. Based on a literature review very few articles have been published on (1R,2S,7R,10R,11R,14S,15R,17R)-14-[(2E,4S,5S)-4,5-dihydroxy-6-methylhepta-2,6-dien-2-yl]-17-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292202562D          

 34 37  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8764    4.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3155    2.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109    3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3282    3.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    3.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 17 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 20 29  1  0  0  0  0
 12 30  1  1  0  0  0
  9 31  1  6  0  0  0
  6 32  1  6  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END


  Mrv1652304292202562D          

 34 37  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873    3.2668    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8764    4.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1540    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3155    2.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109    3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3282    3.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2000    4.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5528    3.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  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
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 17 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 20 29  1  0  0  0  0
 12 30  1  1  0  0  0
  9 31  1  6  0  0  0
  6 32  1  6  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H](O)[C@@H](O)\C=C(/C)[C@H]1CC[C@]2(C)[C@@H]1C[C@@H](O)[C@@H]1[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-17(2)25(34)21(31)15-18(3)19-9-13-29(7)20(19)16-22(32)26-28(6)12-11-24(33)27(4,5)23(28)10-14-30(26,29)8/h15,19-23,25-26,31-32,34H,1,9-14,16H2,2-8H3/b18-15+/t19-,20-,21+,22-,23+,25+,26-,28+,29-,30-/m1/s1

> <INCHI_KEY>
SWQUQBOEMZQZKH-NTMOXBPZSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.48845505655622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,7R,10R,11R,14S,15R,17R)-14-[(2E,4S,5S)-4,5-dihydroxy-6-methylhepta-2,6-dien-2-yl]-17-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
4.913219710666667

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.823331818445766

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.365651289236961

> <JCHEM_PKA_STRONGEST_BASIC>
-0.26051625839228787

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
137.23200000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7R,10R,11R,14S,15R,17R)-14-[(2E,4S,5S)-4,5-dihydroxy-6-methylhepta-2,6-dien-2-yl]-17-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

> <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       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.374   6.011   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.138   4.882   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.503   7.525   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.609   5.887   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.189   4.461   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.554   7.103   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.079   6.893   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.973   8.530   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.331   0.781   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.241  -0.130   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.601   0.361   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33   34                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   32                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   12   31                                             
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   19   30                                             
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   12                                                       
CONECT   20   17   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   20                                                            
CONECT   30   12                                                            
CONECT   31    9                                                            
CONECT   32    6                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(1R,2S,7R,10R,11R,14S,15R,17R)-14-[(2E,4S,5S)-4,5-dihydroxy-6-methylhepta-2,6-dien-2-yl]-17-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

Traditional Name

(1R,2S,7R,10R,11R,14S,15R,17R)-14-[(2E,4S,5S)-4,5-dihydroxy-6-methylhepta-2,6-dien-2-yl]-17-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H](O)[C@@H](O)\C=C(/C)[C@H]1CC[C@]2(C)[C@@H]1C[C@@H](O)[C@@H]1[C@@]3(C)CCC(=O)C(C)(C)[C@@H]3CC[C@@]21C

InChI Identifier

InChI=1S/C30H48O4/c1-17(2)25(34)21(31)15-18(3)19-9-13-29(7)20(19)16-22(32)26-28(6)12-11-24(33)27(4,5)23(28)10-14-30(26,29)8/h15,19-23,25-26,31-32,34H,1,9-14,16H2,2-8H3/b18-15+/t19-,20-,21+,22-,23+,25+,26-,28+,29-,30-/m1/s1

InChI Key

SWQUQBOEMZQZKH-NTMOXBPZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cordia multispicata	Plant	KNApSAcK
Varronia multispicata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
24-hydroxysteroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-alpha-hydroxysteroid
11-hydroxysteroid
3-oxo-5-alpha-steroid
14-alpha-methylsteroid
Steroid
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.25	ALOGPS
logP	4.91	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.23 m³·mol⁻¹	ChemAxon
Polarizability	55.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

163012993

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Cordianol H (NP0079856)

MOL for NP0079856 ((+)-Cordianol H)

3D MOL for NP0079856 ((+)-Cordianol H)

3D SDF for NP0079856 ((+)-Cordianol H)

3D-SDF for NP0079856 ((+)-Cordianol H)

PDB for NP0079856 ((+)-Cordianol H)

3D PDB for NP0079856 ((+)-Cordianol H)

SMILES for NP0079856 ((+)-Cordianol H)

INCHI for NP0079856 ((+)-Cordianol H)

Structure for NP0079856 ((+)-Cordianol H)

3D Structure for NP0079856 ((+)-Cordianol H)