NP-MRD: Showing NP-Card for [(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid (NP0161699)

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Record Information

Version

2.0

Created at

2022-09-02 19:56:30 UTC

Updated at

2022-09-02 19:56:30 UTC

NP-MRD ID

NP0161699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid

Description

CHEMBL1852217 belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position. Based on a literature review very few articles have been published on CHEMBL1852217.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221562D          

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M  END

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  Mrv1652309022221562D          

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M  END
> <DATABASE_ID>
NP0161699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H](CCC3=CC(=O)O[C@@H]3O)\C(CC[C@H]21)=C\OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O7S/c1-23(2)11-5-12-25(4)19(23)10-13-24(3)18(8-6-16-14-21(26)32-22(16)27)17(7-9-20(24)25)15-31-33(28,29)30/h14-15,18-20,22,27H,5-13H2,1-4H3,(H,28,29,30)/b17-15+/t18-,19-,20-,22-,24+,25-/m0/s1

> <INCHI_KEY>
XJAHYWMEEPSAKY-DZFRPBPISA-N

> <FORMULA>
C25H38O7S

> <MOLECULAR_WEIGHT>
482.63

> <EXACT_MASS>
482.233824738

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.750914414893806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(1R,2E,4aR,4bS,8aS,10aS)-1-{2-[(2S)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]ethyl}-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-2-ylidene]methoxy}sulfonic acid

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
4.966165266666665

> <ALOGPS_LOGS>
-5.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.283663443236014

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4024445202514935

> <JCHEM_PKA_STRONGEST_BASIC>
-4.271552635608409

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
124.17519999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2E,4aR,4bS,8aS,10aS)-1-{2-[(2S)-2-hydroxy-5-oxo-2H-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.420  -5.972   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.724  -7.002   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.563  -8.534   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.058  -6.232   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.738  -4.726   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.768  -3.581   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.516   2.104   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0      -1.746   3.437   0.000  0.00  0.00           S+0
HETATM   28  O   UNK     0      -0.413   2.667   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.080   4.207   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.976   4.771   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   33                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   33                                             
CONECT   13   12                                                            
CONECT   14   12   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   14   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   24   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₇S

Average Mass

482.6300 Da

Monoisotopic Mass

482.23382 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H](CCC3=CC(=O)O[C@@H]3O)\C(CC[C@H]21)=C\OS(O)(=O)=O

InChI Identifier

InChI=1S/C25H38O7S/c1-23(2)11-5-12-25(4)19(23)10-13-24(3)18(8-6-16-14-21(26)32-22(16)27)17(7-9-20(24)25)15-31-33(28,29)30/h14-15,18-20,22,27H,5-13H2,1-4H3,(H,28,29,30)/b17-15+/t18-,19-,20-,22-,24+,25-/m0/s1

InChI Key

XJAHYWMEEPSAKY-DZFRPBPISA-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 cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Cheilanthane sesterterpenoids

Alternative Parents

Substituents

Cheilanthane sesterterpenoid
Steroid
Hydrophenanthrene
Phenanthrene
2-furanone
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Dihydrofuran
Organic sulfuric acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
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	1.36	ALOGPS
logS	-5.8	ALOGPS

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

26628207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56666217

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid (NP0161699)

MOL for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D MOL for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D SDF for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D-SDF for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

PDB for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D PDB for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

SMILES for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

INCHI for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

Structure for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D Structure for NP0161699 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(2s)-2-hydroxy-5-oxo-2h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)