NP-MRD: Showing NP-Card for Licoaurone B (NP0333742)

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Record Information

Version

2.0

Created at

2024-08-23 13:49:41 UTC

Updated at

2025-06-11 04:36:36 UTC

NP-MRD ID

NP0333742

Natural Product DOI

https://doi.org/10.57994/3221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Licoaurone B

Description

Licoaurone B belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Based on a literature review very few articles have been published on Licoaurone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05072316222D          

 23 25  0  0  0  0            999 V2000
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   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    2.2374    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
   -1.8212    2.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    4.3808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6462    4.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    3.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.9519    0.0000 C   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
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  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
  9 10  2  0  0  0  0
 10 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
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
  9 16  1  0  0  0  0
  7 17  1  0  0  0  0
  6 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  5 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333742

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2OC3=CC(O)=CC=C3\C2=C\C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1/C18H16O5/c1-22-13-5-2-11(3-6-13)8-16-15(10-18(20)21)14-7-4-12(19)9-17(14)23-16/h2-7,9-10,16,19H,8H2,1H3,(H,20,21)/b15-10-

> <INCHI_KEY>
BJVQDIZWSUBMBT-GDNBJRDFNA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.59634635094773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3Z)-6-hydroxy-2-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-3-ylidene]acetic acid

> <JCHEM_LOGP>
3.1272803163333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.436152822088625

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4803424245905488

> <JCHEM_PKA_STRONGEST_BASIC>
-4.563513917082795

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
84.8004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3Z)-6-hydroxy-2-[(4-methoxyphenyl)methyl]-2H-1-benzofuran-3-ylidene]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAY-23         0                                  
HETATM    1  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.090   4.177   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.630   4.177   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.400   5.510   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.630   6.844   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.400   8.178   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.940   8.178   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.090   6.844   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.320   5.510   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.333  -1.652   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.887   0.957   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15    9                                                       
CONECT   17    7   22                                                       
CONECT   18    6   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    5   17   23                                                  
CONECT   23   22    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

2-[(3Z)-6-hydroxy-2-[(4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-3-ylidene]acetic acid

Traditional Name

[(3Z)-6-hydroxy-2-[(4-methoxyphenyl)methyl]-2H-1-benzofuran-3-ylidene]acetic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2OC3=CC(O)=CC=C3\C2=C\C(O)=O)C=C1

InChI Identifier

InChI=1/C18H16O5/c1-22-13-5-2-11(3-6-13)8-16-15(10-18(20)21)14-7-4-12(19)9-17(14)23-16/h2-7,9-10,16,19H,8H2,1H3,(H,20,21)/b15-10-

InChI Key

BJVQDIZWSUBMBT-GDNBJRDFNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dicledemir@windowslive.com	Trakya University Faculty of Pharmacy	Dicle Çevik	2024-08-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dicledemir@windowslive.com	Trakya University Faculty of Pharmacy	Dicle Çevik	2024-08-23	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dicledemir@windowslive.com	Trakya University Faculty of Pharmacy	Dicle Çevik	2024-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	dicledemir@windowslive.com	Trakya University Faculty of Pharmacy	Dicle Çevik	2024-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	dicledemir@windowslive.com	Trakya University Faculty of Pharmacy	Dicle Çevik	2024-08-23	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Glycyrrhiza asymmetrica		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as coumarans. These are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Alkyl aryl ether
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Monocyclic benzene moiety
Tetrahydrofuran
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.13	ChemAxon
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.8 m³·mol⁻¹	ChemAxon
Polarizability	32.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Licoaurone B (NP0333742)

MOL for NP0333742 (Licoaurone B)

3D MOL for NP0333742 (Licoaurone B)

3D SDF for NP0333742 (Licoaurone B)

3D-SDF for NP0333742 (Licoaurone B)

PDB for NP0333742 (Licoaurone B)

3D PDB for NP0333742 (Licoaurone B)

SMILES for NP0333742 (Licoaurone B)

INCHI for NP0333742 (Licoaurone B)

Structure for NP0333742 (Licoaurone B)

3D Structure for NP0333742 (Licoaurone B)