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Showing NP-Card for methyl 4-(hydroxymethyl)azulene-1-carboxylate (NP0291393)

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Record Information
Version1.0
Created at2022-09-09 22:27:58 UTC
Updated at2022-09-09 22:27:59 UTC
NP-MRD IDNP0291393
Secondary Accession NumbersNone
Natural Product Identification
Common Namemethyl 4-(hydroxymethyl)azulene-1-carboxylate
DescriptionMethyl 4-(hydroxymethyl)azulene-1-carboxylate belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring. methyl 4-(hydroxymethyl)azulene-1-carboxylate is found in Calypogeia azurea. Methyl 4-(hydroxymethyl)azulene-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)


  Mrv1533004151518412D          

 16 17  0  0  0  0            999 V2000
   -0.3602   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -2.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017   -2.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537   -3.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    0.9983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    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
  3  4  2  0  0  0  0
  3  5  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 16  2  0  0  0  0
  8 16  1  0  0  0  0
M  END
Download

3D MOL for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    4.7643    0.5511    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3606    0.3858    0.1064 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7251   -0.8244    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4787   -1.8515    0.2631 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835   -1.0130    0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871   -2.2102    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7560   -2.0217    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9939   -0.6931    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571   -0.1335    0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3862   -1.0536   -0.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6033   -0.3848   -0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    1.2133    0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7018    2.3018    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3153    2.3316    0.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632    1.3224   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3230   -0.0370    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -0.1070   -0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1117    0.3887    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9451    1.6318   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -3.1541    0.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -2.7556    0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -1.8740    0.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2799   -1.5700   -1.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6822    0.0119   -1.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574    1.4624   -0.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1792    3.2378    0.6701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1457    3.2845    0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5315    1.5605   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12  9  1  0
  9 10  1  0
 10 11  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  8 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 15 28  1  0
 14 27  1  0
 13 26  1  0
 12 25  1  0
 10 22  1  0
 10 23  1  0
 11 24  1  0
  7 21  1  0
  6 20  1  0
M  END
Download

3D SDF for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)


  Mrv1533004151518412D          

 16 17  0  0  0  0            999 V2000
   -0.3602   -3.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053   -2.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017   -2.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537   -3.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566   -0.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -0.5636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    0.9983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485   -0.9761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906   -1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863   -1.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.3886    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
  3  4  2  0  0  0  0
  3  5  1  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 16  2  0  0  0  0
  8 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291393

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2C=CC=CC(CO)=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O3/c1-16-13(15)12-7-6-10-9(8-14)4-2-3-5-11(10)12/h2-7,14H,8H2,1H3

> <INCHI_KEY>
DEUFUBQEEUFSGW-UHFFFAOYSA-N

> <FORMULA>
C13H12O3

> <MOLECULAR_WEIGHT>
216.236

> <EXACT_MASS>
216.078644246

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.190246400285517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-(hydroxymethyl)azulene-1-carboxylate

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.198849769333333

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.137252788883565

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7387656301423293

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
61.34940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-(hydroxymethyl)azulene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)

Download
PDB for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)
HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      -0.672  -6.317   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.197  -4.853   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.310  -4.533   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.340  -5.677   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.786  -3.068   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.881  -1.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.786  -0.576   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.250  -1.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.454  -0.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.112   1.409   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.640   1.863   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.956  -0.435   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.624  -1.822   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.956  -3.210   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.454  -3.552   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.250  -2.592   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5    8                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

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3D PDB for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)
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SMILES for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)
COC(=O)C1=C2C=CC=CC(CO)=C2C=C1
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INCHI for NP0291393 (methyl 4-(hydroxymethyl)azulene-1-carboxylate)
InChI=1S/C13H12O3/c1-16-13(15)12-7-6-10-9(8-14)4-2-3-5-11(10)12/h2-7,14H,8H2,1H3
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View in JSmol
Synonyms
ValueSource
Methyl 4-(hydroxymethyl)azulene-1-carboxylic acidGenerator
Chemical FormulaC13H12O3
Average Mass216.2360 Da
Monoisotopic Mass216.07864 Da
IUPAC Namemethyl 4-(hydroxymethyl)azulene-1-carboxylate
Traditional Namemethyl 4-(hydroxymethyl)azulene-1-carboxylate
CAS Registry NumberNot Available
SMILES
COC(=O)C1=C2C=CC=CC(CO)=C2C=C1
InChI Identifier
InChI=1S/C13H12O3/c1-16-13(15)12-7-6-10-9(8-14)4-2-3-5-11(10)12/h2-7,14H,8H2,1H3
InChI KeyDEUFUBQEEUFSGW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Calypogeia azureaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as azulenes. These are polycyclic aromatic compounds containing the azulene skeleton, which consists of the cyclopentadiene ring fused to a cycloheptadiene ring.
KingdomOrganic compounds  
Super ClassHydrocarbons  
ClassUnsaturated hydrocarbons  
Sub ClassOlefins  
Direct ParentAzulenes  
Alternative Parents
Substituents
  • Azulene
    • 

  • Methyl ester
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic alcohol
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
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
logP1.87ALOGPS
logP2.2ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.14ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity61.35 m³·mol⁻¹ChemAxon
Polarizability23.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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 Compound85822405  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]