NP-MRD: Showing NP-Card for (2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one (NP0235016)

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Record Information

Version

2.0

Created at

2022-09-06 17:24:34 UTC

Updated at

2022-09-06 17:24:34 UTC

NP-MRD ID

NP0235016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one

Description

89199-96-2 Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one is found in Dictyota spiralis. Based on a literature review very few articles have been published on 89199-96-2.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062219242D          

 22 24  0  0  1  0            999 V2000
   -1.8983    0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1895    1.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2007    1.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694    0.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393    1.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9594    0.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6681    1.2045    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6569    2.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882    0.8017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0358    1.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    1.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3662    0.5687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1601    0.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697   -0.2506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3885   -1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221   -0.7617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8027   -0.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2916   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5178   -0.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8316    0.1544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506   -1.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448   -1.3514    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
  2  4  2  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  6  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 16 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC=C(C)C)[C@@H]1CC[C@@H](C)[C@@H]2C[C@@H]2C2=C1C(=O)OC2

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-12(2)6-5-7-13(3)15-9-8-14(4)16-10-17(16)18-11-22-20(21)19(15)18/h6,13-17H,5,7-11H2,1-4H3/t13-,14+,15-,16-,17-/m0/s1

> <INCHI_KEY>
GWENPRUHSSRYLN-QEOTZNIISA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
35.222288606954564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,5R,8S)-5-methyl-8-[(2S)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-10-one

> <JCHEM_LOGP>
5.121159961

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.217711575126245

> <JCHEM_PKA_STRONGEST_BASIC>
-6.894298690190303

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
91.23169999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,5R,8S)-5-methyl-8-[(2S)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-10-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.543   1.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.220   2.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.241   3.715   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.876   1.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.447   2.212   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.791   1.460   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.114   2.248   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.093   3.788   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.458   1.497   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.667   2.451   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.196   2.270   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.150   1.062   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.632   1.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.970  -0.468   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.192  -1.992   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.761  -1.422   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.232  -1.242   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.278  -0.033   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.833  -0.567   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.552   0.288   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.894  -2.105   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.377  -2.523   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17    9   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(2S,4S,5R,8S)-5-methyl-8-[(2S)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-10-one

Traditional Name

(2S,4S,5R,8S)-5-methyl-8-[(2S)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0^{2,4}]dodec-1(9)-en-10-one

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC=C(C)C)[C@@H]1CC[C@@H](C)[C@@H]2C[C@@H]2C2=C1C(=O)OC2

InChI Identifier

InChI=1S/C20H30O2/c1-12(2)6-5-7-13(3)15-9-8-14(4)16-10-17(16)18-11-22-20(21)19(15)18/h6,13-17H,5,7-11H2,1-4H3/t13-,14+,15-,16-,17-/m0/s1

InChI Key

GWENPRUHSSRYLN-QEOTZNIISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dictyota spiralis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.12	ChemAxon
pKa (Strongest Acidic)	13.22	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.23 m³·mol⁻¹	ChemAxon
Polarizability	35.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

154303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one (NP0235016)

MOL for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

3D MOL for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

3D SDF for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

3D-SDF for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

PDB for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

3D PDB for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

SMILES for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

INCHI for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

Structure for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)

3D Structure for NP0235016 ((2s,4s,5r,8s)-5-methyl-8-[(2s)-6-methylhept-5-en-2-yl]-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-10-one)