NP-MRD: Showing NP-Card for Neodunol (NP0047725)

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Record Information

Version

2.0

Created at

2022-03-17 20:44:55 UTC

Updated at

2022-03-17 20:44:55 UTC

NP-MRD ID

NP0047725

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neodunol

Description

Neodunol belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, neodunol is considered to be a flavonoid lipid molecule. Neodunol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, neodunol has been detected, but not quantified in, jicama and pulses. Neodunol is found in Calopogonium mucunoides, Neorautanenia amboensis, Neorautanenia edulis and Pachyrrhizus erosus . This could make neodunol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061307202D          

 21 25  0  0  0  0            999 V2000
    0.4790   -1.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1617   -1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0081   -2.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6907   -2.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445   -2.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -2.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1044   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9482   -0.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3565   -2.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5389   -2.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0124   -1.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682   -1.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6365   -1.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924   -0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9641   -2.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2003   -1.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -2.8997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4611   -1.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7603   -0.2771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651   -2.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  1  1  0  0  0  0
 10  6  2  0  0  0  0
 11  2  1  0  0  0  0
 12  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16  6  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 19  4  1  0  0  0  0
 19 14  1  0  0  0  0
 20  8  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047725

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1COC3=C(C=C4C=COC4=C3)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O4/c18-10-1-2-11-13-8-20-15-7-14-9(3-4-19-14)5-12(15)17(13)21-16(11)6-10/h1-7,13,17-18H,8H2

> <INCHI_KEY>
UUDOMPYHVUEXEE-UHFFFAOYSA-N

> <FORMULA>
C17H12O4

> <MOLECULAR_WEIGHT>
280.2748

> <EXACT_MASS>
280.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.989906572147618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,5,8,14(19),15,17-heptaen-17-ol

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
2.826018062666666

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552920891998637

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9768808953323282

> <JCHEM_POLAR_SURFACE_AREA>
51.83000000000001

> <JCHEM_REFRACTIVITY>
75.43900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,5,8,14(19),15,17-heptaen-17-ol

> <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       0.894  -3.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.169  -2.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.215  -4.993   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.489  -4.128   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.483  -4.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.392  -5.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.528  -1.422   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.503  -0.789   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.999  -4.048   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.006  -4.548   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.555  -2.818   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.490  -3.143   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.981  -2.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.521  -2.599   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.012  -1.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.666  -4.354   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.974  -3.414   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.268  -5.413   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.061  -2.649   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.019  -0.517   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.162  -4.723   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1   11                                                       
CONECT    3    4    9                                                       
CONECT    4    3   19                                                       
CONECT    5    9   12                                                       
CONECT    6   10   16                                                       
CONECT    7   14   15                                                       
CONECT    8   13   20                                                       
CONECT    9    3    5   14                                                  
CONECT   10    1    6   18                                                  
CONECT   11    2   13   16                                                  
CONECT   12    5   15   17                                                  
CONECT   13    8   11   17                                                  
CONECT   14    7    9   19                                                  
CONECT   15    7   12   20                                                  
CONECT   16    6   11   21                                                  
CONECT   17   12   13   21                                                  
CONECT   18   10                                                            
CONECT   19    4   14                                                       
CONECT   20    8   15                                                       
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Value	Source
6a,11a-Dihydro-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-9-ol, 9ci	HMDB

Chemical Formula

C₁₇H₁₂O₄

Average Mass

280.2748 Da

Monoisotopic Mass

280.07356 Da

IUPAC Name

7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,5,8,14(19),15,17-heptaen-17-ol

Traditional Name

7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,5,8,14(19),15,17-heptaen-17-ol

CAS Registry Number

53766-53-3

SMILES

OC1=CC2=C(C=C1)C1COC3=C(C=C4C=COC4=C3)C1O2

InChI Identifier

InChI=1S/C17H12O4/c18-10-1-2-11-13-8-20-15-7-14-9(3-4-19-14)5-12(15)17(13)21-16(11)6-10/h1-7,13,17-18H,8H2

InChI Key

UUDOMPYHVUEXEE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Calopogonium mucunoides	LOTUS Database	35616633
Neorautanenia amboensis	Plant	KNApSAcK
Neorautanenia edulis	Plant	KNApSAcK
Pachyrhizus erosus	FooDB	KNAPSACK
Pachyrrhizus erosus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070007 )

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	3.57	ALOGPS
logP	2.83	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.44 m³·mol⁻¹	ChemAxon
Polarizability	28.99 Å³	ChemAxon
Number of Rings	5	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

HMDB0033743

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011873

KNApSAcK ID

C00009637

Chemspider ID

24842981

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Neodunol (NP0047725)

MOL for NP0047725 (Neodunol)

3D MOL for NP0047725 (Neodunol)

3D SDF for NP0047725 (Neodunol)

3D-SDF for NP0047725 (Neodunol)

PDB for NP0047725 (Neodunol)

3D PDB for NP0047725 (Neodunol)

SMILES for NP0047725 (Neodunol)

INCHI for NP0047725 (Neodunol)

Structure for NP0047725 (Neodunol)

3D Structure for NP0047725 (Neodunol)