NP-MRD: Showing NP-Card for 3-(N-Morpholino)propanesulfonic acid (NP0002315)

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Record Information

Version

1.0

Created at

2020-11-13 22:39:47 UTC

Updated at

2021-08-12 19:50:50 UTC

NP-MRD ID

NP0002315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(N-Morpholino)propanesulfonic acid

Provided By

BMRB

Description

3[N-Morpholino]propane sulfonic acid, also known as 3-(N-morpholino)propanesulphonate or MOPS, 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. 3[N-Morpholino]propane sulfonic acid exists in all living organisms, ranging from bacteria to humans. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on 3[N-Morpholino]propane sulfonic acid (PMID: 33922514) (PMID: 32653381) (PMID: 32518977) (PMID: 32210118).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -4.5166   -1.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5682   -0.2037    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.6198    1.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0673   -0.2554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5700   -0.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0709   -0.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4282    0.0028    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2225   -1.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216   -1.2181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4265    0.1060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6322    1.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1331    1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8616    1.0171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0175   -1.6512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1207    1.3470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216    1.3986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184   -1.5996    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3049    1.4328    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -1.5431    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9102   -1.9963    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337   -2.7371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5121   -2.7034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1480   -1.6823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232    1.9397    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210    2.8458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3426    2.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739    1.9615    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  1
  2  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  1  0
 13  8  1  0
  4 14  1  0
  5 15  1  1
  5 16  1  0
  6 17  1  6
  6 18  1  0
  7 19  1  6
  7 20  1  0
  9 21  1  6
  9 22  1  0
 10 23  1  1
 10 24  1  0
 12 25  1  1
 12 26  1  0
 13 27  1  1
 13 28  1  0
M  END
> <DATABASE_ID>
NP0002315

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OS(=O)(=O)CCCN1CCOCC1

> <INCHI_IDENTIFIER>
InChI=1S/C7H15NO4S/c9-13(10,11)7-1-2-8-3-5-12-6-4-8/h1-7H2,(H,9,10,11)

> <INCHI_KEY>
DVLFYONBTKHTER-UHFFFAOYSA-N

> <FORMULA>
C7H15NO4S

> <MOLECULAR_WEIGHT>
209.263

> <EXACT_MASS>
209.072178663

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.781075065036624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(morpholin-4-yl)propane-1-sulfonic acid

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-2.425969059909364

> <ALOGPS_LOGS>
-0.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.9625622930346376

> <JCHEM_PKA_STRONGEST_BASIC>
6.882464284801161

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
48.614300000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
morpholinopropanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    2  S   UNK     0      -4.001  -3.850   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      -3.231  -5.184   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.771  -2.516   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.334  -3.850   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    NP0002315
HETATM    1  O1  UNL     1       4.173   0.095  -0.397  1.00  0.00           O  
HETATM    2  S1  UNL     1       2.915   0.672  -1.002  1.00  0.00           S  
HETATM    3  O2  UNL     1       3.374   1.775  -1.938  1.00  0.00           O  
HETATM    4  O3  UNL     1       2.177  -0.486  -1.941  1.00  0.00           O  
HETATM    5  C1  UNL     1       1.886   1.341   0.245  1.00  0.00           C  
HETATM    6  C2  UNL     1       1.420   0.292   1.197  1.00  0.00           C  
HETATM    7  C3  UNL     1       0.631  -0.812   0.559  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.513  -0.261  -0.073  1.00  0.00           N  
HETATM    9  C4  UNL     1      -1.475   0.246   0.853  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.544   0.979   0.065  1.00  0.00           C  
HETATM   11  O4  UNL     1      -3.197   0.107  -0.792  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.654  -1.150  -0.864  1.00  0.00           C  
HETATM   13  C7  UNL     1      -1.140  -1.019  -1.094  1.00  0.00           C  
HETATM   14  H1  UNL     1       2.699  -1.331  -1.965  1.00  0.00           H  
HETATM   15  H2  UNL     1       1.018   1.849  -0.228  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.453   2.159   0.744  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.319  -0.193   1.672  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.894   0.799   2.035  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.272  -1.437  -0.052  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.258  -1.463   1.415  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.926  -0.569   1.468  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.080   0.980   1.586  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.016   1.731  -0.561  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.244   1.520   0.735  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.891  -1.824  -0.041  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.043  -1.615  -1.805  1.00  0.00           H  
HETATM   27  H14 UNL     1      -0.685  -1.983  -1.333  1.00  0.00           H  
HETATM   28  H15 UNL     1      -1.080  -0.400  -2.041  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8   19   20
CONECT    8    9   13
CONECT    9   10   21   22
CONECT   10   11   23   24
CONECT   11   12
CONECT   12   13   25   26
CONECT   13   27   28
END

View in JSmol

Synonyms

Value	Source
3[N-Morpholino]propane sulfonate	Generator
3[N-Morpholino]propane sulphonate	Generator
3[N-Morpholino]propane sulphonic acid	Generator
3-(N-Morpholino)propanesulfonic acid	HMDB
3-(N-Morpholino)propanesulphonate	HMDB
3-(N-Morpholino)propanesulphonic acid	HMDB
Morpholinopropane sulfonic acid	HMDB
Morpholine propanesulphonic acid	HMDB
MOPS	HMDB

Chemical Formula

C₇H₁₅NO₄S

Average Mass

209.2630 Da

Monoisotopic Mass

209.07218 Da

IUPAC Name

3-(morpholin-4-yl)propane-1-sulfonic acid

Traditional Name

morpholinopropanesulfonic acid

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)CCCN1CCOCC1

InChI Identifier

InChI=1S/C7H15NO4S/c9-13(10,11)7-1-2-8-3-5-12-6-4-8/h1-7H2,(H,9,10,11)

InChI Key

DVLFYONBTKHTER-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not 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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Morpholines

Alternative Parents

Not Available

Substituents

Not Available

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	-1.6	ALOGPS
logP	-2.4	ChemAxon
logS	-0.75	ALOGPS
pKa (Strongest Acidic)	-0.96	ChemAxon
pKa (Strongest Basic)	6.88	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.61 m³·mol⁻¹	ChemAxon
Polarizability	20.78 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0254880

DrugBank ID

DB03434

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

63972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70807

PDB ID

Not Available

ChEBI ID

39076

Good Scents ID

Not Available

References

General References

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 ]
Liu Y, Zhang D, Ding J, Hayat K, Yang X, Zhan X, Zhang D, Lu Y, Zhou P: A Facile Aptasensor for Instantaneous Determination of Cadmium Ions Based on Fluorescence Amplification Effect of MOPS on FAM-Labeled Aptamer. Biosensors (Basel). 2021 Apr 23;11(5). pii: bios11050133. doi: 10.3390/bios11050133. [PubMed:33922514 ]
Gonzalez-Durruthy M, Scanavachi G, Rial R, Liu Z, Cordeiro MNDS, Itri R, Ruso JM: Mapping the underlying mechanisms of fibrinogen benzothiazole drug interactions using computational and experimental approaches. Int J Biol Macromol. 2020 Nov 15;163:730-744. doi: 10.1016/j.ijbiomac.2020.07.044. Epub 2020 Jul 9. [PubMed:32653381 ]
Zhou L, Cai L, Lun J, Zhao M, Guo X: Hydroxypropyl beta-cyclodextrin nanohybrid monoliths for use in capillary electrochromatography with UV detection: application to the enantiomeric separation of adrenergic drugs, anticholinergic drugs, antidepressants, azoles, and antihistamine. Mikrochim Acta. 2020 Jun 10;187(7):381. doi: 10.1007/s00604-020-04317-4. [PubMed:32518977 ]
Du W, Slany M, Wang X, Chen G, Zhang J: The Inhibition Property and Mechanism of a Novel Low Molecular Weight Zwitterionic Copolymer for Improving Wellbore Stability. Polymers (Basel). 2020 Mar 23;12(3). pii: polym12030708. doi: 10.3390/polym12030708. [PubMed:32210118 ]

Showing NP-Card for 3-(N-Morpholino)propanesulfonic acid (NP0002315)

MOL for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

3D MOL for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

3D SDF for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

3D-SDF for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

PDB for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

3D PDB for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

SMILES for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

INCHI for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

Structure for NP0002315 (3-(N-Morpholino)propanesulfonic acid)

3D Structure for NP0002315 (3-(N-Morpholino)propanesulfonic acid)