NP-MRD: Showing NP-Card for 13alpha-Hydroxydolineone (NP0046011)

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Record Information

Version

2.0

Created at

2022-03-17 19:46:56 UTC

Updated at

2022-03-17 19:46:56 UTC

NP-MRD ID

NP0046011

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13alpha-Hydroxydolineone

Description

13Alpha-Hydroxydolineone 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, 13alpha-hydroxydolineone is considered to be a flavonoid lipid molecule. 13Alpha-Hydroxydolineone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 13alpha-Hydroxydolineone has been detected, but not quantified in, jicama and pulses. 13alpha-Hydroxydolineone is found in Neorautanenia amboensis, Neorautanenia mitis , Pachyrhizus tuberosus and Pachyrrhizus erosus . This could make 13alpha-hydroxydolineone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305292D          

 26 31  0  0  0  0            999 V2000
    5.9868    3.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950    3.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464    3.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1946    5.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    5.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    6.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514    4.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9183    4.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896    4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755    5.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    5.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    4.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    4.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    5.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323    4.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7374    4.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082    3.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4132    4.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5113    4.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    6.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003    3.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    4.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806    5.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  1  0  0  0  0
 23  7  1  0  0  0  0
 23 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
M  END


  Mrv0541 05061305292D          

 26 31  0  0  0  0            999 V2000
    5.9868    3.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950    3.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5464    3.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    4.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1946    5.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042    5.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5665    6.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4881    3.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3654    3.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514    4.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9183    4.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896    4.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3755    5.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    5.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    4.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    4.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    5.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323    4.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7374    4.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9082    3.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4132    4.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5113    4.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7474    6.2845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003    3.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    4.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8806    5.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 16  6  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22 12  1  0  0  0  0
 23  7  1  0  0  0  0
 23 14  1  0  0  0  0
 24  8  1  0  0  0  0
 24 15  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
 26 13  1  0  0  0  0
 26 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046011

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O7/c20-18-10-3-9-1-2-22-12(9)5-13(10)26-17-7-23-14-6-16-15(24-8-25-16)4-11(14)19(17,18)21/h1-6,17,21H,7-8H2

> <INCHI_KEY>
HLEAVDSSZUIWQI-UHFFFAOYSA-N

> <FORMULA>
C19H12O7

> <MOLECULAR_WEIGHT>
352.2944

> <EXACT_MASS>
352.058302738

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.33459463152187

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
1.9097641453333332

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.026236562356312

> <JCHEM_PKA_STRONGEST_BASIC>
-3.045826688824046

> <JCHEM_POLAR_SURFACE_AREA>
87.36000000000001

> <JCHEM_REFRACTIVITY>
85.75219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12a-hydroxydolineone

> <JCHEM_VEBER_RULE>
0

$$$$

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      11.175   6.158   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.497   6.948   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.487   6.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.976   7.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.697   9.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.128  10.131   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.791  11.915   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.911   6.677   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.015   7.171   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.563   8.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.581   9.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.621   8.587   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.168   9.635   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.657  10.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.447   7.483   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.523   8.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.715  10.683   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.034   8.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.110   9.267   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.429   6.619   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.505   7.851   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.154   8.449   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.262  11.731   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.561   6.223   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.934   8.217   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.244  10.867   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   22                                                       
CONECT    3    9   10                                                       
CONECT    4   11   15                                                       
CONECT    5   12   13                                                       
CONECT    6   14   16                                                       
CONECT    7   17   23                                                       
CONECT    8   24   25                                                       
CONECT    9    1    3   12                                                  
CONECT   10    3   13   18                                                  
CONECT   11    4   14   19                                                  
CONECT   12    5    9   22                                                  
CONECT   13    5   10   26                                                  
CONECT   14    6   11   23                                                  
CONECT   15    4   16   24                                                  
CONECT   16    6   15   25                                                  
CONECT   17    7   19   26                                                  
CONECT   18   10   19   20                                                  
CONECT   19   11   17   18   21                                             
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22    2   12                                                       
CONECT   23    7   14                                                       
CONECT   24    8   15                                                       
CONECT   25    8   16                                                       
CONECT   26   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Value	Source
13a-Hydroxydolineone	Generator
13Α-hydroxydolineone	Generator

Chemical Formula

C₁₉H₁₂O₇

Average Mass

352.2944 Da

Monoisotopic Mass

352.05830 Da

IUPAC Name

1-hydroxy-5,7,11,14,18-pentaoxahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁷,²¹]tetracosa-2,4(8),9,15(23),16,19,21-heptaen-24-one

Traditional Name

12a-hydroxydolineone

CAS Registry Number

28617-71-2

SMILES

OC12C(COC3=CC4=C(OCO4)C=C13)OC1=C(C=C3C=COC3=C1)C2=O

InChI Identifier

InChI=1S/C19H12O7/c20-18-10-3-9-1-2-22-12(9)5-13(10)26-17-7-23-14-6-16-15(24-8-25-16)4-11(14)19(17,18)21/h1-6,17,21H,7-8H2

InChI Key

HLEAVDSSZUIWQI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Neorautanenia amboensis	Plant	KNApSAcK
Neorautanenia mitis	Plant	KNApSAcK
Pachyrhizus erosus	FooDB	KNAPSACK
Pachyrhizus tuberosus	Plant	KNApSAcK
Pachyrrhizus erosus	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Rotenoids

Direct Parent

Rotenones

Alternative Parents

Substituents

Rotenone or derivatives
Isoflavanone
Isoflavan
Furanochromone
Chromone
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Benzofuran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
Benzenoid
Furan
Heteroaromatic compound
Tertiary alcohol
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Rotenoid flavonoids (LMPK12060033 )

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	2.08	ALOGPS
logP	1.91	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.03	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	87.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.75 m³·mol⁻¹	ChemAxon
Polarizability	34.33 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030756

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002688

KNApSAcK ID

C00009582

Chemspider ID

24842945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13885696

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 13alpha-Hydroxydolineone (NP0046011)

MOL for NP0046011 (13alpha-Hydroxydolineone)

3D MOL for NP0046011 (13alpha-Hydroxydolineone)

3D SDF for NP0046011 (13alpha-Hydroxydolineone)

3D-SDF for NP0046011 (13alpha-Hydroxydolineone)

PDB for NP0046011 (13alpha-Hydroxydolineone)

3D PDB for NP0046011 (13alpha-Hydroxydolineone)

SMILES for NP0046011 (13alpha-Hydroxydolineone)

INCHI for NP0046011 (13alpha-Hydroxydolineone)

Structure for NP0046011 (13alpha-Hydroxydolineone)

3D Structure for NP0046011 (13alpha-Hydroxydolineone)