NP-MRD: Showing NP-Card for Rescinnaminol (NP0067456)

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Record Information

Version

2.0

Created at

2022-04-28 12:18:36 UTC

Updated at

2022-04-28 12:18:36 UTC

NP-MRD ID

NP0067456

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rescinnaminol

Description

(1S)-1-{[(1R,15S,17S,20S)-6-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4(9),5,7-tetraen-17-yl]oxy}-3-(3,4,5-trimethoxyphenyl)propan-1-ol belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Rescinnaminol is found in Rauvolfia serpentina . Based on a literature review very few articles have been published on (1S)-1-{[(1R,15S,17S,20S)-6-methoxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]Henicosa-2(10),4(9),5,7-tetraen-17-yl]oxy}-3-(3,4,5-trimethoxyphenyl)propan-1-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214182D          

 40 45  0  0  1  0            999 V2000
    6.4079    0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3397   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7299    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2229    1.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845    0.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1127   -0.1288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8740    0.7301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
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  1  6  1  0  0  0  0
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  7 13  1  0  0  0  0
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 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282214182D          

 40 45  0  0  1  0            999 V2000
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   -0.6404    2.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9893    1.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2615    2.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720    2.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6104    1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4210    2.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6931    2.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    3.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442    3.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4269    4.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8885    4.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5037    3.0462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7758    3.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9594    1.4886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7699    1.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0177   -0.5277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7638   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 11 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 10 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  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
 27 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(NC3=C2CCN2C[C@H]4C[C@H](CC[C@H]4C[C@H]32)O[C@H](O)CCC2=CC(OC)=C(OC)C(OC)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H42N2O6/c1-36-22-8-9-24-25-11-12-34-18-21-15-23(7-6-20(21)16-27(34)31(25)33-26(24)17-22)40-30(35)10-5-19-13-28(37-2)32(39-4)29(14-19)38-3/h8-9,13-14,17,20-21,23,27,30,33,35H,5-7,10-12,15-16,18H2,1-4H3/t20-,21+,23-,27+,30-/m0/s1

> <INCHI_KEY>
CACUDZIKDKWSSF-CCNLXKQESA-N

> <FORMULA>
C32H42N2O6

> <MOLECULAR_WEIGHT>
550.696

> <EXACT_MASS>
550.30428708

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
63.42432221935351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S)-1-{[(1R,15S,17S,20S)-6-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-17-yl]oxy}-3-(3,4,5-trimethoxyphenyl)propan-1-ol

> <ALOGPS_LOGP>
4.24

> <JCHEM_LOGP>
4.4513312513333325

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.290184840300793

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.457417088971305

> <JCHEM_PKA_STRONGEST_BASIC>
7.393935222060177

> <JCHEM_POLAR_SURFACE_AREA>
85.41000000000001

> <JCHEM_REFRACTIVITY>
154.48889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S)-1-{[(1R,15S,17S,20S)-6-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-17-yl]oxy}-3-(3,4,5-trimethoxyphenyl)propan-1-ol

> <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      11.961   1.427   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.834  -0.108   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.441  -0.765   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.176   0.113   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.303   1.648   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.696   2.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.883   2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.878   1.076   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.677  -0.240   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.365   1.363   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.857   2.817   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       5.862   3.984   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.375   3.697   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.344   3.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.339   1.937   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.847   0.483   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.360   0.196   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.842  -0.684   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.329  -0.397   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.179   1.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.826   2.224   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.692   1.344   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.200   2.798   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.195   3.965   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.713   3.085   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.221   4.538   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.734   4.825   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.739   3.659   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -8.252   3.946   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.760   5.399   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.755   6.566   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.242   6.279   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -8.263   8.020   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.258   9.187   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -10.274   5.686   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0     -10.782   7.140   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -9.258   2.779   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -10.771   3.066   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      13.100  -0.985   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.492  -0.328   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8   11   17                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   10                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   30   36                                                       
CONECT   36   35                                                            
CONECT   37   29   38                                                       
CONECT   38   37                                                            
CONECT   39    2   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂N₂O₆

Average Mass

550.6960 Da

Monoisotopic Mass

550.30429 Da

IUPAC Name

(1S)-1-{[(1R,15S,17S,20S)-6-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-17-yl]oxy}-3-(3,4,5-trimethoxyphenyl)propan-1-ol

Traditional Name

(1S)-1-{[(1R,15S,17S,20S)-6-methoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-17-yl]oxy}-3-(3,4,5-trimethoxyphenyl)propan-1-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(NC3=C2CCN2C[C@H]4C[C@H](CC[C@H]4C[C@H]32)O[C@H](O)CCC2=CC(OC)=C(OC)C(OC)=C2)=C1

InChI Identifier

InChI=1S/C32H42N2O6/c1-36-22-8-9-24-25-11-12-34-18-21-15-23(7-6-20(21)16-27(34)31(25)33-26(24)17-22)40-30(35)10-5-19-13-28(37-2)32(39-4)29(14-19)38-3/h8-9,13-14,17,20-21,23,27,30,33,35H,5-7,10-12,15-16,18H2,1-4H3/t20-,21+,23-,27+,30-/m0/s1

InChI Key

CACUDZIKDKWSSF-CCNLXKQESA-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
Rauvolfia serpentina	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
3-alkylindole
Indole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Hemiacetal
Tertiary amine
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
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	4.24	ALOGPS
logP	4.45	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.46	ChemAxon
pKa (Strongest Basic)	7.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.41 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	154.49 m³·mol⁻¹	ChemAxon
Polarizability	63.42 Å³	ChemAxon
Number of Rings	6	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

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

162855105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rescinnaminol (NP0067456)

MOL for NP0067456 (Rescinnaminol)

3D MOL for NP0067456 (Rescinnaminol)

3D SDF for NP0067456 (Rescinnaminol)

3D-SDF for NP0067456 (Rescinnaminol)

PDB for NP0067456 (Rescinnaminol)

3D PDB for NP0067456 (Rescinnaminol)

SMILES for NP0067456 (Rescinnaminol)

INCHI for NP0067456 (Rescinnaminol)

Structure for NP0067456 (Rescinnaminol)

3D Structure for NP0067456 (Rescinnaminol)