NP-MRD: Showing NP-Card for 5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one (NP0305900)

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Record Information

Version

2.0

Created at

2022-09-10 22:03:49 UTC

Updated at

2022-09-10 22:03:49 UTC

NP-MRD ID

NP0305900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one

Description

5,7-Dihydroxy-2,15-dimethyl-14-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-8-one 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. 5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one is found in Fritillaria ebeiensis. 5,7-Dihydroxy-2,15-dimethyl-14-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-8-one is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191517362D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191517362D          

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M  END
> <DATABASE_ID>
NP0305900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CCC2C3CC(=O)C4(O)CC(O)CCC4(C)C3CCC12C)C1=NCC(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO3/c1-16-5-8-23(28-15-16)17(2)20-6-7-21-19-13-24(30)27(31)14-18(29)9-12-26(27,4)22(19)10-11-25(20,21)3/h16-22,29,31H,5-15H2,1-4H3

> <INCHI_KEY>
OXSDZAAZDQVKSD-UHFFFAOYSA-N

> <FORMULA>
C27H43NO3

> <MOLECULAR_WEIGHT>
429.645

> <EXACT_MASS>
429.324294249

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.740935585116894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,7-dihydroxy-2,15-dimethyl-14-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
4.247938057333332

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.25156973876112

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.60613273049782

> <JCHEM_PKA_STRONGEST_BASIC>
3.8306958349004905

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
123.00169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2,15-dimethyl-14-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         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       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       2.312  -6.868   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   11   19   20                                             
CONECT   19   18                                                            
CONECT   20   18    7   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    3    6   24                                             
CONECT   24   23                                                            
CONECT   25    2   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₃NO₃

Average Mass

429.6450 Da

Monoisotopic Mass

429.32429 Da

IUPAC Name

5,7-dihydroxy-2,15-dimethyl-14-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

Traditional Name

5,7-dihydroxy-2,15-dimethyl-14-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-8-one

CAS Registry Number

Not Available

SMILES

CC(C1CCC2C3CC(=O)C4(O)CC(O)CCC4(C)C3CCC12C)C1=NCC(C)CC1

InChI Identifier

InChI=1S/C27H43NO3/c1-16-5-8-23(28-15-16)17(2)20-6-7-21-19-13-24(30)27(31)14-18(29)9-12-26(27,4)22(19)10-11-25(20,21)3/h16-22,29,31H,5-15H2,1-4H3

InChI Key

OXSDZAAZDQVKSD-UHFFFAOYSA-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

Species Name	Source	Reference
Fritillaria ebeiensis	LOTUS Database	35616633

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-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Oxosteroid
6-oxosteroid
Tetrahydropyridine
Hydropyridine
Cyclic alcohol
Tertiary alcohol
Ketimine
Secondary alcohol
Ketone
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Imine
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen 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	4.07	ALOGPS
logP	4.25	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.61	ChemAxon
pKa (Strongest Basic)	3.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	123 m³·mol⁻¹	ChemAxon
Polarizability	50.74 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

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

78384864

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one (NP0305900)

MOL for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D MOL for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D SDF for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D-SDF for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

PDB for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D PDB for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

SMILES for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

INCHI for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

Structure for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)

3D Structure for NP0305900 (5a,7-dihydroxy-9a,11a-dimethyl-1-[1-(5-methyl-3,4,5,6-tetrahydropyridin-2-yl)ethyl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one)