Showing NP-Card for beta-Dolabrin (NP0057811)

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Record Information
Version2.0
Created at2022-04-28 03:11:38 UTC
Updated at2022-04-28 03:11:38 UTC
NP-MRD IDNP0057811
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-Dolabrin
DescriptionBeta-dolabrin belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. Thus, Beta-dolabrin is considered to be an isoprenoid lipid molecule. beta-Dolabrin is found in Cupressus spp., Cupressus torulosa, Juniperus spp., Thuja plicata and Thujopsis dolabrata. Beta-dolabrin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057811 (beta-Dolabrin)

  Mrv1533004251512082D          

 12 12  0  0  0  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861   -1.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746    0.0174    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
  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for NP0057811 (beta-Dolabrin)

     RDKit          3D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -2.5905   -1.0398    0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8087   -0.0036    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4173    1.3175   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3674   -0.1465    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429   -1.3358    0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -1.9716    0.3793 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4545   -1.3782   -0.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -0.0395   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7766    0.3029   -0.9365 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7916    1.0184   -0.3044 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3549    2.2807   -0.3770 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    0.9577   -0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971   -1.9972    0.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6511   -0.9215    0.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5185    1.2170   -0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0409    2.0375    0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.6262   -1.2666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4921   -1.8257    1.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3579   -3.0092    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2978   -2.0238   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7345    3.0687   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1292    1.8660   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 12  4  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  1 13  1  0
  1 14  1  0
  5 18  1  0
  6 19  1  0
  7 20  1  0
 11 21  1  0
 12 22  1  0
M  END
Download

3D SDF for NP0057811 (beta-Dolabrin)

  Mrv1533004251512082D          

 12 12  0  0  0  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861   -1.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8746    0.0174    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
  2  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057811

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-6H,1H2,2H3,(H,11,12)

> <INCHI_KEY>
ZXPADFNEYYDQFL-UHFFFAOYSA-N

> <FORMULA>
C10H10O2

> <MOLECULAR_WEIGHT>
162.188

> <EXACT_MASS>
162.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.238323501500297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-4-(prop-1-en-2-yl)cyclohepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.7148004596666664

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.173542331667146

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8409525841287904

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
51.32810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-(prop-1-en-2-yl)cyclohepta-2,4,6-trien-1-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0057811 (beta-Dolabrin)

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PDB for NP0057811 (beta-Dolabrin)
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       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.265   4.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.986   1.876   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.161  -2.216   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.211   1.876   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.633   0.032   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0057811 (beta-Dolabrin)
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SMILES for NP0057811 (beta-Dolabrin)
CC(=C)C1=CC=CC(=O)C(O)=C1
Download
INCHI for NP0057811 (beta-Dolabrin)
InChI=1S/C10H10O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-6H,1H2,2H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
b-DolabrinGenerator
Β-dolabrinGenerator
Chemical FormulaC10H10O2
Average Mass162.1880 Da
Monoisotopic Mass162.06808 Da
IUPAC Name2-hydroxy-4-(prop-1-en-2-yl)cyclohepta-2,4,6-trien-1-one
Traditional Name2-hydroxy-4-(prop-1-en-2-yl)cyclohepta-2,4,6-trien-1-one
CAS Registry NumberNot Available
SMILES
CC(=C)C1=CC=CC(=O)C(O)=C1
InChI Identifier
InChI=1S/C10H10O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-6H,1H2,2H3,(H,11,12)
InChI KeyZXPADFNEYYDQFL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cupressus spp.Plant
Cupressus torulosaLOTUS Database
Juniperus spp.Plant
Thuja plicataPlant
Thujopsis dolabrataPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.
KingdomOrganic compounds  
Super ClassHydrocarbon derivatives  
ClassTropones  
Sub ClassTropolones  
Direct ParentTropolones  
Alternative Parents
Substituents
  • Tropolone
    • 

  • Cyclic ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.58ALOGPS
logP1.71ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.17ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.33 m³·mol⁻¹ChemAxon
Polarizability17.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound188981  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available