NP-MRD: Showing NP-Card for (3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol (NP0260586)

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Record Information

Version

2.0

Created at

2022-09-08 02:47:42 UTC

Updated at

2022-09-08 02:47:42 UTC

NP-MRD ID

NP0260586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol

Description

Didehydrofalcarinol 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. (3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol is found in Hedera helix. (3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol was first documented in 2009 (PMID: 19429313). Based on a literature review a small amount of articles have been published on Didehydrofalcarinol (PMID: 29268964) (PMID: 31343078) (PMID: 19953523).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 37  0  0  0  0  0  0  0  0999 V2000
    6.9876   -0.8510   -0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3622   -0.0455    0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9178    0.1982   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6808    1.6862   -0.2826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1717    1.8473   -0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4436    1.4218    0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394    0.4553    0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1783   -0.2823   -0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2791   -1.2371   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4383   -1.6445    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8842   -1.4083    0.4948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   -1.2387    0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4199   -1.0484   -0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5829   -0.8922   -0.3173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9882   -0.7118   -0.6751 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.1222   -1.0794   -2.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3298    0.7290   -0.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9035    1.1210    0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4987   -1.3767   -1.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0513   -1.0214   -0.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9060    0.4497    0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3246   -0.1397    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5629   -0.3127   -0.9577 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156    1.9171   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1068    2.3181    0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9536    2.9421   -0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9010    1.2867   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    1.8793    1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    0.2001    1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6532   -0.0696   -1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0451   -1.7737   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558   -2.7825    0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1514   -1.2045    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6752   -1.3063   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0030   -2.0571   -2.0821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1159    1.4669   -1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1228    0.4115    1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1589    2.1530    0.7693 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  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 16 35  1  0
 15 34  1  1
 17 36  1  0
 18 37  1  0
 18 38  1  0
 10 32  1  0
 10 33  1  0
  9 31  1  0
  8 30  1  0
  7 29  1  0
  6 28  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


  Mrv1652309082204482D          

 18 17  0  0  1  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    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
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5243   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2388   -0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6677   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3822   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967   -2.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8112   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0967   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8112   -3.4105    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  2  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>
NP0260586

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h3-4,8-11,17-18H,1-2,5-7,12H2/b9-8-,11-10-/t17-/m1/s1

> <INCHI_KEY>
ADKVNLJOJPLERM-GMBPKHMRSA-N

> <FORMULA>
C17H20O

> <MOLECULAR_WEIGHT>
240.346

> <EXACT_MASS>
240.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.059068030827085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,9Z,11Z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol

> <JCHEM_LOGP>
4.784083644

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.289381076777047

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5470247170177185

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
82.4249

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,9Z,11Z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.311   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.645   1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.978  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.312  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.646  -0.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.979  -1.746   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.313  -2.516   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.647  -3.286   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.980  -4.056   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      18.314  -3.286   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.980  -5.596   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.314  -6.366   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

C₁₇H₂₀O

Average Mass

240.3460 Da

Monoisotopic Mass

240.15142 Da

IUPAC Name

(3R,9Z,11Z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol

Traditional Name

(3R,9Z,11Z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H20O/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)4-2/h3-4,8-11,17-18H,1-2,5-7,12H2/b9-8-,11-10-/t17-/m1/s1

InChI Key

ADKVNLJOJPLERM-GMBPKHMRSA-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
Hedera helix	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

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	4.78	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	10	ChemAxon
Refractivity	82.42 m³·mol⁻¹	ChemAxon
Polarizability	30.06 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4946120

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6442009

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gutierrez-Rebolledo GA, Drier-Jonas S, Jimenez-Arellanes MA: Natural compounds and extracts from Mexican medicinal plants with anti-leishmaniasis activity: An update. Asian Pac J Trop Med. 2017 Dec;10(12):1105-1110. doi: 10.1016/j.apjtm.2017.10.016. Epub 2017 Nov 7. [PubMed:29268964 ]
Larque-Garcia H, Torres-Tapia LW, Vera-Ku M, Gamboa-Leon R, Novelo-Castilla S, Coral-Martinez TI, Peraza-Sanchez SR: Quantitative seasonal variation of the falcarinol-type polyacetylene (3S)-16,17-didehydrofalcarinol and its spatial tissue distribution in Tridax procumbens. Phytochem Anal. 2020 Mar;31(2):183-190. doi: 10.1002/pca.2878. Epub 2019 Jul 25. [PubMed:31343078 ]
Martin-Quintal Z, del Rosario Garcia-Miss M, Mut-Martin M, Matus-Moo A, Torres-Tapia LW, Peraza-Sanchez SR: The leishmanicidal effect of (3S)-16,17-didehydrofalcarinol, an oxylipin isolated from Tridax procumbens, is independent of NO production. Phytother Res. 2010 Jul;24(7):1004-8. doi: 10.1002/ptr.3052. [PubMed:19953523 ]
Martin-Quintal Z, Moo-Puc R, Gonzalez-Salazar F, Chan-Bacab MJ, Torres-Tapia LW, Peraza-Sanchez SR: In vitro activity of Tridax procumbens against promastigotes of Leishmania mexicana. J Ethnopharmacol. 2009 Apr 21;122(3):463-7. doi: 10.1016/j.jep.2009.01.037. Epub 2009 Feb 10. [PubMed:19429313 ]
LOTUS database [Link]

Showing NP-Card for (3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol (NP0260586)

MOL for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

3D MOL for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

3D SDF for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

3D-SDF for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

PDB for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

3D PDB for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

SMILES for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

INCHI for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

Structure for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)

3D Structure for NP0260586 ((3r,9z,11z)-heptadeca-1,9,11,16-tetraen-4,6-diyn-3-ol)