NP-MRD: Showing NP-Card for Valerenic acid (NP0051830)

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Record Information

Version

2.0

Created at

2022-04-27 23:02:54 UTC

Updated at

2025-02-11 15:46:58 UTC

NP-MRD ID

NP0051830

Natural Product DOI

https://doi.org/10.57994/0494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Valerenic acid

Description

SCHEMBL23164072 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Valerenic acid is found in Nardostachys jatamansi, Valeriana hardwickii and Valeriana officinalis . Based on a literature review very few articles have been published on SCHEMBL23164072.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    0.5193    2.3655    1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5314    1.6873    0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4924    0.4757    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373   -0.6210    0.1993 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7929   -0.2714    0.7397 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9588   -0.1967    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1399    0.2209    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.3763   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5091   -0.2926   -1.4803 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4416   -0.6274   -2.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2589   -1.5350   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -2.2468   -0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1927   -1.2444   -0.4180 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0121   -1.4967    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501    0.1841   -0.5121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7272    1.1101    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8502    2.3481    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364    1.9935    2.4892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3385    3.4563    1.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987    2.1975    0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596   -1.2556    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270    0.0106    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7231    1.0504    1.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3160   -0.6740    1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907    0.5242    0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    0.0706   -2.8121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9234   -2.3883   -1.0608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0424   -0.9717   -1.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9859   -2.8442    0.3494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2306   -2.9500   -1.4194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9238   -1.4108   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794   -1.1671    1.7571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2280   -2.5912    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9799   -0.9745    0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    0.5337   -1.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9494    0.7459    1.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    1.3223   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918    2.9394   -0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2088    2.8995    1.2320 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 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 15  3  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 13 31  1  6
 12 29  1  0
 12 30  1  0
 11 27  1  0
 11 28  1  0
  4 21  1  1
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
 10 26  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 17 38  1  0
 17 39  1  0
 16 36  1  0
 16 37  1  0
 15 35  1  6
M  END


  Mrv1652304282201022D          

 17 18  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    2.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  3  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  1  0  0  0
  7 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051830

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H](\C=C(\C)C(O)=O)C2=C(C)CC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8-/t9-,12+,13-/m1/s1

> <INCHI_KEY>
FEBNTWHYQKGEIQ-JWRGBUJQSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.755402907209863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
3.5963824719999993

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.055677709266172

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.04899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valerenic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   1.777   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   2.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864   4.087   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.531   2.547   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
CONECT    1    2    5   10                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1                                                       
CONECT    6    3                                                            
CONECT    7    2    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3390 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

(2Z)-3-[(4S,7R,7aR)-3,7-dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl]-2-methylprop-2-enoic acid

Traditional Name

valerenic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H](\C=C(\C)C(O)=O)C2=C(C)CC[C@H]12

InChI Identifier

InChI=1S/C15H22O2/c1-9-4-6-12(8-11(3)15(16)17)14-10(2)5-7-13(9)14/h8-9,12-13H,4-7H2,1-3H3,(H,16,17)/b11-8-/t9-,12+,13-/m1/s1

InChI Key

FEBNTWHYQKGEIQ-JWRGBUJQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 300 MHz, CDCl3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, CDCl3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 300 MHz, CDCl3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)	john.cort@pnnl.gov	Not Available	Not Available	2023-03-02	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 300.13, CDCl₃, simulated)	john.cort@pnnl.gov	Not Available	Not Available	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Nardostachys jatamansi	LOTUS Database	35616633
Valeriana hardwickii	Plant	KNApSAcK
Valeriana officinalis	Plant	KNApSAcK

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
Monocarboxylic acid or derivatives
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

Valerenane sesquiterpenoids (C09743 )
Sesquiterpenoids (C15) (C09743 )

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	4.15	ALOGPS
logP	3.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	5.06	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.05 m³·mol⁻¹	ChemAxon
Polarizability	26.76 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444870

KEGG Compound ID

C09743

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281538

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Valerenic acid (NP0051830)

MOL for NP0051830 (Valerenic acid)

3D MOL for NP0051830 (Valerenic acid)

3D SDF for NP0051830 (Valerenic acid)

3D-SDF for NP0051830 (Valerenic acid)

PDB for NP0051830 (Valerenic acid)

3D PDB for NP0051830 (Valerenic acid)

SMILES for NP0051830 (Valerenic acid)

INCHI for NP0051830 (Valerenic acid)

Structure for NP0051830 (Valerenic acid)

3D Structure for NP0051830 (Valerenic acid)