NP-MRD: Showing NP-Card for (11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol (NP0321952)

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Record Information

Version

2.0

Created at

2022-09-12 00:26:22 UTC

Updated at

2022-09-12 00:26:22 UTC

NP-MRD ID

NP0321952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol

Description

(11R,13R,14R)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]Pentadeca-1,3(8),4,6-tetraene-5,13-diol belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. (11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol is found in Givotia madagascariensis. Based on a literature review very few articles have been published on (11R,13R,14R)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]Pentadeca-1,3(8),4,6-tetraene-5,13-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122202262D          

 21 23  0  0  1  0            999 V2000
    5.8461    2.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    2.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647    2.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742    1.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.8219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378    1.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897    1.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014    1.3830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0034    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178    2.1873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3705    2.4305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226    2.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3649    3.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989    3.4826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109    2.5053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3253    3.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503    3.1503    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 10  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC2=CC3=C(CC[C@H]2C(C)(C)[C@@H]1O)C=C(C)C(O)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O2/c1-11-7-13-5-6-16-15(9-14(13)10-17(11)20)8-12(2)18(21)19(16,3)4/h7,9-10,12,16,18,20-21H,5-6,8H2,1-4H3/t12-,16-,18-/m1/s1

> <INCHI_KEY>
VXNHAUUBOYBIGK-XHBKTUGNSA-N

> <FORMULA>
C19H26O2

> <MOLECULAR_WEIGHT>
286.415

> <EXACT_MASS>
286.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
33.887045716891365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11R,13R,14R)-6,12,12,14-tetramethyltricyclo[9.4.0.0^{3,8}]pentadeca-1,3(8),4,6-tetraene-5,13-diol

> <JCHEM_LOGP>
4.477722869000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.077357135976587

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5379820346261331

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
87.52109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11R,13R,14R)-6,12,12,14-tetramethyltricyclo[9.4.0.0^{3,8}]pentadeca-1,3(8),4,6-tetraene-5,13-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.913   4.537   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.441   4.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.312   5.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.841   4.677   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.498   3.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.627   2.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.099   2.582   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.227   1.534   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.111   2.507   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.723   3.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.594   2.128   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.123   2.582   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.006   1.534   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.780   4.083   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.692   4.537   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.909   5.130   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.681   6.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.611   6.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.380   4.677   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.341   5.881   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.881   5.881   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₂

Average Mass

286.4150 Da

Monoisotopic Mass

286.19328 Da

IUPAC Name

(11R,13R,14R)-6,12,12,14-tetramethyltricyclo[9.4.0.0^{3,8}]pentadeca-1,3(8),4,6-tetraene-5,13-diol

Traditional Name

(11R,13R,14R)-6,12,12,14-tetramethyltricyclo[9.4.0.0^{3,8}]pentadeca-1,3(8),4,6-tetraene-5,13-diol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC2=CC3=C(CC[C@H]2C(C)(C)[C@@H]1O)C=C(C)C(O)=C3

InChI Identifier

InChI=1S/C19H26O2/c1-11-7-13-5-6-16-15(9-14(13)10-17(11)20)8-12(2)18(21)19(16,3)4/h7,9-10,12,16,18,20-21H,5-6,8H2,1-4H3/t12-,16-,18-/m1/s1

InChI Key

VXNHAUUBOYBIGK-XHBKTUGNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Givotia madagascariensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.48	ChemAxon
pKa (Strongest Acidic)	10.08	ChemAxon
pKa (Strongest Basic)	-0.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.52 m³·mol⁻¹	ChemAxon
Polarizability	33.89 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

163012218

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol (NP0321952)

MOL for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

3D MOL for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

3D SDF for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

3D-SDF for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

PDB for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

3D PDB for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

SMILES for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

INCHI for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

Structure for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)

3D Structure for NP0321952 ((11r,13r,14r)-6,12,12,14-tetramethyltricyclo[9.4.0.0³,⁸]pentadeca-1,3(8),4,6-tetraene-5,13-diol)