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Showing NP-Card for α chlorohydrin (NP0236312)

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Record Information
Version1.0
Created at2022-09-06 19:10:53 UTC
Updated at2022-09-06 19:10:53 UTC
NP-MRD IDNP0236312
Secondary Accession NumbersNone
Natural Product Identification
Common Nameα chlorohydrin
DescriptionGlycerol alpha-monochlorohydrin, also known as (RS)-3-chloro-1,2-propanediol or a-chlorohydrin, 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. Glycerol alpha-monochlorohydrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glycerol alpha-monochlorohydrin has been detected, but not quantified in, herbs and spices. This could make glycerol alpha-monochlorohydrin a potential biomarker for the consumption of these foods. α chlorohydrin is found in Eunicea mammosa. It was first documented in 1983 (PMID: 6612740). A chloropropane-1,2-diol that is propane-1,2-diol substituted by a chloro group at position 3.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0236312 (α chlorohydrin)


  Mrv0541 05061305532D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
M  END
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3D MOL for NP0236312 (α chlorohydrin)

     RDKit          3D

 13 12  0  0  0  0  0  0  0  0999 V2000
    1.4652    0.5586   -0.7931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1236   -0.4102    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3727   -0.5763    0.2446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8950   -0.9390   -1.0044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    0.6999    0.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    0.3424    0.7622 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9948    1.2853   -0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5683   -1.3882   -0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5190   -0.1407    1.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6110   -1.3742    0.9539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2634   -0.6432   -1.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.4812   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7070    1.1043    1.6102 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
  3  5  1  0
  5  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  1
  4 11  1  0
  5 12  1  0
  5 13  1  0
M  END
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3D SDF for NP0236312 (α chlorohydrin)


  Mrv0541 05061305532D          

  6  5  0  0  0  0            999 V2000
    1.2375   -0.7145    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
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2

> <INCHI_KEY>
SSZWWUDQMAHNAQ-UHFFFAOYSA-N

> <FORMULA>
C3H7ClO2

> <MOLECULAR_WEIGHT>
110.539

> <EXACT_MASS>
110.013457175

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
10.017440298851746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-chloropropane-1,2-diol

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
-0.48442216666666665

> <ALOGPS_LOGS>
0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.588312058743615

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.571293127286452

> <JCHEM_PKA_STRONGEST_BASIC>
-2.95311795610489

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
23.567099999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.05e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α chlorohydrin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0236312 (α chlorohydrin)

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PDB for NP0236312 (α chlorohydrin)
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       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       1.540  -2.667   0.000  0.00  0.00          Cl+0
HETATM    5  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2    6                                                  
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0236312 (α chlorohydrin)
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SMILES for NP0236312 (α chlorohydrin)
OCC(O)CCl
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INCHI for NP0236312 (α chlorohydrin)
InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
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View in JSmol
Synonyms
ValueSource
(RS)-3-Chloro-1,2-propanediolChEBI
1-Chloro-2,3-propanediolChEBI
3-Chloro-1,2-propanediolChEBI
3-Monochloro-1,2-propanediolChEBI
alpha-ChlorohydrinChEBI
ChlorodeoxyglycerolChEBI
a-ChlorohydrinGenerator
Α-chlorohydrinGenerator
Glycerol a-monochlorohydrinGenerator
Glycerol α-monochlorohydrinGenerator
(+-)-2,3-DihydroxychloropropaneHMDB
(+/-)-3-chloro-1,2-propanediolHMDB
1,2-Dihydroxy-3-chloropropaneHMDB
1-Chloro-1-deoxyglycerolHMDB
1-Chloro-2,3-dihydroxypropaneHMDB
1-Chloropropane-2,3-diolHMDB
2,3-Dihydroxypropyl chlorideHMDB
3-Chloro-1,2-dihydroxypropaneHMDB
3-Chloro-1,2-propandiolHMDB
3-Chloro-1,2-propylene glycolHMDB
3-Chloropropane-1,2-diolHMDB
3-ChloropropanediolHMDB
3-Chloropropylene glycolHMDB
3-Dichloro-1,2-propanediolHMDB
3-MCPDHMDB
3-Monochloropropane-1,2-diolHMDB
a-Glycerol chlorohydrinHMDB
a-MonochlorohydrinHMDB
alpha-ChlorohydrineHMDB
alpha-Glycerol chlorohydrinHMDB
alpha-MonochlorohydrinHMDB
beta,Beta'-dihydroxyisopropyl chlorideHMDB
Chloro-1,2-dihydroxypropaneHMDB
Chloro-1,2-propanediolHMDB
ChloropropanediolHMDB
Chloropropylene glycolHMDB
EpiblocHMDB
Glycerin alpha -monochlorhydrinHMDB
Glycerin alpha-monochlorhydrinHMDB
Glycerin epichlorohydrinHMDB
Glycerine alpha-monochlorohydrinHMDB
Glycerol 3-chlorohydrinHMDB
Glycerol alpha -chlorohydrinHMDB
Glycerol chlorohydrinHMDB
Glycerol-alpha -monochlorohydrinHMDB
Glyceryl alpha -chlorohydrinHMDB
Glyceryl alpha-chlorohydrinHMDB
Glyceryl chlorideHMDB
Glyceryl-alpha-chlorohydrinHMDB
3 Chloro 1,2 propanediolMeSH
3 ChloropropanediolMeSH
Glycerol alpha-monochlorohydrinMeSH
alpha ChlorohydrinMeSH
alpha-ChlorhydrinMeSH
Glycerol alpha monochlorohydrinMeSH
3 Monochloropropane 1,2 diolMeSH
alpha ChlorhydrinMeSH
alpha-Monochlorohydrin, glycerolMeSH
Chemical FormulaC3H7ClO2
Average Mass110.5390 Da
Monoisotopic Mass110.01346 Da
IUPAC Name3-chloropropane-1,2-diol
Traditional Nameα chlorohydrin
CAS Registry NumberNot Available
SMILES
OCC(O)CCl
InChI Identifier
InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2
InChI KeySSZWWUDQMAHNAQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eunicea mammosaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganohalogen compounds  
ClassHalohydrins  
Sub ClassChlorohydrins  
Direct ParentChlorohydrins  
Alternative Parents
Substituents
  • Secondary alcohol
    • 

  • Chlorohydrin
    • 

  • 1,2-diol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Alkyl halide
    • 

  • Alkyl chloride
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.71ALOGPS
logP-0.48ChemAxon
logS0.66ALOGPS
pKa (Strongest Acidic)13.57ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.57 m³·mol⁻¹ChemAxon
Polarizability10.02 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031334  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003397  
KNApSAcK IDNot Available
Chemspider ID7018  
KEGG Compound IDC18676  
BioCyc IDCPD0-1953  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7290  
PDB IDNot Available
ChEBI ID18721  
Good Scents IDNot Available
References
General References
  1. Kluwe WM, Gupta BN, Lamb JC 4th: The comparative effects of 1,2-dibromo-3-chloropropane (DBCP) and its metabolites, 3-chloro-1,2-propaneoxide (epichlorohydrin), 3-chloro-1,2-propanediol (alphachlorohydrin), and oxalic acid, on the urogenital system of male rats. Toxicol Appl Pharmacol. 1983 Aug;70(1):67-86. doi: 10.1016/0041-008x(83)90180-1. [PubMed:6612740  ] 
  2. LOTUS database [Link]