NP-MRD: Showing NP-Card for (z)-falcarinol (NP0304331)

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Record Information

Version

2.0

Created at

2022-09-10 19:21:06 UTC

Updated at

2022-09-10 19:21:07 UTC

NP-MRD ID

NP0304331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(z)-falcarinol

Description

Falcarinol, also known as panaxynol, 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. (z)-falcarinol is found in Angelica japonica, Bunium paucifolium, Chaerophyllum aureum, Crithmum maritimum, Cussonia arborea, Daucus carota, Dendropanax arboreus, Deverra tortuosa, Eleutherococcus koreanus, Eryngium campestre, Eryngium dilatatum, Fatsia japonica, Glehnia littoralis, Hedera helix, Heracleum moellendorffii, Levisticum officinale, Niphogeton ternata, Oenanthe javanica, Oplopanax horridus, Panax ginseng, Panax pseudoginseng, Panax quinquefolius, Petroselinum crispum, Saposhnikovia divaricata, Schefflera arboricola and Todaroa aurea. (z)-falcarinol was first documented in 2022 (PMID: 35560192). Based on a literature review a small amount of articles have been published on Falcarinol (PMID: 35232393) (PMID: 36088746) (PMID: 35745662) (PMID: 35620873).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    7.5745    1.5356    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8653    0.3789   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1322   -0.0830   -1.3567 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8264   -1.0722   -2.0515 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8176   -0.5619   -0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7364   -0.9347   -0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657   -1.3536   -0.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -1.7090    0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.1539    0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0536   -1.0761    0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    0.0892    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5669    1.2296    0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9973    1.0236    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6202    0.0133   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0576   -0.2419   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333    1.0332   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2805    0.6858    0.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7754   -0.3501   -0.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7990    2.1752    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1110    1.8759    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6466   -0.2317    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9360    0.7389   -2.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5656   -1.9450   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2649   -2.4032    1.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7652   -3.0953    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9065   -1.3131    1.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3908    0.2033   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1342    2.0792    0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316    1.4914   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1404    0.7756    1.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5016    2.0102    0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -0.8823   -0.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    0.5418   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5181   -0.9915   -0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1166   -0.6114    0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7900    1.4122   -1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4387    1.7656    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2608    0.2826    1.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9032    1.6005    0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8511   -0.2370   -1.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6681   -1.3498   -0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2222   -0.3448   -1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  1  0
  8  7  3  0
  7  6  1  0
  6  5  3  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
 18 40  1  0
 18 41  1  0
 18 42  1  0
 17 38  1  0
 17 39  1  0
 16 36  1  0
 16 37  1  0
 15 34  1  0
 15 35  1  0
 14 32  1  0
 14 33  1  0
 13 30  1  0
 13 31  1  0
 12 28  1  0
 12 29  1  0
 11 27  1  0
 10 26  1  0
  9 24  1  0
  9 25  1  0
  3 22  1  6
  4 23  1  0
  2 21  1  0
  1 19  1  0
  1 20  1  0
M  END


  Mrv1652309102221212D          

 18 17  0  0  1  0            999 V2000
   -5.3842    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6697    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9552    3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9552    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2408    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  3  0  0  0  0
  6  7  1  0  0  0  0
  7  8  3  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304331

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10+/t17-/m1/s1

> <INCHI_KEY>
UGJAEDFOKNAMQD-SXSDINLZSA-N

> <FORMULA>
C17H24O

> <MOLECULAR_WEIGHT>
244.378

> <EXACT_MASS>
244.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.836238426064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,9E)-heptadeca-1,9-dien-4,6-diyn-3-ol

> <JCHEM_LOGP>
5.449993287000001

> <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>
81.2642

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,9E)-heptadeca-1,9-dien-4,6-diyn-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.050   6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.717   5.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.383   6.517   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.383   8.057   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -6.049   5.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.716   4.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.382   4.207   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.048   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.715   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.619   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.286   3.437   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       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    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                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
Falcarinol, (Z)-isomer	MeSH
Panaxynol	MeSH

Chemical Formula

C₁₇H₂₄O

Average Mass

244.3780 Da

Monoisotopic Mass

244.18272 Da

IUPAC Name

(3R,9E)-heptadeca-1,9-dien-4,6-diyn-3-ol

Traditional Name

(3R,9E)-heptadeca-1,9-dien-4,6-diyn-3-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H24O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h4,10-11,17-18H,2-3,5-9,12H2,1H3/b11-10+/t17-/m1/s1

InChI Key

UGJAEDFOKNAMQD-SXSDINLZSA-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
Angelica japonica	LOTUS Database	35616633
Bunium paucifolium	LOTUS Database	35616633
Chaerophyllum aureum	LOTUS Database	35616633
Crithmum maritimum	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Dendropanax arboreus	LOTUS Database	35616633
Deverra tortuosa	LOTUS Database	35616633
Eleutherococcus koreanus	LOTUS Database	35616633
Eryngium campestre	LOTUS Database	35616633
Eryngium dilatatum	LOTUS Database	35616633
Fatsia japonica	LOTUS Database	35616633
Glehnia littoralis	LOTUS Database	35616633
Hedera helix	LOTUS Database	35616633
Heracleum moellendorffii Hance	LOTUS Database	35616633
Levisticum officinale	LOTUS Database	35616633
Niphogeton ternata	LOTUS Database	35616633
Oenanthe javanica	LOTUS Database	35616633
Oplopanax horridus	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Panax pseudoginseng	LOTUS Database	35616633
Panax quinquefolius	LOTUS Database	35616633
Petroselinum crispum	LOTUS Database	35616633
Saposhnikovia divaricata	LOTUS Database	35616633
Schefflera arboricola	LOTUS Database	35616633
Todaroa aurea	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

Fatty alcohols (LMFA05000530 )

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	5.45	ChemAxon
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	-3.5	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	11	ChemAxon
Refractivity	81.26 m³·mol⁻¹	ChemAxon
Polarizability	31.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00001284

Chemspider ID

57578578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Falcarinol

METLIN ID

Not Available

PubChem Compound

56935896

PDB ID

Not Available

ChEBI ID

137840

Good Scents ID

Not Available

References

General References

Santos P, Busta L, Yim WC, Cahoon EB, Kosma DK: Structural diversity, biosynthesis, and function of plant falcarin-type polyacetylenic lipids. J Exp Bot. 2022 May 13;73(9):2889-2904. doi: 10.1093/jxb/erac006. [PubMed:35560192 ]
Dunemann F, He W, Bottcher C, Reichardt S, Nothnagel T, Heuvelmans P, Hermans F: The genetic control of polyacetylenes involved in bitterness of carrots (Daucus carota L.): Identification of QTLs and candidate genes from the plant fatty acid metabolism. BMC Plant Biol. 2022 Mar 2;22(1):92. doi: 10.1186/s12870-022-03484-1. [PubMed:35232393 ]
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LOTUS database [Link]

Showing NP-Card for (z)-falcarinol (NP0304331)

MOL for NP0304331 ((z)-falcarinol)

3D MOL for NP0304331 ((z)-falcarinol)

3D SDF for NP0304331 ((z)-falcarinol)

3D-SDF for NP0304331 ((z)-falcarinol)

PDB for NP0304331 ((z)-falcarinol)

3D PDB for NP0304331 ((z)-falcarinol)

SMILES for NP0304331 ((z)-falcarinol)

INCHI for NP0304331 ((z)-falcarinol)

Structure for NP0304331 ((z)-falcarinol)

3D Structure for NP0304331 ((z)-falcarinol)