NP-MRD: Showing NP-Card for articulin A (NP0333257)

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Record Information

Version

2.0

Created at

2024-05-16 14:45:18 UTC

Updated at

2024-11-01 00:35:43 UTC

NP-MRD ID

NP0333257

Natural Product DOI

https://doi.org/10.57994/2594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

articulin A

Description

Articulin A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on articulin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01282317212D          

 22 24  0  0  0  0            999 V2000
   -2.2539   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6336   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9336   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0789   -0.8250    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 11 15  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333257

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC1=C(C=C)C2=C(C=C1O)C1=CC=C(O)C(C)=C1CC2

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-4-12-14-6-5-13-11(2)18(20)8-7-15(13)16(14)9-19(21)17(12)10-22-3/h4,7-9,20-21H,1,5-6,10H2,2-3H3

> <INCHI_KEY>
TXVHHSWUJBKZJY-UHFFFAOYSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.366

> <EXACT_MASS>
296.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.755048526594834

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-ethenyl-7-(methoxymethyl)-1-methyl-9,10-dihydrophenanthrene-2,6-diol

> <JCHEM_LOGP>
4.702357604333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.373809782998961

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.160763692141895

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1331507505911524

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
89.7308

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
8-ethenyl-7-(methoxymethyl)-1-methyl-9,10-dihydrophenanthrene-2,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JAN-23         0                                  
HETATM    1  C   UNK     0      -4.207  -4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.437  -2.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.897  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.127  -4.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.413  -4.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.183  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.183  -0.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.723  -0.206   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.493   1.127   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.493  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.033  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.803  -2.874   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.343  -2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.723  -2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.493  -4.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.723  -5.541   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.747  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   11    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    3    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3660 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

8-ethenyl-7-(methoxymethyl)-1-methyl-9,10-dihydrophenanthrene-2,6-diol

Traditional Name

8-ethenyl-7-(methoxymethyl)-1-methyl-9,10-dihydrophenanthrene-2,6-diol

CAS Registry Number

Not Available

SMILES

COCC1=C(C=C)C2=C(C=C1O)C1=CC=C(O)C(C)=C1CC2

InChI Identifier

InChI=1S/C19H20O3/c1-4-12-14-6-5-13-11(2)18(20)8-7-15(13)16(14)9-19(21)17(12)10-22-3/h4,7-9,20-21H,1,5-6,10H2,2-3H3

InChI Key

TXVHHSWUJBKZJY-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	vasas.andrea@szte.hu	University of Szeged	Andrea Vasas	2024-05-16	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	vasas.andrea@szte.hu	University of Szeged	Andrea Vasas	2024-05-16	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	vasas.andrea@szte.hu	University of Szeged	Andrea Vasas	2024-05-16	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	vasas.andrea@szte.hu	University of Szeged	Andrea Vasas	2024-05-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	vasas.andrea@szte.hu	University of Szeged	Andrea Vasas	2024-05-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	vasas.andrea@szte.hu	University of Szeged	Andrea Vasas	2024-05-16	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
Juncus articulatus		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Phenanthrene
2-naphthol
Naphthalene
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.7	ChemAxon
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.73 m³·mol⁻¹	ChemAxon
Polarizability	33.76 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

Not Available

Showing NP-Card for articulin A (NP0333257)

MOL for NP0333257 (articulin A)

3D MOL for NP0333257 (articulin A)

3D SDF for NP0333257 (articulin A)

3D-SDF for NP0333257 (articulin A)

PDB for NP0333257 (articulin A)

3D PDB for NP0333257 (articulin A)

SMILES for NP0333257 (articulin A)

INCHI for NP0333257 (articulin A)

Structure for NP0333257 (articulin A)

3D Structure for NP0333257 (articulin A)