NP-MRD: Showing NP-Card for articulin E (NP0333261)

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Record Information

Version

2.0

Created at

2024-05-16 14:56:48 UTC

Updated at

2024-11-01 00:35:47 UTC

NP-MRD ID

NP0333261

Natural Product DOI

https://doi.org/10.57994/2598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

articulin E

Description

Articulin E 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 E.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01282317332D          

 21 23  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
    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
    2.6961   -2.2539    0.0000 O   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  2  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
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  3 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=C(C)C(O)=CC2=C1C=CC1=C(C)C(O)=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O3/c1-9-12-4-5-14-15(13(12)6-7-16(9)20)8-17(21)10(2)18(14)11(3)19/h4-8,20-21H,1-3H3

> <INCHI_KEY>
FVLVUCAYBXCUGV-UHFFFAOYSA-N

> <FORMULA>
C18H16O3

> <MOLECULAR_WEIGHT>
280.323

> <EXACT_MASS>
280.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.844434585625095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3,7-dihydroxy-2,8-dimethylphenanthren-1-yl)ethan-1-one

> <JCHEM_LOGP>
3.929558983333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.19867501295213

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.066331090231717

> <JCHEM_PKA_STRONGEST_BASIC>
-5.481003941029044

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
83.4054

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-(3,7-dihydroxy-2,8-dimethylphenanthren-1-yl)ethanone

> <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  C   UNK     0       2.723  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.493  -4.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.723  -5.541   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.033  -4.207   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.437  -0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -5.747  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    3    7   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₃

Average Mass

280.3230 Da

Monoisotopic Mass

280.10994 Da

IUPAC Name

1-(3,7-dihydroxy-2,8-dimethylphenanthren-1-yl)ethan-1-one

Traditional Name

1-(3,7-dihydroxy-2,8-dimethylphenanthren-1-yl)ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1=C(C)C(O)=CC2=C1C=CC1=C(C)C(O)=CC=C21

InChI Identifier

InChI=1S/C18H16O3/c1-9-12-4-5-14-15(13(12)6-7-16(9)20)8-17(21)10(2)18(14)11(3)19/h4-8,20-21H,1-3H3

InChI Key

FVLVUCAYBXCUGV-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
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
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
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
Phenanthrol
Phenanthrene
2-naphthol
Naphthalene
Acetophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
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	3.93	ChemAxon
pKa (Strongest Acidic)	9.07	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.41 m³·mol⁻¹	ChemAxon
Polarizability	30.84 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 articulin E (NP0333261)

MOL for NP0333261 (articulin E)

3D MOL for NP0333261 (articulin E)

3D SDF for NP0333261 (articulin E)

3D-SDF for NP0333261 (articulin E)

PDB for NP0333261 (articulin E)

3D PDB for NP0333261 (articulin E)

SMILES for NP0333261 (articulin E)

INCHI for NP0333261 (articulin E)

Structure for NP0333261 (articulin E)

3D Structure for NP0333261 (articulin E)