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Showing NP-Card for 12alpha-Hydroxyerosone (NP0047869)

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Record Information
Version2.0
Created at2022-03-17 20:47:18 UTC
Updated at2022-03-17 20:47:18 UTC
NP-MRD IDNP0047869
Secondary Accession NumbersNone
Natural Product Identification
Common Name12alpha-Hydroxyerosone
Description12Alpha-Hydroxyerosone belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton. Thus, 12alpha-hydroxyerosone is considered to be a flavonoid lipid molecule. 12Alpha-Hydroxyerosone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 12alpha-hydroxyerosone has been detected, but not quantified in, jicama and pulses. 12alpha-Hydroxyerosone is found in Neorautanenia amboensis and Pachyrrhizus erosus . This could make 12alpha-hydroxyerosone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047869 (12alpha-Hydroxyerosone)


  Mrv0541 05061307362D          

 27 31  0  0  0  0            999 V2000
   -0.4873    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778    1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696    2.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4043    2.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    2.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049    2.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    4.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    3.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163    4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722    2.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    3.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    3.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    2.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    2.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5067    4.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029    3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    1.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    2.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069    1.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    2.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    3.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    4.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    4.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
 22 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23 16  1  0  0  0  0
 24  2  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 13  1  0  0  0  0
 26  9  1  0  0  0  0
 26 15  1  0  0  0  0
 27 14  1  0  0  0  0
 27 18  1  0  0  0  0
M  END
Download

3D MOL for NP0047869 (12alpha-Hydroxyerosone)

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3D SDF for NP0047869 (12alpha-Hydroxyerosone)

  Mrv0541 05061307362D          

 27 31  0  0  0  0            999 V2000
   -0.4873    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778    1.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696    2.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4043    2.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780    2.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049    2.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    4.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1240    3.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163    4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722    2.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876    2.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5087    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    3.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    3.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5107    2.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798    2.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5067    4.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934    2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3029    3.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    1.9583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0991    2.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069    1.2886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8740    2.4410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    3.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1220    4.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    4.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  2  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 17  8  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 19  2  0  0  0  0
 22 20  1  0  0  0  0
 23  1  1  0  0  0  0
 23 16  1  0  0  0  0
 24  2  1  0  0  0  0
 24 17  1  0  0  0  0
 25  4  1  0  0  0  0
 25 13  1  0  0  0  0
 26  9  1  0  0  0  0
 26 15  1  0  0  0  0
 27 14  1  0  0  0  0
 27 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(OCC3OC4=C(C=C5C=COC5=C4)C(=O)C23O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O7/c1-23-16-6-12-15(8-17(16)24-2)26-9-18-20(12,22)19(21)11-5-10-3-4-25-13(10)7-14(11)27-18/h3-8,18,22H,9H2,1-2H3

> <INCHI_KEY>
SXKFYDWIBCRCRI-UHFFFAOYSA-N

> <FORMULA>
C20H16O7

> <MOLECULAR_WEIGHT>
368.3368

> <EXACT_MASS>
368.089602866

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
36.956455253190356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-12-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
1.9711881463333332

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.041322542805128

> <JCHEM_PKA_STRONGEST_BASIC>
-3.042236988937175

> <JCHEM_POLAR_SURFACE_AREA>
87.36000000000001

> <JCHEM_REFRACTIVITY>
92.9117

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047869 (12alpha-Hydroxyerosone)
Download
PDB for NP0047869 (12alpha-Hydroxyerosone)
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      -0.910   1.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.012   3.064   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.770   4.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.955   5.066   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.986   4.489   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.436   4.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.746   7.474   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.231   6.466   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.577   8.791   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.468   4.906   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.884   5.565   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.816   5.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.849   6.398   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.264   7.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.714   6.882   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.953   3.898   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.149   4.973   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.679   7.716   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.401   5.148   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.299   6.223   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.021   3.655   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.918   4.731   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.573   2.405   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.631   4.557   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.385   6.497   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.094   8.375   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.162   8.132   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3    4   10                                                       
CONECT    4    3   25                                                       
CONECT    5   10   11                                                       
CONECT    6   12   16                                                       
CONECT    7   13   14                                                       
CONECT    8   15   17                                                       
CONECT    9   18   26                                                       
CONECT   10    3    5   13                                                  
CONECT   11    5   14   19                                                  
CONECT   12    6   15   20                                                  
CONECT   13    7   10   25                                                  
CONECT   14    7   11   27                                                  
CONECT   15    8   12   26                                                  
CONECT   16    6   17   23                                                  
CONECT   17    8   16   24                                                  
CONECT   18    9   20   27                                                  
CONECT   19   11   20   21                                                  
CONECT   20   12   18   19   22                                             
CONECT   21   19                                                            
CONECT   22   20                                                            
CONECT   23    1   16                                                       
CONECT   24    2   17                                                       
CONECT   25    4   13                                                       
CONECT   26    9   15                                                       
CONECT   27   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

Download
3D PDB for NP0047869 (12alpha-Hydroxyerosone)
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SMILES for NP0047869 (12alpha-Hydroxyerosone)
COC1=C(OC)C=C2C(OCC3OC4=C(C=C5C=COC5=C4)C(=O)C23O)=C1
Download
INCHI for NP0047869 (12alpha-Hydroxyerosone)
InChI=1S/C20H16O7/c1-23-16-6-12-15(8-17(16)24-2)26-9-18-20(12,22)19(21)11-5-10-3-4-25-13(10)7-14(11)27-18/h3-8,18,22H,9H2,1-2H3
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View in JSmol
Synonyms
ValueSource
12a-HydroxyerosoneGenerator
12Α-hydroxyerosoneGenerator
6a,13a-Dihydro-13a-hydroxy-2,3-dimethoxy[1]benzopyrano[3,4-b]furo[3,2-g][1]benzopyran-13(6H)-one, 9ciHMDB
Chemical FormulaC20H16O7
Average Mass368.3368 Da
Monoisotopic Mass368.08960 Da
IUPAC Name13-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-12-one
Traditional Name13-hydroxy-16,17-dimethoxy-2,6,20-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-3(11),4,7,9,14,16,18-heptaen-12-one
CAS Registry Number66322-32-5
SMILES
COC1=C(OC)C=C2C(OCC3OC4=C(C=C5C=COC5=C4)C(=O)C23O)=C1
InChI Identifier
InChI=1S/C20H16O7/c1-23-16-6-12-15(8-17(16)24-2)26-9-18-20(12,22)19(21)11-5-10-3-4-25-13(10)7-14(11)27-18/h3-8,18,22H,9H2,1-2H3
InChI KeySXKFYDWIBCRCRI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Neorautanenia amboensisPlant
Pachyrhizus erosusFooDB
Pachyrrhizus erosusPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rotenones. These are rotenoids with a structure based on a 6a,12a-dihydrochromeno[3,4-b]chromen-12(6H)-one skeleton.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassRotenoids  
Direct ParentRotenones  
Alternative Parents
Substituents
  • Rotenone or derivatives
    • 

  • Isoflavanone
    • 

  • Isoflavan
    • 

  • Furanochromone
    • 

  • Chromone
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Benzofuran
    • 

  • Anisole
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Furan
    • 

  • Heteroaromatic compound
    • 

  • Tertiary alcohol
    • 

  • Ketone
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • 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
logP2.27ALOGPS
logP1.97ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.04ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area87.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability36.96 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034141  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012416  
KNApSAcK IDC00009584  
Chemspider ID24842947  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257408  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available