NP-MRD: Showing NP-Card for Vulgarin (NP0048461)

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Record Information

Version

2.0

Created at

2022-03-17 20:56:50 UTC

Updated at

2022-03-17 20:56:50 UTC

NP-MRD ID

NP0048461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Vulgarin

Description

Vulgarin, also known as tauremisin or barrelin, belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Vulgarin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Vulgarin has been detected, but not quantified in, mugworts. Vulgarin is found in Achillea fragrantissima, Achillea millefolium, Achillea pratensis, Artemisia barrelieri, Artemisia cana, Artemisia canariensis, Artemisia judaica , Artemisia ludoviciana, Artemisia maritima, Artemisia taurica, Artemisia vallesiaca, Cicer bijugum, Cicer judaicum, Echinops ritro, Gymnosporia cassinoides, Tanacetum achilleifolium and Xanthium pungens. This could make vulgarin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308532D          

 19 21  0  0  0  0            999 V2000
    4.2295    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8705   -0.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9359   -1.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  2  1  0  0  0  0
 14  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  2  0  0  0  0
 17 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3

> <INCHI_KEY>
NGPDZEACIWDCKX-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.773741506211408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-2,6-dione

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
1.7767635190000004

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.252761655446307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1256420519077857

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
69.83229999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
judaicin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.895   2.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.417   3.436   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.492  -1.159   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.141  -0.731   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.747  -2.095   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    6    9                                                       
CONECT    5    7   10                                                       
CONECT    6    4   14                                                       
CONECT    7    5   15                                                       
CONECT    8    1    9   13                                                  
CONECT    9    4    8   11                                                  
CONECT   10    5   14   16                                                  
CONECT   11    9   12   19                                                  
CONECT   12   11   14   15                                                  
CONECT   13    8   17   19                                                  
CONECT   14    2    6   10   12                                             
CONECT   15    3    7   12   18                                             
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19   11   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Barrelin	HMDB
Judaicin	HMDB
Judaicin (eudesmane naphthofuran)	HMDB
Judaicin (sesquiterpene)	HMDB
Tauremisin	HMDB
Tauremisin a	HMDB
Tauremizin	HMDB
Tauresmin	HMDB

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

9-hydroxy-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,6H,9H,9aH,9bH-naphtho[1,2-b]furan-2,6-dione

Traditional Name

judaicin

CAS Registry Number

3162-56-9

SMILES

CC1C2CCC3(C)C(C2OC1=O)C(C)(O)C=CC3=O

InChI Identifier

InChI=1S/C15H20O4/c1-8-9-4-6-14(2)10(16)5-7-15(3,18)12(14)11(9)19-13(8)17/h5,7-9,11-12,18H,4,6H2,1-3H3

InChI Key

NGPDZEACIWDCKX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea fragrantissima	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea pratensis	LOTUS Database	35616633
Artemisia barrelieri	LOTUS Database	35616633
Artemisia cana	LOTUS Database	35616633
Artemisia canariensis	Plant	KNApSAcK
Artemisia judaica	Plant	KNApSAcK
Artemisia ludoviciana	LOTUS Database	35616633
Artemisia maritima	LOTUS Database	35616633
Artemisia taurica	LOTUS Database	35616633
Artemisia vallesiaca	LOTUS Database	35616633
Artemisia vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cicer bijugum	LOTUS Database	35616633
Cicer judaicum	LOTUS Database	35616633
Echinops ritro	LOTUS Database	35616633
Gymnosporia cassinoides	LOTUS Database	35616633
Tanacetum achilleifolium	LOTUS Database	35616633
Xanthium pungens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Cyclohexenone
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.75	ALOGPS
logP	1.78	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.83 m³·mol⁻¹	ChemAxon
Polarizability	27.77 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

HMDB0036130

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

619337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Vulgarin (NP0048461)

MOL for NP0048461 (Vulgarin)

3D MOL for NP0048461 (Vulgarin)

3D SDF for NP0048461 (Vulgarin)

3D-SDF for NP0048461 (Vulgarin)

PDB for NP0048461 (Vulgarin)

3D PDB for NP0048461 (Vulgarin)

SMILES for NP0048461 (Vulgarin)

INCHI for NP0048461 (Vulgarin)

Structure for NP0048461 (Vulgarin)

3D Structure for NP0048461 (Vulgarin)