NP-MRD: Showing NP-Card for Erosnin (NP0045374)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:51 UTC

Updated at

2022-03-17 19:18:51 UTC

NP-MRD ID

NP0045374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erosnin

Description

Erosnin belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, erosnin is considered to be a flavonoid lipid molecule. Erosnin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, erosnin has been detected, but not quantified in, jicama and pulses. Erosnin is found in Pachyrrhizus erosus . This could make erosnin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 37  0  0  0  0  0  0  0  0999 V2000
   -0.2825   -3.0964    1.2282 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -2.0982    0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505   -2.1045    0.6215 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353   -1.0728    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7086   -1.1275    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4682   -0.0883   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751    0.0661   -0.6945 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0128    1.2523   -1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8074    1.9093   -1.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8092    1.0735   -0.8715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4273    1.1563   -0.7496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025    0.0900   -0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3305    0.1363   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545    1.0555   -0.3766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7773    0.6414   -0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0181    1.2730   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1593    0.6067    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0308   -0.6743    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8308   -1.3254    0.8156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818   -0.6423    0.4181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3412   -0.9674    0.3963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3074   -1.1513    1.0238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2127   -0.0915    0.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5218    0.9493    0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2406   -2.0328    0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9801    1.6718   -1.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6271    2.9114   -1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9173    2.0560   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0832    2.2909   -0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7157   -2.3323    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0752   -0.4590    0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5510    0.2038    1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 21  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 17  2  0
 17 24  1  0
 24 23  1  0
 23 22  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 21  2  1  0
 15 20  1  0
 12  4  1  0
 14 13  1  0
  7  6  1  0
 22 18  1  0
  5 25  1  0
  9 27  1  0
  8 26  1  0
 11 28  1  0
 19 30  1  0
 23 31  1  0
 23 32  1  0
 16 29  1  0
M  END


  Mrv0541 02241216252D          

 24 29  0  0  0  0            999 V2000
   -0.2824    1.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832    2.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832    3.1957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    3.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772    2.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064    0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205    1.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6064    0.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205   -0.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -0.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922   -1.4158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832   -1.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3631   -1.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818   -2.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8199   -3.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -3.4382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213   -2.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9818   -0.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 24  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 23  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OC2=CC3=C(C=CO3)C=C2C2=C1C1=CC3=C(OCO3)C=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C18H8O6/c19-18-16-9-4-14-15(22-7-21-14)6-12(9)23-17(16)10-3-8-1-2-20-11(8)5-13(10)24-18/h1-6H,7H2

> <INCHI_KEY>
YQXNKHVPEJJBTJ-UHFFFAOYSA-N

> <FORMULA>
C18H8O6

> <MOLECULAR_WEIGHT>
320.2525

> <EXACT_MASS>
320.032087988

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.94304579306551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,11,17,19,23-pentaoxahexacyclo[11.10.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁶,²⁰]tricosa-1(13),2,4(8),5,9,14,16(20),21-octaen-12-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.786808834

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.236473942834555

> <JCHEM_POLAR_SURFACE_AREA>
71.03999999999999

> <JCHEM_REFRACTIVITY>
80.26570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11,17,19,23-pentaoxahexacyclo[11.10.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁶,²⁰]tricosa-1(13),2,4(8),5,9,14,16(20),21-octaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.527   3.398   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.529   4.454   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.529   5.965   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.039   6.418   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.944   5.210   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.039   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.341   2.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.132   1.433   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.225   1.888   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.132   0.679   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.225  -0.528   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.132  -0.077   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.341  -1.133   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.039  -2.643   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.529  -3.095   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.678  -2.038   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.037  -2.491   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.340  -4.001   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.699  -4.757   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.397  -6.268   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.887  -6.418   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.282  -5.058   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.226  -4.605   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.699  -0.679   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    2    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12    8   11   13                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   11   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   18   21   23                                                  
CONECT   23   15   22                                                       
CONECT   24   13                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Value	Source
Erosinin	HMDB
Erosnine	HMDB

Chemical Formula

C₁₈H₈O₆

Average Mass

320.2525 Da

Monoisotopic Mass

320.03209 Da

IUPAC Name

7,11,17,19,23-pentaoxahexacyclo[11.10.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁶,²⁰]tricosa-1(13),2,4(8),5,9,14,16(20),21-octaen-12-one

Traditional Name

7,11,17,19,23-pentaoxahexacyclo[11.10.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁶,²⁰]tricosa-1(13),2,4(8),5,9,14,16(20),21-octaen-12-one

CAS Registry Number

Not Available

SMILES

O=C1OC2=CC3=C(C=CO3)C=C2C2=C1C1=CC3=C(OCO3)C=C1O2

InChI Identifier

InChI=1S/C18H8O6/c19-18-16-9-4-14-15(22-7-21-14)6-12(9)23-17(16)10-3-8-1-2-20-11(8)5-13(10)24-18/h1-6H,7H2

InChI Key

YQXNKHVPEJJBTJ-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
Pachyrhizus erosus	FooDB	KNAPSACK
Pachyrrhizus erosus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Linear furanocoumarin
Psoralen
Coumarin
1-benzopyran
Benzopyran
Benzodioxole
Benzofuran
Furopyran
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090021 )

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	3.01	ALOGPS
logP	2.79	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.04 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	80.27 m³·mol⁻¹	ChemAxon
Polarizability	31.94 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

HMDB0029465

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000586

KNApSAcK ID

C00009773

Chemspider ID

4476095

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317189

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Erosnin (NP0045374)

MOL for NP0045374 (Erosnin)

3D MOL for NP0045374 (Erosnin)

3D SDF for NP0045374 (Erosnin)

3D-SDF for NP0045374 (Erosnin)

PDB for NP0045374 (Erosnin)

3D PDB for NP0045374 (Erosnin)

SMILES for NP0045374 (Erosnin)

INCHI for NP0045374 (Erosnin)

Structure for NP0045374 (Erosnin)

3D Structure for NP0045374 (Erosnin)