NP-MRD: Showing NP-Card for (1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol (NP0290939)

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Record Information

Version

1.0

Created at

2022-09-09 21:50:49 UTC

Updated at

2022-09-09 21:50:49 UTC

NP-MRD ID

NP0290939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol

Description

ZINC255260714 belongs to the class of organic compounds known as 22,26-epiminocholestanes. These are steroid alkaloids obtained by reduction of spirosolane through opening of the E-ring. Based on a literature review very few articles have been published on ZINC255260714.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223502D          

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M  END

     RDKit          3D

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  Mrv1652309092223502D          

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 16 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 30  1  0  0  0  0
 11 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0290939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1[C@H](O)C[C@H]2[C@@H]3CC=C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC[C@@H](C)CN1C

> <INCHI_IDENTIFIER>
InChI=1S/C28H47NO2/c1-17-6-9-24(29(5)16-17)18(2)26-25(31)15-23-21-8-7-19-14-20(30)10-12-27(19,3)22(21)11-13-28(23,26)4/h7,17-18,20-26,30-31H,6,8-16H2,1-5H3/t17-,18-,20-,21-,22+,23+,24-,25-,26+,27+,28+/m1/s1

> <INCHI_KEY>
QFHXSIDXKCKLAC-PPCQHUCNSA-N

> <FORMULA>
C28H47NO2

> <MOLECULAR_WEIGHT>
429.689

> <EXACT_MASS>
429.360679757

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.95514809418367

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5R,10S,11S,13R,14R,15S)-14-[(1S)-1-[(2R,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,13-diol

> <JCHEM_LOGP>
4.3639581530000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.204289505503816

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.912079244259754

> <JCHEM_PKA_STRONGEST_BASIC>
10.207208059990833

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
129.1187

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5R,10S,11S,13R,14R,15S)-14-[(1S)-1-[(2R,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,13-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.312  -6.868   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12   30                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   30                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   16   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   15   11   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₇NO₂

Average Mass

429.6890 Da

Monoisotopic Mass

429.36068 Da

IUPAC Name

(1S,2R,5R,10S,11S,13R,14R,15S)-14-[(1S)-1-[(2R,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,13-diol

Traditional Name

(1S,2R,5R,10S,11S,13R,14R,15S)-14-[(1S)-1-[(2R,5R)-1,5-dimethylpiperidin-2-yl]ethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,13-diol

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1[C@H](O)C[C@H]2[C@@H]3CC=C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H]1CC[C@@H](C)CN1C

InChI Identifier

InChI=1S/C28H47NO2/c1-17-6-9-24(29(5)16-17)18(2)26-25(31)15-23-21-8-7-19-14-20(30)10-12-27(19,3)22(21)11-13-28(23,26)4/h7,17-18,20-26,30-31H,6,8-16H2,1-5H3/t17-,18-,20-,21-,22+,23+,24-,25-,26+,27+,28+/m1/s1

InChI Key

QFHXSIDXKCKLAC-PPCQHUCNSA-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 22,26-epiminocholestanes. These are steroid alkaloids obtained by reduction of spirosolane through opening of the E-ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

22,26-epiminocholestanes

Alternative Parents

Substituents

22,26-epiminocholestane skeleton
Progestogin-skeleton
Pregnane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-alpha-hydroxysteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Delta-5-steroid
Piperidine
Cyclic alcohol
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Alcohol
Organopnictogen 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	4.36	ChemAxon
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	10.21	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.12 m³·mol⁻¹	ChemAxon
Polarizability	52.96 Å³	ChemAxon
Number of Rings	5	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

73994003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124928662

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol (NP0290939)

MOL for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

3D MOL for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

3D SDF for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

3D-SDF for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

PDB for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

3D PDB for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

SMILES for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

INCHI for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

Structure for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)

3D Structure for NP0290939 ((1r,2r,3as,3bs,7r,9ar,9bs,11as)-1-[(1s)-1-[(2r,5r)-1,5-dimethylpiperidin-2-yl]ethyl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-2,7-diol)