NP-MRD: Showing NP-Card for Dolineone (NP0047825)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:35 UTC

Updated at

2022-03-17 20:46:35 UTC

NP-MRD ID

NP0047825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dolineone

Description

Dolineone, also known as dolichone, 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, dolineone is considered to be a flavonoid lipid molecule. Dolineone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Dolineone has been detected, but not quantified in, jicama and pulses. Dolineone is found in Neorautanenia mitis , Neorautanenia pseudopachyrrhiza, Pachyrhizus tuberosus and Pachyrrhizus erosus . This could make dolineone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307312D          

 25 30  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
    1.9183    4.8658    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
    5.6896    4.6003    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
    4.3755    5.1617    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
    2.7374    4.9645    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
    2.9082    3.5458    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  4  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  2  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
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24 16  1  0  0  0  0
 25 14  1  0  0  0  0
 25 17  1  0  0  0  0
M  END

  Mrv0541 05061307312D          

 25 30  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
    1.9183    4.8658    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
    5.6896    4.6003    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
    4.3755    5.1617    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
    2.7374    4.9645    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
    2.9082    3.5458    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  4  2  0  0  0  0
 11  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  2  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
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  2  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
 24  8  1  0  0  0  0
 24 16  1  0  0  0  0
 25 14  1  0  0  0  0
 25 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O6/c20-19-11-3-9-1-2-21-12(9)5-14(11)25-17-7-22-13-6-16-15(23-8-24-16)4-10(13)18(17)19/h1-6,17-18H,7-8H2

> <INCHI_KEY>
RAJDDCCSNZAPCH-UHFFFAOYSA-N

> <FORMULA>
C19H12O6

> <MOLECULAR_WEIGHT>
336.295

> <EXACT_MASS>
336.063388116

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.566620389959624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
3.07

> <JCHEM_LOGP>
2.5012818083333332

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.42933693141694

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0298270169827544

> <JCHEM_POLAR_SURFACE_AREA>
67.13000000000001

> <JCHEM_REFRACTIVITY>
84.50619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dolineone

> <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       3.581   9.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.563   8.219   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       2.657  10.315   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.168   9.635   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       5.110   9.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.034   8.035   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      12.154   8.449   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.262  11.731   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.561   6.223   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.934   8.217   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.244  10.867   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1   21                                                       
CONECT    3    9   11                                                       
CONECT    4   10   15                                                       
CONECT    5   12   14                                                       
CONECT    6   13   16                                                       
CONECT    7   17   22                                                       
CONECT    8   23   24                                                       
CONECT    9    1    3   12                                                  
CONECT   10    4   13   18                                                  
CONECT   11    3   14   19                                                  
CONECT   12    5    9   21                                                  
CONECT   13    6   10   22                                                  
CONECT   14    5   11   25                                                  
CONECT   15    4   16   23                                                  
CONECT   16    6   15   24                                                  
CONECT   17    7   18   25                                                  
CONECT   18   10   17   19                                                  
CONECT   19   11   18   20                                                  
CONECT   20   19                                                            
CONECT   21    2   12                                                       
CONECT   22    7   13                                                       
CONECT   23    8   15                                                       
CONECT   24    8   16                                                       
CONECT   25   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   60    0
END

View in JSmol

Synonyms

Value	Source
(+)-Dolineone	HMDB
6a,13a-Dihydro-1,3-dioxolo[6,7][1]benzopyrano[3,4-b]furo[3,2-g][1]benzopyran-13(6H)-one, 9ci	HMDB
Dolichone	HMDB

Chemical Formula

C₁₉H₁₂O₆

Average Mass

336.2950 Da

Monoisotopic Mass

336.06339 Da

IUPAC Name

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

dolineone

CAS Registry Number

10065-28-8

SMILES

O=C1C2C(COC3=CC4=C(OCO4)C=C23)OC2=C1C=C1C=COC1=C2

InChI Identifier

InChI=1S/C19H12O6/c20-19-11-3-9-1-2-21-12(9)5-14(11)25-17-7-22-13-6-16-15(23-8-24-16)4-10(13)18(17)19/h1-6,17-18H,7-8H2

InChI Key

RAJDDCCSNZAPCH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Neorautanenia mitis	Plant	KNApSAcK
Neorautanenia pseudopachyrrhiza	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
Ketone
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Rotenoid flavonoids (LMPK12060008 )

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	3.07	ALOGPS
logP	2.5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	10.43	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	67.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.51 m³·mol⁻¹	ChemAxon
Polarizability	33.57 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

HMDB0034039

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012281

KNApSAcK ID

C00009568

Chemspider ID

4475907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316959

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dolineone (NP0047825)

MOL for NP0047825 (Dolineone)

3D MOL for NP0047825 (Dolineone)

3D SDF for NP0047825 (Dolineone)

3D-SDF for NP0047825 (Dolineone)

PDB for NP0047825 (Dolineone)

3D PDB for NP0047825 (Dolineone)

SMILES for NP0047825 (Dolineone)

INCHI for NP0047825 (Dolineone)

Structure for NP0047825 (Dolineone)

3D Structure for NP0047825 (Dolineone)