NP-MRD: Showing NP-Card for 5-Pentacosyl-1,3-benzenediol (NP0049141)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:07:46 UTC

Updated at

2022-03-17 21:07:46 UTC

NP-MRD ID

NP0049141

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Pentacosyl-1,3-benzenediol

Description

5-Pentacosyl-1,3-benzenediol, also known as 5-N-pentadecylresorcinol, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 5-Pentacosyl-1,3-benzenediol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Pentacosyl-1,3-benzenediol is found, on average, in the highest concentration within a few different foods, such as rye bread, breakfast cereals, and ryes and in a lower concentration in hard wheats, common wheats, and barley. 5-Pentacosyl-1,3-benzenediol has also been detected, but not quantified in, several different foods, such as wild rices, rices, red rices, tartary buckwheats, and wheats. 5-Pentacosyl-1,3-benzenediol is found in Avena sativa and Triticum turgidum. This could make 5-pentacosyl-1,3-benzenediol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309111715542D          

 33 33  0  0  0  0            999 V2000
    7.1447  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0025  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0051  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -17.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 27  1  0  0  0  0
 30 26  1  0  0  0  0
 30 28  2  0  0  0  0
 31 27  2  0  0  0  0
 31 28  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
M  END


  Mrv1652309111715542D          

 33 33  0  0  0  0            999 V2000
    7.1447  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0025  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4328  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1473  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8618  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0051  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -14.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354  -16.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -16.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1499  -14.8500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210  -17.3250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 25 24  1  0  0  0  0
 29 25  1  0  0  0  0
 29 26  2  0  0  0  0
 29 27  1  0  0  0  0
 30 26  1  0  0  0  0
 30 28  2  0  0  0  0
 31 27  2  0  0  0  0
 31 28  1  0  0  0  0
 32 30  1  0  0  0  0
 33 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049141

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H56O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-26-30(32)28-31(33)27-29/h26-28,32-33H,2-25H2,1H3

> <INCHI_KEY>
GDJMJAKVVSGNLA-UHFFFAOYSA-N

> <FORMULA>
C31H56O2

> <MOLECULAR_WEIGHT>
460.7751

> <EXACT_MASS>
460.428031036

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.746840987688415

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-pentacosylbenzene-1,3-diol

> <ALOGPS_LOGP>
10.40

> <JCHEM_LOGP>
12.549184522

> <ALOGPS_LOGS>
-7.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.811350807010252

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.359032641624808

> <JCHEM_PKA_STRONGEST_BASIC>
-5.665057916048593

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
145.485

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.46e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-pentacosylbenzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-17         0                                  
HETATM    1  C   UNK     0      13.337 -27.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671 -28.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004 -27.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.338 -28.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.671 -27.720   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.005 -28.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.339 -27.720   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.673 -28.490   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.006 -27.720   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.340 -28.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.674 -27.720   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.007 -28.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.341 -27.720   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.675 -28.490   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.008 -27.720   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      33.342 -28.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.676 -27.720   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      36.009 -28.490   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      37.343 -27.720   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.677 -28.490   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      40.010 -27.720   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.344 -28.490   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      42.678 -27.720   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.011 -28.490   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      45.345 -27.720   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      48.013 -27.720   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      46.679 -30.030   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      49.346 -30.030   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      46.679 -28.490   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      49.346 -28.490   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      48.013 -30.800   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      50.680 -27.720   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      48.013 -32.340   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   29                                                       
CONECT   26   29   30                                                       
CONECT   27   29   31                                                       
CONECT   28   30   31                                                       
CONECT   29   25   26   27                                                  
CONECT   30   26   28   32                                                  
CONECT   31   27   28   33                                                  
CONECT   32   30                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
5-N-Pentadecylresorcinol	HMDB
5-Pentacosylresorcinol	HMDB

Chemical Formula

C₃₁H₅₆O₂

Average Mass

460.7751 Da

Monoisotopic Mass

460.42803 Da

IUPAC Name

5-pentacosylbenzene-1,3-diol

Traditional Name

5-pentacosylbenzene-1,3-diol

CAS Registry Number

70110-61-1

SMILES

CCCCCCCCCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C31H56O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-26-30(32)28-31(33)27-29/h26-28,32-33H,2-25H2,1H3

InChI Key

GDJMJAKVVSGNLA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Avena sativa	LOTUS Database	35616633
Avena sativa L.	FooDB	PHENOL EXPLORER
Hordeum vulgare	FooDB	PHENOL EXPLORER
Oryza sativa	FooDB	PHENOL EXPLORER
Secale cereale	FooDB	PHENOL EXPLORER
Triticum aestivum	FooDB	PHENOL EXPLORER
Triticum durum	FooDB	PHENOL EXPLORER
Triticum turgidum	LOTUS Database	35616633
Zea mays L.	FooDB	PHENOL EXPLORER

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	10.4	ALOGPS
logP	12.55	ChemAxon
logS	-7.3	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	145.48 m³·mol⁻¹	ChemAxon
Polarizability	63.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038485

DrugBank ID

Not Available

Phenol Explorer Compound ID

696

FoodDB ID

FDB017853

KNApSAcK ID

Not Available

Chemspider ID

136954

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155463

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5-Pentacosyl-1,3-benzenediol (NP0049141)

MOL for NP0049141 (5-Pentacosyl-1,3-benzenediol)

3D MOL for NP0049141 (5-Pentacosyl-1,3-benzenediol)

3D SDF for NP0049141 (5-Pentacosyl-1,3-benzenediol)

3D-SDF for NP0049141 (5-Pentacosyl-1,3-benzenediol)

PDB for NP0049141 (5-Pentacosyl-1,3-benzenediol)

3D PDB for NP0049141 (5-Pentacosyl-1,3-benzenediol)

SMILES for NP0049141 (5-Pentacosyl-1,3-benzenediol)

INCHI for NP0049141 (5-Pentacosyl-1,3-benzenediol)

Structure for NP0049141 (5-Pentacosyl-1,3-benzenediol)

3D Structure for NP0049141 (5-Pentacosyl-1,3-benzenediol)