NP-MRD: Showing NP-Card for (3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one (NP0195210)

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Record Information

Version

2.0

Created at

2022-09-04 13:01:50 UTC

Updated at

2022-09-04 13:01:51 UTC

NP-MRD ID

NP0195210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one

Description

(3AS)-3abeta,6alpha-Dihydroxy-4,4,7aalpha-trimethyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one is found in Undaria pinnatifida. Based on a literature review very few articles have been published on (3aS)-3abeta,6alpha-Dihydroxy-4,4,7aalpha-trimethyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.1603   -0.9254   -1.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0885   -0.2419   -0.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3203   -0.6960    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1905    1.2486   -0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2227    2.0651    0.2511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2470    3.3662   -0.3083 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1977    1.6028    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677    0.1304    0.1409 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9369   -0.3929   -1.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152   -0.3726    1.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8785   -1.7286    1.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318   -2.6168    1.7779 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4888   -1.9340    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0777   -0.5189    0.5523 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2023   -0.0215    1.8521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4859   -1.7945   -1.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1945   -1.3406   -1.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227   -0.1959   -2.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1876   -0.7729   -0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0706   -1.7207    0.8770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4677   -0.0634    1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0519    1.4921   -1.6106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149    1.5866   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881    2.2152    1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0126    3.8864    0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414    2.0507   -0.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7046    1.9760    1.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3362   -0.2361   -2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9117    0.1204   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1477   -1.4771   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6177   -2.5257   -0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367   -2.4502    1.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6113    0.2849    2.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  6
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 14  1  0
 14 15  1  1
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 14  8  1  0
 10  8  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
  7 26  1  0
  7 27  1  0
  5 24  1  1
  6 25  1  0
  4 22  1  0
  4 23  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
 15 33  1  0
 13 31  1  0
 13 32  1  0
M  END


  Mrv1652309042215012D          

 15 16  0  0  1  0            999 V2000
    3.8092    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7486    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4782    1.6455    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0195210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@@H](O)CC(C)(C)[C@@]1(O)CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O4/c1-9(2)4-7(12)5-10(3)11(9,14)6-8(13)15-10/h7,12,14H,4-6H2,1-3H3/t7-,10+,11-/m0/s1

> <INCHI_KEY>
XSZPDSCYNQJNEM-XROYCOCOSA-N

> <FORMULA>
C11H18O4

> <MOLECULAR_WEIGHT>
214.261

> <EXACT_MASS>
214.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
22.01205349814157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6S,7aR)-3a,6-dihydroxy-4,4,7a-trimethyl-octahydro-1-benzofuran-2-one

> <JCHEM_LOGP>
0.0730635506666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.156233623246205

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.064388280713409

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7376435690571954

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
52.952200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6S,7aR)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.111   3.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.131   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.626  -1.532   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   14                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   14                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    2    8   15                                             
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
(3AS)-3abeta,6a-dihydroxy-4,4,7aalpha-trimethyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one	Generator
(3AS)-3abeta,6α-dihydroxy-4,4,7aalpha-trimethyl-3a,4,5,6,7,7a-hexahydrobenzofuran-2(3H)-one	Generator

Chemical Formula

C₁₁H₁₈O₄

Average Mass

214.2610 Da

Monoisotopic Mass

214.12051 Da

IUPAC Name

(3aS,6S,7aR)-3a,6-dihydroxy-4,4,7a-trimethyl-octahydro-1-benzofuran-2-one

Traditional Name

(3aS,6S,7aR)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@@H](O)CC(C)(C)[C@@]1(O)CC(=O)O2

InChI Identifier

InChI=1S/C11H18O4/c1-9(2)4-7(12)5-10(3)11(9,14)6-8(13)15-10/h7,12,14H,4-6H2,1-3H3/t7-,10+,11-/m0/s1

InChI Key

XSZPDSCYNQJNEM-XROYCOCOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Undaria pinnatifida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	0.073	ChemAxon
pKa (Strongest Acidic)	13.06	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.95 m³·mol⁻¹	ChemAxon
Polarizability	22.01 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9238942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11063789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one (NP0195210)

MOL for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

3D MOL for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

3D SDF for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

3D-SDF for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

PDB for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

3D PDB for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

SMILES for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

INCHI for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

Structure for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)

3D Structure for NP0195210 ((3as,6s,7ar)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one)