NP-MRD: Showing NP-Card for 11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one (NP0273927)

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Record Information

Version

2.0

Created at

2022-09-08 21:07:51 UTC

Updated at

2022-09-08 21:07:51 UTC

NP-MRD ID

NP0273927

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one

Description

11-Hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]Tetradec-9-en-5-one belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one is found in Warionia saharae. 11-Hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]Tetradec-9-en-5-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161518452D          

 19 22  0  0  0  0            999 V2000
    0.7798    2.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    2.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525    2.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8669    2.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9897    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284    0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8300    0.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6395    0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442   -0.3443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7382    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6057    0.8401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1009    0.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -0.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3243    0.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3492    1.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8629    0.8331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411    1.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    1.6447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  5 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273927

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2C(OC(=O)C2=C)C2C3(C)CC(O3)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-7-4-5-9-8(2)13(16)18-11(9)12-14(3)6-10(19-14)15(7,12)17/h4,9-12,17H,2,5-6H2,1,3H3

> <INCHI_KEY>
LDGHSQJVMCMJNB-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.629825047719493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.1291484753333332

> <ALOGPS_LOGS>
-1.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.944439211187845

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6979022890264366

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
67.9018

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one

> <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       1.456   5.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.584   4.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.018   4.875   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.352   4.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.581   2.582   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.533   1.453   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.283   0.108   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.794   0.405   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.922  -0.643   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.978   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.323   2.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.997   1.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.055   0.350   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.487  -1.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.605   0.870   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.652   2.409   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.611   1.555   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.130   2.841   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.653   3.070   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13   18                                                  
CONECT   13   12   14   15   17                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   13                                                       
CONECT   18   16    2   12   19                                             
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one

Traditional Name

11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one

CAS Registry Number

Not Available

SMILES

CC1=CCC2C(OC(=O)C2=C)C2C3(C)CC(O3)C12O

InChI Identifier

InChI=1S/C15H18O4/c1-7-4-5-9-8(2)13(16)18-11(9)12-14(3)6-10(19-14)15(7,12)17/h4,9-12,17H,2,5-6H2,1,3H3

InChI Key

LDGHSQJVMCMJNB-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Warionia saharae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Oxetane
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
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	1.22	ALOGPS
logP	1.13	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.9 m³·mol⁻¹	ChemAxon
Polarizability	27.63 Å³	ChemAxon
Number of Rings	4	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

75072242

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one (NP0273927)

MOL for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

3D MOL for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

3D SDF for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

3D-SDF for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

PDB for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

3D PDB for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

SMILES for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

INCHI for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

Structure for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)

3D Structure for NP0273927 (11-hydroxy-1,10-dimethyl-6-methylidene-4,13-dioxatetracyclo[10.1.1.0²,¹¹.0³,⁷]tetradec-9-en-5-one)