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Showing NP-Card for Epsilon-caprolactone (NP0002758)

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Record Information
Version2.0
Created at2020-11-23 19:39:40 UTC
Updated at2021-08-19 23:59:19 UTC
NP-MRD IDNP0002758
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpsilon-caprolactone
Provided ByBMRBBMRB logo
DescriptionEpsilon-Caprolactone, also known as 6-hexanolide or 1-oxa-2-oxocycloheptane, belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. Epsilon-Caprolactone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Epsilon-caprolactone was first documented in 2014 (PMID: 24453135). Based on a literature review a small amount of articles have been published on epsilon-Caprolactone (PMID: 34378381) (PMID: 34372160).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002758 (Epsilon-caprolactone)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.1693   -2.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798   -1.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661   -0.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523    0.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515    0.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808   -1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2652   -2.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057    0.4943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9817   -1.2293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1647    2.4646    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.5443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    2.2538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105    2.6751    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    0.0205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.4662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -2.6352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9785   -1.1721    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  1  0
  3  9  1  6
  3 10  1  0
  4 11  1  6
  4 12  1  0
  5 13  1  1
  5 14  1  0
  6 15  1  6
  6 16  1  0
  7 17  1  1
  7 18  1  0
M  END
Download

3D MOL for NP0002758 (Epsilon-caprolactone)

NP0002758
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.7606    1.9219    1.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927    1.2305    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557    0.1028   -0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7101   -0.9875   -0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -0.9181    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512   -0.3940    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669    1.0311   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162    1.6367    0.2440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692    0.3813   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.3594    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2140   -0.7085   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1835   -1.9802   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -1.9053    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -0.2119    1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8117   -1.0258   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -0.5505    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428    1.6005    0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    1.1365   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
M  END
Download

3D SDF for NP0002758 (Epsilon-caprolactone)


     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
    2.1693   -2.8584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798   -1.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661   -0.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523    0.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515    0.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808   -1.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2652   -2.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0057    0.4943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9817   -1.2293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1647    2.4646    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375    1.5443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    2.2538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105    2.6751    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0348    0.0205    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    1.4662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0672   -2.6352    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9785   -1.1721    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  1  0
  3  9  1  6
  3 10  1  0
  4 11  1  6
  4 12  1  0
  5 13  1  1
  5 14  1  0
  6 15  1  6
  6 16  1  0
  7 17  1  1
  7 18  1  0
M  END
> <DATABASE_ID>
NP0002758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCCCCO1

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2

> <INCHI_KEY>
PAPBSGBWRJIAAV-UHFFFAOYSA-N

> <FORMULA>
C6H10O2

> <MOLECULAR_WEIGHT>
114.1424

> <EXACT_MASS>
114.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
11.987251306226336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxepan-2-one

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
1.0386886356666667

> <ALOGPS_LOGS>
-0.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032727987178912

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
29.5101

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caprolactone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0002758 (Epsilon-caprolactone)

NP0002758
     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
    1.7606    1.9219    1.1882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0927    1.2305    0.3834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7557    0.1028   -0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7101   -0.9875   -0.5173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -0.9181    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5512   -0.3940    0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3669    1.0311   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162    1.6367    0.2440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2692    0.3813   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5136   -0.3594    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2140   -0.7085   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1835   -1.9802   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413   -1.9053    1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1060   -0.2119    1.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8117   -1.0258   -0.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -0.5505    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428    1.6005    0.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599    1.1365   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  1  0
  3  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
  7 17  1  0
  7 18  1  0
M  END
Download

PDB for NP0002758 (Epsilon-caprolactone)

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.986   1.877   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.599   4.085   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.211   1.877   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    8                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for NP0002758 (Epsilon-caprolactone)

COMPND    NP0002758
HETATM    1  O1  UNL     1       1.761   1.922   1.188  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.093   1.230   0.383  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.756   0.103  -0.299  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.710  -0.988  -0.517  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.237  -0.918   0.646  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.551  -0.394   0.137  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.367   1.031  -0.287  1.00  0.00           C  
HETATM    8  O2  UNL     1      -0.216   1.637   0.244  1.00  0.00           O  
HETATM    9  H1  UNL     1       2.269   0.381  -1.217  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.514  -0.359   0.399  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.214  -0.708  -1.492  1.00  0.00           H  
HETATM   12  H4  UNL     1       1.184  -1.980  -0.647  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.341  -1.905   1.171  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.106  -0.212   1.444  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.812  -1.026  -0.763  1.00  0.00           H  
HETATM   16  H8  UNL     1      -2.378  -0.551   0.850  1.00  0.00           H  
HETATM   17  H9  UNL     1      -2.243   1.600   0.145  1.00  0.00           H  
HETATM   18  H10 UNL     1      -1.460   1.136  -1.385  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    9   10
CONECT    4    5   11   12
CONECT    5    6   13   14
CONECT    6    7   15   16
CONECT    7    8   17   18
END
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SMILES for NP0002758 (Epsilon-caprolactone)

O=C1CCCCCO1
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INCHI for NP0002758 (Epsilon-caprolactone)

InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
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View in JSmol
Synonyms
ValueSource
1,6-HexanolideChEBI
1-Oxa-2-oxocycloheptaneChEBI
2-OxacycloheptanoneChEBI
2-OxepanoneChEBI
2-Oxohexamethylene oxideChEBI
6-HexanolactoneChEBI
6-HexanolideChEBI
6-Hydroxyhexanoic acid lactoneChEBI
6-Hydroxyhexanoic acid, epsilon-lactoneChEBI
CaprolactoneChEBI
epsilon-Caprolactone monomerChEBI
Hexan-6-olideChEBI
Hexanoic acid, epsilon-lactoneChEBI
Hexano-6-lactoneKegg
6-Hydroxyhexanoate lactoneGenerator
6-Hydroxyhexanoate, epsilon-lactoneGenerator
Hexanoate, epsilon-lactoneGenerator
epsilon-Captolactamium hydrogen sulfateHMDB
epsilon-CaprolactoneChEBI
Chemical FormulaC6H10O2
Average Mass114.1424 Da
Monoisotopic Mass114.06808 Da
IUPAC Nameoxepan-2-one
Traditional Namecaprolactone
CAS Registry NumberNot Available
SMILES
O=C1CCCCCO1
InChI Identifier
InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
InChI KeyPAPBSGBWRJIAAV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassNot Available
Direct ParentLactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point-1.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point215.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility27860 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.422 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.51ALOGPS
logP1.04ChemAxon
logS-0.69ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.51 m³·mol⁻¹ChemAxon
Polarizability11.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060476
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9972
KEGG Compound IDC01880
BioCyc IDCPD-101
BiGG IDNot Available
Wikipedia LinkCaprolactone
METLIN IDNot Available
PubChem Compound10401
PDB IDNot Available
ChEBI ID17915
Good Scents IDrw1242691
References
General References
  1. Romain DC, Williams CK: Chemoselective polymerization control: from mixed-monomer feedstock to copolymers. Angew Chem Int Ed Engl. 2014 Feb 3;53(6):1607-10. doi: 10.1002/anie.201309575. Epub 2014 Jan 22. [PubMed:24453135 ]
  2. Rungrod A, Kapanya A, Punyodom W, Molloy R, Meerak J, Somsunan R: Synthesis of Poly(epsilon-caprolactone) Diacrylate for Micelle-Cross-Linked Sodium AMPS Hydrogel for Use as Controlled Drug Delivery Wound Dressing. Biomacromolecules. 2021 Aug 11. doi: 10.1021/acs.biomac.1c00683. [PubMed:34378381 ]
  3. Vollrath A, Kretzer C, Beringer-Siemers B, Shkodra B, Czaplewska JA, Bandelli D, Stumpf S, Hoeppener S, Weber C, Werz O, Schubert US: Effect of Crystallinity on the Properties of Polycaprolactone Nanoparticles Containing the Dual FLAP/mPEGS-1 Inhibitor BRP-187. Polymers (Basel). 2021 Jul 31;13(15). pii: polym13152557. doi: 10.3390/polym13152557. [PubMed:34372160 ]