NP-MRD: Showing NP-Card for 16-B1-phytoprostane (NP0050076)

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Record Information

Version

2.0

Created at

2022-03-17 21:22:50 UTC

Updated at

2022-03-17 21:22:50 UTC

NP-MRD ID

NP0050076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-B1-phytoprostane

Description

16-B1-phytop 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, 16-b1-phytop is considered to be an octadecanoid lipid molecule. 16-B1-phytop is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652301212022243D          

 22 22  0  0  0  0            999 V2000
   -5.9579    2.2410   -1.3969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8550    0.8324   -1.8831 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652   -0.8051   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -1.4892   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -1.6660   -0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2475   -0.5988    0.7687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757   -1.1759   -0.9540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233   -1.2461    0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833    0.1049   -1.6206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6830   -0.0905   -0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8824    0.8299    2.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8295    0.4654   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2885    0.2812    3.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2070    0.0740    1.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3989    0.3629   -1.9833 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0861   -0.4327    1.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -0.0962    3.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6198    1.3231   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4554   -0.9672   -2.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238   -0.1259    3.6746 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9911    2.1547   -1.7888 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7400    1.6231    0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 16  1  0  0  0  0
  9 18  1  0  0  0  0
 10 12  2  0  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 17  1  0  0  0  0
 14 16  2  0  0  0  0
 15 19  1  0  0  0  0
 16 17  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  2  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](O)\C=C\C1=C(CCCCCCCC(O)=O)C(=O)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C18H28O4/c1-2-15(19)12-10-14-11-13-17(20)16(14)8-6-4-3-5-7-9-18(21)22/h10,12,15,19H,2-9,11,13H2,1H3,(H,21,22)/b12-10+/t15-/m0/s1

> <INCHI_KEY>
WJSAFQZKYVRPGM-PABFRNLHSA-N

> <FORMULA>
C18H28O4

> <MOLECULAR_WEIGHT>
308.418

> <EXACT_MASS>
308.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.34845793371728

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-{2-[(1E,3S)-3-hydroxypent-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}octanoic acid

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.657641676666667

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.52287919119239

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.817523872625718

> <JCHEM_PKA_STRONGEST_BASIC>
-1.694914318384272

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
88.28729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-{2-[(1E,3S)-3-hydroxypent-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}octanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0      -5.958   2.241  -1.397  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.855   0.832  -1.883  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.565  -0.805  -0.098  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.175  -1.489  -0.044  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.500  -1.666  -0.872  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.248  -0.599   0.769  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.876  -1.176  -0.954  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.123  -1.246   0.838  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.183   0.105  -1.621  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.683  -0.091  -0.246  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.882   0.830   2.220  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.829   0.465  -0.614  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.289   0.281   3.489  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.207   0.074   1.147  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.399   0.363  -1.983  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.086  -0.433   1.621  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.928  -0.096   3.026  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.620   1.323  -1.050  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.455  -0.967  -2.367  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.124  -0.126   3.675  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.991   2.155  -1.789  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.740   1.623   0.285  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   15                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   16                                                       
CONECT    9    7   18                                                       
CONECT   10   12   14                                                       
CONECT   11   13   14                                                       
CONECT   12   10   15                                                       
CONECT   13   11   17                                                       
CONECT   14   10   11   16                                                  
CONECT   15    2   12   19                                                  
CONECT   16    8   14   17                                                  
CONECT   17   13   16   20                                                  
CONECT   18    9   21   22                                                  
CONECT   19   15                                                            
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   18                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₈O₄

Average Mass

308.4180 Da

Monoisotopic Mass

308.19876 Da

IUPAC Name

8-{2-[(1E,3S)-3-hydroxypent-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}octanoic acid

Traditional Name

8-{2-[(1E,3S)-3-hydroxypent-1-en-1-yl]-5-oxocyclopent-1-en-1-yl}octanoic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](O)\C=C\C1=C(CCCCCCCC(O)=O)C(=O)CC1

InChI Identifier

InChI=1S/C18H28O4/c1-2-15(19)12-10-14-11-13-17(20)16(14)8-6-4-3-5-7-9-18(21)22/h10,12,15,19H,2-9,11,13H2,1H3,(H,21,22)/b12-10+/t15-/m0/s1

InChI Key

WJSAFQZKYVRPGM-PABFRNLHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Olea europaea	FooDB	PHYTOHUB
Prunus dulcis	FooDB	PHYTOHUB

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

Molecular Framework

Aliphatic homomonocyclic compounds

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	3.17	ALOGPS
logP	3.66	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	88.29 m³·mol⁻¹	ChemAxon
Polarizability	36.35 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50906754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 16-B1-phytoprostane (NP0050076)

MOL for NP0050076 (16-B1-phytoprostane)

3D MOL for NP0050076 (16-B1-phytoprostane)

3D SDF for NP0050076 (16-B1-phytoprostane)

3D-SDF for NP0050076 (16-B1-phytoprostane)

PDB for NP0050076 (16-B1-phytoprostane)

3D PDB for NP0050076 (16-B1-phytoprostane)

SMILES for NP0050076 (16-B1-phytoprostane)

INCHI for NP0050076 (16-B1-phytoprostane)

Structure for NP0050076 (16-B1-phytoprostane)

3D Structure for NP0050076 (16-B1-phytoprostane)