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Showing NP-Card for Sphagnum acid (NP0051575)

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Record Information
Version2.0
Created at2022-04-27 22:53:18 UTC
Updated at2022-04-27 22:53:18 UTC
NP-MRD IDNP0051575
Secondary Accession NumbersNone
Natural Product Identification
Common NameSphagnum acid
DescriptionSphagnum acid belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Sphagnum acid is found in Sphagnum megallanicum. Sphagnum acid was first documented in 2009 (PMID: 19413769). Based on a literature review a small amount of articles have been published on Sphagnum acid (PMID: 31555245) (PMID: 28729228).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051575 (Sphagnum acid)


  Mrv1652304282200532D          

 16 16  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
Download

3D MOL for NP0051575 (Sphagnum acid)

     RDKit          3D

 26 26  0  0  0  0  0  0  0  0999 V2000
   -3.6394   -1.0732   -0.4624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6778   -1.8256   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0151   -3.1940   -0.1919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3041   -1.4050   -0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8145   -0.1928   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    0.9668   -0.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9190    1.8017    0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291    2.6343    1.1410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1342    1.6344    1.3801 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6416    0.0393   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5193   -0.9544    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8959   -0.7832    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893    0.4621    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7796    0.6790    0.1581 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    1.4965   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1974    1.2725   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306   -3.6217   -0.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5796   -2.2273   -0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177    1.6634   -1.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451    0.6603   -1.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2273    0.9947    2.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -1.9342    0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209   -1.6092    0.6724 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3998   -0.0422    0.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976    2.4715   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5819    2.0864   -0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 10  1  0
  9 21  1  0
  6 19  1  0
  6 20  1  0
  4 18  1  0
  3 17  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
 15 25  1  0
 16 26  1  0
M  END
Download

3D SDF for NP0051575 (Sphagnum acid)


  Mrv1652304282200532D          

 16 16  0  0  0  0            999 V2000
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C\C(=C/C(O)=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O5/c12-9-3-1-7(2-4-9)8(5-10(13)14)6-11(15)16/h1-5,12H,6H2,(H,13,14)(H,15,16)/b8-5+

> <INCHI_KEY>
VOWYJJSQRYBVGK-VMPITWQZSA-N

> <FORMULA>
C11H10O5

> <MOLECULAR_WEIGHT>
222.196

> <EXACT_MASS>
222.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.18386993810964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(4-hydroxyphenyl)pent-2-enedioic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.2562424433333335

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.210428111013096

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.491665072562529

> <JCHEM_PKA_STRONGEST_BASIC>
-5.964039482347585

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
55.589200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sphagnum acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0051575 (Sphagnum acid)

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PDB for NP0051575 (Sphagnum acid)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

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3D PDB for NP0051575 (Sphagnum acid)
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SMILES for NP0051575 (Sphagnum acid)
OC(=O)C\C(=C/C(O)=O)C1=CC=C(O)C=C1
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INCHI for NP0051575 (Sphagnum acid)
InChI=1S/C11H10O5/c12-9-3-1-7(2-4-9)8(5-10(13)14)6-11(15)16/h1-5,12H,6H2,(H,13,14)(H,15,16)/b8-5+
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H10O5
Average Mass222.1960 Da
Monoisotopic Mass222.05282 Da
IUPAC Name(2E)-3-(4-hydroxyphenyl)pent-2-enedioic acid
Traditional Namesphagnum acid
CAS Registry NumberNot Available
SMILES
OC(=O)C\C(=C/C(O)=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C11H10O5/c12-9-3-1-7(2-4-9)8(5-10(13)14)6-11(15)16/h1-5,12H,6H2,(H,13,14)(H,15,16)/b8-5+
InChI KeyVOWYJJSQRYBVGK-VMPITWQZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Sphagnum megallanicumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentHydroxycinnamic acids  
Alternative Parents
Substituents
  • Cinnamic acid
    • 

  • Coumaric acid
    • 

  • Coumaric acid or derivatives
    • 

  • Hydroxycinnamic acid
    • 

  • 3-phenylpropanoic-acid
    • 

  • Styrene
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Monocyclic benzene moiety
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP1.46ALOGPS
logP1.26ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.49ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.59 m³·mol⁻¹ChemAxon
Polarizability21.18 ųChemAxon
Number of Rings1ChemAxon
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 IDC00002779  
Chemspider ID4445107  
KEGG Compound IDC10496  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281795  
PDB IDNot Available
ChEBI ID9220  
Good Scents IDNot Available
References
General References
  1. Hamard S, Robroek BJM, Allard PM, Signarbieux C, Zhou S, Saesong T, de Baaker F, Buttler A, Chiapusio G, Wolfender JL, Bragazza L, Jassey VEJ: Effects of Sphagnum Leachate on Competitive Sphagnum Microbiome Depend on Species and Time. Front Microbiol. 2019 Sep 6;10:2042. doi: 10.3389/fmicb.2019.02042. eCollection 2019. [PubMed:31555245  ] 
  2. Drobnik J, Stebel A: Tangled history of the European uses of Sphagnum moss and sphagnol. J Ethnopharmacol. 2017 Sep 14;209:41-49. doi: 10.1016/j.jep.2017.07.025. Epub 2017 Jul 18. [PubMed:28729228  ] 
  3. Mellegard H, Stalheim T, Hormazabal V, Granum PE, Hardy SP: Antibacterial activity of sphagnum acid and other phenolic compounds found in Sphagnum papillosum against food-borne bacteria. Lett Appl Microbiol. 2009 Jul;49(1):85-90. doi: 10.1111/j.1472-765X.2009.02622.x. Epub 2009 Apr 22. [PubMed:19413769  ]