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Showing NP-Card for 12alpha-Hydroxymunduserone (NP0048141)

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Record Information
Version2.0
Created at2022-03-17 20:51:45 UTC
Updated at2022-03-17 20:51:45 UTC
NP-MRD IDNP0048141
Secondary Accession NumbersNone
Natural Product Identification
Common Name12alpha-Hydroxymunduserone
Description12Alpha-Hydroxymunduserone 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-hydroxymunduserone is considered to be a flavonoid lipid molecule. 12Alpha-Hydroxymunduserone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 12alpha-Hydroxymunduserone has been detected, but not quantified in, jicama and pulses. 12alpha-Hydroxymunduserone is found in Millettia oblata ssp. teitensis , Pachyrrhizus erosus and Tephrosia fulvinervis. This could make 12alpha-hydroxymunduserone a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048141 (12alpha-Hydroxymunduserone)


  Mrv0541 02241210242D          

 26 29  0  0  0  0            999 V2000
   -1.0666   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0666   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -2.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3523   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4994   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0749    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -2.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606    0.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9280    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878    1.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749    2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -1.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
  9 21  1  0  0  0  0
 10 20  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  2  0  0  0  0
 17 24  1  0  0  0  0
 19 26  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
Download

3D MOL for NP0048141 (12alpha-Hydroxymunduserone)

Download
3D SDF for NP0048141 (12alpha-Hydroxymunduserone)

  Mrv0541 02241210242D          

 26 29  0  0  0  0            999 V2000
   -1.0666   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0666   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -2.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606   -1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749   -2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878   -1.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878   -0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994   -0.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4994    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878    0.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137   -2.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523    0.4115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3606    0.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9280    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878    1.6474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0749    2.0603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -1.6460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  1  0  0  0  0
  9 21  1  0  0  0  0
 10 20  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 22  1  0  0  0  0
 17 18  2  0  0  0  0
 17 24  1  0  0  0  0
 19 26  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O2

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O7/c1-22-10-4-5-11-13(6-10)26-17-9-25-14-8-16(24-3)15(23-2)7-12(14)19(17,21)18(11)20/h4-8,17,21H,9H2,1-3H3

> <INCHI_KEY>
APAWOEBSLLGWDF-UHFFFAOYSA-N

> <FORMULA>
C19H18O7

> <MOLECULAR_WEIGHT>
358.342

> <EXACT_MASS>
358.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
36.12535692284469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12a-hydroxy-2,3,9-trimethoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphen-12-one

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.6543934800000002

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.075003440920117

> <JCHEM_PKA_STRONGEST_BASIC>
-4.193060464043405

> <JCHEM_POLAR_SURFACE_AREA>
83.45000000000002

> <JCHEM_REFRACTIVITY>
90.53380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12a-hydroxymunduserone

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048141 (12alpha-Hydroxymunduserone)
Download
PDB for NP0048141 (12alpha-Hydroxymunduserone)
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  C   UNK     0      -1.991  -3.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.991  -1.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.327  -0.763   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.663  -1.534   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.663  -3.075   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.327  -3.846   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.658  -3.846   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.673  -3.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.673  -1.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.658  -0.763   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.006  -3.846   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.337  -3.075   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.337  -1.534   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.006  -0.763   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.666  -0.763   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.666   0.768   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.337   1.534   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.006   0.768   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.999  -3.846   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.658   0.768   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.673   0.008   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.002   1.534   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.332   0.768   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.337   3.075   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.006   3.846   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.332  -3.073   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10   14   21                                             
CONECT   10    2    9   20                                                  
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14    9   13   18                                                  
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   24                                                  
CONECT   18   14   17                                                       
CONECT   19    5   26                                                       
CONECT   20   10                                                            
CONECT   21    9                                                            
CONECT   22   16   23                                                       
CONECT   23   22                                                            
CONECT   24   17   25                                                       
CONECT   25   24                                                            
CONECT   26   19                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

Download
3D PDB for NP0048141 (12alpha-Hydroxymunduserone)
Download
SMILES for NP0048141 (12alpha-Hydroxymunduserone)
COC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O2
Download
INCHI for NP0048141 (12alpha-Hydroxymunduserone)
InChI=1S/C19H18O7/c1-22-10-4-5-11-13(6-10)26-17-9-25-14-8-16(24-3)15(23-2)7-12(14)19(17,21)18(11)20/h4-8,17,21H,9H2,1-3H3
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View in JSmol
Synonyms
ValueSource
12a-HydroxymunduseroneGenerator
12Α-hydroxymunduseroneGenerator
Chemical FormulaC19H18O7
Average Mass358.3420 Da
Monoisotopic Mass358.10525 Da
IUPAC Name12a-hydroxy-2,3,9-trimethoxy-6,6a,12,12a-tetrahydro-5,7-dioxatetraphen-12-one
Traditional Name12a-hydroxymunduserone
CAS Registry Number66280-24-8
SMILES
COC1=CC2=C(C=C1)C(=O)C1(O)C(COC3=C1C=C(OC)C(OC)=C3)O2
InChI Identifier
InChI=1S/C19H18O7/c1-22-10-4-5-11-13(6-10)26-17-9-25-14-8-16(24-3)15(23-2)7-12(14)19(17,21)18(11)20/h4-8,17,21H,9H2,1-3H3
InChI KeyAPAWOEBSLLGWDF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Millettia oblata ssp. teitensisPlant
Pachyrhizus erosusFooDB
Pachyrrhizus erosusPlant
Tephrosia fulvinervisPlant
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
    • 

  • Chromone
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • 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
logP1.98ALOGPS
logP1.65ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.08ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.53 m³·mol⁻¹ChemAxon
Polarizability36.13 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035070  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013694  
KNApSAcK IDC00009580  
Chemspider ID24842959  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14427372  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available