Np mrd loader

Showing NP-Card for Trigofoenoside A (NP0049423)

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Record Information
Version2.0
Created at2022-03-17 21:12:19 UTC
Updated at2022-03-17 21:12:19 UTC
NP-MRD IDNP0049423
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrigofoenoside A
DescriptionChrysophanol 8-gentiobioside belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Chrysophanol 8-gentiobioside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chrysophanol 8-gentiobioside has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and pulses. Trigofoenoside A is found in Dioscorea cayenensis , Dioscorea deltoidea var.orbiculata , Dioscorea nipponica , Dioscorea spongiosa, Dioscorea villosa , Lilium regale, Ophiopogon planiscapus, Paris polyphylla, Maianthemum atropurpureum and Solanum tuberosum. This could make chrysophanol 8-gentiobioside a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0049423 (Trigofoenoside A)


  Mrv0541 02241208152D          

 63 70  0  0  0  0            999 V2000
    2.2376    2.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0659    1.4862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D MOL for NP0049423 (Trigofoenoside A)

Download
3D SDF for NP0049423 (Trigofoenoside A)

  Mrv0541 02241208152D          

 63 70  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0049423

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)OC2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C45H74O18/c1-19(18-57-40-37(54)35(52)32(49)28(16-46)60-40)8-13-45(56)20(2)30-27(63-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)59-42-39(36(53)33(50)29(17-47)61-42)62-41-38(55)34(51)31(48)21(3)58-41/h6,19-21,23-42,46-56H,7-18H2,1-5H3

> <INCHI_KEY>
KNZSXKKCTOYLSV-UHFFFAOYSA-N

> <FORMULA>
C45H74O18

> <MOLECULAR_WEIGHT>
903.0583

> <EXACT_MASS>
902.487515564

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
98.6884344495312

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4,5-dihydroxy-2-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.4999950886666654

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.044153158266138

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.557688997767045

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6483772987566265

> <JCHEM_POLAR_SURFACE_AREA>
287.13999999999993

> <JCHEM_REFRACTIVITY>
219.47220000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(4,5-dihydroxy-2-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049423 (Trigofoenoside A)
Download
PDB for NP0049423 (Trigofoenoside A)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       4.177   4.281   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.856   2.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.388   2.612   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.015   1.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.547   1.044   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.453   2.292   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.977   0.760   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.977  -0.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.311  -0.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.646  -0.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.646  -2.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.311  -3.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.977  -2.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.645  -3.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.310  -2.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.310  -0.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.645  -0.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.645   1.530   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.310   2.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.024   1.530   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.183   3.059   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.916   4.714   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.393   3.249   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.487   2.004   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.393   0.760   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.856   1.234   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.487  -0.488   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.024  -0.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.173  -0.362   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.705  -0.521   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.331  -1.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.861  -2.089   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.490  -3.496   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.020  -3.657   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      14.646  -5.064   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       7.893  -3.013   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.426  -3.175   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.052  -4.581   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.584  -4.743   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.210  -6.149   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.146  -5.829   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -7.978  -3.090   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -9.312  -2.320   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0     -10.644  -3.090   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0     -11.979  -2.320   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -13.314  -3.090   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0     -14.646  -2.320   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -5.311   1.530   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -6.646   2.300   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.646   3.840   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -5.311   4.609   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0     -10.644   4.609   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -9.312   3.840   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -9.312   2.300   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -7.978   1.530   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -7.978  -0.010   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -9.312  -0.780   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -10.644  -0.010   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -10.644   1.530   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -7.978   4.609   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -7.978   6.149   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0     -11.979  -0.780   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0     -13.314  -0.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    7    9   13   17                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   42                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17    8   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24   28                                             
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23    2   22   24                                                  
CONECT   24   20   23   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26    2   25                                                       
CONECT   27   25   28                                                       
CONECT   28   16   20   27                                                  
CONECT   29    5   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   37                                                            
CONECT   37   31   36   38                                                  
CONECT   38   37   39   41                                                  
CONECT   39   33   38   40                                                  
CONECT   40   39                                                            
CONECT   41   38                                                            
CONECT   42   11   43                                                       
CONECT   43   42   44   57                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   62                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   49                                                            
CONECT   49   48   50   55                                                  
CONECT   50   49   51   60                                                  
CONECT   51   50                                                            
CONECT   52   53                                                            
CONECT   53   52   54   60                                                  
CONECT   54   53   55                                                       
CONECT   55   49   54   56                                                  
CONECT   56   55   57                                                       
CONECT   57   43   56   58                                                  
CONECT   58   57   59   62                                                  
CONECT   59   58                                                            
CONECT   60   50   53   61                                                  
CONECT   61   60                                                            
CONECT   62   45   58   63                                                  
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  140    0
END

Download
3D PDB for NP0049423 (Trigofoenoside A)
Download
SMILES for NP0049423 (Trigofoenoside A)
CC(CCC1(O)OC2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O
Download
INCHI for NP0049423 (Trigofoenoside A)
InChI=1S/C45H74O18/c1-19(18-57-40-37(54)35(52)32(49)28(16-46)60-40)8-13-45(56)20(2)30-27(63-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)59-42-39(36(53)33(50)29(17-47)61-42)62-41-38(55)34(51)31(48)21(3)58-41/h6,19-21,23-42,46-56H,7-18H2,1-5H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC45H74O18
Average Mass903.0583 Da
Monoisotopic Mass902.48752 Da
IUPAC Name2-[(4,5-dihydroxy-2-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol
Traditional Name2-[(4,5-dihydroxy-2-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-16-yl]oxy}-6-(hydroxymethyl)oxan-3-yl)oxy]-6-methyloxane-3,4,5-triol
CAS Registry Number99705-66-5
SMILES
CC(CCC1(O)OC2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(O)C(O)C1OC1OC(C)C(O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C45H74O18/c1-19(18-57-40-37(54)35(52)32(49)28(16-46)60-40)8-13-45(56)20(2)30-27(63-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)59-42-39(36(53)33(50)29(17-47)61-42)62-41-38(55)34(51)31(48)21(3)58-41/h6,19-21,23-42,46-56H,7-18H2,1-5H3
InChI KeyKNZSXKKCTOYLSV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dioscorea cayenensisPlant
Dioscorea deltoidea var.orbiculataPlant
Dioscorea nipponicaPlant
Dioscorea spongiosaLOTUS Database
Dioscorea villosaPlant
Lilium regaleLOTUS Database
Ophiopogon planiscapusLOTUS Database
Paris polyphyllaLOTUS Database
Smilacina atropurpureaLOTUS Database
Solanum tuberosumLOTUS Database
Trigonella foenum-graecumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassAnthracenes  
Sub ClassAnthraquinones  
Direct ParentAnthraquinones  
Alternative Parents
Substituents
  • 9,10-anthraquinone
    • 

  • Anthraquinone
    • 

  • Phenolic glycoside
    • 

  • O-glycosyl compound
    • 

  • Glycosyl compound
    • 

  • Disaccharide
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Oxane
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP0.11ALOGPS
logP-0.5ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.56ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area287.14 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity219.47 m³·mol⁻¹ChemAxon
Polarizability98.69 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0039488  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019094  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752659  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available