NP-MRD: Showing NP-Card for 8'-hydroxy-3,4-dihydrovernoniyne (NP0042637)

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Record Information

Version

2.0

Created at

2021-06-21 00:15:11 UTC

Updated at

2021-06-30 00:17:50 UTC

NP-MRD ID

NP0042637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8'-hydroxy-3,4-dihydrovernoniyne

Provided By

JEOL Database JEOL Logo

Description

(5S)-5-(8-hydroxyocta-2,4,6-triyn-1-yl)oxolan-2-one 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. 8'-hydroxy-3,4-dihydrovernoniyne is found in Vernonia scorpioides (Asteraceae). 8'-hydroxy-3,4-dihydrovernoniyne was first documented in 2013 (Pollo, L.A.E., et al.). Based on a literature review very few articles have been published on (5S)-5-(8-hydroxyocta-2,4,6-triyn-1-yl)oxolan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102153D          

 25 25  0  0  0  0            999 V2000
    3.6528   -4.6753    0.5953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -3.9936    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834   -3.2246    1.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1434   -2.2687    0.1305 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1342   -3.0789   -1.1500 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1291   -2.2340   -2.4230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1278   -1.4925   -2.5873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549   -0.8854   -2.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4729   -0.1075   -2.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5005    0.4988   -3.0165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8190    1.2768   -3.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8469    1.8838   -3.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0992    2.6210   -3.4634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0200    3.8630   -2.7787 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3421   -3.8500   -1.0873 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534   -3.9126    1.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3310   -2.6935    1.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1475   -1.9412    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769   -1.3788    0.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -3.7839   -1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816   -1.5437   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -2.8891   -3.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9397    2.0577   -3.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3125    2.8211   -4.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2151    4.3074   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  7  8  3  0  0  0  0
  5 15  1  0  0  0  0
  8  9  1  0  0  0  0
 15  2  1  0  0  0  0
  9 10  3  0  0  0  0
  2  3  1  0  0  0  0
 10 11  1  0  0  0  0
  3  4  1  0  0  0  0
 11 12  3  0  0  0  0
  5  6  1  0  0  0  0
 12 13  1  0  0  0  0
  2  1  2  0  0  0  0
  6  7  1  0  0  0  0
 13 14  1  0  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  4 18  1  0  0  0  0
  4 19  1  0  0  0  0
  5 20  1  1  0  0  0
  6 21  1  0  0  0  0
  6 22  1  0  0  0  0
 13 23  1  0  0  0  0
 13 24  1  0  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C#CC#CC#CC([H])([H])[C@@]1([H])OC(=O)C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O3/c13-10-6-4-2-1-3-5-7-11-8-9-12(14)15-11/h11,13H,7-10H2/t11-/m1/s1

> <INCHI_KEY>
SYVUUEJXFHQEFM-LLVKDONJSA-N

> <FORMULA>
C12H10O3

> <MOLECULAR_WEIGHT>
202.209

> <EXACT_MASS>
202.062994182

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.047651720467456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-5-(8-hydroxyocta-2,4,6-triyn-1-yl)oxolan-2-one

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.2294095526666662

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.359813132462985

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.474126435763846

> <JCHEM_PKA_STRONGEST_BASIC>
-3.903617072277446

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
56.7158

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-(8-hydroxyocta-2,4,6-triyn-1-yl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  O   UNK     0       3.653  -4.675   0.595  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.714  -3.994   0.220  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.783  -3.225   1.107  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.143  -2.269   0.131  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.134  -3.079  -1.150  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.129  -2.234  -2.423  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.128  -1.492  -2.587  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.155  -0.885  -2.721  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.473  -0.108  -2.888  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.501   0.499  -3.017  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.819   1.277  -3.180  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.847   1.884  -3.308  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.099   2.621  -3.463  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.020   3.863  -2.779  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.342  -3.850  -1.087  0.00  0.00           O+0
HETATM   16  H   UNK     0       1.053  -3.913   1.543  0.00  0.00           H+0
HETATM   17  H   UNK     0       2.331  -2.693   1.889  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.148  -1.941   0.442  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.777  -1.379   0.026  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.292  -3.784  -1.160  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.982  -1.544  -2.421  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.288  -2.889  -3.289  0.00  0.00           H+0
HETATM   23  H   UNK     0      -7.940   2.058  -3.048  0.00  0.00           H+0
HETATM   24  H   UNK     0      -7.313   2.821  -4.518  0.00  0.00           H+0
HETATM   25  H   UNK     0      -6.215   4.307  -3.095  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   15    3    1                                                  
CONECT    3    2    4   16   17                                             
CONECT    4    5    3   18   19                                             
CONECT    5    4   15    6   20                                             
CONECT    6    5    7   21   22                                             
CONECT    7    8    6                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   23   24                                             
CONECT   14   13   25                                                       
CONECT   15    5    2                                                       
CONECT   16    3                                                            
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19    4                                                            
CONECT   20    5                                                            
CONECT   21    6                                                            
CONECT   22    6                                                            
CONECT   23   13                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₀O₃

Average Mass

202.2090 Da

Monoisotopic Mass

202.06299 Da

IUPAC Name

(5S)-5-(8-hydroxyocta-2,4,6-triyn-1-yl)oxolan-2-one

Traditional Name

(5S)-5-(8-hydroxyocta-2,4,6-triyn-1-yl)oxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C#CC#CC#CC([H])([H])[C@@]1([H])OC(=O)C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C12H10O3/c13-10-6-4-2-1-3-5-7-11-8-9-12(14)15-11/h11,13H,7-10H2/t11-/m1/s1

InChI Key

SYVUUEJXFHQEFM-LLVKDONJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Vernonia scorpioides (Asteraceae)	JEOL database	Pollo, L.A.E., et al, Phytochem. 95, 375 (2013)

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
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Primary 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	2.12	ALOGPS
logP	1.23	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.72 m³·mol⁻¹	ChemAxon
Polarizability	22.05 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

73212485

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pollo, L.A.E., et al. (2013). Pollo, L.A.E., et al, Phytochem. 95, 375 (2013). Phytochem..

Showing NP-Card for 8'-hydroxy-3,4-dihydrovernoniyne (NP0042637)

MOL for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

3D MOL for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

3D SDF for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

3D-SDF for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

PDB for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

3D PDB for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

SMILES for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

INCHI for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

Structure for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)

3D Structure for NP0042637 (8'-hydroxy-3,4-dihydrovernoniyne)