NP-MRD: Showing NP-Card for Chloropanaxydiol (NP0085317)

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Record Information

Version

2.0

Created at

2022-04-29 05:53:08 UTC

Updated at

2022-04-29 05:53:08 UTC

NP-MRD ID

NP0085317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chloropanaxydiol

Description

Chloropanaxydiol, also known as CEHD, belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups. Chloropanaxydiol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Chloropanaxydiol has been detected, but not quantified in, tea. Chloropanaxydiol is found in Panax ginseng . This could make chloropanaxydiol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 46  0  0  0  0  0  0  0  0999 V2000
   -5.6591    0.7622    1.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4476    0.0939    0.4912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5396   -0.1063   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3674   -0.9710   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913   -1.1769   -1.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0108    0.1456   -2.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    0.9146   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8733    0.4267   -0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1742    0.2934   -1.6183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4351   -0.9280   -0.9926 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5073   -1.5685    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345   -0.7821    0.1767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7615   -0.1439    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9690    0.5811    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0131    1.1881    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2858    1.9199    0.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9773    1.8903   -0.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0999    1.2571    1.7298 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2999    1.9530    1.8465 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3704   -0.1762    1.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2598   -0.1811   -0.2139 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.2011    0.0005    2.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730    1.4275    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3877    1.3772    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3093    0.7219    0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7435   -0.9052    0.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0994   -0.5853   -1.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1774    0.9164   -0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7760   -0.5982    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7521   -1.9924   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7016   -1.8615   -1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1272   -1.6875   -2.3759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3932   -0.0246   -3.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8707    0.7548   -2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8159    1.0097   -0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0876    2.0091   -1.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251    0.8535    0.2685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6511   -1.5546   -1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758   -2.6125   -0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -1.4690    1.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1277    2.9947    0.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3305    1.5982   -1.2653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5671    1.3235    2.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0505    1.3285    2.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9345   -0.7354    2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -0.6823    1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 13 14  1  0
 14 15  3  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10  8  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  1
 10 38  1  6
 11 39  1  0
 11 40  1  0
 16 41  1  1
 17 42  1  0
 18 43  1  1
 19 44  1  0
 20 45  1  0
 20 46  1  0
M  END


  Mrv0541 05061306372D          

 21 21  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
   -3.6020   -1.7309    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
    2.2243   -5.4434    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
    2.9388   -7.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2243   -6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388   -6.6809    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   -7.9184    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5099   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533   -6.2684    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
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  3  0  0  0  0
 10  7  3  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC1OC1CC#CC#CC(O)C(O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C17H25ClO3/c1-2-3-4-5-8-11-16-17(21-16)12-9-6-7-10-14(19)15(20)13-18/h14-17,19-20H,2-5,8,11-13H2,1H3

> <INCHI_KEY>
BPRJTLAULHNDLP-UHFFFAOYSA-N

> <FORMULA>
C17H25ClO3

> <MOLECULAR_WEIGHT>
312.832

> <EXACT_MASS>
312.149222373

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.698039818648404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-chloro-8-(3-heptyloxiran-2-yl)octa-4,6-diyne-2,3-diol

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.8149014606666656

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.951873880013085

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.282355857961928

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6833313976939426

> <JCHEM_POLAR_SURFACE_AREA>
52.99

> <JCHEM_REFRACTIVITY>
85.8116

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-chloro-8-(3-heptyloxiran-2-yl)octa-4,6-diyne-2,3-diol

> <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      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.152  -7.081   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.152  -8.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.152  -5.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.152 -10.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.152  -4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.486 -14.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.152 -11.701   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.486 -12.471   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 Cl   UNK     0       6.819 -14.781   0.000  0.00  0.00          Cl+0
HETATM   19  O   UNK     0       2.818 -12.471   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.819 -11.701   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.048  -1.897   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    5   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   14                                                       
CONECT   11    8   16                                                       
CONECT   12    9   17                                                       
CONECT   13   15   18                                                       
CONECT   14   10   15   19                                                  
CONECT   15   13   14   20                                                  
CONECT   16   11   17   21                                                  
CONECT   17   12   16   21                                                  
CONECT   18   13                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
1-Chloro-8-(3-heptyloxiranyl)-4,6-octadiyne-2,3-diol	HMDB
1-Chloro-9,10-epoxy-4,6-heptadecadiyne-2,3-diol	HMDB
CEHD	HMDB

Chemical Formula

C₁₇H₂₅ClO₃

Average Mass

312.8320 Da

Monoisotopic Mass

312.14922 Da

IUPAC Name

1-chloro-8-(3-heptyloxiran-2-yl)octa-4,6-diyne-2,3-diol

Traditional Name

1-chloro-8-(3-heptyloxiran-2-yl)octa-4,6-diyne-2,3-diol

CAS Registry Number

Not Available

SMILES

CCCCCCCC1OC1CC#CC#CC(O)C(O)CCl

InChI Identifier

InChI=1S/C17H25ClO3/c1-2-3-4-5-8-11-16-17(21-16)12-9-6-7-10-14(19)15(20)13-18/h14-17,19-20H,2-5,8,11-13H2,1H3

InChI Key

BPRJTLAULHNDLP-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Halohydrins

Sub Class

Chlorohydrins

Direct Parent

Chlorohydrins

Alternative Parents

Substituents

1,2-diol
Chlorohydrin
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organochloride
Organooxygen compound
Alkyl chloride
Alkyl halide
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	4.13	ALOGPS
logP	3.81	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.28	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	85.81 m³·mol⁻¹	ChemAxon
Polarizability	36.7 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

HMDB0032676

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010630

KNApSAcK ID

Not Available

Chemspider ID

115645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

130756

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Chloropanaxydiol (NP0085317)

MOL for NP0085317 (Chloropanaxydiol)

3D MOL for NP0085317 (Chloropanaxydiol)

3D SDF for NP0085317 (Chloropanaxydiol)

3D-SDF for NP0085317 (Chloropanaxydiol)

PDB for NP0085317 (Chloropanaxydiol)

3D PDB for NP0085317 (Chloropanaxydiol)

SMILES for NP0085317 (Chloropanaxydiol)

INCHI for NP0085317 (Chloropanaxydiol)

Structure for NP0085317 (Chloropanaxydiol)

3D Structure for NP0085317 (Chloropanaxydiol)