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Showing NP-Card for (2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid (NP0226697)

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Record Information
Version2.0
Created at2022-09-06 05:49:23 UTC
Updated at2022-09-06 05:49:23 UTC
NP-MRD IDNP0226697
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid
Description (2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid is found in Electranthera mutica.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)


  Mrv1652309062207492D          

 24 26  0  0  0  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -1.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141    0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    0.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088    1.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3569    0.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1694    0.2898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747   -0.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -1.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676   -1.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8855   -2.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -3.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -2.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  9 24  1  0  0  0  0
  4 24  1  0  0  0  0
M  END
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3D MOL for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)

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3D SDF for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)

  Mrv1652309062207492D          

 24 26  0  0  0  0            999 V2000
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -1.0585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.1400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0141    0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8266    0.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088    1.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3569    0.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1694    0.2898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747   -0.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623   -0.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9801   -1.5472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676   -1.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8855   -2.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158   -3.0977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -2.6090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  9 24  1  0  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226697

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC1(C)C(O)(C2)C1=CC(O)=C(O)C=C1\C=C\C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-17(2)12-6-7-18(17,3)19(24,10-12)13-9-15(21)14(20)8-11(13)4-5-16(22)23/h4-5,8-9,12,20-21,24H,6-7,10H2,1-3H3,(H,22,23)/b5-4+

> <INCHI_KEY>
KQXBAAPBTURYGB-SNAWJCMRSA-N

> <FORMULA>
C19H24O5

> <MOLECULAR_WEIGHT>
332.396

> <EXACT_MASS>
332.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.36922859625474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid

> <JCHEM_LOGP>
3.1934095159999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.180425791732576

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.104623186842862

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4079365800331

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
90.78019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)
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PDB for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.389   0.683   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864   0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.389  -0.201   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.249   1.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.916   1.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.916  -0.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.249  -1.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.249  -2.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.583  -0.529   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.110  -1.976   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.100  -0.261   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.626   1.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.143   1.453   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.670   2.900   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.133   0.274   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.649   0.541   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.606  -1.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.090  -1.441   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.563  -2.888   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.046  -3.156   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.520  -4.603   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.509  -5.782   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.003  -4.870   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.583   1.011   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   24                                             
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

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3D PDB for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)
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SMILES for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)
CC1(C)C2CCC1(C)C(O)(C2)C1=CC(O)=C(O)C=C1\C=C\C(O)=O
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INCHI for NP0226697 ((2e)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid)
InChI=1S/C19H24O5/c1-17(2)12-6-7-18(17,3)19(24,10-12)13-9-15(21)14(20)8-11(13)4-5-16(22)23/h4-5,8-9,12,20-21,24H,6-7,10H2,1-3H3,(H,22,23)/b5-4+
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SynonymsNot Available
Chemical FormulaC19H24O5
Average Mass332.3960 Da
Monoisotopic Mass332.16237 Da
IUPAC Name(2E)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid
Traditional Name(2E)-3-(4,5-dihydroxy-2-{2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}phenyl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
CC1(C)C2CCC1(C)C(O)(C2)C1=CC(O)=C(O)C=C1\C=C\C(O)=O
InChI Identifier
InChI=1S/C19H24O5/c1-17(2)12-6-7-18(17,3)19(24,10-12)13-9-15(21)14(20)8-11(13)4-5-16(22)23/h4-5,8-9,12,20-21,24H,6-7,10H2,1-3H3,(H,22,23)/b5-4+
InChI KeyKQXBAAPBTURYGB-SNAWJCMRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coreopsis muticaLOTUS Database
Chemical Taxonomy
ClassificationNot classified
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
logP3.19ChemAxon
pKa (Strongest Acidic)4.1ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.78 m³·mol⁻¹ChemAxon
Polarizability35.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External LinksNot Available
References
General References
  1. LOTUS database [Link]