NP-MRD: Showing NP-Card for (2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid (NP0249633)

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Record Information

Version

2.0

Created at

2022-09-07 12:14:38 UTC

Updated at

2022-09-07 12:14:39 UTC

NP-MRD ID

NP0249633

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid

Description

CHEMBL337494 belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group. (2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid is found in Sarcococca saligna. Based on a literature review very few articles have been published on CHEMBL337494.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214142D          

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M  END

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  Mrv1652309072214142D          

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  5  6  1  4  0  0  0
  5  7  2  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 21 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
 17 31  1  0  0  0  0
 12 31  1  0  0  0  0
 14 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0249633

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(O)=N[C@H]1[C@@H](O)C[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC=C32)[C@H](C)N(C)C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46N2O3/c1-8-16(2)26(33)29-24-23(31)15-28(5)21-13-14-27(4)19(17(3)30(6)7)11-12-20(27)18(21)9-10-22(28)25(24)32/h8,12,17-19,21-25,31-32H,9-11,13-15H2,1-7H3,(H,29,33)/b16-8+/t17-,18-,19+,21-,22?,23-,24-,25+,27+,28+/m0/s1

> <INCHI_KEY>
QVNOTNUGUHMPDI-AIWDQZKNSA-N

> <FORMULA>
C28H46N2O3

> <MOLECULAR_WEIGHT>
458.687

> <EXACT_MASS>
458.350843349

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.350756433109645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-[(1S,2R,4S,5S,6R,10R,14S,15R)-14-[(1S)-1-(dimethylamino)ethyl]-4,6-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl]-2-methylbut-2-enimidic acid

> <JCHEM_LOGP>
1.3636744778170522

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.058116088515458

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.473524325680815

> <JCHEM_PKA_STRONGEST_BASIC>
10.408640329770337

> <JCHEM_POLAR_SURFACE_AREA>
76.29

> <JCHEM_REFRACTIVITY>
135.45889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[(1S,2R,4S,5S,6R,10R,14S,15R)-14-[(1S)-1-(dimethylamino)ethyl]-4,6-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl]-2-methylbut-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.776   2.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.260   2.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.264   0.722   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.729  -0.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.780   0.451   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.772   1.628   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.303  -0.998   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.349  -3.895   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.408  -3.579   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      13.303  -5.217   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      14.248  -6.432   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.777  -5.427   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.288   1.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   31                                             
CONECT   13   12                                                            
CONECT   14   12   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21   18   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   17   12                                                  
CONECT   32   14    8   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆N₂O₃

Average Mass

458.6870 Da

Monoisotopic Mass

458.35084 Da

IUPAC Name

(2E)-N-[(1S,2R,4S,5S,6R,10R,14S,15R)-14-[(1S)-1-(dimethylamino)ethyl]-4,6-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl]-2-methylbut-2-enimidic acid

Traditional Name

(2E)-N-[(1S,2R,4S,5S,6R,10R,14S,15R)-14-[(1S)-1-(dimethylamino)ethyl]-4,6-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl]-2-methylbut-2-enimidic acid

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(O)=N[C@H]1[C@@H](O)C[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](CC=C32)[C@H](C)N(C)C)[C@H]1O

InChI Identifier

InChI=1S/C28H46N2O3/c1-8-16(2)26(33)29-24-23(31)15-28(5)21-13-14-27(4)19(17(3)30(6)7)11-12-20(27)18(21)9-10-22(28)25(24)32/h8,12,17-19,21-25,31-32H,9-11,13-15H2,1-7H3,(H,29,33)/b16-8+/t17-,18-,19+,21-,22?,23-,24-,25+,27+,28+/m0/s1

InChI Key

QVNOTNUGUHMPDI-AIWDQZKNSA-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
Sarcococca saligna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxysteroids. Hydroxysteroids are compounds containing an steroid backbone, with at least one hydrogen substituted by a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

Hydroxysteroids

Alternative Parents

Substituents

22-azasteroid
4-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
Azasteroid
N-acyl-amine
Cyclic alcohol
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Alcohol
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	ChemAxon
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	10.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	76.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.46 m³·mol⁻¹	ChemAxon
Polarizability	55.35 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

23214216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44358199

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid (NP0249633)

MOL for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

3D MOL for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

3D SDF for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

3D-SDF for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

PDB for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

3D PDB for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

SMILES for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

INCHI for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

Structure for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)

3D Structure for NP0249633 ((2e)-n-[(1s,3br,6r,7s,8s,9ar,9bs,11ar)-1-[(1s)-1-(dimethylamino)ethyl]-6,8-dihydroxy-9a,11a-dimethyl-1h,2h,3bh,4h,5h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]-2-methylbut-2-enimidic acid)