NP-MRD: Showing NP-Card for Longistylin A (NP0336254)

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Record Information

Version

2.0

Created at

2024-09-11 05:24:45 UTC

Updated at

2024-09-11 05:24:46 UTC

NP-MRD ID

NP0336254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Longistylin A

Description

Longistylin A belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Longistylin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Longistylin A has been detected, but not quantified in, pulses. This could make longistylin a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310312D          

 22 23  0  0  0  0            999 V2000
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    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
    3.5724   -1.2375    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
    3.5724   -0.4125    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
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 11 10  2  0  0  0  0
 12  9  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  9  2  0  0  0  0
 16  7  2  0  0  0  0
 16  8  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 19 18  2  0  0  0  0
 20 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  3  1  0  0  0  0
 22 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C/C2=CC=CC=C2)=CC(O)=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O2/c1-15(2)9-12-18-19(21)13-17(14-20(18)22-3)11-10-16-7-5-4-6-8-16/h4-11,13-14,21H,12H2,1-3H3/b11-10-

> <INCHI_KEY>
MPDBOKIOROLWQP-KHPPLWFESA-N

> <FORMULA>
C20H22O2

> <MOLECULAR_WEIGHT>
294.3875

> <EXACT_MASS>
294.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.15339100763393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methoxy-2-(3-methylbut-2-en-1-yl)-5-[(Z)-2-phenylethenyl]phenol

> <ALOGPS_LOGP>
5.48

> <JCHEM_LOGP>
5.580417263333334

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.188877489348751

> <JCHEM_PKA_STRONGEST_BASIC>
-4.849115183653439

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
94.19969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methoxy-2-(3-methylbut-2-en-1-yl)-5-[(Z)-2-phenylethenyl]phenol

> <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      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   16                                                       
CONECT    8    6   16                                                       
CONECT    9   12   15                                                       
CONECT   10   11   16                                                       
CONECT   11   10   17                                                       
CONECT   12    9   18                                                       
CONECT   13   17   19                                                       
CONECT   14   17   20                                                       
CONECT   15    1    2    9                                                  
CONECT   16    7    8   10                                                  
CONECT   17   11   13   14                                                  
CONECT   18   12   19   20                                                  
CONECT   19   13   18   21                                                  
CONECT   20   14   18   22                                                  
CONECT   21   19                                                            
CONECT   22    3   20                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-4-isopentenyl-5-methoxystilbene	HMDB
3-Hydroxy-5-methoxy-4-prenylstilbene	HMDB
3-Methoxy-2-(3-methyl-2-butenyl)-5-(2-phenylethenyl)phenol, 9ci	HMDB
5-Cinnamyl-3-methoxy-2-prenylphenol	HMDB
Longistyline a	HMDB

Chemical Formula

C₂₀H₂₂O₂

Average Mass

294.3875 Da

Monoisotopic Mass

294.16198 Da

IUPAC Name

3-methoxy-2-(3-methylbut-2-en-1-yl)-5-[(Z)-2-phenylethenyl]phenol

Traditional Name

3-methoxy-2-(3-methylbut-2-en-1-yl)-5-[(Z)-2-phenylethenyl]phenol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C/C2=CC=CC=C2)=CC(O)=C1CC=C(C)C

InChI Identifier

InChI=1S/C20H22O2/c1-15(2)9-12-18-19(21)13-17(14-20(18)22-3)11-10-16-7-5-4-6-8-16/h4-11,13-14,21H,12H2,1-3H3/b11-10-

InChI Key

MPDBOKIOROLWQP-KHPPLWFESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	5.48	ALOGPS
logP	5.58	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.2 m³·mol⁻¹	ChemAxon
Polarizability	34.15 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038543

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017929

KNApSAcK ID

C00015435

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

131752397

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Longistylin A (NP0336254)

MOL for NP0336254 (Longistylin A)

3D MOL for NP0336254 (Longistylin A)

3D SDF for NP0336254 (Longistylin A)

3D-SDF for NP0336254 (Longistylin A)

PDB for NP0336254 (Longistylin A)

3D PDB for NP0336254 (Longistylin A)

SMILES for NP0336254 (Longistylin A)

INCHI for NP0336254 (Longistylin A)

Structure for NP0336254 (Longistylin A)

3D Structure for NP0336254 (Longistylin A)