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Showing NP-Card for Homodolicholide (NP0047783)

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Record Information
Version2.0
Created at2022-03-17 20:45:54 UTC
Updated at2022-03-17 20:45:54 UTC
NP-MRD IDNP0047783
Secondary Accession NumbersNone
Natural Product Identification
Common NameHomodolicholide
DescriptionArtonin K belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Thus, artonin K is considered to be a flavonoid lipid molecule. Artonin K is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Artonin K has been detected, but not quantified in, fruits and jackfruits. This could make artonin K a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047783 (Homodolicholide)


  Mrv0541 05061307262D          

 35 38  0  0  0  0            999 V2000
   10.0616    2.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9040    4.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1143    3.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780    3.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7858    2.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    2.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6327    0.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9997    0.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163    1.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9098    2.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439    0.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001    1.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4277   -0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2899    3.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7638    2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8513    3.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5074    0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3252    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009    0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6687    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753    1.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5882    2.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0268    3.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5021    1.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0968    1.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6224    1.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    2.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9741    1.6276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6410    3.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360   -0.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  7  2  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 10  1  0  0  0  0
 21 18  1  0  0  0  0
 22 12  1  0  0  0  0
 23 12  1  0  0  0  0
 24 13  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27 22  1  0  0  0  0
 28  5  1  0  0  0  0
 28 11  1  0  0  0  0
 28 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29  6  1  0  0  0  0
 29 13  1  0  0  0  0
 29 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  1  0  0  0  0
 33 26  1  0  0  0  0
 34 27  2  0  0  0  0
 35 14  1  0  0  0  0
 35 27  1  0  0  0  0
M  END
Download

3D MOL for NP0047783 (Homodolicholide)

Download
3D SDF for NP0047783 (Homodolicholide)

  Mrv0541 05061307262D          

 35 38  0  0  0  0            999 V2000
   10.0616    2.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9040    4.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1143    3.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3780    3.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7858    2.4073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2371    2.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6327    0.9230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9997    0.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163    1.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9098    2.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8439    0.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001    1.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4277   -0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2899    3.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7638    2.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8513    3.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5074    0.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3252    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009    0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9151    1.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6687    0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4472    1.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753    1.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5882    2.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0268    3.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9532   -0.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5021    1.6327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0968    1.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6224    1.1304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4786    2.5409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9741    1.6276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6410    3.7848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789   -0.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7360   -0.6640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 16  4  1  0  0  0  0
 17  7  2  0  0  0  0
 17 15  1  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 19 16  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21 10  1  0  0  0  0
 21 18  1  0  0  0  0
 22 12  1  0  0  0  0
 23 12  1  0  0  0  0
 24 13  1  0  0  0  0
 24 23  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 26 25  1  0  0  0  0
 27 22  1  0  0  0  0
 28  5  1  0  0  0  0
 28 11  1  0  0  0  0
 28 19  1  0  0  0  0
 28 20  1  0  0  0  0
 29  6  1  0  0  0  0
 29 13  1  0  0  0  0
 29 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 25  1  0  0  0  0
 33 26  1  0  0  0  0
 34 27  2  0  0  0  0
 35 14  1  0  0  0  0
 35 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047783

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h7,15-16,18-26,30-33H,8-14H2,1-6H3/b17-7+

> <INCHI_KEY>
LRRBQWHWKJDDAW-REZTVBANSA-N

> <FORMULA>
C29H48O6

> <MOLECULAR_WEIGHT>
492.6878

> <EXACT_MASS>
492.345089268

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
56.411342624787366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[(5E)-3,4-dihydroxy-5-(propan-2-yl)hept-5-en-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.247009798666668

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.969514932578353

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.299443851487059

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1531432845161893

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
135.7806

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[(5E)-3,4-dihydroxy-5-isopropylhept-5-en-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047783 (Homodolicholide)
Download
PDB for NP0047783 (Homodolicholide)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      18.782   4.229   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.621   8.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.880   6.895   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.906   5.817   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.800   4.494   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.479   3.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.243   4.286   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.381   1.723   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.199   0.735   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.684   3.698   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.165   4.120   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.442   0.726   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.040   3.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.265  -0.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.341   6.951   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.626   4.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.522   5.647   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.414   1.133   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.807   3.152   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.895   1.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.308   2.205   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.982   0.692   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.701   2.076   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.501   3.393   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.165   4.400   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.983   5.704   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.513  -0.753   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.271   3.048   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.781   2.009   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.162   2.110   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.760   4.743   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      14.885   3.038   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      14.263   7.065   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.441  -1.859   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.974  -1.239   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7    1   17                                                       
CONECT    8    9   19                                                       
CONECT    9    8   20                                                       
CONECT   10   11   21                                                       
CONECT   11   10   28                                                       
CONECT   12   22   23                                                       
CONECT   13   24   29                                                       
CONECT   14   18   35                                                       
CONECT   15    2    3   17                                                  
CONECT   16    4   19   25                                                  
CONECT   17    7   15   26                                                  
CONECT   18   14   20   21                                                  
CONECT   19    8   16   28                                                  
CONECT   20    9   18   28                                                  
CONECT   21   10   18   29                                                  
CONECT   22   12   27   29                                                  
CONECT   23   12   24   30                                                  
CONECT   24   13   23   31                                                  
CONECT   25   16   26   32                                                  
CONECT   26   17   25   33                                                  
CONECT   27   22   34   35                                                  
CONECT   28    5   11   19   20                                             
CONECT   29    6   13   21   22                                             
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32   25                                                            
CONECT   33   26                                                            
CONECT   34   27                                                            
CONECT   35   14   27                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

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3D PDB for NP0047783 (Homodolicholide)
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SMILES for NP0047783 (Homodolicholide)
C\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
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INCHI for NP0047783 (Homodolicholide)
InChI=1S/C29H48O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h7,15-16,18-26,30-33H,8-14H2,1-6H3/b17-7+
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View in JSmol
Synonyms
ValueSource
5a,6-Dihydro-1,3,8-trihydroxy-10-methoxy-5,5-dimethyl-5H,7H-benzofuro[3,4-BC]xanthen-7-oneHMDB
28-HomodolicholideHMDB
2a,3a,22R,23R-Tetrahydroxy-b-homo-7-oxa-5a-stigmast-24(28)-en-6-oneHMDB
Chemical FormulaC29H48O6
Average Mass492.6878 Da
Monoisotopic Mass492.34509 Da
IUPAC Name15-[(5E)-3,4-dihydroxy-5-(propan-2-yl)hept-5-en-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one
Traditional Name15-[(5E)-3,4-dihydroxy-5-isopropylhept-5-en-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0²,⁷.0¹²,¹⁶]octadecan-8-one
CAS Registry Number86630-40-2
SMILES
C\C=C(/C(C)C)C(O)C(O)C(C)C1CCC2C3COC(=O)C4CC(O)C(O)CC4(C)C3CCC12C
InChI Identifier
InChI=1S/C29H48O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h7,15-16,18-26,30-33H,8-14H2,1-6H3/b17-7+
InChI KeyLRRBQWHWKJDDAW-REZTVBANSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lablab purpureusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class1-benzopyrans  
Direct ParentXanthones  
Alternative Parents
Substituents
  • Naphthopyranone
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  • Xanthone
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  • Naphthopyran
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  • Chromone
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  • 1-naphthol
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  • Naphthalene
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  • Coumaran
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  • Anisole
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  • 1-hydroxy-4-unsubstituted benzenoid
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  • 1-hydroxy-2-unsubstituted benzenoid
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  • Alkyl aryl ether
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  • Pyranone
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  • Benzenoid
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  • Pyran
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  • Vinylogous acid
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  • Heteroaromatic compound
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  • Oxacycle
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  • Ether
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  • Polyol
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  • Organooxygen compound
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  • Organic oxygen compound
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  • Hydrocarbon derivative
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  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.36ALOGPS
logP3.25ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.3ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity135.78 m³·mol⁻¹ChemAxon
Polarizability56.41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040673  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020470  
KNApSAcK IDC00013480  
Chemspider ID24844322  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15340661  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available