NP-MRD: Showing NP-Card for 1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one (NP0324248)

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Record Information

Version

2.0

Created at

2022-09-12 04:12:28 UTC

Updated at

2022-09-12 04:12:28 UTC

NP-MRD ID

NP0324248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one

Description

1-{4,12-Dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]Dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one belongs to the class of organic compounds known as xeniaphyllane and xenicane diterpenoids. These are diterpenoids with a structure based either on the xeniaphyllane or the xenicane skeleton. 1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one is found in Sinularia gibberosa. 1-{4,12-Dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]Dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251506592D          

 24 26  0  0  0  0            999 V2000
    7.0694    2.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7069    2.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3445    1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2306    2.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0445    2.6345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1833    1.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3694    1.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8458    0.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1361    0.2190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972    0.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666    1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    2.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179    1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    0.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666    0.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291    1.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241    0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509    1.5126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773    2.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    2.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    3.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326    2.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4562    3.4222    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  2  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
 13 14  1  0  0  0  0
 10 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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0324248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(CO)C=CC(=O)C1(C)CC2C1CCC1(C)OC1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-13-5-6-17-20(4,24-17)10-7-15-14(13)11-19(15,3)16(22)8-9-18(2,23)12-21/h8-9,14-15,17,21,23H,1,5-7,10-12H2,2-4H3

> <INCHI_KEY>
JDMFCROXXFSLJV-UHFFFAOYSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.484182365426705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.6522445763333335

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.311480362821833

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.750946764852127

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0871676247165416

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
94.17779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      13.196   4.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.386   3.979   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.576   3.002   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      15.364   5.169   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.883   4.918   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      13.409   2.789   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.890   3.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.912   1.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.454   0.409   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.393   2.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.141   0.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.644   3.621   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.125   3.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.873   2.353   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.704   1.351   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.164   1.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.974   2.312   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.218   0.970   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.522   2.824   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.691   3.826   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.447   5.168   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.888   5.709   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.341   5.198   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.318   6.388   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   14                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   23                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   17   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   13   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one

Traditional Name

1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(O)(CO)C=CC(=O)C1(C)CC2C1CCC1(C)OC1CCC2=C

InChI Identifier

InChI=1S/C20H30O4/c1-13-5-6-17-20(4,24-17)10-7-15-14(13)11-19(15,3)16(22)8-9-18(2,23)12-21/h8-9,14-15,17,21,23H,1,5-7,10-12H2,2-4H3

InChI Key

JDMFCROXXFSLJV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sinularia gibberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xeniaphyllane and xenicane diterpenoids. These are diterpenoids with a structure based either on the xeniaphyllane or the xenicane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Xeniaphyllane and xenicane diterpenoids

Alternative Parents

Substituents

Xeniaphyllane diterpenoid
Fatty alcohol
Fatty acyl
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
1,2-diol
Ketone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Primary alcohol
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	2.19	ALOGPS
logP	2.65	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.18 m³·mol⁻¹	ChemAxon
Polarizability	37.48 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

74082903

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one (NP0324248)

MOL for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

3D MOL for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

3D SDF for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

3D-SDF for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

PDB for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

3D PDB for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

SMILES for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

INCHI for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

Structure for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)

3D Structure for NP0324248 (1-{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}-4,5-dihydroxy-4-methylpent-2-en-1-one)