NP-MRD: Showing NP-Card for Tetraethylenepentamine crosslinked with epichlorohydrin (NP0334569)

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Record Information

Version

2.0

Created at

2024-09-10 18:56:47 UTC

Updated at

2024-09-10 18:56:47 UTC

NP-MRD ID

NP0334569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetraethylenepentamine crosslinked with epichlorohydrin

Description

Colestipol belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Colestipol is a very strong basic compound (based on its pKa). Such substances include:Thiazide diuretics, furosemidegemfibrozilbenzylpenicillin, tetracyclinedigoxinlipid-soluble vitamins (A, D, E, K)Colestipol is contraindicated in hypertriglyceridemia (high level of triglycerides in the blood). Colestipol is a copolymer of diethylenetriamine (DETA) —or tetraethylenepentamine according to some sources— and epichlorohydrin. The following notable side effects may occur:Gastrointestinal tract disturbances, especially (mild, occasionally severe) constipationsometimes increase in VLDL and triglyceride synthesisColestipol can bind to a number of drugs and nutrients in the gut and inhibit or delay their absorption. It is also used to reduce stool volume and frequency, and in the treatment of chronic diarrhea. Colestipol (trade names Colestid, Cholestabyl) is a bile acid sequestrant used to lower blood cholesterol, specifically low-density lipoprotein (LDL). This leads to decreased enterohepatic recirculation of bile acids, increased synthesis of new bile acids by the liver from cholesterol, decreased liver cholesterol, increased LDL receptor expression, and decreasing LDL in blood. The structure drawing (top right) shows the DETA moieties in blue and the epichlorohydrin moieties in red. Like cholestyramine, colestipol works in the gut by trapping bile acids and preventing them from being reabsorbed.

Structure

MOL SDF PDB SMILES InChI

375
  Mrv0541 02231214382D          

 18 17  0  0  1  0            999 V2000
    3.3626    0.8043    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2040    1.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7299    3.6804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8734    4.0929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5864    4.0929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0168    3.6804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4430    3.6804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7915    0.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166    0.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0771    0.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4444    4.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0154    4.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588    3.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3009    3.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5879    3.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8720    3.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3023    4.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1575    4.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  3 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
  4 15  1  0  0  0  0
  5 14  1  0  0  0  0
  5 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClCC1CO1.NCCNCCNCCNCCN

> <INCHI_IDENTIFIER>
InChI=1S/C8H23N5.C3H5ClO/c9-1-3-11-5-7-13-8-6-12-4-2-10;4-1-3-2-5-3/h11-13H,1-10H2;3H,1-2H2

> <INCHI_KEY>
GMRWGQCZJGVHKL-UHFFFAOYSA-N

> <FORMULA>
C11H28ClN5O

> <MOLECULAR_WEIGHT>
281.826

> <EXACT_MASS>
281.19823825

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
23.970034700248945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2-aminoethyl)[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]amine; 2-(chloromethyl)oxirane

> <JCHEM_LOGP>
-2.515652919

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA_STRONGEST_BASIC>
9.814480476075257

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
56.041800000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
epichlorohydrin; tetraethylenepentamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 375                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       6.277   1.501   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       9.714   2.835   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       8.829   6.870   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      12.830   7.640   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.828   7.640   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      16.831   6.870   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.827   6.870   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.944   1.501   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.484   1.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.611   0.731   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.163   7.640   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.495   7.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.496   6.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.162   6.870   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.164   6.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.494   6.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.498   7.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.161   7.640   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    8    9                                                       
CONECT    3   11   12                                                       
CONECT    4   13   15                                                       
CONECT    5   14   16                                                       
CONECT    6   17                                                            
CONECT    7   18                                                            
CONECT    8    2    9   10                                                  
CONECT    9    2    8                                                       
CONECT   10    1    8                                                       
CONECT   11    3   13                                                       
CONECT   12    3   14                                                       
CONECT   13    4   11                                                       
CONECT   14    5   12                                                       
CONECT   15    4   17                                                       
CONECT   16    5   18                                                       
CONECT   17    6   15                                                       
CONECT   18    7   16                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
Epichlorohydrin-tetraethylenepentamine polymer	Kegg
HCL, Colestipol	MeSH
Colestid	MeSH
Hydrochloride, colestipol	MeSH
Colestipol hydrochloride	MeSH
Colestipol HCL	MeSH

Chemical Formula

C₁₁H₂₈ClN₅O

Average Mass

281.8260 Da

Monoisotopic Mass

281.19824 Da

IUPAC Name

(2-aminoethyl)[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]amine; 2-(chloromethyl)oxirane

Traditional Name

epichlorohydrin; tetraethylenepentamine

CAS Registry Number

Not Available

SMILES

ClCC1CO1.NCCNCCNCCNCCN

InChI Identifier

InChI=1S/C8H23N5.C3H5ClO/c9-1-3-11-5-7-13-8-6-12-4-2-10;4-1-3-2-5-3/h11-13H,1-10H2;3H,1-2H2

InChI Key

GMRWGQCZJGVHKL-UHFFFAOYSA-N

Experimental Spectra

Not Available

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 epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Not Available

Direct Parent

Epoxides

Alternative Parents

Substituents

Dialkyl ether
Secondary aliphatic amine
Oxirane
Ether
Secondary amine
Oxacycle
Primary amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Amine
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Not Available

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	-2.5	ChemAxon
pKa (Strongest Basic)	9.81	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	56.04 m³·mol⁻¹	ChemAxon
Polarizability	23.97 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

HMDB0014519

DrugBank ID

DB00375

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010378

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C06925

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Colestipol

METLIN ID

Not Available

PubChem Compound

62816

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tetraethylenepentamine crosslinked with epichlorohydrin (NP0334569)

MOL for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

3D MOL for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

3D SDF for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

3D-SDF for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

PDB for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

3D PDB for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

SMILES for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

INCHI for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

Structure for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)

3D Structure for NP0334569 (Tetraethylenepentamine crosslinked with epichlorohydrin)