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Showing NP-Card for Marasmal (NP0048614)

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Record Information
Version2.0
Created at2022-03-17 20:59:16 UTC
Updated at2022-03-17 20:59:16 UTC
NP-MRD IDNP0048614
Secondary Accession NumbersNone
Natural Product Identification
Common NameMarasmal
DescriptionMarasmal belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Marasmal is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Marasmal has been detected, but not quantified in, mushrooms. Marasmal is found in Marasmius oreades . This could make marasmal a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048614 (Marasmal)


  Mrv0541 01101310242D          

 22 24  0  0  0  0            999 V2000
   -2.3571   -2.6812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0716   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -3.9188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3571   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9282   -2.6812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6427   -3.0937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3571   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -2.2687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2152   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861   -4.3313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -5.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -4.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1 11  1  0  0  0  0
 11  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
 10  8  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 11 12  1  1  0  0  0
 10 11  1  0  0  0  0
 12 14  2  0  0  0  0
  9 15  1  6  0  0  0
 10 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  1 19  1  6  0  0  0
  3 20  1  6  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
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3D MOL for NP0048614 (Marasmal)

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3D SDF for NP0048614 (Marasmal)

  Mrv0541 01101310242D          

 22 24  0  0  0  0            999 V2000
   -2.3571   -2.6812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0716   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -3.9188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3571   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -4.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -3.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282   -1.8563    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9282   -2.6812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6427   -3.0937    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3571   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -1.6427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -1.4438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2137   -2.2687    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007   -2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2152   -3.0938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -2.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861   -4.3313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3571   -5.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0716   -4.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1 11  1  0  0  0  0
 11  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
 10  8  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 11 12  1  1  0  0  0
 10 11  1  0  0  0  0
 12 14  2  0  0  0  0
  9 15  1  6  0  0  0
 10 16  1  6  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  1 19  1  6  0  0  0
  3 20  1  6  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048614

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](O)OC(=O)[C@@]11[C@@H](O)C[C@@H](O)C(C)(C)C1CC=C2C=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O6/c1-14(2)8-4-3-7(6-16)11-12(19)21-13(20)15(8,11)10(18)5-9(14)17/h3,6,8-12,17-19H,4-5H2,1-2H3/t8?,9-,10+,11-,12+,15+/m1/s1

> <INCHI_KEY>
OLGMJXURWXVYKR-JAIRQZCISA-N

> <FORMULA>
C15H20O6

> <MOLECULAR_WEIGHT>
296.3157

> <EXACT_MASS>
296.125988372

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.866562822363626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,8R,10S,10aR,10bS)-3,8,10-trihydroxy-7,7-dimethyl-1-oxo-1H,3H,6H,6aH,7H,8H,9H,10H,10bH-naphtho[1,8a-c]furan-4-carbaldehyde

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
-0.7600419733333338

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.47161080232468

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.274119961724636

> <JCHEM_PKA_STRONGEST_BASIC>
-2.963379592276959

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
72.49000000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,8R,10S,10aR,10bS)-3,8,10-trihydroxy-7,7-dimethyl-1-oxo-3H,6H,6aH,8H,9H,10H,10bH-naphtho[1,8a-c]furan-4-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048614 (Marasmal)
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PDB for NP0048614 (Marasmal)
HEADER    PROTEIN                                 10-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JAN-13         0                                  
HETATM    1  C   UNK     0      -4.400  -5.005   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.734  -5.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.734  -7.315   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.400  -8.085   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.066  -7.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.733  -8.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.399  -7.315   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.399  -5.775   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.733  -3.465   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.733  -5.005   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.066  -5.775   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.400  -3.465   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.066  -2.695   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -5.887  -3.066   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.399  -2.695   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      -0.399  -4.235   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       0.935  -5.005   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.268  -5.775   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.734  -4.235   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -7.067  -8.085   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.400  -9.625   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.734  -8.855   0.000  0.00  0.00           C+0
CONECT    1    2   11   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   21   22                                             
CONECT    5    4   11    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   10   17                                                  
CONECT    9   10   13   15                                                  
CONECT   10    8    9   11   16                                             
CONECT   11    1    5   12   10                                             
CONECT   12   13   11   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12                                                            
CONECT   15    9                                                            
CONECT   16   10                                                            
CONECT   17    8   18                                                       
CONECT   18   17                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

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3D PDB for NP0048614 (Marasmal)
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SMILES for NP0048614 (Marasmal)
[H][C@@]12[C@@H](O)OC(=O)[C@@]11[C@@H](O)C[C@@H](O)C(C)(C)C1CC=C2C=O
Download
INCHI for NP0048614 (Marasmal)
InChI=1S/C15H20O6/c1-14(2)8-4-3-7(6-16)11-12(19)21-13(20)15(8,11)10(18)5-9(14)17/h3,6,8-12,17-19H,4-5H2,1-2H3/t8?,9-,10+,11-,12+,15+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H20O6
Average Mass296.3157 Da
Monoisotopic Mass296.12599 Da
IUPAC Name(3S,8R,10S,10aR,10bS)-3,8,10-trihydroxy-7,7-dimethyl-1-oxo-1H,3H,6H,6aH,7H,8H,9H,10H,10bH-naphtho[1,8a-c]furan-4-carbaldehyde
Traditional Name(3S,8R,10S,10aR,10bS)-3,8,10-trihydroxy-7,7-dimethyl-1-oxo-3H,6H,6aH,8H,9H,10H,10bH-naphtho[1,8a-c]furan-4-carbaldehyde
CAS Registry Number124869-10-9
SMILES
[H][C@@]12[C@@H](O)OC(=O)[C@@]11[C@@H](O)C[C@@H](O)C(C)(C)C1CC=C2C=O
InChI Identifier
InChI=1S/C15H20O6/c1-14(2)8-4-3-7(6-16)11-12(19)21-13(20)15(8,11)10(18)5-9(14)17/h3,6,8-12,17-19H,4-5H2,1-2H3/t8?,9-,10+,11-,12+,15+/m1/s1
InChI KeyOLGMJXURWXVYKR-JAIRQZCISA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Marasmius oreadesFungi
Pleurotus ostreatusFooDB
    • 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 naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon  made up of two fused benzene rings.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassNaphthofurans  
Sub ClassNot Available
Direct ParentNaphthofurans  
Alternative Parents
Substituents
  • Naphthofuran
    • 

  • Gamma butyrolactone
    • 

  • Cyclic alcohol
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Hemiacetal
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Aldehyde
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.5ALOGPS
logP-0.76ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)5.27ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity72.49 m³·mol⁻¹ChemAxon
Polarizability28.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036867  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015821  
KNApSAcK IDC00020308  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752070  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available