NP-MRD: Showing NP-Card for [(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid (NP0185746)

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Record Information

Version

2.0

Created at

2022-09-04 01:16:54 UTC

Updated at

2022-09-04 01:16:54 UTC

NP-MRD ID

NP0185746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL1852064 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 CHEMBL1852064.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042203162D          

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 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  8 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1OC(=O)C(CC[C@H]2\C(CC[C@H]3[C@]2(C)CC[C@H]2C(C)(C)CCC[C@]32C)=C\OS(O)(=O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O7S/c1-24(2)12-6-13-26(4)20(24)11-14-25(3)19(9-7-17-15-22(31-5)33-23(17)27)18(8-10-21(25)26)16-32-34(28,29)30/h15-16,19-22H,6-14H2,1-5H3,(H,28,29,30)/b18-16+/t19-,20-,21-,22+,25+,26-/m0/s1

> <INCHI_KEY>
LNWZALYQTMHQIK-MENYEORKSA-N

> <FORMULA>
C26H40O7S

> <MOLECULAR_WEIGHT>
496.66

> <EXACT_MASS>
496.249474802

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.96757579145056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
5.761480987999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.372184305187695

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4454769722509928

> <JCHEM_PKA_STRONGEST_BASIC>
-4.32308932171884

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
129.00149999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <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      -5.936 -11.676   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.775 -10.145   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.368  -9.518   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.048  -8.012   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -7.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.746  -6.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -6.517   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.746  -3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.516  -2.516   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0      -1.746  -1.183   0.000  0.00  0.00           S+0
HETATM   13  O   UNK     0      -0.413  -1.953   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.080  -0.413   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.976   0.151   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.171  -5.710   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.456  -6.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -6.517   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.890  -9.258   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.384  -9.578   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -3.034 -10.288   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20   21   27                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    8   18   31                                             
CONECT   31   30                                                            
CONECT   32    5   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    3                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀O₇S

Average Mass

496.6600 Da

Monoisotopic Mass

496.24947 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CO[C@@H]1OC(=O)C(CC[C@H]2\C(CC[C@H]3[C@]2(C)CC[C@H]2C(C)(C)CCC[C@]32C)=C\OS(O)(=O)=O)=C1

InChI Identifier

InChI=1S/C26H40O7S/c1-24(2)12-6-13-26(4)20(24)11-14-25(3)19(9-7-17-15-22(31-5)33-23(17)27)18(8-10-21(25)26)16-32-34(28,29)30/h15-16,19-22H,6-14H2,1-5H3,(H,28,29,30)/b18-16+/t19-,20-,21-,22+,25+,26-/m0/s1

InChI Key

LNWZALYQTMHQIK-MENYEORKSA-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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	5.76	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	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129 m³·mol⁻¹	ChemAxon
Polarizability	53.97 Å³	ChemAxon
Number of Rings	4	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

26628851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53494118

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-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid (NP0185746)

MOL for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D MOL for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D SDF for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D-SDF for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

PDB for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D PDB for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

SMILES for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

INCHI for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

Structure for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D Structure for NP0185746 ([(1r,2e,4ar,4bs,8as,10as)-1-{2-[(5r)-5-methoxy-2-oxo-5h-furan-3-yl]ethyl}-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)