NP-MRD: Showing NP-Card for (2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid (NP0211356)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 09:36:31 UTC

Updated at

2022-09-05 09:36:31 UTC

NP-MRD ID

NP0211356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid

Description

Valerenolic acid, also known as valerenolate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Valerenolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Valerenolic acid has been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and tea. (2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid is found in Valeriana officinalis. This could make valerenolic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    1.1731    2.0151   -1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1662    1.4493   -0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    0.2076   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4521   -0.9782   -0.4566 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7945   -0.6287    0.0735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018   -0.8006   -0.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720   -1.3644   -1.9489 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1619   -0.4168    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2356   -0.5742   -0.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2328    0.1157    1.2994 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1220   -2.0481    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0150   -1.3597    1.4594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2758   -0.9547    0.7227 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2849   -0.4749    1.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9049    0.1217   -0.2557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2040    1.5069    0.2778 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5399    1.8233    0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    2.3139   -0.7584 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1268    3.0984   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859    1.9002   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5846    1.5373   -2.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5251   -1.3673   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975   -0.2063    1.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9203   -1.6894   -2.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2696   -2.2937   -1.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5383   -0.5859   -2.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997    1.1122    1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7389   -2.7812   -0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -2.5557    0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5637   -0.4457    1.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -2.1037    2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7400   -1.7963    0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2332   -0.1593    1.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873   -1.3516    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8408    0.3082    2.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393    0.0282   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7275    1.6035    1.2741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7788    2.2401    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1714    3.3164   -0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    2.2382   -1.6938 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8 10  1  0
  8  9  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 13  1  0
 15  3  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
 13 32  1  6
 12 30  1  0
 12 31  1  0
 11 28  1  0
 11 29  1  0
  4 22  1  6
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
 10 27  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 39  1  0
 18 40  1  0
 16 37  1  1
 17 38  1  0
 15 36  1  6
M  END


  Mrv0541 05061309122D          

 18 19  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
    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
    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
    0.8838    0.0709    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
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  4  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211356

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-8-4-5-11(6-10(3)15(17)18)13-9(2)7-12(16)14(8)13/h6,8,11-12,14,16H,4-5,7H2,1-3H3,(H,17,18)/b10-6+

> <INCHI_KEY>
XJNQXTISSHEQKD-UXBLZVDNSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.897795828871295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.88

> <JCHEM_LOGP>
2.287617675000001

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.234472361271965

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.877750020411587

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9466425113911193

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
71.6415

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(1-hydroxy-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       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.924   9.003   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6   10   11                                                       
CONECT    7    9   12                                                       
CONECT    8    1    4   14                                                  
CONECT    9    2    7   13                                                  
CONECT   10    3    6   15                                                  
CONECT   11    5    6   13                                                  
CONECT   12    7   14   16                                                  
CONECT   13    9   11   14                                                  
CONECT   14    8   12   13                                                  
CONECT   15   10   17   18                                                  
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Valerenolate	Generator
Hydroxyvalerenic acid	HMDB
(2E)-3-(1-Hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylprop-2-enoate	Generator
Valerenolic acid	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3334 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

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

Traditional Name

(2E)-3-(1-hydroxy-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(O)C12

InChI Identifier

InChI=1S/C15H22O3/c1-8-4-5-11(6-10(3)15(17)18)13-9(2)7-12(16)14(8)13/h6,8,11-12,14,16H,4-5,7H2,1-3H3,(H,17,18)/b10-6+

InChI Key

XJNQXTISSHEQKD-UXBLZVDNSA-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
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.88	ALOGPS
logP	2.29	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-0.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.64 m³·mol⁻¹	ChemAxon
Polarizability	27.9 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

HMDB0036563

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015467

KNApSAcK ID

C00021291

Chemspider ID

4943985

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6439586

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid (NP0211356)

MOL for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

3D MOL for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

3D SDF for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

3D-SDF for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

PDB for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

3D PDB for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

SMILES for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

INCHI for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

Structure for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)

3D Structure for NP0211356 ((2e)-3-(1-hydroxy-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1h-inden-4-yl)-2-methylprop-2-enoic acid)