NP-MRD: Showing NP-Card for Prostaglandin F2a (NP0334676)

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Record Information

Version

2.0

Created at

2024-09-10 19:28:00 UTC

Updated at

2024-09-10 19:28:01 UTC

NP-MRD ID

NP0334676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prostaglandin F2a

Description

Prostaglandin F2a, also known as 9a,11a-PGF2 or enzaprost, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin F2A is considered to be an eicosanoid lipid molecule. The synthesis requires only seven steps, a huge improvement on the original 17-steps synthesis of Corey and Cheng, and uses 2,5-dimethoxytetrahydrofuran as a starting reagent, with S-proline as an asymmetric catalyst. The Arachidonic Acid then reacts with two Cyclooxygenase (COX) receptors, COX-1 and COX-2 to form Prostaglandin H2, an intermediate. Prostaglandin F2α (PGF2α in prostanoid nomenclature), pharmaceutically termed carboprost, is a naturally occurring prostaglandin used in medicine to induce labor and as an abortifacient. Prostaglandin F2a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, prostaglandin F2A participates in a number of enzymatic reactions. In particular, prostaglandin F2A can be biosynthesized from prostaglandin H2 through its interaction with the enzyme prostamide/prostaglandin F synthase. In addition, prostaglandin F2A can be biosynthesized from prostaglandin E2 through its interaction with the enzyme carbonyl reductase [nadph] 1. In humans, prostaglandin F2A is involved in mefenamic acid action pathway. PGF2α and oxytocin also inhibit the production of progesterone, a hormone that facilitates corpus luteum development. The PGF2α isoform 8-iso-PGF2α was found in significantly increased amounts in patients with endometriosis, thus being a potential causative link in endometriosis-associated oxidative stress. Prostaglandin F2a was first documented in 1975 (PMID: 1061097). In small doses (1–4 mg/day), PGF2α acts to stimulate uterine muscle contractions, which aids in the birth process (PMID: 2403792) (PMID: 16475787) (PMID: 7202743) (PMID: 2982905) (PMID: 2539085) (PMID: 1562522).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02231218572D          

 25 25  0  0  1  0            999 V2000
   24.7199  -20.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0695  -18.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6174  -16.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3589  -20.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8005  -18.9899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9499  -19.1606    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6174  -18.6756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2049  -19.9452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   26.2848  -19.1606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.0299  -19.9452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1653  -18.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6174  -17.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5522  -19.4577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3318  -17.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3318  -16.6131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7675  -19.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0463  -16.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0463  -15.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1544  -19.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7609  -14.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3698  -19.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7609  -14.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7567  -20.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4753  -13.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9720  -19.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  9  2  1  6  0  0  0
 15  3  1  1  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  6  0  0  0
  7  9  1  0  0  0  0
  7 12  1  1  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 16  2  0  0  0  0
 14 15  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1

> <INCHI_KEY>
PXGPLTODNUVGFL-UAAPODJFSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.70056243906626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.6110544173333317

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.513964334215405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.355294048784039

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263153076120291

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
100.47070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-trans-PGF2α

> <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      46.144 -38.477   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      50.530 -35.290   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      47.819 -30.241   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      36.137 -37.985   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      36.961 -35.448   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      46.573 -35.766   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.819 -34.861   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.049 -37.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      49.065 -35.766   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      48.589 -37.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.109 -35.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.819 -33.321   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.964 -36.321   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      49.153 -32.551   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      49.153 -31.011   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.499 -35.845   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.486 -30.241   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      50.486 -28.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.355 -36.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      51.820 -27.931   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      39.890 -36.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      51.820 -26.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      38.746 -37.430   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      53.154 -25.621   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      37.281 -36.954   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   25                                                            
CONECT    5   25                                                            
CONECT    6    7    8   11                                                  
CONECT    7    6    9   12                                                  
CONECT    8    1    6   10                                                  
CONECT    9    2    7   10                                                  
CONECT   10    8    9                                                       
CONECT   11    6   13                                                       
CONECT   12    7   14                                                       
CONECT   13   11   16                                                       
CONECT   14   12   15                                                       
CONECT   15    3   14   17                                                  
CONECT   16   13   19                                                       
CONECT   17   15   18                                                       
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22                                                            
CONECT   25    4    5   23                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
(+)-Prostaglandin F2a	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoate	HMDB
(5Z,13E)-(15S)-9-alpha,11-alpha,15-Trihydroxyprosta-5,13-dienoic acid	HMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oate	HMDB
(5Z,13E,15S)-9a,11a,15-Trihydroxyprosta-5,13-dien-1-Oic acid	HMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oate	HMDB
(5Z,9a,11a,13E,15S)-9,11,15-Trihydroxy-prosta-5,13-dien-1-Oic acid	HMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oate	HMDB
(9alpha,11alpha,15)-Trihydroxyprosta-(5Z,13E)-dien-1-Oic acid	HMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoate	HMDB
7-[3,5-Dihydroxy-2-(3-hydroxy-1-octenyl)cyclopentyl]-5-heptenoic acid	HMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oate	HMDB
9,11,15-Trihydroxy-(5Z,9a,11a,13E,15S)-prosta-5,13-dien-1-Oic acid	HMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oate	HMDB
9,11,15-Trihydroxyprosta-5Z,13E-dien-1-Oic acid	HMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoate	HMDB
9a,11a,15(S)-Trihydroxy-5-cis-13-trans-prostadienoic acid	HMDB
9a,11a-PGF2	HMDB
9a,11a-PGF2a	HMDB
Amoglandin	HMDB
Cyclosin	HMDB
Dinifertin	HMDB
Dinoprost	HMDB
Enzaprost	HMDB
Enzaprost F	HMDB
F2a Isoprostane	HMDB
Glandin N	HMDB
L-PGF2-alpha	HMDB
L-Prostaglandin F2-alpha	HMDB
Panacelan	HMDB
PGF2a	HMDB
Prostaglandin F2	HMDB
Prostamate	HMDB
Prostarmon F	HMDB
Prostin F 2 alpha	HMDB
Protamodin	HMDB
9alpha,11beta PGF2	HMDB
9alpha,11beta-PGF2	HMDB
Estrofan	HMDB
F2 alpha, Prostaglandin	HMDB
F2alpha, Prostaglandin	HMDB
PGF2	HMDB
PGF2 alpha	HMDB
PGF2alpha	HMDB
Prostaglandin F2 alpha	HMDB
Prostaglandin F2alpha	HMDB
alpha, PGF2	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Mass

354.4810 Da

Monoisotopic Mass

354.24062 Da

IUPAC Name

(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

5-trans-PGF2α

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4+,13-12+/t15-,16+,17+,18-,19+/m0/s1

InChI Key

PXGPLTODNUVGFL-UAAPODJFSA-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 prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Prostaglandins (LMFA03010077 )

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	3.11	ALOGPS
logP	2.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	100.47 m³·mol⁻¹	ChemAxon
Polarizability	41.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0001139

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022448

KNApSAcK ID

Not Available

Chemspider ID

4446204

KEGG Compound ID

C00639

BioCyc ID

Not Available

BiGG ID

35568

Wikipedia Link

Prostaglandin F2alpha

METLIN ID

6032

PubChem Compound

5283078

PDB ID

Not Available

ChEBI ID

15553

Good Scents ID

Not Available

References

General References

Catanzarite VA: Prophylactic intramyometrial carboprost tromethamine does not substantially reduce blood loss relative to intramyometrial oxytocin at routine cesarean section. Am J Perinatol. 1990 Jan;7(1):39-42. [PubMed:2403792 ]
Komoto J, Yamada T, Watanabe K, Woodward DF, Takusagawa F: Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase (PGFS): crystal structure of PGFS containing bimatoprost. Biochemistry. 2006 Feb 21;45(7):1987-96. doi: 10.1021/bi051861t. [PubMed:16475787 ]
Grinsted J, Byskov AG: Meiosis-inducing and meiosis-preventing substances in human male reproductive organs. Fertil Steril. 1981 Feb;35(2):199-204. [PubMed:7202743 ]
Carr BR, Milburn J Jr, Wright EE, Simpson ER: Adenylate cyclase activity in neocortex and fetal zone membrane fractions of the human fetal adrenal gland. J Clin Endocrinol Metab. 1985 Apr;60(4):718-22. doi: 10.1210/jcem-60-4-718. [PubMed:2982905 ]
Negrel R, Gaillard D, Ailhaud G: Prostacyclin as a potent effector of adipose-cell differentiation. Biochem J. 1989 Jan 15;257(2):399-405. doi: 10.1042/bj2570399. [PubMed:2539085 ]
Hammarstrom S, Hamberg M, Samuelsson B, Duell EA, Stawiski M, Voorhees JJ: Increased concentrations of nonesterified arachidonic acid, 12L-hydroxy-5,8,10,14-eicosatetraenoic acid, prostaglandin E2, and prostaglandin F2alpha in epidermis of psoriasis. Proc Natl Acad Sci U S A. 1975 Dec;72(12):5130-4. doi: 10.1073/pnas.72.12.5130. [PubMed:1061097 ]
Steele GL, Leung PC: Intragonadal signalling mechanisms in the control of steroid hormone production. J Steroid Biochem Mol Biol. 1992 Mar;41(3-8):515-22. doi: 10.1016/0960-0760(92)90376-t. [PubMed:1562522 ]
Ciabattoni G, Pugliese F, Spaldi M, Cinotti GA, Patrono C: Radioimmunoassay measurement of prostaglandins E2 and F2alpha in human urine. J Endocrinol Invest. 1979 Apr-Jun;2(2):173-82. doi: 10.1007/BF03349310. [PubMed:489926 ]
Davi G, Chiarelli F, Santilli F, Pomilio M, Vigneri S, Falco A, Basili S, Ciabattoni G, Patrono C: Enhanced lipid peroxidation and platelet activation in the early phase of type 1 diabetes mellitus: role of interleukin-6 and disease duration. Circulation. 2003 Jul 1;107(25):3199-203. doi: 10.1161/01.CIR.0000074205.17807.D0. Epub 2003 Jun 16. [PubMed:12810609 ]

Showing NP-Card for Prostaglandin F2a (NP0334676)

MOL for NP0334676 (Prostaglandin F2a)

3D MOL for NP0334676 (Prostaglandin F2a)

3D SDF for NP0334676 (Prostaglandin F2a)

3D-SDF for NP0334676 (Prostaglandin F2a)

PDB for NP0334676 (Prostaglandin F2a)

3D PDB for NP0334676 (Prostaglandin F2a)

SMILES for NP0334676 (Prostaglandin F2a)

INCHI for NP0334676 (Prostaglandin F2a)

Structure for NP0334676 (Prostaglandin F2a)

3D Structure for NP0334676 (Prostaglandin F2a)