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Showing NP-Card for Morpholine (NP0338185)

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Record Information
Version2.0
Created at2024-09-11 14:14:29 UTC
Updated at2024-09-11 14:14:30 UTC
NP-MRD IDNP0338185
Secondary Accession NumbersNone
Natural Product Identification
Common NameMorpholine
DescriptionMorpholine, also known as C4H9NO or drewamine, belongs to the class of organic compounds known as morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively. Morpholine decomposes reasonably slowly in the absence of oxygen even at the high temperatures and pressures in these steam systems. Morpholine is often used in conjunction with low concentrations of hydrazine or ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine is a common additive, in ppm concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is a very strong basic compound (based on its pKa). In humans, morpholine is involved in mycophenolic acid metabolism pathway. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. Morpholine was first documented in 1981 (PMID: 7279992). This heterocycle, pictured at right, features both amine and ether functional groups (PMID: 8077515).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0338185 (Morpholine)


  Mrv0541 02241220022D          

  6  6  0  0  0  0            999 V2000
    0.0409   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
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3D MOL for NP0338185 (Morpholine)

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3D SDF for NP0338185 (Morpholine)

  Mrv0541 02241220022D          

  6  6  0  0  0  0            999 V2000
    0.0409   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0338185

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1COCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2

> <INCHI_KEY>
YNAVUWVOSKDBBP-UHFFFAOYSA-N

> <FORMULA>
C4H9NO

> <MOLECULAR_WEIGHT>
87.1204

> <EXACT_MASS>
87.068413915

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.465792629528412

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
morpholine

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-0.41137892333333337

> <ALOGPS_LOGS>
0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.505514632085726

> <JCHEM_POLAR_SURFACE_AREA>
21.259999999999998

> <JCHEM_REFRACTIVITY>
23.7679

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.91e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
morpholine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0338185 (Morpholine)
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PDB for NP0338185 (Morpholine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.076  -1.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.311  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.311   0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.076   1.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.311   0.770   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.311  -0.770   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END

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3D PDB for NP0338185 (Morpholine)
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SMILES for NP0338185 (Morpholine)
C1COCCN1
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INCHI for NP0338185 (Morpholine)
InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
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Synonyms
ValueSource
Tetrahydro-1,4-oxazineChEBI
1-Oxa-4-azacyclohexaneHMDB
C4H9NOHMDB
Diethylene imidoxideHMDB
Diethylene oximideHMDB
Diethyleneimide oxideHMDB
Diethylenimide oxideHMDB
DrewamineHMDB
Morpholine ON rasta resinHMDB
Morpholine, 4-soya alkyl derivs.HMDB
Morpholine, practHMDB
Morpholine,reagHMDB
Tetrahydro-1, 4-isoxazineHMDB
Tetrahydro-1,4-isoxazineHMDB
Tetrahydro-2H-1,4-oxazineHMDB
Tetrahydro-4H-1,4-oxazineHMDB
Tetrahydro-4H-1-4-oxazineHMDB
Tetrahydro-p-isoxazineHMDB
Tetrahydro-p-oxazineHMDB
Tetryhydro-2H-1,4-oxazineHMDB
Morpholine hydroiodideMeSH
Morpholine phosphateMeSH
Morpholine phosphate (3:1)MeSH
Morpholine sulfite (1:1)MeSH
Morpholine phosphonate (1:1)MeSH
Morpholine hydrochlorideMeSH
Chemical FormulaC4H9NO
Average Mass87.1204 Da
Monoisotopic Mass87.06841 Da
IUPAC Namemorpholine
Traditional Namemorpholine
CAS Registry NumberNot Available
SMILES
C1COCCN1
InChI Identifier
InChI=1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2
InChI KeyYNAVUWVOSKDBBP-UHFFFAOYSA-N
Experimental Spectra
Not Available
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 morpholines. These are organic compounds containing a morpholine moiety, which consists of a six-member aliphatic saturated ring with the formula C4H9NO, where the oxygen and nitrogen atoms lie at positions 1 and 4, respectively.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassOxazinanes  
Sub ClassMorpholines  
Direct ParentMorpholines  
Alternative Parents
Substituents
  • Morpholine
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Ether
    • 

  • Secondary aliphatic amine
    • 

  • Dialkyl ether
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • 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
logP-0.75ALOGPS
logP-0.41ChemAxon
logS0.9ALOGPS
pKa (Strongest Basic)8.51ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.77 m³·mol⁻¹ChemAxon
Polarizability9.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031581  
DrugBank IDDB13669  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008207  
KNApSAcK IDNot Available
Chemspider ID13837537  
KEGG Compound IDC14452  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMorpholine  
METLIN IDNot Available
PubChem Compound8083  
PDB IDNot Available
ChEBI ID34856  
Good Scents IDNot Available
References
General References
  1. Kubis A, Witek R, Baran E, Jadach W, Matecka K, Zaba A: [In vivo antimycotic effect of topically applied morpholine (author's transl)]. Pharmazie. 1981 Jun;36(6):429-31. [PubMed:7279992  ] 
  2. Hay RJ: Antifungal drugs on the horizon. J Am Acad Dermatol. 1994 Sep;31(3 Pt 2):S82-6. doi:  10.1016/s0190-9622(08)81275-3. [PubMed:8077515  ]