Showing metabocard for (4R,7R)-4-isopropenyl-7-methyloxepan-2-one (MMDBc0054706)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-06 16:09:56 UTC
Update Date2025-01-15 20:17:46 UTC
Metabolite IDMMDBc0054706
Metabolite Identification
Common Name(4R,7R)-4-isopropenyl-7-methyloxepan-2-one
DescriptionTaurocyamine is a guanidino-taurine analogue derived from taurine. It is an intermediate of taurine and hypotaurine metabolism. The concentration of taurocyamine present in the human urine and serum could be as low as 8-78 pmol/ml. (PMID: 6520173 ) Plasma levels of taurocyamine are significantly increased in patients with chronic renal failure with or without hemodialysis. (PMID: 10516995 ). Taurocyamine is an endogenous alkaline "shifter". It effectively reduces the extent of brain intracellular lactic acidosis brought about by anoxic insult. A pH alkaline shift may protect the brain against the deleterious effects of lactic acidosis. (PMID: 8241459 ). Taurocyamine is an inhibitor of taurine transport and a glycine receptor antagonist in the brain (PMID: 12411417 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000055b2edc43420>


  Mrv0541 02231219462D          

 10  9  0  0  0  0            999 V2000
   17.3552  -15.5970    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6407  -16.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9427  -14.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7677  -16.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698  -12.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4987  -12.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7842  -13.9470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698  -15.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698  -14.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7842  -13.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000055b2edc43420>

HMDB0003584
     RDKit          3D
Taurocyamine
 19 18  0  0  0  0  0  0  0  0999 V2000
    2.4420   -0.1129   -0.8066 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604    0.1413    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412    0.8824    1.4148 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -0.2579    0.6600 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362   -1.0065   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.1407   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    0.4559    0.1048 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.7559    1.2843    1.1870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    0.1892    0.4199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    1.2807   -1.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7418    0.6985   -1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475   -1.0807   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5303    1.9252    1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340    0.3685    2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552   -2.0452   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -0.4722   -1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737   -1.6450    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -1.7102   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    2.2453   -1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 10 19  1  0
M  END
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3D SDF for #<Metabolite:0x000055b2edc43420>


  Mrv0541 02231219462D          

 10  9  0  0  0  0            999 V2000
   17.3552  -15.5970    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6407  -16.0095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9427  -14.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7677  -16.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698  -12.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4987  -12.7095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7842  -13.9470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698  -15.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0698  -14.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7842  -13.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054706

> <DATABASE_NAME>
MIME

> <SMILES>
NC(N)=NCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H9N3O3S/c4-3(5)6-1-2-10(7,8)9/h1-2H2,(H4,4,5,6)(H,7,8,9)

> <INCHI_KEY>
JKLRIMRKZBSSED-UHFFFAOYSA-N

> <FORMULA>
C3H9N3O3S

> <MOLECULAR_WEIGHT>
167.187

> <EXACT_MASS>
167.036461859

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
14.964769025053343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(diaminomethylidene)amino]ethane-1-sulfonic acid

> <ALOGPS_LOGP>
-2.31

> <JCHEM_LOGP>
-2.3847301697798278

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.2187804644980842

> <JCHEM_PKA_STRONGEST_BASIC>
11.766340779660142

> <JCHEM_POLAR_SURFACE_AREA>
118.77

> <JCHEM_REFRACTIVITY>
35.0269

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(diaminomethylidene)amino]ethanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x000055b2edc43420>

HMDB0003584
     RDKit          3D
Taurocyamine
 19 18  0  0  0  0  0  0  0  0999 V2000
    2.4420   -0.1129   -0.8066 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7604    0.1413    0.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412    0.8824    1.4148 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5689   -0.2579    0.6600 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1362   -1.0065   -0.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6033   -1.1407   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841    0.4559    0.1048 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.7559    1.2843    1.1870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    0.1892    0.4199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2455    1.2807   -1.3521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7418    0.6985   -1.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475   -1.0807   -1.1282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5303    1.9252    1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340    0.3685    2.2359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552   -2.0452   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -0.4722   -1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737   -1.6450    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -1.7102   -0.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    2.2453   -1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  3 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
 10 19  1  0
M  END
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PDB for #<Metabolite:0x000055b2edc43420>

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  S   UNK     0      32.396 -29.114   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      31.063 -29.884   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      31.626 -27.781   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      33.166 -30.448   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      33.730 -23.724   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      36.398 -23.724   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      35.064 -26.034   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      33.730 -28.344   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.730 -26.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.064 -24.494   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    8                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   10                                                            
CONECT    6   10                                                            
CONECT    7    9   10                                                       
CONECT    8    1    9                                                       
CONECT    9    7    8                                                       
CONECT   10    5    6    7                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x000055b2edc43420>

COMPND    HMDB0003584
HETATM    1  N1  UNL     1       2.442  -0.113  -0.807  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.760   0.141   0.412  1.00  0.00           C  
HETATM    3  N2  UNL     1       2.441   0.882   1.415  1.00  0.00           N  
HETATM    4  N3  UNL     1       0.569  -0.258   0.660  1.00  0.00           N  
HETATM    5  C2  UNL     1      -0.136  -1.006  -0.336  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.603  -1.141  -0.010  1.00  0.00           C  
HETATM    7  S1  UNL     1      -2.384   0.456   0.105  1.00  0.00           S  
HETATM    8  O1  UNL     1      -1.756   1.284   1.187  1.00  0.00           O  
HETATM    9  O2  UNL     1      -3.848   0.189   0.420  1.00  0.00           O  
HETATM   10  O3  UNL     1      -2.245   1.281  -1.352  1.00  0.00           O  
HETATM   11  H1  UNL     1       2.742   0.698  -1.390  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.648  -1.081  -1.128  1.00  0.00           H  
HETATM   13  H3  UNL     1       2.530   1.925   1.303  1.00  0.00           H  
HETATM   14  H4  UNL     1       2.834   0.368   2.236  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.255  -2.045  -0.461  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.062  -0.472  -1.305  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.774  -1.645   0.964  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.154  -1.710  -0.784  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.259   2.245  -1.129  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    4    4
CONECT    3   13   14
CONECT    4    5
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   19
END
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SMILES for #<Metabolite:0x000055b2edc43420>

NC(N)=NCCS(O)(=O)=O
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INCHI for #<Metabolite:0x000055b2edc43420>

InChI=1S/C3H9N3O3S/c4-3(5)6-1-2-10(7,8)9/h1-2H2,(H4,4,5,6)(H,7,8,9)
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Synonyms
ValueSource
2-{[amino(imino)methyl]amino}ethanesulfonic acidChEBI
Guanidinoethane sulfonic acidChEBI
N-(Aminoiminomethyl) taurineChEBI
2-{[amino(imino)methyl]amino}ethanesulfonateGenerator
2-{[amino(imino)methyl]amino}ethanesulphonateGenerator
2-{[amino(imino)methyl]amino}ethanesulphonic acidGenerator
Guanidinoethane sulfonateGenerator
Guanidinoethane sulphonateGenerator
Guanidinoethane sulphonic acidGenerator
2-{Carbamimidamido}ethanesulfonateHMDB
2-{Carbamimidamido}ethanesulfonic acidHMDB
GuanidinoethanesulfonateHMDB
Guanidinoethanesulfonic acidHMDB
Guanidinoethyl sulfonateHMDB, MeSH
Guanodinoethane sulfonateMeSH, HMDB
Molecular FormulaC3H9N3O3S
Average Mass167.187
Monoisotopic Mass167.036461859
IUPAC Name2-[(diaminomethylidene)amino]ethane-1-sulfonic acid
Traditional Name2-[(diaminomethylidene)amino]ethanesulfonic acid
CAS Registry NumberNot Available
SMILES
NC(N)=NCCS(O)(=O)=O
InChI Identifier
InChI=1S/C3H9N3O3S/c4-3(5)6-1-2-10(7,8)9/h1-2H2,(H4,4,5,6)(H,7,8,9)
InChI KeyJKLRIMRKZBSSED-UHFFFAOYSA-N