NP-MRD: Showing NP-Card for Roxburghine B (NP0050902)

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Record Information

Version

2.0

Created at

2022-04-27 22:22:21 UTC

Updated at

2022-04-27 22:22:21 UTC

NP-MRD ID

NP0050902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Roxburghine B

Description

Methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0²,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁹,³¹.0²⁰,²⁸.0²²,²⁷]Dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylate belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. Roxburghine B is found in Uncaria elliptica and Uncaria gambir . Based on a literature review very few articles have been published on methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0²,¹⁴.0⁴,¹².0⁶,¹¹.0¹⁹,³¹.0²⁰,²⁸.0²²,²⁷]Dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200222D          

 37 44  0  0  1  0            999 V2000
    7.6260   -0.0392    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


  Mrv1652304282200222D          

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  6 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 20 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  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 22 28  2  0  0  0  0
 17 29  1  1  0  0  0
 14 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
  2 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CN2CC3=C(C[C@@]2(C)[C@@H]2CN4CCC5=C(NC6=CC=CC=C56)[C@H]4C[C@H]12)NC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C31H32N4O2/c1-31-14-27-22(19-8-4-5-9-25(19)32-27)15-35(31)16-23(30(36)37-2)21-13-28-29-20(11-12-34(28)17-24(21)31)18-7-3-6-10-26(18)33-29/h3-10,16,21,24,28,32-33H,11-15,17H2,1-2H3/t21-,24-,28-,31+/m1/s1

> <INCHI_KEY>
SSVINUXCSDCQPY-ABXXHBHXSA-N

> <FORMULA>
C31H32N4O2

> <MOLECULAR_WEIGHT>
492.623

> <EXACT_MASS>
492.252526286

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.40890911390444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0^{2,14}.0^{4,12}.0^{6,11}.0^{19,31}.0^{20,28}.0^{22,27}]dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylate

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
4.096538409666665

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.488710323163584

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.738070839917945

> <JCHEM_PKA_STRONGEST_BASIC>
7.016577250750732

> <JCHEM_POLAR_SURFACE_AREA>
64.36

> <JCHEM_REFRACTIVITY>
145.69819999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0^{2,14}.0^{4,12}.0^{6,11}.0^{19,31}.0^{20,28}.0^{22,27}]dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylate

> <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      14.235  -0.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.752   0.194   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.967   1.719   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      14.583   2.394   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      13.513   1.287   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.974   1.341   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      11.157   0.036   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      11.880  -1.324   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.419  -1.379   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.618   0.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.896   1.450   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.712   2.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.251   2.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.990   4.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.451   4.170   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.634   2.864   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       7.357   1.504   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.540   0.199   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.001   0.253   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.278   1.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.095   2.919   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.762   1.346   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.547  -0.179   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       3.931  -0.854   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.119  -0.755   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.094   0.194   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.121   1.719   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.549   2.295   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.079   0.144   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.806   5.421   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.345   5.367   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.084   6.781   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       9.901   8.087   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      17.395   2.295   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.608   1.346   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.393  -0.179   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      16.965  -0.755   0.000  0.00  0.00           C+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    6                                                       
CONECT   14   12   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   11   18   29                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   22                                                       
CONECT   29   17                                                            
CONECT   30   14   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34    3   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    2                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   88    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0,.0,.0,.0,.0,.0,]dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylic acid	Generator

Chemical Formula

C₃₁H₃₂N₄O₂

Average Mass

492.6230 Da

Monoisotopic Mass

492.25253 Da

IUPAC Name

methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0^{2,14}.0^{4,12}.0^{6,11}.0^{19,31}.0^{20,28}.0^{22,27}]dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylate

Traditional Name

methyl (1S,2S,17S,19R)-2-methyl-5,14,21,31-tetraazaoctacyclo[15.15.0.0^{2,14}.0^{4,12}.0^{6,11}.0^{19,31}.0^{20,28}.0^{22,27}]dotriaconta-4(12),6,8,10,15,20(28),22,24,26-nonaene-16-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CN2CC3=C(C[C@@]2(C)[C@@H]2CN4CCC5=C(NC6=CC=CC=C56)[C@H]4C[C@H]12)NC1=CC=CC=C31

InChI Identifier

InChI=1S/C31H32N4O2/c1-31-14-27-22(19-8-4-5-9-25(19)32-27)15-35(31)16-23(30(36)37-2)21-13-28-29-20(11-12-34(28)17-24(21)31)18-7-3-6-10-26(18)33-29/h3-10,16,21,24,28,32-33H,11-15,17H2,1-2H3/t21-,24-,28-,31+/m1/s1

InChI Key

SSVINUXCSDCQPY-ABXXHBHXSA-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
Uncaria elliptica	LOTUS Database	35616633
Uncaria gambir	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Pyridoindole
Beta-carboline
Diazanaphthalene
3-alkylindole
Naphthyridine
Indole or derivatives
Indole
Aralkylamine
Tetrahydropyridine
Benzenoid
Piperidine
Heteroaromatic compound
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Allylamine
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Enamine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	4.19	ALOGPS
logP	4.1	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	15.74	ChemAxon
pKa (Strongest Basic)	7.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	145.7 m³·mol⁻¹	ChemAxon
Polarizability	57.41 Å³	ChemAxon
Number of Rings	8	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

163067947

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Roxburghine B (NP0050902)

MOL for NP0050902 (Roxburghine B)

3D MOL for NP0050902 (Roxburghine B)

3D SDF for NP0050902 (Roxburghine B)

3D-SDF for NP0050902 (Roxburghine B)

PDB for NP0050902 (Roxburghine B)

3D PDB for NP0050902 (Roxburghine B)

SMILES for NP0050902 (Roxburghine B)

INCHI for NP0050902 (Roxburghine B)

Structure for NP0050902 (Roxburghine B)

3D Structure for NP0050902 (Roxburghine B)