NP-MRD: Showing NP-Card for (+)-nerolidol (NP0045076)

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Record Information

Version

2.0

Created at

2022-03-10 18:57:34 UTC

Updated at

2022-03-10 22:16:26 UTC

NP-MRD ID

NP0045076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-nerolidol

Description

Nerolidol also known as peruviol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Nerolidol is a naturally occurring sesquiterpene alcohol found in the essential oils of many types of plants and flowers. It is present in neroli, ginger, jasmine, lavender, tea tree, and lemon grass, and is a dominant scent compound in Brassavola nodosa. Nerolidol has also been reported as one of the volatile components detected in cannabis samples (PMID: 26657499 ). The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers (PMID: 27136520 ). Currently it is also under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs (https://Doi.Org/10.1016/S0939-6411(01)00166-7). Additionally, it is known for various biological activities include antioxidant, anti-fungal, anticancer, and antimicrobial activity (PMID: 27136520 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
   -2.6805    1.0259   -0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8476    0.1006    0.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8967   -1.3303    0.0331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3311   -1.6769   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1236   -1.5841   -1.0857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -2.1439    1.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790   -1.7736    1.5532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -2.1103    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4965   -1.2156   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2477   -1.7124   -1.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5972    0.1982    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0736    0.4571    0.3422 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.8356    0.7287 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    2.5641    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7892    2.0110   -1.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486    3.9569    0.3909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6447    2.0770   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5825    0.7435   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9441    0.3950    1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3747   -2.2951   -1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -2.1991    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8878   -0.7589   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6710   -1.8662   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0965   -1.9305    2.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4534   -3.2102    0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6859   -2.3971    2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0074   -0.7226    1.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -3.1743   -0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074   -2.4186   -1.1236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -0.8810   -2.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5301   -2.2347   -2.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0249    0.5764    0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3531    0.8447   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6013    0.2146   -0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3681   -0.2340    1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911    2.2399    1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909    1.1007   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9959    1.6997   -1.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3884    2.7860   -1.7548 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1231    4.1861    1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5063    4.2355    0.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    4.6208   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  2  3
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  3  1  0
  3  4  1  0
  3  5  1  6
  3  2  1  0
  2  1  2  3
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 13 36  1  0
 12 34  1  0
 12 35  1  0
 11 32  1  0
 11 33  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
  8 28  1  0
  7 26  1  0
  7 27  1  0
  6 24  1  0
  6 25  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  2 19  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv1652309272007292D          

 16 15  0  0  0  0            999 V2000
   -3.9618    1.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6763    0.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9618    1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2473    0.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329    1.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    0.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039    1.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039    1.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895    0.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895   -0.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7538   -0.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683   -0.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -0.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4521    0.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    0.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 11 14  1  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C/CC[C@](C)(O)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-/t15-/m1/s1

> <INCHI_KEY>
FQTLCLSUCSAZDY-QKXCFHHRSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.79242043868361

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6Z)-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>
74.0092

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -7.395   2.041   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.729   1.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.395   3.581   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.062   1.271   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.728   2.041   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.394   1.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.061   2.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.061   3.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.727   1.271   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.727  -0.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.606  -1.039   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.274  -1.039   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.607  -0.269   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.940  -0.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.711   1.064   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.169   1.064   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    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                                                       
CONECT   11   10   14                                                       
CONECT   12   13   14                                                       
CONECT   13   12                                                            
CONECT   14   15   16   11   12                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
(+)-cis-Nerolidol	HMDB
(+)-Nerolidol	HMDB
(6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
(Z)-(S)-(+)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
(Z)-Nerolidol	HMDB
3,7,11-Trimethyl-(3S,6Z)-(+)-1,6,10-dodecatrien-3-ol	HMDB
3,7,11-Trimethyl-(Z)-(S)-(+)-1,6,10-dodecatrien-3-ol	HMDB
D-Nerolidol	HMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	MeSH
Nerolidol, (Z)-isomer	MeSH
Nerolidol, (S-(Z))-isomer	MeSH
Nerolidol	MeSH
Nerolidol, (e)-isomer	MeSH
Nerolidol, (S-(e))-isomer	MeSH
Peruviol	MeSH
[S-(Z)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	PhytoBank
(3S,6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	PhytoBank
folic alcohol	PhytoBank
cis-(+)-Nerolidol	PhytoBank
(3S,6Z)-Nerolidol	PhytoBank
(±)-Nerolidol	PhytoBank
Nerodilol	PhytoBank

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3663 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

142-50-7

SMILES

CC(C)=CCC\C(C)=C/CC[C@](C)(O)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-/t15-/m1/s1

InChI Key

FQTLCLSUCSAZDY-QKXCFHHRSA-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, 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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Angelica gigas	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Cistus creticus	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hedychium coronarium	LOTUS Database	35616633
Lindera benzoin	LOTUS Database	35616633
Myrocarpus fastigiatus	LOTUS Database	35616633
Salvia dorisiana	LOTUS Database	35616633
Syzygiella tasmanica	LOTUS Database	35616633
Tanacetum longifolium	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

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

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	4.55	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	27.79 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

HMDB0035663

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006275

KNApSAcK ID

C00034757

Chemspider ID

4512192

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5356544

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chan WK, Tan LT, Chan KG, Lee LH, Goh BH: Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities. Molecules. 2016 Apr 28;21(5). pii: molecules21050529. doi: 10.3390/molecules21050529. [PubMed:27136520 ]

Showing NP-Card for (+)-nerolidol (NP0045076)

MOL for NP0045076 ((+)-nerolidol)

3D MOL for NP0045076 ((+)-nerolidol)

3D SDF for NP0045076 ((+)-nerolidol)

3D-SDF for NP0045076 ((+)-nerolidol)

PDB for NP0045076 ((+)-nerolidol)

3D PDB for NP0045076 ((+)-nerolidol)

SMILES for NP0045076 ((+)-nerolidol)

INCHI for NP0045076 ((+)-nerolidol)

Structure for NP0045076 ((+)-nerolidol)

3D Structure for NP0045076 ((+)-nerolidol)