NP-MRD: Showing NP-Card for Acetoxyvalerenic acid (NP0137451)

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Record Information

Version

2.0

Created at

2022-05-30 16:52:51 UTC

Updated at

2022-05-30 16:52:51 UTC

NP-MRD ID

NP0137451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetoxyvalerenic acid

Description

Acetylvalerenolic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Acetylvalerenolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Acetylvalerenolic acid is an odorless tasting compound. Outside of the human body, Acetylvalerenolic acid has been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and tea. Acetoxyvalerenic acid is found in Valeriana officinalis. This could make acetylvalerenolic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
    4.6768   -0.0273    2.6534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9734   -0.0172    1.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5994   -0.4499    0.3423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    0.4487    1.2270 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0785    0.4208   -0.0671 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7184    1.7773   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3251    1.6836   -0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4012    2.8051   -1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2132    0.5075   -0.7220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6088   -0.0660   -0.9688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5374    0.7587   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3730    0.4536    0.6826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463   -0.9143    1.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2572    1.5070    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0280    1.1537    2.1682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2436    2.8126    0.8421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790   -1.5111   -0.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2392   -1.9235   -1.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -1.5896   -0.9151 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5116   -2.7469   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8008   -0.3496   -0.0566 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2934    0.8947    2.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9741   -0.1602    3.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3457   -0.9097    2.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8085   -0.0017   -0.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4002    2.1429   -1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8004    2.4725    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3322    3.3620   -2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597    2.4181   -2.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614    3.4532   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6784    0.0675   -2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006    1.8452   -0.5524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3951   -0.9343    1.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455   -1.7051    0.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6789   -1.1534    1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5016    3.0024   -0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2629   -2.1237   -1.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -1.8416    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623   -1.3619   -2.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2844   -3.0128   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -1.3539   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -2.4863    0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655   -3.5257   -0.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832   -3.1875    0.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -0.6338    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 16  1  0
 14 15  2  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 21  1  0
 21 19  1  0
 21  9  1  0
 20 42  1  0
 20 43  1  0
 20 44  1  0
 19 41  1  6
 18 39  1  0
 18 40  1  0
 17 37  1  0
 17 38  1  0
 10 31  1  6
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  6 26  1  0
  6 27  1  0
  5 25  1  6
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 45  1  1
M  END


  Mrv0541 05061308382D          

 21 22  0  0  0  0            999 V2000
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  1  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  2  0  0  0  0
 19 17  2  0  0  0  0
 20 17  1  0  0  0  0
 21 12  1  0  0  0  0
 21 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(OC(C)=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-9-5-6-13(7-11(3)17(19)20)15-10(2)8-14(16(9)15)21-12(4)18/h7,9,13-14,16H,5-6,8H2,1-4H3,(H,19,20)/b11-7+

> <INCHI_KEY>
VBBXZFLAYWAXSK-YRNVUSSQSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.14657298619919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[1-(acetyloxy)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.728743085333333

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.550861492932636

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004607469535601

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
80.793

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[1-(acetyloxy)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

> <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       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.332  -1.653   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.887   0.956   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.924   9.003   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    9                                                       
CONECT    6    5   13                                                       
CONECT    7   11   13                                                       
CONECT    8   10   14                                                       
CONECT    9    1    5   16                                                  
CONECT   10    2    8   15                                                  
CONECT   11    3    7   17                                                  
CONECT   12    4   18   21                                                  
CONECT   13    6    7   15                                                  
CONECT   14    8   16   21                                                  
CONECT   15   10   13   16                                                  
CONECT   16    9   14   15                                                  
CONECT   17   11   19   20                                                  
CONECT   18   12                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Acetylvalerenolate	Generator
Acetoxyvalerenic acid	HMDB
(2E)-3-[1-(Acetyloxy)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoate	Generator
Acetylvalerenolic acid	MeSH

Chemical Formula

C₁₇H₂₄O₄

Average Mass

292.3701 Da

Monoisotopic Mass

292.16746 Da

IUPAC Name

(2E)-3-[1-(acetyloxy)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

Traditional Name

(2E)-3-[1-(acetyloxy)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC1CCC(\C=C(/C)C(O)=O)C2=C(C)CC(OC(C)=O)C12

InChI Identifier

InChI=1S/C17H24O4/c1-9-5-6-13(7-11(3)17(19)20)15-10(2)8-14(16(9)15)21-12(4)18/h7,9,13-14,16H,5-6,8H2,1-4H3,(H,19,20)/b11-7+

InChI Key

VBBXZFLAYWAXSK-YRNVUSSQSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.27	ALOGPS
logP	2.73	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.79 m³·mol⁻¹	ChemAxon
Polarizability	32.15 Å³	ChemAxon
Number of Rings	2	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

HMDB0035687

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014404

KNApSAcK ID

C00021292

Chemspider ID

4943984

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439585

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Acetoxyvalerenic acid (NP0137451)

MOL for NP0137451 (Acetoxyvalerenic acid)

3D MOL for NP0137451 (Acetoxyvalerenic acid)

3D SDF for NP0137451 (Acetoxyvalerenic acid)

3D-SDF for NP0137451 (Acetoxyvalerenic acid)

PDB for NP0137451 (Acetoxyvalerenic acid)

3D PDB for NP0137451 (Acetoxyvalerenic acid)

SMILES for NP0137451 (Acetoxyvalerenic acid)

INCHI for NP0137451 (Acetoxyvalerenic acid)

Structure for NP0137451 (Acetoxyvalerenic acid)

3D Structure for NP0137451 (Acetoxyvalerenic acid)