NP-MRD: Showing NP-Card for 2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione (NP0251324)

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Record Information

Version

2.0

Created at

2022-09-07 14:29:13 UTC

Updated at

2022-09-07 14:29:13 UTC

NP-MRD ID

NP0251324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione

Description

2-Methyl-6-(3-methyl-7-{[4-(4-methylpent-3-en-1-yl)-5-oxo-2,5-dihydrofuran-2-yl]methyl}octa-2,6-dien-1-yl)cyclohexa-2,5-diene-1,4-dione belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione is found in Sargassum sagamianum. 2-Methyl-6-(3-methyl-7-{[4-(4-methylpent-3-en-1-yl)-5-oxo-2,5-dihydrofuran-2-yl]methyl}octa-2,6-dien-1-yl)cyclohexa-2,5-diene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508142D          

 31 32  0  0  0  0            999 V2000
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2398   -6.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9849   -7.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4698   -8.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2903   -8.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7752   -8.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5957   -8.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0806   -9.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9011   -9.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3860   -9.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2065   -9.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6914  -10.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5119  -10.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9968  -11.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8173  -10.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6612  -11.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8408  -11.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5052  -12.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3558  -11.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5354  -11.2892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2366   -8.4470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6258   -7.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599   -7.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9049   -6.6724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1203   -6.4175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  8 28  1  0  0  0  0
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  6 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004161508142D          

 31 32  0  0  0  0            999 V2000
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0251324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC1=CC(CC(C)=CCCC(C)=CCC2=CC(=O)C=C(C)C2=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O4/c1-18(2)8-6-11-23-17-25(31-27(23)30)14-20(4)10-7-9-19(3)12-13-22-16-24(28)15-21(5)26(22)29/h8,10,12,15-17,25H,6-7,9,11,13-14H2,1-5H3

> <INCHI_KEY>
PRJQMQHHBMRRQA-UHFFFAOYSA-N

> <FORMULA>
C27H34O4

> <MOLECULAR_WEIGHT>
422.565

> <EXACT_MASS>
422.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.5699841792147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2,5-dihydrofuran-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
6.868189214999999

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.660684636841072

> <JCHEM_PKA_STRONGEST_BASIC>
-6.836878318591299

> <JCHEM_POLAR_SURFACE_AREA>
60.440000000000005

> <JCHEM_REFRACTIVITY>
130.09289999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2H-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.914 -12.455   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.438 -13.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.344 -15.166   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.875 -15.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.780 -16.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.312 -16.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.217 -17.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.749 -17.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.654 -18.420   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.185 -18.259   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.091 -19.505   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.622 -19.344   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.527 -20.590   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      22.059 -20.429   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.901 -21.997   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.369 -22.158   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.743 -23.565   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.464 -20.912   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      15.933 -21.073   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      15.375 -15.768   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.502 -13.598   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.898 -13.920   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.423 -12.455   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.958 -11.979   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17   25                                                  
CONECT   25   24                                                            
CONECT   26   14                                                            
CONECT   27   10                                                            
CONECT   28    8   29                                                       
CONECT   29   28    6   30                                                  
CONECT   30   29                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₄

Average Mass

422.5650 Da

Monoisotopic Mass

422.24571 Da

IUPAC Name

2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2,5-dihydrofuran-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2H-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC1=CC(CC(C)=CCCC(C)=CCC2=CC(=O)C=C(C)C2=O)OC1=O

InChI Identifier

InChI=1S/C27H34O4/c1-18(2)8-6-11-23-17-25(31-27(23)30)14-20(4)10-7-9-19(3)12-13-22-16-24(28)15-21(5)26(22)29/h8,10,12,15-17,25H,6-7,9,11,13-14H2,1-5H3

InChI Key

PRJQMQHHBMRRQA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sargassum sagamianum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Prenylbenzoquinone
P-benzoquinone
Quinone
2-furanone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	5.79	ALOGPS
logP	6.87	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	130.09 m³·mol⁻¹	ChemAxon
Polarizability	49.57 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

74051840

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione (NP0251324)

MOL for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

PDB for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

SMILES for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

INCHI for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

Structure for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0251324 (2-{3,7-dimethyl-8-[4-(4-methylpent-3-en-1-yl)-5-oxo-2h-furan-2-yl]octa-2,6-dien-1-yl}-6-methylcyclohexa-2,5-diene-1,4-dione)