NP-MRD: Showing NP-Card for [(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid (NP0159607)

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Record Information

Version

2.0

Created at

2022-09-02 17:23:36 UTC

Updated at

2022-09-02 17:23:36 UTC

NP-MRD ID

NP0159607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL1852025 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 CHEMBL1852025.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219232D          

 32 35  0  0  1  0            999 V2000
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309022219232D          

 32 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0159607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H](CCC3=CCN=C3O)\C(CC[C@H]21)=C\OS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO5S/c1-23(2)12-5-13-25(4)20(23)10-14-24(3)19(8-6-17-11-15-26-22(17)27)18(7-9-21(24)25)16-31-32(28,29)30/h11,16,19-21H,5-10,12-15H2,1-4H3,(H,26,27)(H,28,29,30)/b18-16+/t19-,20-,21-,24+,25-/m0/s1

> <INCHI_KEY>
MFNDFSXRNQJSDX-VUVIDIKTSA-N

> <FORMULA>
C25H39NO5S

> <MOLECULAR_WEIGHT>
465.65

> <EXACT_MASS>
465.254894534

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.43360697395011

> <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-(5-hydroxy-2H-pyrrol-4-yl)ethyl]-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-2-ylidene]methoxy}sulfonic acid

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
3.946171266123426

> <ALOGPS_LOGS>
-5.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.211256249209494

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.5154864321120032

> <JCHEM_PKA_STRONGEST_BASIC>
4.044783490545532

> <JCHEM_POLAR_SURFACE_AREA>
96.19000000000001

> <JCHEM_REFRACTIVITY>
125.69189999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2E,4aR,4bS,8aS,10aS)-1-[2-(2-hydroxy-5H-pyrrol-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  N   UNK     0      -2.058  -6.232   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -1.738  -4.726   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.768  -3.581   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.516   2.104   0.000  0.00  0.00           O+0
HETATM   26  S   UNK     0      -1.746   3.437   0.000  0.00  0.00           S+0
HETATM   27  O   UNK     0      -0.413   2.667   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.080   4.207   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.976   4.771   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   32  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   32                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   32                                             
CONECT   13   12                                                            
CONECT   14   12   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21                                                            
CONECT   23   14   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   23   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₉NO₅S

Average Mass

465.6500 Da

Monoisotopic Mass

465.25489 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H](CCC3=CCN=C3O)\C(CC[C@H]21)=C\OS(O)(=O)=O

InChI Identifier

InChI=1S/C25H39NO5S/c1-23(2)12-5-13-25(4)20(23)10-14-24(3)19(8-6-17-11-15-26-22(17)27)18(7-9-21(24)25)16-31-32(28,29)30/h11,16,19-21H,5-10,12-15H2,1-4H3,(H,26,27)(H,28,29,30)/b18-16+/t19-,20-,21-,24+,25-/m0/s1

InChI Key

MFNDFSXRNQJSDX-VUVIDIKTSA-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
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Pyrroline
Organic sulfuric acid or derivatives
Secondary carboxylic acid amide
Lactam
Carboxamide group
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen 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	1.96	ALOGPS
logP	3.95	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	-1.5	ChemAxon
pKa (Strongest Basic)	4.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.19 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.69 m³·mol⁻¹	ChemAxon
Polarizability	51.43 Å³	ChemAxon
Number of Rings	4	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

26629153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53494252

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-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid (NP0159607)

MOL for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D MOL for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D SDF for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D-SDF for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

PDB for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D PDB for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

SMILES for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

INCHI for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

Structure for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)

3D Structure for NP0159607 ([(1r,2e,4ar,4bs,8as,10as)-1-[2-(2-hydroxy-5h-pyrrol-3-yl)ethyl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-2-ylidene]methoxysulfonic acid)