NP-MRD: Showing NP-Card for 3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione (NP0244992)

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Record Information

Version

1.0

Created at

2022-09-07 05:55:00 UTC

Updated at

2022-09-07 05:55:00 UTC

NP-MRD ID

NP0244992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

Description

AC1L1GHZ belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. 3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione is found in Dactylospongia elegans, Dysidea arenaria and Verongula rigida. AC1L1GHZ is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161505422D          

 26 28  0  0  0  0            999 V2000
    1.9411    3.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    2.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8465    2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    2.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    3.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0946    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    1.8960    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  1  0  0  0  0
M  END


  Mrv1533004161505422D          

 26 28  0  0  0  0            999 V2000
    1.9411    3.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590    2.4690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8465    2.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3162    2.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    2.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266    3.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5643    1.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0946    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909    1.8960    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  2  0  0  0  0
  8 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
  7 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(O)=C(CC2(C)C(C)CCC3(C)C2CCCC3=C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3

> <INCHI_KEY>
JJWITJNSXCXULM-UHFFFAOYSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.50201898186398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.367249087666668

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.868666424764576

> <JCHEM_PKA_STRONGEST_BASIC>
-4.944412504654549

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
104.14519999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-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       3.623   6.056   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.097   4.609   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.580   4.341   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.590   5.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.926   5.254   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.916   6.433   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.453   3.807   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.463   2.627   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.990   1.180   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.990   1.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.053   2.894   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.043   1.715   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.970   3.539   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   18                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   10   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
CONECT   24    8    3   25                                                  
CONECT   25   24                                                            
CONECT   26    7                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

3-[(1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(O)=C(CC2(C)C(C)CCC3(C)C2CCCC3=C)C1=O

InChI Identifier

InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3

InChI Key

JJWITJNSXCXULM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dactylospongia elegans	LOTUS Database	35616633
Dysidea arenaria	LOTUS Database	35616633
Verongula rigida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic 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	3.89	ALOGPS
logP	4.37	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	5.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.15 m³·mol⁻¹	ChemAxon
Polarizability	39.5 Å³	ChemAxon
Number of Rings	3	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

3691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione (NP0244992)

MOL for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D MOL for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D SDF for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D-SDF for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

PDB for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D PDB for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

SMILES for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

INCHI for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

Structure for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)

3D Structure for NP0244992 (3-[(1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione)