NP-MRD: Showing NP-Card for dehydrofalcarinol (NP0189846)

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Record Information

Version

2.0

Created at

2022-09-04 06:24:17 UTC

Updated at

2026-02-19 12:04:01 UTC

NP-MRD ID

NP0189846

Natural Product DOI

https://doi.org/10.57994/7666

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dehydrofalcarinol

Description

Dehydrofalcarinol belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. dehydrofalcarinol is found in Artemisia arctica, Artemisia campestris, Artemisia palustris, Conyza scabrida, Dendropanax arboreus, Eriocephalus africanus and Nidorella auriculata. dehydrofalcarinol was first documented in 2007 (PMID: 17885841). Based on a literature review a small amount of articles have been published on Dehydrofalcarinol (PMID: 33021790) (PMID: 20521838).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 39  0  0  0  0  0  0  0  0999 V2000
   -6.2133   -1.5660   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0512   -1.0738   -1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9181    0.4271   -1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567    0.7505   -0.3189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0669    0.2626    1.0644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9452    0.5933    2.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -0.0657    1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    0.2301    2.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5431    0.8410    2.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8657    1.3406    0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0939    0.6847    0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0912    0.1677   -0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2644   -0.4201   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2709   -0.9039   -1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5195   -1.4789   -1.7711 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1005   -2.3567   -0.8291 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4747   -0.3572   -1.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0377    0.8177   -2.3628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2987   -2.6659   -0.8337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0369   -0.9340   -0.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2295   -1.7124   -1.5502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5492    0.6979   -2.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8443    0.9173   -0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8904    0.2127   -0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5521    1.8229   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9926    0.8142    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2708   -0.8398    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875    0.3478    3.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8075    1.7088    1.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8450   -1.1906    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107    0.1168    0.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -0.0804    3.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3235    1.0113    2.8531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1042    1.1855   -0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0907    2.4517    0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3242   -2.0601   -2.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3538   -1.7946   -0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5325   -0.5060   -1.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9895    0.9718   -2.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7211    1.6320   -2.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  2  3
 15 14  1  0
 14 13  3  0
 13 12  1  0
 12 11  3  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 16 37  1  0
 15 36  1  6
 17 38  1  0
 18 39  1  0
 18 40  1  0
 10 34  1  0
 10 35  1  0
  9 33  1  0
  8 32  1  0
  7 30  1  0
  7 31  1  0
  6 28  1  0
  6 29  1  0
  5 26  1  0
  5 27  1  0
  4 24  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
  2 21  1  0
  1 19  1  0
  1 20  1  0
M  END


  Mrv1652309042208242D          

 18 17  0  0  1  0            999 V2000
    1.0461   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605   -1.8414    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
    3.1895   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    1.4586    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3342    2.2836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0487    1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  3  0  0  0  0
 12 13  1  0  0  0  0
 13 14  3  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0189846

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](C=C)C#CC#CC\C=C/CCCCCC=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h3-4,10-11,17-18H,1-2,5-9,12H2/b11-10-/t17-/m1/s1

> <INCHI_KEY>
JRLHSTVTOOELAF-QXPKXGMISA-N

> <FORMULA>
C17H22O

> <MOLECULAR_WEIGHT>
242.362

> <EXACT_MASS>
242.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.795137623261954

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,9Z)-heptadeca-1,9,16-trien-4,6-diyn-3-ol

> <JCHEM_LOGP>
5.146005300666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.289410263002587

> <JCHEM_PKA_STRONGEST_BASIC>
-3.547011950962667

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
81.30829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,9Z)-heptadeca-1,9,16-trien-4,6-diyn-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.953  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286  -3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954  -3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.287  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621  -3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955  -2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.288  -3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.622  -2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.622  -1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.956  -0.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.289   0.413   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.623   1.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.957   1.953   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.290   2.723   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      19.290   4.263   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.624   1.953   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.958   2.723   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O

Average Mass

242.3620 Da

Monoisotopic Mass

242.16707 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@H](C=C)C#CC#CC\C=C/CCCCCC=C

InChI Identifier

InChI=1S/C17H22O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h3-4,10-11,17-18H,1-2,5-9,12H2/b11-10-/t17-/m1/s1

InChI Key

JRLHSTVTOOELAF-QXPKXGMISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

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
Artemisia arctica	LOTUS Database	35616633
Artemisia campestris	LOTUS Database	35616633
Artemisia palustris	LOTUS Database	35616633
Conyza scabrida	LOTUS Database	35616633
Dendropanax arboreus	LOTUS Database	35616633
Eriocephalus africanus	LOTUS Database	35616633
Homo sapiens		Not Available
Nidorella auriculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty alcohol (CHEBI:81289 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00022682

Chemspider ID

30791590

KEGG Compound ID

C17716

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13895593

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Grant CV, Cai S, Risinger AL, Liang H, O'Keefe BR, Doench JG, Cichewicz RH, Mooberry SL: CRISPR-Cas9 Genome-Wide Knockout Screen Identifies Mechanism of Selective Activity of Dehydrofalcarinol in Mesenchymal Stem-like Triple-Negative Breast Cancer Cells. J Nat Prod. 2020 Oct 23;83(10):3080-3092. doi: 10.1021/acs.jnatprod.0c00642. Epub 2020 Oct 6. [PubMed:33021790 ]
Rawson A, Koidis A, Rai DK, Tuohy M, Brunton N: Influence of Sous Vide and water immersion processing on polyacetylene content and instrumental color of parsnip (Pastinaca sativa) disks. J Agric Food Chem. 2010 Jul 14;58(13):7740-7. doi: 10.1021/jf100517p. [PubMed:20521838 ]
Yamazoe S, Hasegawa K, Ito J, Mikami Y, Shigemori H: Hederyne A, a new antimicrobial polyacetylene from galls of Hedera rhombea Bean. J Asian Nat Prod Res. 2007 Sep-Dec;9(6-8):537-40. doi: 10.1080/10286020600882379. [PubMed:17885841 ]
LOTUS database [Link]
DOI: 10.1021/acs.jnatprod.0c00642
PMID: 33021790

Showing NP-Card for dehydrofalcarinol (NP0189846)

MOL for NP0189846 (dehydrofalcarinol)

3D MOL for NP0189846 (dehydrofalcarinol)

3D SDF for NP0189846 (dehydrofalcarinol)

3D-SDF for NP0189846 (dehydrofalcarinol)

PDB for NP0189846 (dehydrofalcarinol)

3D PDB for NP0189846 (dehydrofalcarinol)

SMILES for NP0189846 (dehydrofalcarinol)

INCHI for NP0189846 (dehydrofalcarinol)

Structure for NP0189846 (dehydrofalcarinol)

3D Structure for NP0189846 (dehydrofalcarinol)