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Showing NP-Card for (-)-Blechnic acid (NP0050430)

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Record Information
Version2.0
Created at2022-04-27 21:36:30 UTC
Updated at2022-04-27 21:36:30 UTC
NP-MRD IDNP0050430
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Blechnic acid
DescriptionBlechnic acid, also known as blechnate, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (-)-Blechnic acid is found in Blechnum orientale , Brainea insignis, Struthiopteris amabilis, Struthiopteris niponica, Woodwardia orientalis and Woodwardia prolifera. (-)-Blechnic acid was first documented in 2003 (PMID: 12620363). Based on a literature review very few articles have been published on Blechnic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050430 ((-)-Blechnic acid)


  Mrv1652304272223362D          

 26 28  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
Download

3D MOL for NP0050430 ((-)-Blechnic acid)

Download
3D SDF for NP0050430 ((-)-Blechnic acid)

  Mrv1652304272223362D          

 26 28  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    2.9519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.7771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    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
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  1  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C\C1=C2[C@H]([C@H](OC2=C(O)C=C1)C1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H14O8/c19-10-4-2-9(7-12(10)21)16-15(18(24)25)14-8(3-6-13(22)23)1-5-11(20)17(14)26-16/h1-7,15-16,19-21H,(H,22,23)(H,24,25)/b6-3+/t15-,16-/m1/s1

> <INCHI_KEY>
GJHXGOBGPWPCCK-HFPBVCCTSA-N

> <FORMULA>
C18H14O8

> <MOLECULAR_WEIGHT>
358.302

> <EXACT_MASS>
358.068867411

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.196666812944144

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.2704996963333333

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.76104790398423

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0715363171095107

> <JCHEM_PKA_STRONGEST_BASIC>
-4.967437603600877

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
89.1441

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050430 ((-)-Blechnic acid)
Download
PDB for NP0050430 ((-)-Blechnic acid)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.680  -1.012   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.143  -0.188   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.090   1.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.630   1.509   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.400   2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.400   5.510   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.940   2.843   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.590  -2.547   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924  -3.317   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.257  -3.317   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Download
3D PDB for NP0050430 ((-)-Blechnic acid)
Download
SMILES for NP0050430 ((-)-Blechnic acid)
OC(=O)\C=C\C1=C2[C@H]([C@H](OC2=C(O)C=C1)C1=CC=C(O)C(O)=C1)C(O)=O
Download
INCHI for NP0050430 ((-)-Blechnic acid)
InChI=1S/C18H14O8/c19-10-4-2-9(7-12(10)21)16-15(18(24)25)14-8(3-6-13(22)23)1-5-11(20)17(14)26-16/h1-7,15-16,19-21H,(H,22,23)(H,24,25)/b6-3+/t15-,16-/m1/s1
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Synonyms
ValueSource
BlechnateGenerator
Chemical FormulaC18H14O8
Average Mass358.3020 Da
Monoisotopic Mass358.06887 Da
IUPAC Name(2S,3R)-4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
Traditional Name(2S,3R)-4-[(1E)-2-carboxyeth-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C\C1=C2[C@H]([C@H](OC2=C(O)C=C1)C1=CC=C(O)C(O)=C1)C(O)=O
InChI Identifier
InChI=1S/C18H14O8/c19-10-4-2-9(7-12(10)21)16-15(18(24)25)14-8(3-6-13(22)23)1-5-11(20)17(14)26-16/h1-7,15-16,19-21H,(H,22,23)(H,24,25)/b6-3+/t15-,16-/m1/s1
InChI KeyGJHXGOBGPWPCCK-HFPBVCCTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Blechnum orientalePlant
Brainea insignisPlant
Struthiopteris amabilis-
Struthiopteris niponica-
Woodwardia orientalisPlant
Woodwardia proliferaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
Class2-arylbenzofuran flavonoids  
Sub ClassNot Available
Direct Parent2-arylbenzofuran flavonoids  
Alternative Parents
Substituents
  • 2-arylbenzofuran flavonoid
    • 

  • Cinnamic acid
    • 

  • Cinnamic acid or derivatives
    • 

  • Coumaric acid or derivatives
    • 

  • Coumaran
    • 

  • Catechol
    • 

  • Styrene
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.71ALOGPS
logP2.27ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.14 m³·mol⁻¹ChemAxon
Polarizability34.2 ųChemAxon
Number of Rings3ChemAxon
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 IDC00000623  
Chemspider ID8491790  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10316325  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Davin LB, Wang CZ, Helms GL, Lewis NG: [13C]-Specific labeling of 8-2' linked (-)-cis-blechnic, (-)-trans-blechnic and (-)-brainic acids in the fern Blechnum spicant. Phytochemistry. 2003 Feb;62(3):501-11. doi: 10.1016/s0031-9422(02)00540-x. [PubMed:12620363  ]