NP-MRD: Showing NP-Card for 2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one (NP0219081)

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Record Information

Version

2.0

Created at

2022-09-05 19:57:38 UTC

Updated at

2022-09-05 19:57:39 UTC

NP-MRD ID

NP0219081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one

Description

2-Methoxy-3,5-dimethyl-6-[(1S)-1,3,5-trimethyl-2-[(2E,4S)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]-4H-pyran-4-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one is found in Elysia crispata. Based on a literature review very few articles have been published on 2-methoxy-3,5-dimethyl-6-[(1S)-1,3,5-trimethyl-2-[(2E,4S)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]-4H-pyran-4-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221572D          

 30 31  0  0  1  0            999 V2000
    6.3532   -0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637   -0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9617   -1.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1492   -1.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721   -0.9142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9847   -0.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -1.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0509   -0.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -3.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -3.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3730   -2.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -1.1409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9055   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519    0.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354    1.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251    2.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416    0.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861   -0.9206    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 20 29  2  0  0  0  0
 29 30  1  0  0  0  0
M  END


  Mrv1652309052221572D          

 30 31  0  0  1  0            999 V2000
    6.3532   -0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5637   -0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9617   -1.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1492   -1.9569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1721   -0.9142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9847   -0.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5701   -1.4783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6524   -1.2001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0509   -0.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3939   -3.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9368   -3.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3730   -2.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873   -1.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018   -1.1409    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9055   -0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4891   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0519    0.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4392    1.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354    1.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1251    2.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7009    0.3447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416    0.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0861   -0.9206    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 20 29  2  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219081

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)[C@@H](C)\C=C(/C)C1=C(C)C(=O)C(C)=C[C@]1(C)C1=C(C)C(=O)C(C)=C(OC)O1

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O5/c1-10-19(26)13(2)11-14(3)20-16(5)21(27)15(4)12-25(20,8)23-17(6)22(28)18(7)24(29-9)30-23/h11-13H,10H2,1-9H3/b14-11+/t13-,25-/m0/s1

> <INCHI_KEY>
WKECBESDKQBOQM-UAKQWYECSA-N

> <FORMULA>
C25H32O5

> <MOLECULAR_WEIGHT>
412.526

> <EXACT_MASS>
412.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.51869524623542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxy-3,5-dimethyl-6-[(1S)-1,3,5-trimethyl-2-[(2E,4S)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]-4H-pyran-4-one

> <JCHEM_LOGP>
5.287581363666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.26550947624412

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8605042885275145

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
131.3367

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-3,5-dimethyl-6-[(1S)-1,3,5-trimethyl-2-[(2E,4S)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      11.859  -1.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.386  -1.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.262  -2.153   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.612  -3.653   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.788  -1.706   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.438  -0.207   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.664  -2.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.951  -2.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.695  -0.578   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.390  -2.900   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.469  -5.642   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.057  -5.210   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.749  -6.768   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.696  -5.259   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.723  -2.900   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.057  -2.130   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.690  -0.450   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.780  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.964   0.536   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.687   1.896   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.746   3.302   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.234   3.794   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.226   1.949   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.973   3.428   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.042   0.643   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.798   0.299   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.319  -0.716   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.761  -1.719   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₅

Average Mass

412.5260 Da

Monoisotopic Mass

412.22497 Da

IUPAC Name

2-methoxy-3,5-dimethyl-6-[(1S)-1,3,5-trimethyl-2-[(2E,4S)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]-4H-pyran-4-one

Traditional Name

2-methoxy-3,5-dimethyl-6-[(1S)-1,3,5-trimethyl-2-[(2E,4S)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one

CAS Registry Number

Not Available

SMILES

CCC(=O)[C@@H](C)\C=C(/C)C1=C(C)C(=O)C(C)=C[C@]1(C)C1=C(C)C(=O)C(C)=C(OC)O1

InChI Identifier

InChI=1S/C25H32O5/c1-10-19(26)13(2)11-14(3)20-16(5)21(27)15(4)12-25(20,8)23-17(6)22(28)18(7)24(29-9)30-23/h11-13H,10H2,1-9H3/b14-11+/t13-,25-/m0/s1

InChI Key

WKECBESDKQBOQM-UAKQWYECSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Elysia crispata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Alkyl aryl ether
Pyranone
Pyran
Heteroaromatic compound
Vinylogous ester
Ketone
Cyclic ketone
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	5.29	ChemAxon
pKa (Strongest Acidic)	16.27	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	131.34 m³·mol⁻¹	ChemAxon
Polarizability	45.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163187163

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one (NP0219081)

MOL for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

3D MOL for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

3D SDF for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

3D-SDF for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

PDB for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

3D PDB for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

SMILES for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

INCHI for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

Structure for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)

3D Structure for NP0219081 (2-methoxy-3,5-dimethyl-6-[(1s)-1,3,5-trimethyl-2-[(2e,4s)-4-methyl-5-oxohept-2-en-2-yl]-4-oxocyclohexa-2,5-dien-1-yl]pyran-4-one)