NP-MRD: Showing NP-Card for (4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol (NP0145774)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 01:02:33 UTC

Updated at

2022-09-02 01:02:34 UTC

NP-MRD ID

NP0145774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol

Description

Ginsenoyne I belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Ginsenoyne I is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ginsenoyne I has been detected, but not quantified in, tea. (4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol is found in Panax ginseng. This could make ginsenoyne I a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 45  0  0  0  0  0  0  0  0999 V2000
    8.1562    1.1700    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0681    0.7048    0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7608    0.7847    0.2320 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7188    0.3258    1.0202 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5695    2.1819   -0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3495    2.5843   -0.5257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2802    1.6342   -0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3545    0.8375   -0.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2365   -0.1016   -0.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1812    0.1892   -1.2347 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0651    0.6357   -0.6921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0366   -0.5658   -1.3667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1604   -1.8642   -0.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668   -1.9376    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6575   -1.8492   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9123   -1.9297    0.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0283   -0.8321    1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0266    0.5090    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1445    1.6282    1.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1657    1.6175   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1002    1.1085    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1468    0.2746    1.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8696    0.1094   -0.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454   -0.6676    1.0202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4064    2.8492   -0.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1566    3.6170   -0.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6214   -1.1398   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8302   -0.0318    0.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.7734   -2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5399   -0.5760   -2.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751   -2.6854   -1.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3419   -1.9375    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947   -2.9229    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4538   -1.1526    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323   -2.7027   -1.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836   -0.9331   -1.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9401   -2.9222    0.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7959   -1.8905   -0.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0635   -0.9163    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517   -0.8940    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1051    0.6888   -0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9049    0.5503   -0.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5918    2.5157    1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2136    1.8565    1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775    1.3064    2.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  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  1  0
 10  9  1  0
  9  8  1  0
  8  7  3  0
  7  6  1  0
  6  5  2  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
 10 12  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 18 41  1  0
 18 42  1  0
 17 39  1  0
 17 40  1  0
 16 37  1  0
 16 38  1  0
 15 35  1  0
 15 36  1  0
 14 33  1  0
 14 34  1  0
 13 31  1  0
 13 32  1  0
 12 30  1  6
 10 29  1  6
  9 27  1  0
  9 28  1  0
  6 26  1  0
  5 25  1  0
  3 23  1  6
  4 24  1  0
  2 22  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv0541 05061311472D          

 19 19  0  0  0  0            999 V2000
   -4.3164   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3677   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -5.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  3  0  0  0  0
 12  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC1OC1CC#C\C=C/C(O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C17H26O2/c1-3-5-6-7-10-13-16-17(19-16)14-11-8-9-12-15(18)4-2/h4,9,12,15-18H,2-3,5-7,10,13-14H2,1H3/b12-9-

> <INCHI_KEY>
AOXSLJSDFVRCQA-XFXZXTDPSA-N

> <FORMULA>
C17H26O2

> <MOLECULAR_WEIGHT>
262.3871

> <EXACT_MASS>
262.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
32.52261300052405

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
4.565368060666666

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.68845509581004

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.446468417942015

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1660018665692684

> <JCHEM_POLAR_SURFACE_AREA>
32.76

> <JCHEM_REFRACTIVITY>
81.42369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.057  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.487  -8.621   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.153  -9.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.152  -7.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.152  -8.621   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.152  -5.541   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.486  -9.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.152  -4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.819  -8.621   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.278  -3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.818  -3.231   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.819  -7.081   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.048  -1.897   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2   15                                                       
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   10                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15    4   12   18                                                  
CONECT   16   13   17   19                                                  
CONECT   17   14   16   19                                                  
CONECT   18   15                                                            
CONECT   19   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
9,10-Epoxy-1,4-heptadecadien-6-yn-3-ol	HMDB

Chemical Formula

C₁₇H₂₆O₂

Average Mass

262.3871 Da

Monoisotopic Mass

262.19328 Da

IUPAC Name

(4Z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol

Traditional Name

(4Z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol

CAS Registry Number

Not Available

SMILES

CCCCCCCC1OC1CC#C\C=C/C(O)C=C

InChI Identifier

InChI=1S/C17H26O2/c1-3-5-6-7-10-13-16-17(19-16)14-11-8-9-12-15(18)4-2/h4,9,12,15-18H,2-3,5-7,10,13-14H2,1H3/b12-9-

InChI Key

AOXSLJSDFVRCQA-XFXZXTDPSA-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
Panax ginseng	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.81	ALOGPS
logP	4.57	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	81.42 m³·mol⁻¹	ChemAxon
Polarizability	32.52 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0040374

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020106

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752801

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol (NP0145774)

MOL for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

3D MOL for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

3D SDF for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

3D-SDF for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

PDB for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

3D PDB for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

SMILES for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

INCHI for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

Structure for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)

3D Structure for NP0145774 ((4z)-8-(3-heptyloxiran-2-yl)octa-1,4-dien-6-yn-3-ol)