NP-MRD: Showing NP-Card for (+)-Spiropachysine (NP0082934)

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Record Information

Version

2.0

Created at

2022-04-29 04:00:26 UTC

Updated at

2022-04-29 04:00:26 UTC

NP-MRD ID

NP0082934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Spiropachysine

Description

(1R,1'S,2'S,7'S,10'R,11'S,13'S,14'S,15'S)-14'-[(1S)-1-(dimethylamino)ethyl]-2,2',15'-trimethyl-2,3-dihydrospiro[isoindole-1,5'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane]-13'-ol belongs to the class of organic compounds known as 16-hydroxysteroids. These are steroids carrying a hydroxyl group at the 16-position of the steroid backbone. (+)-Spiropachysine is found in Pachysandra procumbens. Based on a literature review very few articles have been published on (1R,1'S,2'S,7'S,10'R,11'S,13'S,14'S,15'S)-14'-[(1S)-1-(dimethylamino)ethyl]-2,2',15'-trimethyl-2,3-dihydrospiro[isoindole-1,5'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane]-13'-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206002D          

 34 39  0  0  1  0            999 V2000
    4.8801   -1.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292206002D          

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    1.4682    0.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -0.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567   -2.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597   -1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  0  0  0  0
  4  9  1  6  0  0  0
  8 10  1  6  0  0  0
  7 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  1  0  0  0
  5 16  1  6  0  0  0
  3 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 23 32  1  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
 20 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H]1[C@@H](O)C[C@H]2[C@@H]3CC[C@H]4C[C@@]5(CC[C@]4(C)[C@H]3CC[C@]12C)N(C)CC1=CC=CC=C51)N(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H48N2O/c1-20(32(4)5)28-27(34)17-26-23-12-11-22-18-31(24-10-8-7-9-21(24)19-33(31)6)16-15-29(22,2)25(23)13-14-30(26,28)3/h7-10,20,22-23,25-28,34H,11-19H2,1-6H3/t20-,22-,23+,25-,26-,27-,28-,29-,30-,31+/m0/s1

> <INCHI_KEY>
QOPCQMMKSJQFBG-XYGVGCQLSA-N

> <FORMULA>
C31H48N2O

> <MOLECULAR_WEIGHT>
464.738

> <EXACT_MASS>
464.376664174

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
58.16870587328348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,1'S,2'S,7'S,10'R,11'S,13'S,14'S,15'S)-14'-[(1S)-1-(dimethylamino)ethyl]-2,2',15'-trimethyl-2,3-dihydrospiro[isoindole-1,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-13'-ol

> <ALOGPS_LOGP>
4.91

> <JCHEM_LOGP>
5.251237533333333

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.874540404875034

> <JCHEM_PKA_STRONGEST_BASIC>
9.827563861866869

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
142.0159

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.32e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,1'S,2'S,7'S,10'R,11'S,13'S,14'S,15'S)-14'-[(1S)-1-(dimethylamino)ethyl]-2,2',15'-trimethyl-3H-spiro[isoindole-1,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-13'-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.110  -2.043   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.205  -0.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.831   0.609   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.363   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.268  -0.476   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.641  -1.883   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.732  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.733   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.268   2.016   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      13.979   2.445   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.978  -0.905   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      15.385  -0.279   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      16.631  -1.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.546   1.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.817  -2.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.298  -1.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.926   1.855   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.394   1.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.768   0.288   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.673  -0.958   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.046  -2.365   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.515  -2.526   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.610  -1.280   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.236   0.127   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       2.840  -2.613   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       1.333  -2.293   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.173  -0.762   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.073   0.144   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.088   1.675   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.495   2.302   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.741   1.396   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.579  -0.135   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.466  -4.020   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.578  -2.204   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   16                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8                                                            
CONECT   11    7   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
CONECT   16    5                                                            
CONECT   17    3   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19    2   21   34                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   32                                             
CONECT   24   23   19                                                       
CONECT   25   23   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   23   27                                                  
CONECT   33   25                                                            
CONECT   34   20                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₈N₂O

Average Mass

464.7380 Da

Monoisotopic Mass

464.37666 Da

IUPAC Name

(1R,1'S,2'S,7'S,10'R,11'S,13'S,14'S,15'S)-14'-[(1S)-1-(dimethylamino)ethyl]-2,2',15'-trimethyl-2,3-dihydrospiro[isoindole-1,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-13'-ol

Traditional Name

(1R,1'S,2'S,7'S,10'R,11'S,13'S,14'S,15'S)-14'-[(1S)-1-(dimethylamino)ethyl]-2,2',15'-trimethyl-3H-spiro[isoindole-1,5'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-13'-ol

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H]1[C@@H](O)C[C@H]2[C@@H]3CC[C@H]4C[C@@]5(CC[C@]4(C)[C@H]3CC[C@]12C)N(C)CC1=CC=CC=C51)N(C)C

InChI Identifier

InChI=1S/C31H48N2O/c1-20(32(4)5)28-27(34)17-26-23-12-11-22-18-31(24-10-8-7-9-21(24)19-33(31)6)16-15-29(22,2)25(23)13-14-30(26,28)3/h7-10,20,22-23,25-28,34H,11-19H2,1-6H3/t20-,22-,23+,25-,26-,27-,28-,29-,30-,31+/m0/s1

InChI Key

QOPCQMMKSJQFBG-XYGVGCQLSA-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
Pachysandra procumbens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 16-hydroxysteroids. These are steroids carrying a hydroxyl group at the 16-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

16-hydroxysteroids

Alternative Parents

Substituents

22-azasteroid
Pregnane-skeleton
Steroidal alkaloid
16-hydroxysteroid
16-beta-hydroxysteroid
Azasteroid
Alkaloid or derivatives
Isoindole or derivatives
Isoindole
Isoindoline
Aralkylamine
Benzenoid
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.91	ALOGPS
logP	5.25	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	14.87	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.71 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	142.02 m³·mol⁻¹	ChemAxon
Polarizability	58.17 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

163105702

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Spiropachysine (NP0082934)

MOL for NP0082934 ((+)-Spiropachysine)

3D MOL for NP0082934 ((+)-Spiropachysine)

3D SDF for NP0082934 ((+)-Spiropachysine)

3D-SDF for NP0082934 ((+)-Spiropachysine)

PDB for NP0082934 ((+)-Spiropachysine)

3D PDB for NP0082934 ((+)-Spiropachysine)

SMILES for NP0082934 ((+)-Spiropachysine)

INCHI for NP0082934 ((+)-Spiropachysine)

Structure for NP0082934 ((+)-Spiropachysine)

3D Structure for NP0082934 ((+)-Spiropachysine)