NP-MRD: Showing NP-Card for alprostadil (NP0150720)

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Record Information

Version

2.0

Created at

2022-09-02 06:55:03 UTC

Updated at

2022-09-02 06:55:03 UTC

NP-MRD ID

NP0150720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alprostadil

Description

Prostaglandin E1, also known as alprostadil or PGE1, 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 E1 is considered to be an eicosanoid lipid molecule. Caverject and Edex are similarly fast-acting, but instead are injected by syringe directly into the corpus cavernosum of the penis. Prostaglandin E1 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. It works by opening blood vessels by relaxing smooth muscle. alprostadil is found in Larix sibirica and Populus balsamifera. alprostadil was first documented in 1997 (PMID: 9248778). This is primarily useful when the threat of premature closure of the ductus arteriosus exists in an infant with ductal-dependent congenital heart disease, including cyanotic lesions (e.G., Hypoplastic left heart syndrome, pulmonary atresia/stenosis, tricuspid atresia/stenosis, transposition of the great arteries) and acyanotic lesions (e.G., Coarctation of the aorta, critical aortic stenosis, and interrupted aortic arch) (PMID: 16701566) (PMID: 12445486) (PMID: 9612114) (PMID: 15086195).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 59 59  0  0  0  0  0  0  0  0999 V2000
   -6.3045    0.6873   -2.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1257    0.9288   -0.8466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7084    1.3193   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5099    1.5713    0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8184    0.3543    1.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9530   -0.8126    1.3243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3525   -1.8840    2.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5262   -0.4941    1.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5886   -0.3395    0.8060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -0.0281    1.0426 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2417   -0.0718    2.4701 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4082    0.6635    2.7217 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4410   -1.5347    2.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3831   -2.2270    1.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1805   -3.4210    1.3343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6164   -1.2001    0.4531 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1020   -0.9388    0.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661    0.2414   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9603    0.4258   -0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -0.7505   -0.9558 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1879   -0.5753   -0.9515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6964    0.5840   -1.7515 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3653    0.4882   -3.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -0.4853   -3.6603 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433    1.5360   -4.0329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2173    0.0479   -2.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5045    1.6314   -2.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240    0.1945   -2.7930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7780    1.7843   -0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4351    0.0399   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4508    2.2873   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341    0.5277   -0.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4539    1.8652    1.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1732    2.3948    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.5262    2.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8931    0.0519    1.6530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0245   -1.0950    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4831   -1.4515    3.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2660   -0.3955    2.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9572   -0.4667   -0.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0916    0.9283    0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5206    0.3484    3.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132    1.5907    2.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727   -1.6880    3.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3904   -1.8966    3.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1952   -1.5313   -0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5541   -0.8654    1.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.8460   -0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.1356   -1.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    1.1933   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2553    1.3839   -0.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3266    0.5838    0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5101   -1.6110   -0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3382   -0.9665   -1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6096   -0.4801    0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6166   -1.5112   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8186    0.6533   -1.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2365    1.5211   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5615    2.0783   -3.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 25  1  0
 23 24  2  0
 16 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  6
 11 42  1  1
 12 43  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  6
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  0
 21 56  1  0
 22 57  1  0
 22 58  1  0
 25 59  1  0
M  END

      
  Mrv1652303291818252D          

 25 25  0  0  0  0            999 V2000
10001.883810001.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.599110000.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.314210001.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.027310000.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.742410001.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.457610000.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.172710001.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.887810000.8024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.172710002.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.517410002.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.802910002.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.802910003.3693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.088510003.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.374210003.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.659810003.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.943610003.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.229010003.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.517410003.7815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.3771 9999.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.049610001.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.499210001.2965    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.831810000.8113    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.086810000.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.911910000.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.166810000.8113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 19  2  0  0  0  0
 22 20  1  1  0  0  0
 21 10  1  6  0  0  0
 25  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0150720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

> <INCHI_KEY>
GMVPRGQOIOIIMI-DWKJAMRDSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.487

> <EXACT_MASS>
354.240624195

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.130542770300785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

> <JCHEM_LOGP>
3.5871917936666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.680474481265463

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.353232088584439

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263175145935014

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
98.31849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
alprostadil

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-MAR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-MAR-18         0                                  
HETATM    1  C   UNK     0    8670.1838668.932   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.5188668.164   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8672.8538668.932   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8674.1848668.164   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8675.5198668.932   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8676.8548668.164   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8678.1898668.932   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8679.5248668.164   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8678.1898670.471   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8667.6338670.644   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.2998671.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.2998672.956   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.9658673.726   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.6328672.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.2988673.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.9618672.956   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8659.6278673.726   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8667.6338673.726   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8669.2378665.463   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8664.8938668.638   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8667.5998669.087   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8666.3538668.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8666.8298666.716   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8668.3698666.716   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8668.8458668.181   0.000  0.00  0.00           C+0
CONECT    1    2   25                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10   11   21                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   12                                                            
CONECT   19   24                                                            
CONECT   20   22                                                            
CONECT   21   22   25   10                                                  
CONECT   22   21   23   20                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   19                                                  
CONECT   25   21   24    1                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	ChEBI
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	ChEBI
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoic acid	ChEBI
Alprostadil	ChEBI
Alprostadilum	ChEBI
Befar	ChEBI
Caverject	ChEBI
Edex	ChEBI
Muse	ChEBI
PGE-1	ChEBI
PGE1	ChEBI
Prostin VR	ChEBI
Prostin VR pediatric	Kegg
(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11a,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	Generator
(11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oate	Generator
(11Α,13E,15S)-11,15-dihydroxy-9-oxoprost-13-en-1-Oic acid	Generator
(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate	Generator
(13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoate	Generator
(13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acid	Generator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoate	Generator
11a,15a-Dihydroxy-9-oxo-13-trans-prostenoic acid	Generator
11alpha,15alpha-Dihydroxy-9-oxo-13-trans-prostenoate	Generator
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoate	Generator
11Α,15α-dihydroxy-9-oxo-13-trans-prostenoic acid	Generator
Prink	HMDB
Vitaros	HMDB
Caverject impulse	HMDB
U-10136prostin	HMDB
U-10136alprostadil	HMDB
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
(+)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
(-)-3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
(-)-Prostaglandin e1	HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoate	HMDB
(13E)-(15S)-11-alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oate	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid	HMDB
11,15-Dihydroxy-9-oxoprost-13-en-1-Oic acid (acd/name 4.0)	HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoate	HMDB
3-Hydroxy-2-(3-hydroxy-1-octenyl)-5-oxo-cyclopentaneheptanoic acid	HMDB
Alprostadil prostoglandin e1	HMDB
Alprostadil(usan)	HMDB
L-Prostaglandin e1	HMDB
Lipo pge1	HMDB
Lipo-pge1	HMDB
Viridal	HMDB
Prostaglandin e1alpha	HMDB
Sugiran	HMDB
Vasaprostan	HMDB
Minprog	HMDB
PGE1alpha	HMDB
Prostavasin	HMDB
Prostine VR	HMDB
Abbott brand OF alprostadil	HMDB
Paladin brand OF alprostadil	HMDB
Schwarz pharma brand OF alprostadil	HMDB
Astra brand OF alprostadil	HMDB
Hoyer brand OF alprostadil	HMDB
Allphar brand OF alprostadil	HMDB
AstraZeneca brand OF alprostadil	HMDB
Janssen brand OF alprostadil	HMDB
Pharmacia brand 1 OF alprostadil	HMDB
Pharmacia brand 2 OF alprostadil	HMDB
Schwarz brand OF alprostadil	HMDB
Vivus brand OF alprostadil	HMDB
Prostaglandin e1	MeSH, KEGG

Chemical Formula

C₂₀H₃₄O₅

Average Mass

354.4870 Da

Monoisotopic Mass

354.24062 Da

IUPAC Name

7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

Traditional Name

alprostadil

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16+,17+,19+/m0/s1

InChI Key

GMVPRGQOIOIIMI-DWKJAMRDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Larix sibirica	LOTUS Database	35616633
Populus balsamifera	LOTUS Database	35616633

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
Fatty alcohol
Hydroxy fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:15544 )
Prostaglandins (C04741 )
Prostaglandins (LMFA03010134 )

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	3.59	ChemAxon
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	42.13 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

HMDB0001442

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022625

KNApSAcK ID

Not Available

Chemspider ID

4444306

KEGG Compound ID

C04741

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15544

Good Scents ID

Not Available

References

General References

Borsick M, Rajkhowa T, Taub M: Evidence for post-transcriptional regulation of Na,K-ATPase by prostaglandin E1. Biochem Biophys Res Commun. 2006 Jun 30;345(2):739-45. doi: 10.1016/j.bbrc.2006.04.158. Epub 2006 May 5. [PubMed:16701566 ]
Weiss T, Fischer D, Hausmann D, Weiss C: Endothelial function in patients with peripheral vascular disease: influence of prostaglandin E1. Prostaglandins Leukot Essent Fatty Acids. 2002 Nov;67(5):277-81. doi: 10.1054/plef.2002.0429. [PubMed:12445486 ]
Thum J, Caspary L, Creutzig A, Alexander K: Intra-arterial and intravenous administration of prostaglandin E1 cause different changes to skin microcirculation in patients with peripheral arterial occlusive disease. Vasa. 1998 May;27(2):100-5. [PubMed:9612114 ]
Foldvari M, Oguejiofor CJ: Metabolism studies on transdermal prostaglandin E1 in human foreskin in vitro. Eur J Drug Metab Pharmacokinet. 1997 Apr-Jun;22(2):111-20. doi: 10.1007/BF03189793. [PubMed:9248778 ]
Kornberg A, Schotte U, Kupper B, Hommann M, Scheele J: Impact of selective prostaglandin E1 treatment on graft perfusion and function after liver transplantation. Hepatogastroenterology. 2004 Mar-Apr;51(56):526-31. [PubMed:15086195 ]
LOTUS database [Link]

Showing NP-Card for alprostadil (NP0150720)

MOL for NP0150720 (alprostadil)

3D MOL for NP0150720 (alprostadil)

3D SDF for NP0150720 (alprostadil)

3D-SDF for NP0150720 (alprostadil)

PDB for NP0150720 (alprostadil)

3D PDB for NP0150720 (alprostadil)

SMILES for NP0150720 (alprostadil)

INCHI for NP0150720 (alprostadil)

Structure for NP0150720 (alprostadil)

3D Structure for NP0150720 (alprostadil)