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Showing NP-Card for Epichlorohydrin (NP0002873)

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Record Information
Version1.0
Created at2020-11-23 19:42:31 UTC
Updated at2021-08-12 19:52:23 UTC
NP-MRD IDNP0002873
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpichlorohydrin
Provided ByBMRBBMRB logo
Description It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on (S)-epichlorohydrin (PMID: 34278788) (PMID: 34199206) (PMID: 34010561) (PMID: 34002186) (PMID: 33959369) (PMID: 33774776).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002873 (Epichlorohydrin)


     RDKit          2D

 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.8958    0.3536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5385    0.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609    1.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588   -1.3697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1726    1.5906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.6325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    0.9104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681   -1.2582    0.0000 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  3  1  0
  2  6  1  6
  2  7  1  0
  3  8  1  6
  4  9  1  1
  4 10  1  0
M  END
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3D MOL for NP0002873 (Epichlorohydrin)

NP0002873
     RDKit          3D

 10 10  0  0  0  0  0  0  0  0999 V2000
    2.6775   -0.3100   -0.3504 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    0.3068    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.5047   -0.3373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3952    0.0109    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -1.2029    0.5227 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    1.3374   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263    0.4238    1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -0.9307   -1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0534   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.8159    0.8748 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  3  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  6
  4  9  1  0
  4 10  1  0
M  END
Download

3D SDF for NP0002873 (Epichlorohydrin)


     RDKit          2D

 10 10  0  0  0  0  0  0  0  0999 V2000
   -2.8958    0.3536    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4157    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5385    0.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5609    1.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6588   -1.3697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1726    1.5906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -1.6325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8287    0.9104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681   -1.2582    0.0000 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  3  1  0
  2  6  1  6
  2  7  1  0
  3  8  1  6
  4  9  1  1
  4 10  1  0
M  END
> <DATABASE_ID>
NP0002873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CCl)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1

> <INCHI_KEY>
BRLQWZUYTZBJKN-GSVOUGTGSA-N

> <FORMULA>
C3H5ClO

> <MOLECULAR_WEIGHT>
92.52

> <EXACT_MASS>
92.0028925

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
8.381723948729507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(chloromethyl)oxirane

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.6772814056666667

> <ALOGPS_LOGS>
-0.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.187369150675658

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
20.057

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.18e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-epichlorohydrin

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0002873 (Epichlorohydrin)

NP0002873
     RDKit          3D

 10 10  0  0  0  0  0  0  0  0999 V2000
    2.6775   -0.3100   -0.3504 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1168    0.3068    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -0.5047   -0.3373 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3952    0.0109    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -1.2029    0.5227 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0015    1.3374   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0263    0.4238    1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477   -0.9307   -1.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1464    0.0534   -0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    0.8159    0.8748 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  3  1  0
  2  6  1  0
  2  7  1  0
  3  8  1  6
  4  9  1  0
  4 10  1  0
M  END
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PDB for NP0002873 (Epichlorohydrin)

HEADER    PROTEIN                                 25-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-16         0                                  
HETATM    1  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0      -0.889   3.969   0.000  0.00  0.00          Cl+0
HETATM    5  O   UNK     0      -0.325   0.325   0.000  0.00  0.00           O+0
HETATM    6  H   UNK     0      -1.043   2.058   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    3    5                                                       
CONECT    3    1    2    5    6                                             
CONECT    4    1                                                            
CONECT    5    2    3                                                       
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for NP0002873 (Epichlorohydrin)

COMPND    NP0002873
HETATM    1 CL1  UNL     1       2.677  -0.310  -0.350  1.00  0.00          CL  
HETATM    2  C1  UNL     1       1.117   0.307   0.187  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.040  -0.505  -0.337  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.395   0.011   0.115  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.855  -1.203   0.523  1.00  0.00           O  
HETATM    6  H1  UNL     1       1.001   1.337  -0.258  1.00  0.00           H  
HETATM    7  H2  UNL     1       1.026   0.424   1.272  1.00  0.00           H  
HETATM    8  H3  UNL     1       0.048  -0.931  -1.342  1.00  0.00           H  
HETATM    9  H4  UNL     1      -2.146   0.053  -0.684  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.433   0.816   0.875  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    6    7
CONECT    3    4    5    8
CONECT    4    5    9   10
END
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SMILES for NP0002873 (Epichlorohydrin)

[H][C@@]1(CCl)CO1
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INCHI for NP0002873 (Epichlorohydrin)

InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1
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View in JSmol
Synonyms
ValueSource
(S)-(Chloromethyl)oxiraneChEBI
Chemical FormulaC3H5ClO
Average Mass92.5200 Da
Monoisotopic Mass92.00289 Da
IUPAC Name(2S)-2-(chloromethyl)oxirane
Traditional Name(S)-epichlorohydrin
CAS Registry NumberNot Available
SMILES
[H][C@@]1(CCl)CO1
InChI Identifier
InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1
InChI KeyBRLQWZUYTZBJKN-GSVOUGTGSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, benzene, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, benzene, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, benzene, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as epoxides. These are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassEpoxides
Sub ClassNot Available
Direct ParentEpoxides
Alternative Parents
Substituents
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP0.35ALOGPS
logP0.68ChemAxon
logS-0.11ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.06 m³·mol⁻¹ChemAxon
Polarizability8.38 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID131706
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID37145
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Eivazzadeh-Keihan R, Khalili F, Khosropour N, Aliabadi HAM, Radinekiyan F, Sukhtezari S, Maleki A, Madanchi H, Hamblin MR, Mahdavi M, Haramshahi SMA, Shalan AE, Lanceros-Mendez S: Hybrid Bionanocomposite Containing Magnesium Hydroxide Nanoparticles Embedded in a Carboxymethyl Cellulose Hydrogel Plus Silk Fibroin as a Scaffold for Wound Dressing Applications. ACS Appl Mater Interfaces. 2021 Jul 28;13(29):33840-33849. doi: 10.1021/acsami.1c07285. Epub 2021 Jul 18. [PubMed:34278788 ]
  3. Teruel-Juanes R, Pascual-Jose B, Graf R, Reina JA, Giamberini M, Ribes-Greus A: Effect of Dendritic Side Groups on the Mobility of Modified Poly(epichlorohydrin) Copolymers. Polymers (Basel). 2021 Jun 13;13(12). pii: polym13121961. doi: 10.3390/polym13121961. [PubMed:34199206 ]
  4. Li K, Wang Y, Chen X, Bin S, Liu Y: Relatively Independent Motion of a Continuous Nanocellulose Network in a Polymer Matrix. Biomacromolecules. 2021 Jun 14;22(6):2684-2692. doi: 10.1021/acs.biomac.1c00377. Epub 2021 May 19. [PubMed:34010561 ]
  5. Jia X, Zhao J, Wang J, Ren H, Hong Z, Wu K: Amine functionalized polyacrylonitrile fibers for the selective preconcentration of trace metals prior to their on-line determination by ICP-MS. Anal Methods. 2021 Jun 10;13(22):2504-2511. doi: 10.1039/d1ay00511a. [PubMed:34002186 ]
  6. Chen C, Du Y, Chen F: Effect of urea concentration on properties of peanut protein isolate, arachin and conarachin-based adhesives during urea-epichlorohydrin modification. R Soc Open Sci. 2021 Mar 31;8(3):202227. doi: 10.1098/rsos.202227. [PubMed:33959369 ]
  7. Jain S, Desai MR, Nallamothu B, Kuche K, Chaudhari D, Katiyar SS: Partial inclusion complex assisted crosslinked beta-cyclodextrin nanoparticles for improving therapeutic potential of docetaxel against breast cancer. Drug Deliv Transl Res. 2021 Mar 27. pii: 10.1007/s13346-021-00956-z. doi: 10.1007/s13346-021-00956-z. [PubMed:33774776 ]
  8. Yan ZJ, Bartels M, Gollapudi B, Driver J, Himmelstein M, Gehen S, Juberg D, van Wesenbeeck I, Terry C, Rasoulpour R: Weight of evidence analysis of the tumorigenic potential of 1,3-dichloropropene supports a threshold-based risk assessment. Crit Rev Toxicol. 2020 Nov;50(10):836-860. doi: 10.1080/10408444.2020.1845119. Epub 2021 Feb 2. [PubMed:33528302 ]
  9. Xu H, Zhang L, Zhang H, Luo J, Gao X: Green Fabrication of Chitin/Chitosan Composite Hydrogels and Their Potential Applications. Macromol Biosci. 2021 Mar;21(3):e2000389. doi: 10.1002/mabi.202000389. Epub 2021 Jan 18. [PubMed:33458940 ]