NP-MRD: Showing NP-Card for methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate (NP0157248)

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Record Information

Version

2.0

Created at

2022-09-02 14:35:23 UTC

Updated at

2022-09-02 14:35:23 UTC

NP-MRD ID

NP0157248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

Description

12-O-Acetylbromovulone III belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids. methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate is found in Clavularia viridis. Based on a literature review very few articles have been published on 12-O-Acetylbromovulone III.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022216352D          

 29 29  0  0  1  0            999 V2000
   -2.6230   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -2.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418   -2.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744   -1.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345   -2.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -3.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -2.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004   -1.8369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6254   -1.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0379   -2.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629   -2.5514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395   -1.2077    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1330   -0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    0.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6024   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3169   -0.6039    0.0000 C   0  0  0  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  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END


  Mrv1652309022216352D          

 29 29  0  0  1  0            999 V2000
   -2.6230   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9556   -2.9561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0418   -2.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3744   -1.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6207   -1.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5345   -2.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2192   -3.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -2.6574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8004   -1.8369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6254   -1.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0379   -2.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -3.2659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8629   -2.5514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4190   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395   -1.2077    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1330   -0.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385    0.1261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8867   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6011   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3156   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0301   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8880    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6024   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3169   -0.6039    0.0000 C   0  0  0  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  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C[C@@]1(OC(C)=O)C=C(Br)C(=O)\C1=C\C=C\CCCC(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H31BrO5/c1-4-5-6-7-10-13-16-23(29-18(2)25)17-20(24)22(27)19(23)14-11-8-9-12-15-21(26)28-3/h8,10-11,13-14,17H,4-7,9,12,15-16H2,1-3H3/b11-8+,13-10-,19-14-/t23-/m1/s1

> <INCHI_KEY>
PZZGEYIHKTYLQG-IFOWTQMNSA-N

> <FORMULA>
C23H31BrO5

> <MOLECULAR_WEIGHT>
467.4

> <EXACT_MASS>
466.135487

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
48.165629860738406

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (5E)-7-[(1E,2R)-2-(acetyloxy)-4-bromo-2-[(2Z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
5.594437158333332

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.724886071976988

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
121.3543

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5E)-7-[(1E,2R)-2-(acetyloxy)-4-bromo-2-[(2Z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.896  -6.423   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.650  -5.518   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.811  -3.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.565  -3.081   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.159  -3.708   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.998  -5.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.409  -5.866   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.655  -4.960   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.494  -3.429   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.034  -3.429   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.804  -4.763   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.034  -6.096   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.344  -4.763   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.012  -3.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.782  -2.415   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      -2.314  -2.254   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       0.248  -1.271   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.072   0.235   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.655  -1.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.989  -1.127   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.322  -1.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.656  -1.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.990  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.323  -1.127   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.657  -1.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.991  -1.127   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.991   0.413   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.325  -1.897   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.658  -1.127   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14   19                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₁BrO₅

Average Mass

467.4000 Da

Monoisotopic Mass

466.13549 Da

IUPAC Name

methyl (5E)-7-[(1E,2R)-2-(acetyloxy)-4-bromo-2-[(2Z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

Traditional Name

methyl (5E)-7-[(1E,2R)-2-(acetyloxy)-4-bromo-2-[(2Z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C[C@@]1(OC(C)=O)C=C(Br)C(=O)\C1=C\C=C\CCCC(=O)OC

InChI Identifier

InChI=1S/C23H31BrO5/c1-4-5-6-7-10-13-16-23(29-18(2)25)17-20(24)22(27)19(23)14-11-8-9-12-15-21(26)28-3/h8,10-11,13-14,17H,4-7,9,12,15-16H2,1-3H3/b11-8+,13-10-,19-14-/t23-/m1/s1

InChI Key

PZZGEYIHKTYLQG-IFOWTQMNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Clavularia viridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Clavulones and derivatives

Alternative Parents

Substituents

Clavulone
Fatty acid ester
Fatty acid methyl ester
Dicarboxylic acid or derivatives
Alpha-haloketone
Methyl ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Bromoalkene
Haloalkene
Vinyl bromide
Vinyl halide
Carbonyl group
Hydrocarbon derivative
Organohalogen compound
Organobromide
Organooxygen compound
Organic oxygen compound
Organic oxide
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	5.77	ALOGPS
logP	5.59	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	121.35 m³·mol⁻¹	ChemAxon
Polarizability	48.17 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

9560710

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11385797

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate (NP0157248)

MOL for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

3D MOL for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

3D SDF for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

3D-SDF for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

PDB for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

3D PDB for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

SMILES for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

INCHI for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

Structure for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)

3D Structure for NP0157248 (methyl (5e)-7-[(1e,2r)-2-(acetyloxy)-4-bromo-2-[(2z)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate)