MiMeDB: Showing metabocard for Nerolidol (MMDBc0047731)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:40:04 UTC

Update Date

2022-12-15 22:52:16 UTC

Metabolite ID

MMDBc0047731

Metabolite Identification

Common Name

Nerolidol

Description

Nerolidol is found in bitter gourd. Nerolidol is a component of many essential oils. The (S)-enantiomer is the commoner and occurs mostly as the (S)-(E)-isomer. Nerolidol is a flavouring agent. Nerolidol has been shown to exhibit anti-fungal function (PMID 17202684 ). Nerolidol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units.

Structure

MOL SDF PDB SMILES InChI


  Mrv1572004161622512D          

 17 16  0  0  0  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13  9  2  0  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047731

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCC(C)(O)C=C)=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+

> <INCHI_KEY>
FQTLCLSUCSAZDY-SDNWHVSQSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.721938535450253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol

> <ALOGPS_LOGP>
4.55

> <JCHEM_LOGP>
4.307206727666666

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.459388332120984

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2856635435302817

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
74.00919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nerolidol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-16         0                                  
HETATM    1  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.954   1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.390   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6    1   15                                                       
CONECT    7    9   10                                                       
CONECT    8   11   12                                                       
CONECT    9    7   13                                                       
CONECT   10    7   14                                                       
CONECT   11    8   14   17                                                  
CONECT   12    8   15                                                       
CONECT   13    2    3    9                                                  
CONECT   14    4   10   11                                                  
CONECT   15    5    6   12   16                                             
CONECT   16   15                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

Synonyms

Value	Source
trans-Nerolidol	ChEMBL
Nerolidol, (S-(e))-isomer	MeSH
Nerolidol, (Z)-isomer	MeSH
Nerolidol, (e)-isomer	MeSH
Nerolidol, (S-(Z))-isomer	MeSH
Peruviol	MeSH
Nerolidol	MeSH
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	MeSH

Molecular Formula

C₁₅H₂₆O

Average Mass

222.372

Monoisotopic Mass

222.198365457

IUPAC Name

(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol

Traditional Name

nerolidol

CAS Registry Number

Not Available

SMILES

[H]\C(CCC(C)(O)C=C)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+

InChI Key

FQTLCLSUCSAZDY-SDNWHVSQSA-N

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

Farsesane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.55	ALOGPS
logP	4.31	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.46	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.01 m³·mol⁻¹	ChemAxon
Polarizability	28.72 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9610000000-aac55e5ccd9b7c6e5bcd	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0490000000-161e693347ad291e0fbd	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avr-8930000000-9d44e8ed0962b3b4a6e5	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gc0-9200000000-e773e83c3d163f0457dd	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-ccfe5910ac69a0881b78	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fk9-0290000000-472fb15ead3e188bca2a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0q29-8920000000-480ab5d82bb26f770cf2	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016854	Farnesyl pyrophosphate	Nerolidol	R-linalool synthase	Synthesis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown
Bacteria	Actinobacteria	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nerolidol

METLIN ID

Not Available

PubChem Compound

5284507

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for Nerolidol (MMDBc0047731)

MOL for #<Metabolite:0x0000564af1dd8e10>

3D MOL for #<Metabolite:0x0000564af1dd8e10>

3D SDF for #<Metabolite:0x0000564af1dd8e10>

3D-SDF for #<Metabolite:0x0000564af1dd8e10>

PDB for #<Metabolite:0x0000564af1dd8e10>

3D PDB for #<Metabolite:0x0000564af1dd8e10>

SMILES for #<Metabolite:0x0000564af1dd8e10>

INCHI for #<Metabolite:0x0000564af1dd8e10>

Structure for #<Metabolite:0x0000564af1dd8e10>

3D Structure for #<Metabolite:0x0000564af1dd8e10>