NP-MRD: Showing NP-Card for 15-Hydroxymarasmen-3-one (NP0048430)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:56:21 UTC

Updated at

2022-03-17 20:56:21 UTC

NP-MRD ID

NP0048430

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-Hydroxymarasmen-3-one

Description

(Z)-Resveratrol 3-glucoside 5-sulfate belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton (Z)-Resveratrol 3-glucoside 5-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (Z)-Resveratrol 3-glucoside 5-sulfate has been detected, but not quantified in, green vegetables. 15-Hydroxymarasmen-3-one is found in Marasmius oreades . This could make (Z)-resveratrol 3-glucoside 5-sulfate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308512D          

 19 22  0  0  0  0            999 V2000
    1.9507    1.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0173    1.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8663    1.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428   -0.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557   -0.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0597    0.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2581    1.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6087    1.0954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511    0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8251    0.3456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3592   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230   -0.4076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    1.1193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0004    0.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5265    0.4408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9313   -0.6398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223    0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3761   -0.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  8  3  2  0  0  0  0
  8  7  1  0  0  0  0
  9  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 10  2  0  0  0  0
 17 13  1  0  0  0  0
 18  7  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048430

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CC=C3COC4OC(O)C2(CCC1=O)C34

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-14(2)9-4-3-8-7-18-12-11(8)15(9,13(17)19-12)6-5-10(14)16/h3,9,11-13,17H,4-7H2,1-2H3

> <INCHI_KEY>
HFEYLLLUTJYNMH-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.48760409819167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-en-4-one

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.615491624666666

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.11596879724049

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.857725059207024

> <JCHEM_PKA_STRONGEST_BASIC>
-4.125889996775487

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
68.73810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-en-4-one

> <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       3.641   3.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.899   2.658   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.217   3.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.678   3.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.253  -0.577   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.584  -0.559   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.445   1.592   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.948   1.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.870   2.045   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.522   0.778   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.140   0.645   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.137  -0.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.083  -0.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.330   2.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.601   0.690   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.983   0.823   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.605  -1.194   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.562   0.057   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.302  -1.701   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   15                                                       
CONECT    7    8   18                                                       
CONECT    8    3    7   11                                                  
CONECT    9    4   14   15                                                  
CONECT   10    5   14   16                                                  
CONECT   11    8   12   15                                                  
CONECT   12   11   18   19                                                  
CONECT   13   15   17   19                                                  
CONECT   14    1    2    9   10                                             
CONECT   15    6    9   11   13                                             
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18    7   12                                                       
CONECT   19   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
(Z)-Resveratrol 3-glucoside 5-sulfuric acid	Generator
(Z)-Resveratrol 3-glucoside 5-sulphate	Generator
(Z)-Resveratrol 3-glucoside 5-sulphuric acid	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

14-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-en-4-one

Traditional Name

14-hydroxy-5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-en-4-one

CAS Registry Number

124894-86-6

SMILES

CC1(C)C2CC=C3COC4OC(O)C2(CCC1=O)C34

InChI Identifier

InChI=1S/C15H20O4/c1-14(2)9-4-3-8-7-18-12-11(8)15(9,13(17)19-12)6-5-10(14)16/h3,9,11-13,17H,4-7H2,1-2H3

InChI Key

HFEYLLLUTJYNMH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Marasmius oreades	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Hexose monosaccharide
Phenylsulfate
O-glycosyl compound
Glycosyl compound
Arylsulfate
Styrene
Phenol ether
Phenoxy compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Oxane
Organic sulfuric acid or derivatives
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.1	ALOGPS
logP	1.62	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.74 m³·mol⁻¹	ChemAxon
Polarizability	27.49 Å³	ChemAxon
Number of Rings	4	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

HMDB0037074

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016062

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

131752139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 15-Hydroxymarasmen-3-one (NP0048430)

MOL for NP0048430 (15-Hydroxymarasmen-3-one)

3D MOL for NP0048430 (15-Hydroxymarasmen-3-one)

3D SDF for NP0048430 (15-Hydroxymarasmen-3-one)

3D-SDF for NP0048430 (15-Hydroxymarasmen-3-one)

PDB for NP0048430 (15-Hydroxymarasmen-3-one)

3D PDB for NP0048430 (15-Hydroxymarasmen-3-one)

SMILES for NP0048430 (15-Hydroxymarasmen-3-one)

INCHI for NP0048430 (15-Hydroxymarasmen-3-one)

Structure for NP0048430 (15-Hydroxymarasmen-3-one)

3D Structure for NP0048430 (15-Hydroxymarasmen-3-one)