NP-MRD: Showing NP-Card for (3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one (NP0236769)

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Record Information

Version

2.0

Created at

2022-09-06 19:45:21 UTC

Updated at

2022-09-06 19:45:21 UTC

NP-MRD ID

NP0236769

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one

Description

Applanatumol H belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. (3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one is found in Ganoderma applanatum. Based on a literature review very few articles have been published on Applanatumol H.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062221452D          

 23 25  0  0  1  0            999 V2000
    0.0702   -3.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0702   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2549    0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846    0.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6443   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588    0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0733   -1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3588   -3.1424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0236769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@]12COC(=O)[C@]1(CC(=O)C1=CC(O)=CC=C1O)CC[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O7/c17-7-16-8-23-14(22)15(16,4-3-13(16)21)6-12(20)10-5-9(18)1-2-11(10)19/h1-2,5,13,17-19,21H,3-4,6-8H2/t13-,15+,16-/m0/s1

> <INCHI_KEY>
VPMBQAULVONHEM-IMJJTQAJSA-N

> <FORMULA>
C16H18O7

> <MOLECULAR_WEIGHT>
322.313

> <EXACT_MASS>
322.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.906259233369532

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aS)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-hexahydro-1H-cyclopenta[c]furan-1-one

> <JCHEM_LOGP>
0.3822214066666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.02570019040362

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.203814967234232

> <JCHEM_PKA_STRONGEST_BASIC>
-2.833224772242392

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
78.38759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aS)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       0.131  -5.866   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.131  -4.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.465  -3.556   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.476   1.465   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465   1.064   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.798   1.834   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.929  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.405  -3.956   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.203  -3.556   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.203  -2.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.536  -1.246   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.536   0.294   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.870  -2.016   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.870  -3.556   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.536  -4.326   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.536  -5.866   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   14                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    4   10   12                                             
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14                                                            
CONECT   16    2   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₇

Average Mass

322.3130 Da

Monoisotopic Mass

322.10525 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@@]12COC(=O)[C@]1(CC(=O)C1=CC(O)=CC=C1O)CC[C@@H]2O

InChI Identifier

InChI=1S/C16H18O7/c17-7-16-8-23-14(22)15(16,4-3-13(16)21)6-12(20)10-5-9(18)1-2-11(10)19/h1-2,5,13,17-19,21H,3-4,6-8H2/t13-,15+,16-/m0/s1

InChI Key

VPMBQAULVONHEM-IMJJTQAJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ganoderma applanatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aryl alkyl ketone
Hydroquinone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Gamma butyrolactone
Monocyclic benzene moiety
Vinylogous acid
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441473

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132542817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one (NP0236769)

MOL for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

3D MOL for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

3D SDF for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

3D-SDF for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

PDB for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

3D PDB for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

SMILES for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

INCHI for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

Structure for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)

3D Structure for NP0236769 ((3ar,4s,6as)-6a-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-4-hydroxy-3a-(hydroxymethyl)-tetrahydrocyclopenta[c]furan-1-one)