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Showing NP-Card for Licarin B (NP0050464)

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Record Information
Version2.0
Created at2022-04-27 21:44:16 UTC
Updated at2022-04-27 21:44:16 UTC
NP-MRD IDNP0050464
Secondary Accession NumbersNone
Natural Product Identification
Common NameLicarin B
DescriptionLICARIN B belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Licarin B is found in Eupomatia laurina, Iryanthera lancifolia, Licaria guianensis, Machilus thunbergii, Magnolia denudata , Myristica castaneifolia, Myristica fragrans , Ocotea macrophylla, Ocotea porosa and Staudtia kamerunensis. Licarin B was first documented in 2019 (PMID: 30272133). Based on a literature review a small amount of articles have been published on LICARIN B (PMID: 35275149) (PMID: 33529639) (PMID: 29607669).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050464 (Licarin B)


  Mrv1652304272223442D          

 24 27  0  0  1  0            999 V2000
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2430   -2.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9966   -1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
 10  4  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 13 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
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
Download

3D MOL for NP0050464 (Licarin B)

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3D SDF for NP0050464 (Licarin B)

  Mrv1652304272223442D          

 24 27  0  0  1  0            999 V2000
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2430   -2.0255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9966   -1.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104   -0.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.1271    0.0000 C   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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
 10  4  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 13 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
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C)=CC2=C1O[C@H]([C@@H]2C)C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O4/c1-4-5-13-8-15-12(2)19(24-20(15)18(9-13)21-3)14-6-7-16-17(10-14)23-11-22-16/h4-10,12,19H,11H2,1-3H3/b5-4+/t12-,19-/m1/s1

> <INCHI_KEY>
DMMQXURQRMNSBM-YZAYTREXSA-N

> <FORMULA>
C20H20O4

> <MOLECULAR_WEIGHT>
324.376

> <EXACT_MASS>
324.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.474264137493314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2R,3R)-7-methoxy-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl]-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
4.593575335

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3771355357585096

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
92.1751

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2R,3R)-7-methoxy-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl]-2H-1,3-benzodioxole

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0050464 (Licarin B)
Download
PDB for NP0050464 (Licarin B)
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      -5.793  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.023  -2.637   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.054  -3.781   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.460  -3.155   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -7.299  -1.623   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.268  -2.549   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.530  -4.383   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.197  -5.153   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.531  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.865   0.237   0.000  0.00  0.00           C+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    4   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

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3D PDB for NP0050464 (Licarin B)
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SMILES for NP0050464 (Licarin B)
COC1=CC(\C=C\C)=CC2=C1O[C@H]([C@@H]2C)C1=CC=C2OCOC2=C1
Download
INCHI for NP0050464 (Licarin B)
InChI=1S/C20H20O4/c1-4-5-13-8-15-12(2)19(24-20(15)18(9-13)21-3)14-6-7-16-17(10-14)23-11-22-16/h4-10,12,19H,11H2,1-3H3/b5-4+/t12-,19-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H20O4
Average Mass324.3760 Da
Monoisotopic Mass324.13616 Da
IUPAC Name5-[(2R,3R)-7-methoxy-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl]-2H-1,3-benzodioxole
Traditional Name5-[(2R,3R)-7-methoxy-3-methyl-5-[(1E)-prop-1-en-1-yl]-2,3-dihydro-1-benzofuran-2-yl]-2H-1,3-benzodioxole
CAS Registry NumberNot Available
SMILES
COC1=CC(\C=C\C)=CC2=C1O[C@H]([C@@H]2C)C1=CC=C2OCOC2=C1
InChI Identifier
InChI=1S/C20H20O4/c1-4-5-13-8-15-12(2)19(24-20(15)18(9-13)21-3)14-6-7-16-17(10-14)23-11-22-16/h4-10,12,19H,11H2,1-3H3/b5-4+/t12-,19-/m1/s1
InChI KeyDMMQXURQRMNSBM-YZAYTREXSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eupomatia laurinaLOTUS Database
Iryanthera lancifoliaLOTUS Database
Licaria guianensisLOTUS Database
Machilus thunbergiiLOTUS Database
Magnolia denudataPlant
Myristica castaneifoliaLOTUS Database
Myristica fragransPlant
Ocotea macrophyllaLOTUS Database
Ocotea porosaLOTUS Database
Staudtia kamerunensisLOTUS Database
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
    • 

  • Neolignan skeleton
    • 

  • Coumaran
    • 

  • Benzodioxole
    • 

  • Benzofuran
    • 

  • Anisole
    • 

  • Styrene
    • 

  • Alkyl aryl ether
    • 

  • Benzenoid
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen 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
logP4.45ALOGPS
logP4.59ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.18 m³·mol⁻¹ChemAxon
Polarizability36.47 ųChemAxon
Number of Rings4ChemAxon
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 IDC00000696  
Chemspider ID4945284  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6441061  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Chen H, Ji T, Chen J, Li X: Matrix Solid-Phase Dispersion Combined with HPLC-DAD for Simultaneous Determination of Nine Lignans in Saururus chinensis. J Chromatogr Sci. 2019 Feb 1;57(2):186-193. doi: 10.1093/chromsci/bmy090. [PubMed:30272133  ] 
  2. Yoshioka Y, Kono R, Kuse M, Yamashita Y, Ashida H: Phenylpropanoids and neolignans isolated from Myristica fragrans enhance glucose uptake in myotubes. Food Funct. 2022 Apr 4;13(7):3879-3893. doi: 10.1039/d1fo04408g. [PubMed:35275149  ] 
  3. Mbaveng AT, Wamba BEN, Bitchagno GTM, Tankeo SB, Celik I, Atontsa BCK, Nkuete Lonfouo AH, Kuete V, Efferth T: Bioactivity of fractions and constituents of Piper capense fruits towards a broad panel of cancer cells. J Ethnopharmacol. 2021 May 10;271:113884. doi: 10.1016/j.jep.2021.113884. Epub 2021 Jan 30. [PubMed:33529639  ] 
  4. Francis SK, James B, Varughese S, Nair MS: Phytochemical investigation on Myristica fragrans stem bark. Nat Prod Res. 2019 Apr;33(8):1204-1208. doi: 10.1080/14786419.2018.1457670. Epub  2018 Apr 2. [PubMed:29607669  ]