NP-MRD: Showing NP-Card for Pancreatin (NP0334573)

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Record Information

Version

2.0

Created at

2024-09-10 18:57:45 UTC

Updated at

2024-09-10 18:57:45 UTC

NP-MRD ID

NP0334573

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pancreatin

Description

9-Cis-Retinoic acid, also known as alitretinoin or aberel, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. 9-Cis-Retinoic acid is a drug which is used for topical treatment of cutaneous lesions in patients with aids-related kaposi's sarcoma. 9-Cis-Retinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 9-cis-retinoic acid participates in a number of enzymatic reactions. In particular, 9-cis-retinoic acid can be biosynthesized from 9-cis-retinal through its interaction with the enzyme retinal dehydrogenase 1. In addition, 9-cis-retinoic acid can be biosynthesized from 9-cis-retinal through the action of the enzyme retinal dehydrogenase 2. In humans, 9-cis-retinoic acid is involved in retinol metabolism. 9-Cis-Retinoic acid is a potentially toxic compound. Pancreatin was first documented in 1997 (PMID: 9115228). A retinoic acid in which the exocyclic double bonds have 7E,9Z,11E,13E geometry (PMID: 10684759) (PMID: 11978340) (PMID: 12611604) (PMID: 12882648).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305281819482D          

 22 22  0  0  0  0            999 V2000
   -3.8707    0.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8707   -0.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563   -0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7396    1.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729    1.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4418   -0.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273   -0.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4418    0.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7273    0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0128    0.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    0.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -0.5062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -0.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449   -2.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -1.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161   -2.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2984    0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2984    1.5563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1306   -3.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449   -2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5595   -3.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  9  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  7  1  0  0  0  0
  7  9  2  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 18  1  0  0  0  0
 18 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 16  1  0  0  0  0
 16 15  2  0  0  0  0
 15 21  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 21 20  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334573

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+

> <INCHI_KEY>
SHGAZHPCJJPHSC-ZVCIMWCZSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.4351

> <EXACT_MASS>
300.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.88530022493456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

> <ALOGPS_LOGP>
5.66

> <JCHEM_LOGP>
5.014367711

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.996647744997455

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
97.79079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alitretinoin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-18         0                                  
HETATM    1  C   UNK     0      -7.225   0.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.225  -0.945   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.892  -1.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.981   2.454   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.892   1.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.803   2.454   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.558  -0.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.224  -1.715   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.558   0.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.224   1.365   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.891   0.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.777   0.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.777  -0.945   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.110  -1.715   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.444  -4.025   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.110  -3.255   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.777  -4.025   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.557   1.365   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.557   2.905   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.110  -6.335   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.444  -5.565   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.778  -6.335   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    7                                                       
CONECT    4    5                                                            
CONECT    5    1    9    4    6                                             
CONECT    6    5                                                            
CONECT    7    3    9    8                                                  
CONECT    8    7                                                            
CONECT    9    5    7   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   18                                                       
CONECT   12   18   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   16                                                       
CONECT   15   16   21                                                       
CONECT   16   14   15   17                                                  
CONECT   17   16                                                            
CONECT   18   11   12   19                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   15   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid	ChEBI
(7E,9Z,11E,13E)-Retinoic acid	ChEBI
9(Z)-Retinoic acid	ChEBI
9-cis-Tretinoin	ChEBI
Alitretinoin	ChEBI
Alitretinoina	ChEBI
Alitretinoine	ChEBI
Alitretinoinum	ChEBI
Panretin	ChEBI
Panretyn	ChEBI
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate	Generator
(7E,9Z,11E,13E)-Retinoate	Generator
9(Z)-Retinoate	Generator
9-cis-Retinoate	Generator
15-Apo-beta-caroten-15-Oate	HMDB
15-Apo-beta-caroten-15-Oic acid	HMDB
9-Retinoate	HMDB
9-Retinoic acid	HMDB
Aberel	HMDB
Aberela	HMDB
Airol	HMDB
Aknoten	HMDB
all-trans- Vitamin a1 acid	HMDB
all-trans-b-Retinoate	HMDB
all-trans-b-Retinoic acid	HMDB
all-trans-beta-Retinoate	HMDB
all-trans-beta-Retinoic acid	HMDB
all-trans-Vitamin a acid	HMDB
alpha-Vitaminsyre	HMDB
Atragen	HMDB
Avita	HMDB
Avitoin	HMDB
b-Retinoate	HMDB
b-Retinoic acid	HMDB
beta-Retinoate	HMDB
beta-Retinoic acid	HMDB
Dermairol	HMDB
Effederm	HMDB
Epi-aberel	HMDB
Eudyna	HMDB
Isotretinoin retinoate	HMDB
Isotretinoin retinoic acid	HMDB
Panretin gel	HMDB
Panrexin	HMDB
Renova	HMDB
Retacnyl	HMDB
Retin a	HMDB
Retin-a	HMDB
Retin-a micro	HMDB
Retinoate	HMDB
Retinoic acid	HMDB
Retinova	HMDB
trans-Retinoate	HMDB
trans-Retinoic acid	HMDB
trans-Vitamin a acid	HMDB
Tretinoin	HMDB
Tretinoin/all-trans retinoate	HMDB
Tretinoin/all-trans retinoic acid	HMDB
Tretinon	HMDB
Vesanoid	HMDB
Vesnaroid	HMDB
Toctino	HMDB
9CRA compound	HMDB
9 cis Retinoic acid	HMDB

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4351 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid

Traditional Name

alitretinoin

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C1=C(C)CCCC1(C)C)=C\C=C\C(\C)=C\C(O)=O

InChI Identifier

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+

InChI Key

SHGAZHPCJJPHSC-ZVCIMWCZSA-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 retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Retinoids

Direct Parent

Retinoids

Alternative Parents

Substituents

Retinoic acid
Diterpenoid
Retinoid skeleton
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

retinoic acid (CHEBI:50648 )
Retinoids (C15493 )
Retinoids (LMPR01090022 )

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	5.66	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	97.79 m³·mol⁻¹	ChemAxon
Polarizability	35.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0002369

DrugBank ID

DB00523

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001084

KNApSAcK ID

Not Available

Chemspider ID

395778

KEGG Compound ID

C15493

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alitretinoin

METLIN ID

Not Available

PubChem Compound

449171

PDB ID

Not Available

ChEBI ID

50648

Good Scents ID

Not Available

References

General References

Mertz JR, Shang E, Piantedosi R, Wei S, Wolgemuth DJ, Blaner WS: Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. J Biol Chem. 1997 May 2;272(18):11744-9. doi: 10.1074/jbc.272.18.11744. [PubMed:9115228 ]
Hong SH, Mochizuki M, Nishimura R, Sasaki N, Kadosawa T, Matsunaga S: Differentiation induction of canine osteosarcoma cell lines by retinoids. Res Vet Sci. 2000 Feb;68(1):57-62. doi: 10.1053/rvsc.1999.0338. [PubMed:10684759 ]
Serghides L, Kain KC: Mechanism of protection induced by vitamin A in falciparum malaria. Lancet. 2002 Apr 20;359(9315):1404-6. doi: 10.1016/S0140-6736(02)08360-5. [PubMed:11978340 ]
Hidalgo CO, Diez C, Duque P, Facal N, Gomez E: Pregnancies and improved early embryonic development with bovine oocytes matured in vitro with 9-cis-retinoic acid. Reproduction. 2003 Mar;125(3):409-16. [PubMed:12611604 ]
Antonio V, Janvier B, Brouillet A, Andreani M, Raymondjean M: Oxysterol and 9-cis-retinoic acid stimulate the group IIA secretory phospholipase A2 gene in rat smooth-muscle cells. Biochem J. 2003 Dec 1;376(Pt 2):351-60. doi: 10.1042/BJ20030098. [PubMed:12882648 ]

Showing NP-Card for Pancreatin (NP0334573)

MOL for NP0334573 (Pancreatin)

3D MOL for NP0334573 (Pancreatin)

3D SDF for NP0334573 (Pancreatin)

3D-SDF for NP0334573 (Pancreatin)

PDB for NP0334573 (Pancreatin)

3D PDB for NP0334573 (Pancreatin)

SMILES for NP0334573 (Pancreatin)

INCHI for NP0334573 (Pancreatin)

Structure for NP0334573 (Pancreatin)

3D Structure for NP0334573 (Pancreatin)