NP-MRD: Showing NP-Card for (3s)-3,7-dimethyloct-6-enoic acid (NP0264301)

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Record Information

Version

2.0

Created at

2022-09-08 07:46:41 UTC

Updated at

2022-09-08 07:46:41 UTC

NP-MRD ID

NP0264301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3,7-dimethyloct-6-enoic acid

Description

(S)-citronellic acid, also known as (S)-citronellate, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. (3s)-3,7-dimethyloct-6-enoic acid is found in Chamaecyparis obtusa. (3s)-3,7-dimethyloct-6-enoic acid was first documented in 2013 (PMID: 24130034). Based on a literature review very few articles have been published on (S)-citronellic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
    3.6788   -1.3598    0.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514   -0.5574    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2420    0.4882    1.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208   -0.7005   -0.7942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2934    0.1414   -0.8142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9542   -0.7252   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2060    0.1745   -0.7222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2126    0.9313   -2.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    1.0464    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2047    0.2311    1.7417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925   -0.6624    1.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573    0.4107    2.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464   -1.9878    1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5485   -0.6763    0.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8407   -2.0161   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421    0.4610    1.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2895    0.3549    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2811    1.5076    0.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6460   -1.4388   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2779    0.7028   -1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3513    0.8501    0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0467   -1.3789   -1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809   -1.2814    0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0672   -0.5425   -0.7107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550    0.4353   -2.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579    1.9777   -1.8290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2374    0.9753   -2.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1294    1.6710    0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615    1.7466    0.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7429   -0.4304    3.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  7  9  1  0
  9 10  1  0
 10 12  1  0
 10 11  2  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  7 24  1  1
  6 22  1  0
  6 23  1  0
  5 20  1  0
  5 21  1  0
  4 19  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  9 28  1  0
  9 29  1  0
 12 30  1  0
M  END

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   5.747   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol

Synonyms

Value	Source
(-)-Citronellic acid	ChEBI
(3S)-3,7-Dimethyl-6-octenoic acid	ChEBI
(S)-(-)-3,7-Dimethyl-6-octenoic acid	ChEBI
(S)-(-)-Citronellic acid	ChEBI
(S)-3,7-Dimethyl-6-octenoic acid	ChEBI
(-)-Citronellate	Generator
(3S)-3,7-Dimethyl-6-octenoate	Generator
(S)-(-)-3,7-Dimethyl-6-octenoate	Generator
(S)-(-)-Citronellate	Generator
(S)-3,7-Dimethyl-6-octenoate	Generator
(S)-Citronellate	Generator

Chemical Formula

C₁₀H₁₈O₂

Average Mass

170.2520 Da

Monoisotopic Mass

170.13068 Da

IUPAC Name

(3S)-3,7-dimethyloct-6-enoic acid

Traditional Name

(3S)-3,7-dimethyloct-6-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC=C(C)C)CC(O)=O

InChI Identifier

InChI=1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)/t9-/m0/s1

InChI Key

GJWSUKYXUMVMGX-VIFPVBQESA-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
Chamaecyparis obtusa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.87	ChemAxon
pKa (Strongest Acidic)	5.19	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	5	ChemAxon
Refractivity	50.22 m³·mol⁻¹	ChemAxon
Polarizability	20.11 Å³	ChemAxon
Number of Rings	0	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

C00010311

Chemspider ID

5367467

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6999955

PDB ID

Not Available

ChEBI ID

144575

Good Scents ID

Not Available

References

General References

Moreno Rueda MG, Guerrini A, Giovannini PP, Medici A, Grandini A, Sacchetti G, Pedrini P: Biotransformations of terpenes by fungi from Amazonian citrus plants. Chem Biodivers. 2013 Oct;10(10):1909-19. doi: 10.1002/cbdv.201300112. [PubMed:24130034 ]
LOTUS database [Link]

Showing NP-Card for (3s)-3,7-dimethyloct-6-enoic acid (NP0264301)

MOL for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

3D MOL for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

3D SDF for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

3D-SDF for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

PDB for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

3D PDB for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

SMILES for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

INCHI for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

Structure for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)

3D Structure for NP0264301 ((3s)-3,7-dimethyloct-6-enoic acid)