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Showing NP-Card for Tranexamic acid (NP0136933)

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Record Information
Version2.0
Created at2022-05-30 16:28:51 UTC
Updated at2022-05-30 16:28:51 UTC
NP-MRD IDNP0136933
Secondary Accession NumbersNone
Natural Product Identification
Common NameTranexamic acid
DescriptionTranexamic Acid, also known as tranexmate or acido tranexamico, belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group. Tranexamic Acid is a drug which is used for use in patients with hemophilia for short term use (two to eight days) to reduce or prevent hemorrhage and reduce the need for replacement therapy during and following tooth extraction. It can also be used for excessive bleeding in menstruation, surgery, or trauma cases. Tranexamic Acid is only found in individuals that have used or taken this drug. Tranexamic Acid is a very strong basic compound (based on its pKa). In humans, tranexamic Acid is involved in tranexamic acid action pathway. It is an antifibrinolytic hemostatic used in severe hemorrhage. Oral LD50 in mice is >10 gm/kg. In patients with hereditary angioedema, inhibition of the formation and activity of plasmin by tranexamic acid may prevent attacks of angioedema by decreasing plasmin-induced activation of the first complement protein (C1). Tranexamic acid in a concentration of 1 mg per mL does not aggregate platelets in vitro. Tranexamic acid is about 10 times more potent in vitro than aminocaproic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0136933 (Tranexamic acid)


  Mrv0541 04191212112D          

 11 11  0  0  0  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  5  1  1  0  0  0  0
  5  4  1  0  0  0  0
  5  8  1  1  0  0  0
  2  6  1  0  0  0  0
  6  3  1  0  0  0  0
  6 10  1  6  0  0  0
  8  7  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0136933 (Tranexamic acid)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -3.3295    0.0628   -0.5842 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4252   -0.7224    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    0.1285    0.5095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5615    0.4750   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8311    1.0110   -0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6851   -0.2292   -0.2007 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8610    0.1913    0.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0642   -0.3447    1.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7138    1.1478    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670   -1.2795    0.4834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -0.5970    1.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5507    0.9719   -0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9295    0.2242   -1.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257   -1.0712    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894   -1.5793   -0.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5423    1.0682    0.9929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.4566   -1.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480    1.2093   -1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601    1.6138    0.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2569    1.5847   -1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0519   -0.5775   -1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5982    2.1323    0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188   -1.8498    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3796   -1.9687   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273   -1.3203    2.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697    0.1755    1.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 11  1  0
 11 10  1  0
 10  6  1  0
  6  5  1  0
  5  4  1  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  4  3  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  1
 11 25  1  0
 11 26  1  0
 10 23  1  0
 10 24  1  0
  6 21  1  6
  5 19  1  0
  5 20  1  0
  4 17  1  0
  4 18  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0136933 (Tranexamic acid)


  Mrv0541 04191212112D          

 11 11  0  0  0  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  4  1  0  0  0  0
  5  1  1  0  0  0  0
  5  4  1  0  0  0  0
  5  8  1  1  0  0  0
  2  6  1  0  0  0  0
  6  3  1  0  0  0  0
  6 10  1  6  0  0  0
  8  7  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC[C@H]1CC[C@@H](CC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-

> <INCHI_KEY>
GYDJEQRTZSCIOI-LJGSYFOKSA-N

> <FORMULA>
C8H15NO2

> <MOLECULAR_WEIGHT>
157.2102

> <EXACT_MASS>
157.110278729

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
17.2788240013345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
-1.42

> <JCHEM_LOGP>
-1.5523915649706275

> <ALOGPS_LOGS>
-0.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.55825346408191

> <JCHEM_PKA_STRONGEST_BASIC>
10.220233332069741

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
41.9037

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tranexamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0136933 (Tranexamic acid)

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PDB for NP0136933 (Tranexamic acid)
HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -3.850   0.000  0.00  0.00           N+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    6                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    8                                                  
CONECT    6    2    3   10                                                  
CONECT    7    8                                                            
CONECT    8    5    7    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0136933 (Tranexamic acid)
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SMILES for NP0136933 (Tranexamic acid)
NC[C@H]1CC[C@@H](CC1)C(O)=O
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INCHI for NP0136933 (Tranexamic acid)
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-
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View in JSmol
Synonyms
ValueSource
Acide tranexamiqueChEBI
Acido tranexamicoChEBI
Acidum tranexamicumChEBI
CyklokapronChEBI
TranexamsaeureChEBI
Tranexmic acidChEBI
Tranhexamic acidChEBI
trans AMCHAChEBI
trans-4-(Aminomethyl)cyclohexanecarboxylic acidChEBI
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylIC ACIDChEBI
trans-AmchaChEBI
trans-Tranexamic acidChEBI
TranexmateGenerator
TranhexamateGenerator
trans-4-(Aminomethyl)cyclohexanecarboxylateGenerator
trans-4-AMINOMETHYLCYCLOHEXANE-1-carboxylateGenerator
trans-TranexamateGenerator
TranexamateGenerator
Chemical FormulaC8H15NO2
Average Mass157.2102 Da
Monoisotopic Mass157.11028 Da
IUPAC Name(1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid
Traditional Nametranexamic acid
CAS Registry NumberNot Available
SMILES
NC[C@H]1CC[C@@H](CC1)C(O)=O
InChI Identifier
InChI=1S/C8H15NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h6-7H,1-5,9H2,(H,10,11)/t6-,7-
InChI KeyGYDJEQRTZSCIOI-LJGSYFOKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as amino acids. These are organic compounds that contain at least one carboxyl group and one amino group.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAmino acids  
Alternative Parents
Substituents
  • Amino acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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-1.4ALOGPS
logP-1.6ChemAxon
logS-0.94ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)10.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.9 m³·mol⁻¹ChemAxon
Polarizability17.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014447  
DrugBank IDDB00302  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482000  
KEGG Compound IDC12535  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTranexamic_Acid  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48669  
Good Scents IDNot Available
References
General ReferencesNot Available