NP-MRD: Showing NP-Card for (2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine (NP0219863)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 20:59:51 UTC

Updated at

2022-09-05 20:59:51 UTC

NP-MRD ID

NP0219863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine

Description

(2S,3S,8Z)-8-(1-bromopropylidene)-3-chloro-2-[(2Z)-pent-2-en-4-yn-1-yl]-3,4,7,8-tetrahydro-2H-oxocine belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. (2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine is found in Laurencia venusta. Based on a literature review very few articles have been published on (2S,3S,8Z)-8-(1-bromopropylidene)-3-chloro-2-[(2Z)-pent-2-en-4-yn-1-yl]-3,4,7,8-tetrahydro-2H-oxocine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222592D          

 18 18  0  0  1  0            999 V2000
    1.7103    4.3779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    3.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    3.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    2.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    2.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.4904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7581    1.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0738    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8988    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113    1.1270    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3113   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959   -0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -0.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337    1.1747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3497    1.7581    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C(Br)=C1/C\C=C/C[C@H](Cl)[C@H](C\C=C/C#C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18BrClO/c1-3-5-6-11-15-13(17)9-7-8-10-14(18-15)12(16)4-2/h1,5-8,13,15H,4,9-11H2,2H3/b6-5-,8-7-,14-12-/t13-,15-/m0/s1

> <INCHI_KEY>
FMCNCJZDZVGTHG-AWVRWISKSA-N

> <FORMULA>
C15H18BrClO

> <MOLECULAR_WEIGHT>
329.66

> <EXACT_MASS>
328.022956

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.438151945873777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,8Z)-8-(1-bromopropylidene)-3-chloro-2-[(2Z)-pent-2-en-4-yn-1-yl]-3,4,7,8-tetrahydro-2H-oxocine

> <JCHEM_LOGP>
4.182519553

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.834058185077649

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
84.935

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,8Z)-8-(1-bromopropylidene)-3-chloro-2-[(2Z)-pent-2-en-4-yn-1-yl]-2,3,4,7-tetrahydrooxocine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.193   8.172   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.859   7.402   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.525   6.632   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.525   5.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.859   4.322   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.859   2.782   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.282   2.193   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.871   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.411   0.770   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0       6.181   2.104   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0       6.181  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.721  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.282  -0.653   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.859  -1.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.436  -0.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.153   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.436   2.193   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -0.653   3.282   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    6   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈BrClO

Average Mass

329.6600 Da

Monoisotopic Mass

328.02296 Da

IUPAC Name

(2S,3S,8Z)-8-(1-bromopropylidene)-3-chloro-2-[(2Z)-pent-2-en-4-yn-1-yl]-3,4,7,8-tetrahydro-2H-oxocine

Traditional Name

(2S,3S,8Z)-8-(1-bromopropylidene)-3-chloro-2-[(2Z)-pent-2-en-4-yn-1-yl]-2,3,4,7-tetrahydrooxocine

CAS Registry Number

Not Available

SMILES

CC\C(Br)=C1/C\C=C/C[C@H](Cl)[C@H](C\C=C/C#C)O1

InChI Identifier

InChI=1S/C15H18BrClO/c1-3-5-6-11-15-13(17)9-7-8-10-14(18-15)12(16)4-2/h1,5-8,13,15H,4,9-11H2,2H3/b6-5-,8-7-,14-12-/t13-,15-/m0/s1

InChI Key

FMCNCJZDZVGTHG-AWVRWISKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Laurencia venusta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxocins

Sub Class

Not Available

Direct Parent

Oxocins

Alternative Parents

Substituents

Oxocin
Vinyl bromide
Vinyl halide
Haloalkene
Bromoalkene
Oxacycle
Acetylide
Organic oxygen compound
Organooxygen compound
Alkyl chloride
Alkyl halide
Organohalogen compound
Organobromide
Hydrocarbon derivative
Organochloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.18	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.94 m³·mol⁻¹	ChemAxon
Polarizability	30.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

34981494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162954128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine (NP0219863)

MOL for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

3D MOL for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

3D SDF for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

3D-SDF for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

PDB for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

3D PDB for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

SMILES for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

INCHI for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

Structure for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)

3D Structure for NP0219863 ((2z,4z,7s,8s)-2-(1-bromopropylidene)-7-chloro-8-[(2z)-pent-2-en-4-yn-1-yl]-3,6,7,8-tetrahydrooxocine)