NP-MRD: Showing NP-Card for 3alpha,15-Dihydroxymarasmene (NP0048426)

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Record Information

Version

2.0

Created at

2022-03-17 20:56:17 UTC

Updated at

2022-03-17 20:56:17 UTC

NP-MRD ID

NP0048426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3alpha,15-Dihydroxymarasmene

Description

3Alpha,15-Dihydroxymarasmene belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 3Alpha,15-Dihydroxymarasmene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3alpha,15-dihydroxymarasmene has been detected, but not quantified in, mushrooms. 3alpha,15-Dihydroxymarasmene is found in Marasmius oreades . This could make 3alpha,15-dihydroxymarasmene 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  1  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>
NP0048426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(O)CCC23C(O)OC4OCC(=CCC12)C34

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-14(2)9-4-3-8-7-18-12-11(8)15(9,13(17)19-12)6-5-10(14)16/h3,9-13,16-17H,4-7H2,1-2H3

> <INCHI_KEY>
INMDHOFDLKYMSO-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.284998602745716

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-diol

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
1.0519639189999996

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.55394050353686

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.858872647084203

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8066982137205269

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
69.5604

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-diol

> <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
3a,15-Dihydroxymarasmene	Generator
3Α,15-dihydroxymarasmene	Generator
3,4-Dimethyl-(1,2)dithiolo(1,5-b)(1,2)dithiole-7-S(IV)	HMDB

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3328 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-diol

Traditional Name

5,5-dimethyl-11,13-dioxatetracyclo[7.5.1.0¹,⁶.0¹²,¹⁵]pentadec-8-ene-4,14-diol

CAS Registry Number

124869-03-0

SMILES

CC1(C)C(O)CCC23C(O)OC4OCC(=CCC12)C34

InChI Identifier

InChI=1S/C15H22O4/c1-14(2)9-4-3-8-7-18-12-11(8)15(9,13(17)19-12)6-5-10(14)16/h3,9-13,16-17H,4-7H2,1-2H3

InChI Key

INMDHOFDLKYMSO-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 furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Hemiacetal
Oxacycle
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	0.83	ALOGPS
logP	1.05	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.56 m³·mol⁻¹	ChemAxon
Polarizability	28.28 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

HMDB0036039

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014859

KNApSAcK ID

C00020313

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

14433060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3alpha,15-Dihydroxymarasmene (NP0048426)

MOL for NP0048426 (3alpha,15-Dihydroxymarasmene)

3D MOL for NP0048426 (3alpha,15-Dihydroxymarasmene)

3D SDF for NP0048426 (3alpha,15-Dihydroxymarasmene)

3D-SDF for NP0048426 (3alpha,15-Dihydroxymarasmene)

PDB for NP0048426 (3alpha,15-Dihydroxymarasmene)

3D PDB for NP0048426 (3alpha,15-Dihydroxymarasmene)

SMILES for NP0048426 (3alpha,15-Dihydroxymarasmene)

INCHI for NP0048426 (3alpha,15-Dihydroxymarasmene)

Structure for NP0048426 (3alpha,15-Dihydroxymarasmene)

3D Structure for NP0048426 (3alpha,15-Dihydroxymarasmene)