NP-MRD: Showing NP-Card for nerolidol (NP0277070)

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Record Information

Version

2.0

Created at

2022-09-09 01:31:32 UTC

Updated at

2025-02-11 15:47:19 UTC

NP-MRD ID

NP0277070

Natural Product DOI

https://doi.org/10.57994/2610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nerolidol

Description

Nerolidol, also known as (+/-)-nerolidol or humbertiol?, Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Additionally, it is known for various biological activities include antioxidant, anti fungal, anticancer, and antimicrobial activity. Nerolidyl compounds involve joining nerolidol at the oxygen atom to other groups, and include Nerolidyl diphosphate. Nerolidol is an extremely weak basic (essentially neutral) compound (based on its pKa). Because of its hydrophobic nature, nerolidol is easily permeable across the plasma membrane and can interact with intracellular proteins. Nerolidol is a citrus, floral, and green tasting compound. Outside of the human body, Nerolidol is found, on average, in the highest concentration within a few different foods, such as tea, cardamoms, and common thymes and in a lower concentration in orange mints, star anises, and sweet basils. Nerolidol has also been detected, but not quantified in, several different foods, such as tarragons, lindens, roman camomiles, sweet oranges, and bitter gourds. This could make nerolidol a potential biomarker for the consumption of these foods. There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. Petraea flower in response to insect feeding. It is one of several organic volatiles produced by the A. Lyrata ssp. Nerolidol is a potentially toxic compound. nerolidol is found in Abies nephrolepis, Abies sachalinensis, Abies sibirica, Achillea abrotanoides, Achillea millefolium, Achillea moschata, Acokanthera oblongifolia, Aframomum sceptrum, Ageratum conyzoides, Aloysia citrodora, Aloysia triphylla, Alpinia chinensis, Alpinia latilabris, Alpinia zerumbet, Arctotis aspera, Aristolochia triangularis, Artemisia dolosa, Artemisia dracunculus, Artemisia judaica, Artemisia ludoviciana, Artemisia schmidtiana, Artemisia thuscula, Artemisia tridentata, Artemisia xanthochroa, Asarum asperum, Atalantia buxifolia, Athamanta macedonica, Austromyrtus dulcis, Betonica macrantha, Blepharocalyx salicifolius, Bupleurum gibraltaricum, Callitropsis nootkatensis, Camellia sinensis, Canella winterana, Cannabis sativa, Cassinia subtropica, Castanopsis cuspidata, Cedrela odorata, Centella asiatica, Cineraria parvifolia, Cinnamomum camphora, Cinnamomum sieboldii, Citrus aurantium, Citrus iyo, Citrus paradisi, Cleistopholis patens, Comptonia peregrina, Coreopsis senaria, Cryptomeria japonica, Cymbopogon distans, Dalbergia decipularis, Daphne genkwa, Daphne odora, Dittrichia viscosa, Elettaria cardamomum, Elsholtzia ciliata, Erigeron canadensis, Erigeron philadelphicus, Etlingera elatior, Eucalyptus nova-anglica, Euploea sylvester, Ferula feruloides, Foveolina dichotoma, Geigeria ornativa, Gossypium hirsutum, Hedychium coronarium, Helichrysum mimetes, Heracleum dissectum, Hyalosperma glutinosum, Hypericum perforatum, Hyssopus officinalis, Ilex paraguariensis, Illicium verum, Inula germanica, Juniperus communis, Larix lyallii, Lavandula angustifolia, Lavandula stoechas, Libanotis buchtormensis, Lonicera japonica, Loxodonta africana, Matricaria matricarioides, Melissa officinalis, Mentha aquatica, Micromeria cristata, Micromeria juliana, Micromeria myrtifolia, Micromeria sinaica, Minuria cunninghamii, Mosla cavaleriei, Myrocarpus fastigiatus, Myrtus communis, Nectandra amazonum, Ocimum basilicum, Origanum cordifolium, Origanum vulgare, Osteospermum rigidum, Otoba parvifolia, Parasenecio petasitoides, Pelargonium quercifolium, Perilla frutescens, Persicaria minor, Phyla dulcis, Picea koraiensis, Pinus densiflora, Piper aduncum, Piper gaudichaudianum, Piper guineense, Piper lolot, Piper marginatum, Piper nigrum, Piper rusbyi, Polemannia montana, Psiadia altissima, Psidium guajava, Renealmia alpinia, Rhanterium epapposum, Rhododendron calostrotum, Roldana aschenborniana, Salmea scandens, Salvia absconditiflora, Salvia sclarea, Santolina chamaecyparissus, Sarcandra glabra, Saussurea involucrata, Schistostephium crataegifolium, Senecio lydenburgensis, Sideritis athoa, Sideritis ferrensis, Sideritis tragoriganum, Siparuna guianensis, Stachys recta, Stevia rebaudiana, Strychnos spinosa, Swertia japonica, Syzygiella tasmanica, Syzygium nervosum, Thulinella chrysantha, Thymus praecox, Tithonia diversifolia, Tordylium apulum, Ursinia nana, Uvariopsis tripetala, Vitex agnus-castus, Vitex negundo, Warburgia ugandensis, Xanthium strumarium, Zingiber officinale and Ziziphora hispanica. nerolidol was first documented in 2007 (PMID: 17202684). The aroma of nerolidol is woody and reminiscent of fresh bark.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    5.4455   -0.6656   -1.3563 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0130    0.0967   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773    0.5680   -0.3491 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5372    1.8477   -1.1054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8563   -0.4069   -1.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    0.6567    1.0651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7178    1.1150    1.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6732    0.2892    0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2986   -0.3119    1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107   -0.1225    2.8033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3412   -1.1421    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6837   -0.5159    0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8050   -1.2381    0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6054   -0.6463   -0.4967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4001    0.7943   -0.8988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7521   -1.3898   -1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8034   -0.9730   -2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723   -0.9903   -1.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6501    0.4115    0.4448 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    2.7143   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923    1.7203   -2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5151    2.0473   -1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7820   -1.2072   -0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743   -0.2848    1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7750    1.4124    1.5775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5233    1.0893    2.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5803    2.1963    0.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6754    0.1494   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544   -0.5648    3.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1485   -0.6703    3.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.9536    3.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2594   -2.1803    1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -1.1328   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513    0.5131    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7980   -0.5230    2.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9904   -2.2693    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1863    1.1091   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4186    1.3998    0.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675    0.8899   -1.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8957   -2.3475   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6809   -0.7839   -0.9423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6129   -1.6074   -2.1636 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


  Mrv0541 02241220202D          

 16 15  0  0  0  0            999 V2000
   -3.9318   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0723   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0722   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7872   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2170   -0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9318   -0.2073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2170    0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3575    0.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0889    0.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153    0.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 13  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  3  0  0  0
  6 14  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
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0277070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)=CCCC(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

> <INCHI_KEY>
FQTLCLSUCSAZDY-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.71035715485764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.339  -1.156   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.005  -0.387   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.671  -1.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.336  -0.387   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.002  -1.156   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -0.387   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -1.156   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001  -0.387   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.336  -1.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.671  -0.387   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.005  -1.156   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.339  -0.387   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.005   1.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.667   1.156   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.899   0.950   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.442   0.950   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   16                                             
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    2                                                            
CONECT   14    6                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-nerolidol	HMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol	HMDB
3-Hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene	HMDB
Humbertiol?	HMDB
Melaleucol	HMDB
Peruviol	HMDB
Stirrup	HMDB
Nerolidol, (S-(Z))-isomer	MeSH
Nerolidol, (Z)-isomer	MeSH
Nerolidol	MeSH
Nerolidol, (e)-isomer	MeSH
Nerolidol, (S-(e))-isomer	MeSH

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3663 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

3,7,11-trimethyldodeca-1,6,10-trien-3-ol

Traditional Name

nerolidol

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)=CCCC(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

InChI Key

FQTLCLSUCSAZDY-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CDCl₃, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-16	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abies nephrolepis	LOTUS Database	35616633
Abies sachalinensis	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Achillea abrotanoides	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea moschata	LOTUS Database	35616633
Acokanthera oblongifolia	LOTUS Database	35616633
Aframomum sceptrum	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Aloysia citrodora	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Alpinia chinensis	LOTUS Database	35616633
Alpinia latilabris	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Arctotis aspera	LOTUS Database	35616633
Aristolochia triangularis	LOTUS Database	35616633
Artemisia dolosa	LOTUS Database	35616633
Artemisia dracunculus	LOTUS Database	35616633
Artemisia judaica	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Artemisia schmidtiana	LOTUS Database	35616633
Artemisia thuscula	LOTUS Database	35616633
Artemisia tridentata	LOTUS Database	35616633
Artemisia xanthochroa	LOTUS Database	35616633
Asarum asperum	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Athamanta macedonica	LOTUS Database	35616633
Austromyrtus dulcis	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Blepharocalyx salicifolius	LOTUS Database	35616633
Bupleurum gibraltaricum	LOTUS Database	35616633
Callitropsis nootkatensis	LOTUS Database	35616633
Camellia sinensis	LOTUS Database	35616633
Canella winterana	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Cassinia subtropica	LOTUS Database	35616633
Castanopsis cuspidata	LOTUS Database	35616633
Cedrela odorata	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Cineraria parvifolia	LOTUS Database	35616633
Cinnamomum camphora	LOTUS Database	35616633
Cinnamomum sieboldii	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus iyo	LOTUS Database	35616633
Citrus paradisi	LOTUS Database	35616633
Cleistopholis patens	LOTUS Database	35616633
Comptonia peregrina	LOTUS Database	35616633
Coreopsis senaria	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cymbopogon distans	LOTUS Database	35616633
Dalbergia decipularis	LOTUS Database	35616633
Daphne genkwa	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Dittrichia viscosa	LOTUS Database	35616633
Elettaria cardamomum	LOTUS Database	35616633
Elsholtzia ciliata	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Erigeron philadelphicus	LOTUS Database	35616633
Etlingera elatior	LOTUS Database	35616633
Eucalyptus nova-anglica	LOTUS Database	35616633
Euploea sylvester	LOTUS Database	35616633
Ferula feruloides	LOTUS Database	35616633
Foveolina dichotoma	LOTUS Database	35616633
Geigeria ornativa	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Hedychium coronarium	LOTUS Database	35616633
Helichrysum mimetes	LOTUS Database	35616633
Heracleum dissectum	LOTUS Database	35616633
Hyalosperma glutinosum	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Hyssopus officinalis L.	LOTUS Database	35616633
Ilex paraguariensis	LOTUS Database	35616633
Illicium verum	LOTUS Database	35616633
Inula germanica	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Larix lyallii	LOTUS Database	35616633
Lavandula angustifolia	LOTUS Database	35616633
Lavandula stoechas	LOTUS Database	35616633
Libanotis buchtormensis	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Loxodonta africana	LOTUS Database	35616633
Matricaria matricarioides	LOTUS Database	35616633
Melissa officinalis	LOTUS Database	35616633
Mentha aquatica	LOTUS Database	35616633
Micromeria cristata	LOTUS Database	35616633
Micromeria juliana	LOTUS Database	35616633
Micromeria myrtifolia	LOTUS Database	35616633
Micromeria sinaica	LOTUS Database	35616633
Minuria cunninghamii	LOTUS Database	35616633
Mosla cavaleriei	LOTUS Database	35616633
Myrocarpus fastigiatus	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Nectandra amazonum	LOTUS Database	35616633
Ocimum basilicum	LOTUS Database	35616633
Origanum cordifolium	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Osteospermum rigidum	LOTUS Database	35616633
Otoba parvifolia	LOTUS Database	35616633
Parasenecio petasitoides	LOTUS Database	35616633
Pelargonium quercifolium	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Persicaria minor	LOTUS Database	35616633
Phyla dulcis	LOTUS Database	35616633
Picea koraiensis	LOTUS Database	35616633
Pinus densiflora	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Piper gaudichaudianum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper lolot	LOTUS Database	35616633
Piper marginatum	LOTUS Database	35616633
Piper nigrum	LOTUS Database	35616633
Piper rusbyi	LOTUS Database	35616633
Polemannia montana	LOTUS Database	35616633
Psiadia altissima	LOTUS Database	35616633
Psidium guajava	LOTUS Database	35616633
Renealmia alpinia	LOTUS Database	35616633
Rhanterium epapposum	LOTUS Database	35616633
Rhododendron calostrotum	LOTUS Database	35616633
Roldana aschenborniana	LOTUS Database	35616633
Salmea scandens	LOTUS Database	35616633
Salvia absconditiflora	LOTUS Database	35616633
Salvia sclarea	LOTUS Database	35616633
Santolina chamaecyparissus	LOTUS Database	35616633
Sarcandra glabra	LOTUS Database	35616633
Saussurea involucrata	LOTUS Database	35616633
Schistostephium crataegifolium	LOTUS Database	35616633
Senecio lydenburgensis	LOTUS Database	35616633
Sideritis athoa	LOTUS Database	35616633
Sideritis ferrensis	LOTUS Database	35616633
Sideritis tragoriganum	LOTUS Database	35616633
Siparuna guianensis	LOTUS Database	35616633
Stachys recta	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Strychnos spinosa	LOTUS Database	35616633
Swertia japonica	LOTUS Database	35616633
Syzygiella tasmanica	LOTUS Database	35616633
Syzygium nervosum	LOTUS Database	35616633
Thulinella chrysantha	LOTUS Database	35616633
Thymus praecox	LOTUS Database	35616633
Tithonia diversifolia	LOTUS Database	35616633
Tordylium apulum	LOTUS Database	35616633
Ursinia nana	LOTUS Database	35616633
Uvariopsis tripetala	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Warburgia ugandensis	LOTUS Database	35616633
Xanthium strumarium	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633
Ziziphora hispanica	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

<i>E</i>-nerolidol (CPD-8843 )

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	28.71 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

HMDB0035662

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014378

KNApSAcK ID

C00003166

Chemspider ID

8549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nerolidol

METLIN ID

Not Available

PubChem Compound

8888

PDB ID

Not Available

ChEBI ID

7524

Good Scents ID

Not Available

References

General References

Lee SJ, Han JI, Lee GS, Park MJ, Choi IG, Na KJ, Jeung EB: Antifungal effect of eugenol and nerolidol against Microsporum gypseum in a guinea pig model. Biol Pharm Bull. 2007 Jan;30(1):184-8. doi: 10.1248/bpb.30.184. [PubMed:17202684 ]
LOTUS database [Link]

Showing NP-Card for nerolidol (NP0277070)

MOL for NP0277070 (nerolidol)

3D MOL for NP0277070 (nerolidol)

3D SDF for NP0277070 (nerolidol)

3D-SDF for NP0277070 (nerolidol)

PDB for NP0277070 (nerolidol)

3D PDB for NP0277070 (nerolidol)

SMILES for NP0277070 (nerolidol)

INCHI for NP0277070 (nerolidol)

Structure for NP0277070 (nerolidol)

3D Structure for NP0277070 (nerolidol)