NP-MRD: Showing NP-Card for 4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone (NP0244614)

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Record Information

Version

2.0

Created at

2022-09-07 05:27:39 UTC

Updated at

2022-09-07 05:27:39 UTC

NP-MRD ID

NP0244614

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone

Description

4,4'-Dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. 4,4'-Dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500182D          

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M  END

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  Mrv1533004171500182D          

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 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 24 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  2  0  0  0  0
 23 35  1  0  0  0  0
 14 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)C1=C(O)C(=O)C(C)=C(C1=O)C1=C(C)C(=O)C(O)=C(C(C)CCC=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O6/c1-15(2)11-9-13-17(5)21-27(33)23(19(7)25(31)29(21)35)24-20(8)26(32)30(36)22(28(24)34)18(6)14-10-12-16(3)4/h11-12,17-18,35-36H,9-10,13-14H2,1-8H3

> <INCHI_KEY>
QFOBPJPOYMETCQ-UHFFFAOYSA-N

> <FORMULA>
C30H38O6

> <MOLECULAR_WEIGHT>
494.628

> <EXACT_MASS>
494.266838944

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
55.7438065197326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-5-[4-hydroxy-2-methyl-5-(6-methylhept-5-en-2-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]-6-methyl-3-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
6.813956036

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.281957696882795

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.61501935666126

> <JCHEM_PKA_STRONGEST_BASIC>
-5.140580013292937

> <JCHEM_POLAR_SURFACE_AREA>
108.74

> <JCHEM_REFRACTIVITY>
147.0352

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-5-[4-hydroxy-2-methyl-5-(6-methylhept-5-en-2-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]-6-methyl-3-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   36                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16                                                            
CONECT   18   15   19   33                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   35                                                  
CONECT   24   23   25   33                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   24   18   34                                                  
CONECT   34   33                                                            
CONECT   35   23                                                            
CONECT   36   14                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₈O₆

Average Mass

494.6280 Da

Monoisotopic Mass

494.26684 Da

IUPAC Name

2-hydroxy-5-[4-hydroxy-2-methyl-5-(6-methylhept-5-en-2-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]-6-methyl-3-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione

Traditional Name

2-hydroxy-5-[4-hydroxy-2-methyl-5-(6-methylhept-5-en-2-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl]-6-methyl-3-(6-methylhept-5-en-2-yl)cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C)C1=C(O)C(=O)C(C)=C(C1=O)C1=C(C)C(=O)C(O)=C(C(C)CCC=C(C)C)C1=O

InChI Identifier

InChI=1S/C30H38O6/c1-15(2)11-9-13-17(5)21-27(33)23(19(7)25(31)29(21)35)24-20(8)26(32)30(36)22(28(24)34)18(6)14-10-12-16(3)4/h11-12,17-18,35-36H,9-10,13-14H2,1-8H3

InChI Key

QFOBPJPOYMETCQ-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Prenylbenzoquinone
Quinone
P-benzoquinone
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	4.05	ALOGPS
logP	6.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	5.62	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.74 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	147.04 m³·mol⁻¹	ChemAxon
Polarizability	55.74 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone (NP0244614)

MOL for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

3D MOL for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

3D SDF for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

3D-SDF for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

PDB for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

3D PDB for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

SMILES for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

INCHI for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

Structure for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)

3D Structure for NP0244614 (4,4'-dihydroxy-6,6'-dimethyl-3,3'-bis(6-methylhept-5-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),1'(6'),3,3'-tetraene-2,2',5,5'-tetrone)