NP-MRD: Showing NP-Card for (+)-Epoxynepapakistamine A (NP0072875)

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Record Information

Version

2.0

Created at

2022-04-28 18:09:28 UTC

Updated at

2022-04-28 18:09:28 UTC

NP-MRD ID

NP0072875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Epoxynepapakistamine A

Description

(20S)-2beta,4beta-Diacetoxy-3beta-(tigloylamino)-20-(methylamino)-16alpha,17alpha-epoxy-5alpha-pregnane belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton. (+)-Epoxynepapakistamine A is found in Sarcococca coriacea. Based on a literature review very few articles have been published on (20S)-2beta,4beta-Diacetoxy-3beta-(tigloylamino)-20-(methylamino)-16alpha,17alpha-epoxy-5alpha-pregnane.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220092D          

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M  END

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M  END


  Mrv1652304282220092D          

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    0.9090    3.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4421    3.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2182    0.8030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0367    0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5359    1.3559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2166    2.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7158    2.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3966    3.5342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5342    2.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0334    3.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8518    3.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8535    1.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5781    3.6381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2589    4.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7581    5.0557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4404    4.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  6  0  0  0
 16 18  1  1  0  0  0
 15 18  1  0  0  0  0
 15 19  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 23  1  6  0  0  0
  5 24  1  6  0  0  0
  3 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  2 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 32 35  1  0  0  0  0
  1 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H](C)[C@@]12O[C@@H]1C[C@H]1[C@@H]3CC[C@H]4[C@@H](OC(C)=O)[C@@H](NC(=O)C(\C)=C\C)[C@H](C[C@]4(C)[C@H]3CC[C@]21C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H48N2O6/c1-9-16(2)28(36)33-26-24(37-18(4)34)15-29(6)21-12-13-30(7)23(14-25-31(30,39-25)17(3)32-8)20(21)10-11-22(29)27(26)38-19(5)35/h9,17,20-27,32H,10-15H2,1-8H3,(H,33,36)/b16-9+/t17-,20+,21-,22-,23-,24-,25+,26-,27+,29+,30-,31+/m0/s1

> <INCHI_KEY>
WMEAPXSFCMQXCW-SJXBBCLOSA-N

> <FORMULA>
C31H48N2O6

> <MOLECULAR_WEIGHT>
544.733

> <EXACT_MASS>
544.351237274

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
62.38498829895157

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,6R,7S,10S,11R,13S,14S,15R,16R)-13-(acetyloxy)-7,11-dimethyl-6-[(1S)-1-(methylamino)ethyl]-14-[(2E)-2-methylbut-2-enamido]-5-oxapentacyclo[8.8.0.0^{2,7}.0^{4,6}.0^{11,16}]octadecan-15-yl acetate

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
3.3273377536666664

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.319629220077584

> <JCHEM_PKA_STRONGEST_BASIC>
9.918320915612512

> <JCHEM_POLAR_SURFACE_AREA>
106.26000000000002

> <JCHEM_REFRACTIVITY>
146.24400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,6R,7S,10S,11R,13S,14S,15R,16R)-13-(acetyloxy)-7,11-dimethyl-6-[(1S)-1-(methylamino)ethyl]-14-[(2E)-2-methylbut-2-enamido]-5-oxapentacyclo[8.8.0.0^{2,7}.0^{4,6}.0^{11,16}]octadecan-15-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       9.481   5.565   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.077   4.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.145   2.919   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.617   3.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.021   4.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.953   5.759   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.493   4.727   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.562   3.501   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.157   2.081   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.685   1.887   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.034   3.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.438   5.115   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.370   6.341   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.897   6.147   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.903   4.987   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.551   3.488   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.867   2.689   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.571   4.543   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.616   6.500   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.782   7.505   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -0.838   7.007   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      -1.126   8.520   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.697   6.465   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.425   5.953   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.741   1.499   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.268   1.305   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.200   2.531   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      11.864  -0.115   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      11.604   3.951   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      12.536   5.177   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.940   6.597   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.064   4.983   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.996   6.209   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.523   6.015   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.660   3.563   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.412   6.791   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.817   8.211   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.748   9.437   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.289   8.405   0.000  0.00  0.00           C+0
CONECT    1    2    6   36                                                  
CONECT    2    1    3   29                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   24                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17                                                  
CONECT   12   11   13   15   23                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   18   19                                             
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   15                                                       
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   12                                                            
CONECT   24    5                                                            
CONECT   25    3   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    2   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36    1   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
(20S)-2b,4b-Diacetoxy-3b-(tigloylamino)-20-(methylamino)-16a,17a-epoxy-5a-pregnane	Generator
(20S)-2Β,4β-diacetoxy-3β-(tigloylamino)-20-(methylamino)-16α,17α-epoxy-5α-pregnane	Generator

Chemical Formula

C₃₁H₄₈N₂O₆

Average Mass

544.7330 Da

Monoisotopic Mass

544.35124 Da

IUPAC Name

(1R,2S,4R,6R,7S,10S,11R,13S,14S,15R,16R)-13-(acetyloxy)-7,11-dimethyl-6-[(1S)-1-(methylamino)ethyl]-14-[(2E)-2-methylbut-2-enamido]-5-oxapentacyclo[8.8.0.0^{2,7}.0^{4,6}.0^{11,16}]octadecan-15-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CN[C@@H](C)[C@@]12O[C@@H]1C[C@H]1[C@@H]3CC[C@H]4[C@@H](OC(C)=O)[C@@H](NC(=O)C(\C)=C\C)[C@H](C[C@]4(C)[C@H]3CC[C@]21C)OC(C)=O

InChI Identifier

InChI=1S/C31H48N2O6/c1-9-16(2)28(36)33-26-24(37-18(4)34)15-29(6)21-12-13-30(7)23(14-25-31(30,39-25)17(3)32-8)20(21)10-11-22(29)27(26)38-19(5)35/h9,17,20-27,32H,10-15H2,1-8H3,(H,33,36)/b16-9+/t17-,20+,21-,22-,23-,24-,25+,26-,27+,29+,30-,31+/m0/s1

InChI Key

WMEAPXSFCMQXCW-SJXBBCLOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 coriacea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

16-oxosteroids

Alternative Parents

Substituents

22-azasteroid
Steroid ester
Pregnane-skeleton
Pregnane-type alkaloid
Steroidal alkaloid
16-oxosteroid
Azasteroid
Naphthopyran
Naphthalene
Alkaloid or derivatives
Oxane
Pyran
Dicarboxylic acid or derivatives
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Secondary amine
Amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen 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	3.33	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.32	ChemAxon
pKa (Strongest Basic)	9.92	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.26 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	146.24 m³·mol⁻¹	ChemAxon
Polarizability	62.38 Å³	ChemAxon
Number of Rings	5	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

9235790

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11060634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Epoxynepapakistamine A (NP0072875)

MOL for NP0072875 ((+)-Epoxynepapakistamine A)

3D MOL for NP0072875 ((+)-Epoxynepapakistamine A)

3D SDF for NP0072875 ((+)-Epoxynepapakistamine A)

3D-SDF for NP0072875 ((+)-Epoxynepapakistamine A)

PDB for NP0072875 ((+)-Epoxynepapakistamine A)

3D PDB for NP0072875 ((+)-Epoxynepapakistamine A)

SMILES for NP0072875 ((+)-Epoxynepapakistamine A)

INCHI for NP0072875 ((+)-Epoxynepapakistamine A)

Structure for NP0072875 ((+)-Epoxynepapakistamine A)

3D Structure for NP0072875 ((+)-Epoxynepapakistamine A)