NP-MRD: Showing NP-Card for (6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one (NP0044084)

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Record Information

Version

1.0

Created at

2021-11-12 23:49:10 UTC

Updated at

2021-11-26 17:45:15 UTC

NP-MRD ID

NP0044084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one

Description

It was first documented in 2013 (PMID: 23650961). Based on a literature review very few articles have been published on (6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.7721   -0.2387   -1.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.2973   -0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4587    1.1553    0.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7473    1.0770   -1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390    1.4767   -0.2768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9635    0.1927    0.2921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874   -0.4514    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3036   -0.0238   -0.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    0.1165    0.3952 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9600   -1.6854    0.9934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8162   -2.5808    1.1833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.7142    1.4976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -0.5438    1.1507 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2508   -0.8915    0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2321   -1.2861    1.2698 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3607   -1.1840   -1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7408   -0.4244   -0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8978    0.4975   -2.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3590    0.8490    0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3733    0.4582   -1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2022    2.0000   -1.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1891    1.9280   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558    2.1426    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945    0.8992   -1.0753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -0.8104   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2007    0.9733    0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2275    0.0254    2.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9814   -1.6610   -0.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3023   -0.5931    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  1
  2 14  1  0
 14 15  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  7  1  0
 13  6  1  0
  9 26  1  0
  8 24  1  0
  8 25  1  0
  5 22  1  0
  5 23  1  0
  4 20  1  0
  4 21  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
 14 28  1  6
 15 29  1  0
 13 27  1  1
M  END


  Mrv1652311132100492D          

 15 16  0  0  1  0            999 V2000
    0.0768    0.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1648   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6345   -1.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   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  2  0  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  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)CCC2=C(CO)C(=O)O[C@@H]2[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O5/c1-10(14)3-2-5-6(4-11)9(13)15-7(5)8(10)12/h7-8,11-12,14H,2-4H2,1H3/t7-,8+,10-/m0/s1

> <INCHI_KEY>
LQKMEMNNLDQFHY-XKSSXDPKSA-N

> <FORMULA>
C10H14O5

> <MOLECULAR_WEIGHT>
214.217

> <EXACT_MASS>
214.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.950800320802436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-1.0545341706666664

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.66268388354348

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.269735265781135

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859752471072518

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
50.764

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-4,5,7,7a-tetrahydro-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0       0.143   1.728   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.774  -1.805   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.784  -3.520   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.126  -2.549   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₄O₅

Average Mass

214.2170 Da

Monoisotopic Mass

214.08412 Da

IUPAC Name

(6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

(6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-4,5,7,7a-tetrahydro-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@]1(O)CCC2=C(CO)C(=O)O[C@@H]2[C@H]1O

InChI Identifier

InChI=1S/C10H14O5/c1-10(14)3-2-5-6(4-11)9(13)15-7(5)8(10)12/h7-8,11-12,14H,2-4H2,1H3/t7-,8+,10-/m0/s1

InChI Key

LQKMEMNNLDQFHY-XKSSXDPKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Pleurotus cornucopiae

Chemical Taxonomy

Classification

Not classified

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	-0.9	ALOGPS
logP	-1.1	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	11.27	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	50.76 m³·mol⁻¹	ChemAxon
Polarizability	20.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

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

71655107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang S, Bao L, Zhao F, Wang Q, Li S, Ren J, Li L, Wen H, Guo L, Liu H: Isolation, Identification, and Bioactivity of Monoterpenoids and Sesquiterpenoids from the Mycelia of Edible Mushroom Pleurotus cornucopiae. J Agric Food Chem. 2013 May 29;61(21):5122-9. doi: 10.1021/jf401612t. Epub 2013 May 16. [PubMed:23650961 ]

Showing NP-Card for (6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one (NP0044084)

MOL for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

3D MOL for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

3D SDF for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

3D-SDF for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

PDB for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

3D PDB for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

SMILES for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

INCHI for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

Structure for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)

3D Structure for NP0044084 ((6S,7R,7aS)-6,7-dihydroxy-3-(hydroxymethyl)-6-methyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one)