NP-MRD: Showing NP-Card for Hulupinic acid (NP0084106)

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Record Information

Version

2.0

Created at

2022-04-29 04:56:34 UTC

Updated at

2022-04-29 04:56:35 UTC

NP-MRD ID

NP0084106

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hulupinic acid

Description

Hulupinic acid, also known as hulupinate, belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. Hulupinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Hulupinic acid has been detected, but not quantified in, alcoholic beverages. Hulupinic acid is found in Humulus lupulus . This could make hulupinic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -3.8425    0.0499   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -1.2290   -0.2515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273   -2.4995   -0.8758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0836   -1.2025    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180    0.0394    1.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239    0.4459    0.8431 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8452   -0.4907    1.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    0.0344    0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0306   -0.5810    0.0889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6499   -1.8783   -0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471    0.0107   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0665    1.8035    1.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1905    2.1931    2.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    2.5996    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    3.8508    0.4960 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592    1.9386   -0.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0218    2.3545   -2.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319    0.6851   -0.6187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -0.1020   -1.4737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6529   -0.1300   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.7917   -1.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3088    0.4488    0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9314   -2.3290   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5185   -2.7907   -0.2928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -3.2253   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5802   -2.1250    0.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6766   -0.0830    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438    0.8496    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8536   -0.5568    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -1.5110    0.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4718    0.9854    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.8655   -0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3127   -2.0789   -1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7975   -2.7153    0.2055 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    0.0211   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1723   -0.6074    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4088    1.0699    0.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954    4.5198    1.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873    3.3091   -2.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  6  5  1  6
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 18  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061305002D          

 19 19  0  0  0  0            999 V2000
   -2.1503    1.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0883    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619    3.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2239    2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912    1.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433    2.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169    3.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  5  2  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  6  2  0  0  0  0
 12 11  2  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0084106

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-9(2)5-7-15(8-6-10(3)4)13(18)11(16)12(17)14(15)19/h5-6,16-17H,7-8H2,1-4H3

> <INCHI_KEY>
KKNXLCGOZLVUHL-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.665253335352816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dihydroxy-2,2-bis(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
3.2258873120000002

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.550137670039021

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.323060571417498

> <JCHEM_PKA_STRONGEST_BASIC>
-4.393482785958573

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
76.82309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-2,2-bis(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

> <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      -4.014   3.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.031   5.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.169   7.298   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.151   5.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.477   2.904   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.507   4.049   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.645   5.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    7    9                                                       
CONECT    6    8   10                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9    1    2    5                                                  
CONECT   10    3    4    6                                                  
CONECT   11   12   13   16                                                  
CONECT   12   11   14   17                                                  
CONECT   13   11   15   18                                                  
CONECT   14   12   15   19                                                  
CONECT   15    7    8   13   14                                             
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
Hulupinate	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

4,5-dihydroxy-2,2-bis(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

Traditional Name

4,5-dihydroxy-2,2-bis(3-methylbut-2-en-1-yl)cyclopent-4-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1(CC=C(C)C)C(=O)C(O)=C(O)C1=O

InChI Identifier

InChI=1S/C15H20O4/c1-9(2)5-7-15(8-6-10(3)4)13(18)11(16)12(17)14(15)19/h5-6,16-17H,7-8H2,1-4H3

InChI Key

KKNXLCGOZLVUHL-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
Humulus lupulus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous acids

Sub Class

Not Available

Direct Parent

Vinylogous acids

Alternative Parents

Substituents

Vinylogous acid
Cyclic ketone
Ketone
Enediol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	1.6	ALOGPS
logP	3.23	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.82 m³·mol⁻¹	ChemAxon
Polarizability	28.67 Å³	ChemAxon
Number of Rings	1	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

HMDB0030102

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001900

KNApSAcK ID

Not Available

Chemspider ID

10182038

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12310637

PDB ID

Not Available

ChEBI ID

581942

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hulupinic acid (NP0084106)

MOL for NP0084106 (Hulupinic acid)

3D MOL for NP0084106 (Hulupinic acid)

3D SDF for NP0084106 (Hulupinic acid)

3D-SDF for NP0084106 (Hulupinic acid)

PDB for NP0084106 (Hulupinic acid)

3D PDB for NP0084106 (Hulupinic acid)

SMILES for NP0084106 (Hulupinic acid)

INCHI for NP0084106 (Hulupinic acid)

Structure for NP0084106 (Hulupinic acid)

3D Structure for NP0084106 (Hulupinic acid)