NP-MRD: Showing NP-Card for 4,5-Dihydroniveusin A (NP0047476)

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Record Information

Version

2.0

Created at

2022-03-17 20:40:50 UTC

Updated at

2022-03-17 20:40:50 UTC

NP-MRD ID

NP0047476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-Dihydroniveusin A

Description

4,5-Dihydroniveusin A belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 4,5-Dihydroniveusin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4,5-dihydroniveusin a has been detected, but not quantified in, fats and oils and sunflowers. This could make 4,5-dihydroniveusin a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306452D          

 28 30  0  0  0  0            999 V2000
    4.5580    3.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664    5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    2.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    3.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224    4.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677    0.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830    2.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830   -0.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    4.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830    0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    3.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5221    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    0.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -1.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0711    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966    3.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3471    1.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    0.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    3.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284    1.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  2  0  0  0  0
 11  3  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19  4  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  1  0  0  0  0
 20  8  1  0  0  0  0
 20 12  1  0  0  0  0
 21  9  1  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26 13  1  0  0  0  0
 26 18  1  0  0  0  0
 27 14  1  0  0  0  0
 27 17  1  0  0  0  0
 28 19  1  0  0  0  0
 28 20  1  0  0  0  0
M  END


  Mrv0541 05061306452D          

 28 30  0  0  0  0            999 V2000
    4.5580    3.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0664    5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    2.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    3.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224    4.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677    0.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830    2.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830   -0.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020    4.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9830    0.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    0.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135    1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9170    3.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5221    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1984    0.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6975   -1.1778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0711    2.0620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966    3.9818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3471    1.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7135   -0.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    0.7271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    3.1419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9284    1.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  2  0  0  0  0
 11  3  2  0  0  0  0
 12  6  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19  4  1  0  0  0  0
 19  7  1  0  0  0  0
 19 15  1  0  0  0  0
 20  8  1  0  0  0  0
 20 12  1  0  0  0  0
 21  9  1  0  0  0  0
 22 15  1  0  0  0  0
 23 17  2  0  0  0  0
 24 18  2  0  0  0  0
 25 20  1  0  0  0  0
 26 13  1  0  0  0  0
 26 18  1  0  0  0  0
 27 14  1  0  0  0  0
 27 17  1  0  0  0  0
 28 19  1  0  0  0  0
 28 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OC1CC2(C)OC(O)(CC2O)C(CO)CC2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O8/c1-5-10(2)17(23)27-14-7-19(4)15(22)8-20(25,28-19)12(9-21)6-13-16(14)11(3)18(24)26-13/h5,12-16,21-22,25H,3,6-9H2,1-2,4H3/b10-5-

> <INCHI_KEY>
SNUZCOSRHAIVKC-YHYXMXQVSA-N

> <FORMULA>
C20H28O8

> <MOLECULAR_WEIGHT>
396.4315

> <EXACT_MASS>
396.178417872

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.36398269824217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradecan-9-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
1.309188927

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.921957127976913

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.66907037319674

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6685916263733347

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
97.59349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradecan-9-yl (2Z)-2-methylbut-2-enoate

> <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       8.508   6.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.724   9.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.012   5.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.332   5.865   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.882   8.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.166   0.587   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.702   5.095   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.332   1.833   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.702  -1.429   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.350   8.518   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.536   3.849   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.702   0.111   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.072   1.833   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.166   4.619   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.332   3.373   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.072   3.373   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.445   7.272   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.441   2.603   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.237   4.619   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.237   0.587   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.035  -2.199   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.133   3.849   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.914   7.433   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       9.981   2.603   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.332  -0.659   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.536   1.357   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.072   5.865   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.733   2.603   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   19                                                            
CONECT    5    1   10                                                       
CONECT    6   12   13                                                       
CONECT    7   14   19                                                       
CONECT    8   15   20                                                       
CONECT    9   12   21                                                       
CONECT   10    2    5   17                                                  
CONECT   11    3   16   18                                                  
CONECT   12    6    9   20                                                  
CONECT   13    6   16   26                                                  
CONECT   14    7   16   27                                                  
CONECT   15    8   19   22                                                  
CONECT   16   11   13   14                                                  
CONECT   17   10   23   27                                                  
CONECT   18   11   24   26                                                  
CONECT   19    4    7   15   28                                             
CONECT   20    8   12   25   28                                             
CONECT   21    9                                                            
CONECT   22   15                                                            
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   20                                                            
CONECT   26   13   18                                                       
CONECT   27   14   17                                                       
CONECT   28   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
1,12-Dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradecan-9-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₈O₈

Average Mass

396.4315 Da

Monoisotopic Mass

396.17842 Da

IUPAC Name

1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradecan-9-yl (2Z)-2-methylbut-2-enoate

Traditional Name

1,12-dihydroxy-2-(hydroxymethyl)-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradecan-9-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

98204-96-7

SMILES

C\C=C(\C)C(=O)OC1CC2(C)OC(O)(CC2O)C(CO)CC2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H28O8/c1-5-10(2)17(23)27-14-7-19(4)15(22)8-20(25,28-19)12(9-21)6-13-16(14)11(3)18(24)26-13/h5,12-16,21-22,25H,3,6-9H2,1-2,4H3/b10-5-

InChI Key

SNUZCOSRHAIVKC-YHYXMXQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.38	ALOGPS
logP	1.31	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.59 m³·mol⁻¹	ChemAxon
Polarizability	40.36 Å³	ChemAxon
Number of Rings	3	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

HMDB0032844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010821

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751333

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4,5-Dihydroniveusin A (NP0047476)

MOL for NP0047476 (4,5-Dihydroniveusin A)

3D MOL for NP0047476 (4,5-Dihydroniveusin A)

3D SDF for NP0047476 (4,5-Dihydroniveusin A)

3D-SDF for NP0047476 (4,5-Dihydroniveusin A)

PDB for NP0047476 (4,5-Dihydroniveusin A)

3D PDB for NP0047476 (4,5-Dihydroniveusin A)

SMILES for NP0047476 (4,5-Dihydroniveusin A)

INCHI for NP0047476 (4,5-Dihydroniveusin A)

Structure for NP0047476 (4,5-Dihydroniveusin A)

3D Structure for NP0047476 (4,5-Dihydroniveusin A)