NP-MRD: Showing NP-Card for Petasalbin (NP0048280)

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Record Information

Version

2.0

Created at

2022-03-17 20:53:57 UTC

Updated at

2022-03-17 20:53:57 UTC

NP-MRD ID

NP0048280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Petasalbin

Description

Petasalbin, also known as ligularol, belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Petasalbin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Petasalbin has been detected, but not quantified in, a few different foods, such as giant butterburs, green vegetables, and tea. Petasalbin is found in Ligularia fischeri, Ligularia kanaitzensis, Ligularia lamarum, Ligularia sibirica, Ligularia subspicata, Ligularia vellerea, Ligularia virgaurea and Petasites albus. This could make petasalbin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308372D          

 17 19  0  0  0  0            999 V2000
    4.6119   -2.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  8  2  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9-8-17-12-7-11-6-4-5-10(2)15(11,3)14(16)13(9)12/h8,10-11,14,16H,4-7H2,1-3H3

> <INCHI_KEY>
ANKFPIBCTISOBX-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.26934201354274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-ol

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
3.3548728246666677

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.607063852011933

> <JCHEM_PKA_STRONGEST_BASIC>
-2.077224639081559

> <JCHEM_POLAR_SURFACE_AREA>
33.370000000000005

> <JCHEM_REFRACTIVITY>
68.00850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.609  -4.251   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7   11   12                                                       
CONECT    8    9   17                                                       
CONECT    9    1    8   13                                                  
CONECT   10    2    5   15                                                  
CONECT   11    6    7   15                                                  
CONECT   12    7   13   17                                                  
CONECT   13    9   12   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15    3   10   11   14                                             
CONECT   16   14                                                            
CONECT   17    8   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxyfuranoeremophilane	HMDB
Ligularol	HMDB
Methyl 2-oxoheptanoate	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Mass

234.3340 Da

Monoisotopic Mass

234.16198 Da

IUPAC Name

3,4a,5-trimethyl-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-ol

Traditional Name

3,4a,5-trimethyl-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-4-ol

CAS Registry Number

4176-11-8

SMILES

CC1CCCC2CC3=C(C(O)C12C)C(C)=CO3

InChI Identifier

InChI=1S/C15H22O2/c1-9-8-17-12-7-11-6-4-5-10(2)15(11,3)14(16)13(9)12/h8,10-11,14,16H,4-7H2,1-3H3

InChI Key

ANKFPIBCTISOBX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia fischeri	Plant	KNApSAcK
Ligularia kanaitzensis	LOTUS Database	35616633
Ligularia lamarum	LOTUS Database	35616633
Ligularia sibirica	Plant	KNApSAcK
Ligularia subspicata	LOTUS Database	35616633
Ligularia vellerea	LOTUS Database	35616633
Ligularia virgaurea	LOTUS Database	35616633
Petasites albus	LOTUS Database	35616633
Petasites japonicus	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Heteroaromatic compound
Furan
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.56	ALOGPS
logP	3.35	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.01 m³·mol⁻¹	ChemAxon
Polarizability	27.27 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035639

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014349

KNApSAcK ID

C00017368

Chemspider ID

434155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

495921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Petasalbin (NP0048280)

MOL for NP0048280 (Petasalbin)

3D MOL for NP0048280 (Petasalbin)

3D SDF for NP0048280 (Petasalbin)

3D-SDF for NP0048280 (Petasalbin)

PDB for NP0048280 (Petasalbin)

3D PDB for NP0048280 (Petasalbin)

SMILES for NP0048280 (Petasalbin)

INCHI for NP0048280 (Petasalbin)

Structure for NP0048280 (Petasalbin)

3D Structure for NP0048280 (Petasalbin)