NP-MRD: Showing NP-Card for (1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione (NP0222995)

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Record Information

Version

2.0

Created at

2022-09-06 00:58:09 UTC

Updated at

2022-09-06 00:58:09 UTC

NP-MRD ID

NP0222995

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione

Description

(1R,2S,4R,9R,10R,14S,16S)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]Hexadec-5-ene-7,12-dione belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review very few articles have been published on (1R,2S,4R,9R,10R,14S,16S)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]Hexadec-5-ene-7,12-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202582D          

 20 24  0  0  1  0            999 V2000
    0.7745    1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509    1.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7782    2.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    2.6840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630    3.1348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972    2.7584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8681    3.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080    2.5313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7517    3.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4896    2.6132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3048    2.7402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0072    1.9707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7096    1.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8944    1.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4433    0.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7370   -0.3874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.5991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059    1.4231    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3768    1.7168    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9660    1.9439    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 14  1  1  0  0  0
  8 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20  2  1  6  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222995

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@@H]3OC(=O)C(=C)[C@H]3[C@@H]3OC(=O)C(=C[C@H]4O[C@@H]14)[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-5-9-8(19-13(5)16)4-15(2)10-6(3-7-12(15)18-7)14(17)20-11(9)10/h3,7-12H,1,4H2,2H3/t7-,8+,9-,10+,11+,12-,15-/m1/s1

> <INCHI_KEY>
SDDUXDYWCUNMAR-MPCKERLOSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.272

> <EXACT_MASS>
274.084123551

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
26.50121353843476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4R,9R,10R,14S,16S)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0^{2,4}.0^{6,16}.0^{10,14}]hexadec-5-ene-7,12-dione

> <JCHEM_LOGP>
1.1342269969999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.234840860893362

> <JCHEM_POLAR_SURFACE_AREA>
65.13

> <JCHEM_REFRACTIVITY>
66.20150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,9R,10R,14S,16S)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0^{2,4}.0^{6,16}.0^{10,14}]hexadec-5-ene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.446   2.021   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.148   3.392   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.453   4.765   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.068   5.010   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.544   5.852   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.915   5.149   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.354   5.697   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.548   4.725   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.003   6.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.381   4.878   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.902   5.115   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.347   3.679   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.791   2.242   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.270   2.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.428   0.716   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.976  -0.723   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.941   1.118   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.864   2.656   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.303   3.205   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.670   3.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14    8                                                  
CONECT   20   18    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2720 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

(1R,2S,4R,9R,10R,14S,16S)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0^{2,4}.0^{6,16}.0^{10,14}]hexadec-5-ene-7,12-dione

Traditional Name

(1R,2S,4R,9R,10R,14S,16S)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0^{2,4}.0^{6,16}.0^{10,14}]hexadec-5-ene-7,12-dione

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@@H]3OC(=O)C(=C)[C@H]3[C@@H]3OC(=O)C(=C[C@H]4O[C@@H]14)[C@H]23

InChI Identifier

InChI=1S/C15H14O5/c1-5-9-8(19-13(5)16)4-15(2)10-6(3-7-12(15)18-7)14(17)20-11(9)10/h3,7-12H,1,4H2,2H3/t7-,8+,9-,10+,11+,12-,15-/m1/s1

InChI Key

SDDUXDYWCUNMAR-MPCKERLOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Ether
Oxirane
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
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	1.13	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.2 m³·mol⁻¹	ChemAxon
Polarizability	26.5 Å³	ChemAxon
Number of Rings	5	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

162886458

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione (NP0222995)

MOL for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

3D MOL for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

3D SDF for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

3D-SDF for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

PDB for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

3D PDB for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

SMILES for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

INCHI for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

Structure for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)

3D Structure for NP0222995 ((1r,2s,4r,9r,10r,14s,16s)-1-methyl-11-methylidene-3,8,13-trioxapentacyclo[7.6.1.0²,⁴.0⁶,¹⁶.0¹⁰,¹⁴]hexadec-5-ene-7,12-dione)