NP-MRD: Showing NP-Card for [(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid (NP0242617)

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Record Information

Version

1.0

Created at

2022-09-07 02:58:13 UTC

Updated at

2022-09-07 02:58:13 UTC

NP-MRD ID

NP0242617

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid

Description

{[(2R)-2-{2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulfonic acid belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. Based on a literature review very few articles have been published on {[(2R)-2-{2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulfonic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204582D          

 33 35  0  0  1  0            999 V2000
   -2.1933   -0.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178   -0.3549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.2795    0.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2296   -1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072204582D          

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 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  1  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  2  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242617

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CC[C@@H](CCCC1=CC(=O)O[C@H]1O)COS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O7S/c1-17-10-11-20-21(9-6-13-24(20,2)3)25(17,4)14-12-18(16-31-33(28,29)30)7-5-8-19-15-22(26)32-23(19)27/h9,15,17-18,20,23,27H,5-8,10-14,16H2,1-4H3,(H,28,29,30)/t17-,18+,20-,23+,25-/m0/s1

> <INCHI_KEY>
UTGHYWBAVNHHJG-DKBPJWHKSA-N

> <FORMULA>
C25H40O7S

> <MOLECULAR_WEIGHT>
484.65

> <EXACT_MASS>
484.249474802

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.88395478054381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R)-2-{2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulfonic acid

> <JCHEM_LOGP>
5.4360153113333345

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.290995384591775

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.3602204854826985

> <JCHEM_PKA_STRONGEST_BASIC>
-4.271543244317873

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
127.10219999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-2-{2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]pentyl]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.094  -0.609   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.633  -0.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.449   0.643   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.988   0.590   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.711  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.895  -2.076   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.618  -3.436   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.157  -3.489   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -10.973  -2.183   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.250  -0.824   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.584  -0.054   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.358   0.713   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.356  -2.022   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.249  -3.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.022  -2.792   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.689  -2.022   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.355  -2.792   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.021  -2.022   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.312  -2.792   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.646  -2.022   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.980  -2.792   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.386  -2.166   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.417  -3.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.948  -3.149   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.647  -4.644   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.141  -4.324   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.996  -5.354   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.355  -4.332   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.021  -5.102   0.000  0.00  0.00           O+0
HETATM   30  S   UNK     0      -1.021  -6.642   0.000  0.00  0.00           S+0
HETATM   31  O   UNK     0      -2.561  -6.642   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.519  -6.642   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.021  -8.182   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    6    2   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   17   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
{[(2R)-2-{2-[(1S,2S,4ar)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulfonate	Generator
{[(2R)-2-{2-[(1S,2S,4ar)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulphonate	Generator
{[(2R)-2-{2-[(1S,2S,4ar)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulphonic acid	Generator

Chemical Formula

C₂₅H₄₀O₇S

Average Mass

484.6500 Da

Monoisotopic Mass

484.24947 Da

IUPAC Name

{[(2R)-2-{2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]pentyl]oxy}sulfonic acid

Traditional Name

[(2R)-2-{2-[(1S,2S,4aR)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]pentyl]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@H]2C(=CCCC2(C)C)[C@@]1(C)CC[C@@H](CCCC1=CC(=O)O[C@H]1O)COS(O)(=O)=O

InChI Identifier

InChI=1S/C25H40O7S/c1-17-10-11-20-21(9-6-13-24(20,2)3)25(17,4)14-12-18(16-31-33(28,29)30)7-5-8-19-15-22(26)32-23(19)27/h9,15,17-18,20,23,27H,5-8,10-14,16H2,1-4H3,(H,28,29,30)/t17-,18+,20-,23+,25-/m0/s1

InChI Key

UTGHYWBAVNHHJG-DKBPJWHKSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Organic sulfuric acid or derivatives
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.44	ChemAxon
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	127.1 m³·mol⁻¹	ChemAxon
Polarizability	52.88 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162818897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid (NP0242617)

MOL for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

3D MOL for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

3D SDF for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

3D-SDF for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

PDB for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

3D PDB for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

SMILES for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

INCHI for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

Structure for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)

3D Structure for NP0242617 ([(2r)-2-{2-[(1s,2s,4ar)-1,2,5,5-tetramethyl-2,3,4,4a,6,7-hexahydronaphthalen-1-yl]ethyl}-5-[(2r)-2-hydroxy-5-oxo-2h-furan-3-yl]pentyl]oxysulfonic acid)