NP-MRD: Showing NP-Card for (+)-12-Methoxy-Na-methylvellosimine (NP0074885)

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Record Information

Version

2.0

Created at

2022-04-28 20:11:59 UTC

Updated at

2022-04-28 20:12:00 UTC

NP-MRD ID

NP0074885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-12-Methoxy-Na-methylvellosimine

Description

(1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. (+)-12-Methoxy-Na-methylvellosimine is found in Rauvolfia bahiensis. Based on a literature review very few articles have been published on (1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282222122D          

 25 29  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957    0.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7925    0.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068   -2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165   -3.0358    0.0000 O   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  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 18  1  0  0  0  0
  5 19  1  0  0  0  0
  1 19  1  6  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  6  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1652304282222122D          

 25 29  0  0  1  0            999 V2000
   -0.7779   -0.9460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2774   -1.6159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5479   -1.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6531   -0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.2226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9861   -0.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -1.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784   -1.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3569   -1.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -1.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828   -0.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957    0.7849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7925    0.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -0.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    0.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6957   -0.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3127    0.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0955    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6068   -2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1165   -3.0358    0.0000 O   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  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  8 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 18  1  0  0  0  0
  5 19  1  0  0  0  0
  1 19  1  6  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  6  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0074885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2N(C)C3=C(C[C@H]4[C@H](C=O)[C@@H]5C[C@@H]3N4C\C5=C\C)C2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O2/c1-4-12-10-23-17-9-15-13-6-5-7-19(25-3)21(13)22(2)20(15)18(23)8-14(12)16(17)11-24/h4-7,11,14,16-18H,8-10H2,1-3H3/b12-4-/t14-,16-,17+,18+/m1/s1

> <INCHI_KEY>
RBNBEKDCSALFTN-JNSISUEASA-N

> <FORMULA>
C21H24N2O2

> <MOLECULAR_WEIGHT>
336.435

> <EXACT_MASS>
336.183778021

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.444206540046096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

> <ALOGPS_LOGP>
3.02

> <JCHEM_LOGP>
2.5246369520000007

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.113635864778583

> <JCHEM_PKA_STRONGEST_BASIC>
5.634282279081362

> <JCHEM_POLAR_SURFACE_AREA>
34.47

> <JCHEM_REFRACTIVITY>
99.53970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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      -1.452  -1.766   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.518  -3.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.023  -2.850   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.243  -1.321   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.408  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.086  -0.555   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.282   0.416   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.574  -0.422   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.177  -1.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.639  -1.992   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.573  -3.212   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.266  -2.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.754  -2.599   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.151  -1.111   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.061  -0.023   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.459   1.465   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.946   1.865   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.200   1.953   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.357  -0.555   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.323   0.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.299  -0.235   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.450   0.787   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.912   0.301   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.133  -4.428   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.217  -5.667   0.000  0.00  0.00           O+0
CONECT    1    2   19   21                                                  
CONECT    2    1    3   24                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10    3                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    7                                                            
CONECT   19    5    1                                                       
CONECT   20    4   21                                                       
CONECT   21   20    1   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    2   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₂

Average Mass

336.4350 Da

Monoisotopic Mass

336.18378 Da

IUPAC Name

(1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

Traditional Name

(1S,12S,13R,14S,15E)-15-ethylidene-5-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

CAS Registry Number

Not Available

SMILES

COC1=C2N(C)C3=C(C[C@H]4[C@H](C=O)[C@@H]5C[C@@H]3N4C\C5=C\C)C2=CC=C1

InChI Identifier

InChI=1S/C21H24N2O2/c1-4-12-10-23-17-9-15-13-6-5-7-19(25-3)21(13)22(2)20(15)18(23)8-14(12)16(17)11-24/h4-7,11,14,16-18H,8-10H2,1-3H3/b12-4-/t14-,16-,17+,18+/m1/s1

InChI Key

RBNBEKDCSALFTN-JNSISUEASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rauvolfia bahiensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Vobasan skeleton
Sarpagine-skeleton
Pyridoindole
Beta-carboline
N-alkylindole
3-alkylindole
Indole or derivatives
Indole
Quinuclidine
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Substituted pyrrole
Piperidine
N-methylpyrrole
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aldehyde
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	3.02	ALOGPS
logP	2.52	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	5.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.54 m³·mol⁻¹	ChemAxon
Polarizability	39.44 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162995542

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-12-Methoxy-Na-methylvellosimine (NP0074885)

MOL for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

3D MOL for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

3D SDF for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

3D-SDF for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

PDB for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

3D PDB for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

SMILES for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

INCHI for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

Structure for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)

3D Structure for NP0074885 ((+)-12-Methoxy-Na-methylvellosimine)