NP-MRD: Showing NP-Card for (2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol (NP0179321)

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Record Information

Version

2.0

Created at

2022-09-03 17:29:22 UTC

Updated at

2022-09-03 17:29:22 UTC

NP-MRD ID

NP0179321

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol

Description

(2S,13S,15R,20S,21S)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]Henicosa-4(12),5,7,9-tetraen-17-ol 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. (2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol is found in Rauvolfia caffra, Rauvolfia mannii, Rauvolfia sumatrana and Rauvolfia volkensii. Based on a literature review very few articles have been published on (2S,13S,15R,20S,21S)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]Henicosa-4(12),5,7,9-tetraen-17-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032219292D          

 23 28  0  0  1  0            999 V2000
    1.2658   -1.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -1.1649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2083   -0.9592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0607   -0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198    0.2058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7138    0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8828    1.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0914    0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760    0.4995    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8355    0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4426    0.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -0.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8559   -1.1784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230   -0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3301   -0.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817   -0.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8192    0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676    0.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432   -0.9684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3264   -1.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0451   -0.3696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0576   -0.2785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 20 12  1  6  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
  8 22  1  0  0  0  0
  3 22  1  0  0  0  0
 20 23  1  0  0  0  0
  9 23  1  6  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179321

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2COC(O)C3[C@@H]2C[C@@H]2N1[C@H]3CC1=C2NC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O2/c1-9-13-8-23-19(22)17-11(13)6-16-18-12(7-15(17)21(9)16)10-4-2-3-5-14(10)20-18/h2-5,9,11,13,15-17,19-20,22H,6-8H2,1H3/t9-,11+,13+,15-,16-,17?,19?/m0/s1

> <INCHI_KEY>
LVOPRJWLXUCHRL-RDKYAOAVSA-N

> <FORMULA>
C19H22N2O2

> <MOLECULAR_WEIGHT>
310.397

> <EXACT_MASS>
310.168127956

> <ALOGPS_LOGP>
2.05

> <ALOGPS_LOGS>
-2.73

> <ALOGPS_SOLUBILITY>
5.78e-01 g/l

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.363  -3.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.544  -2.174   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.389  -1.791   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.980  -1.179   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.464   0.384   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.332   1.467   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.648   2.975   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.171   0.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.822   0.932   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.426   1.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.559   0.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.085  -1.295   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       5.331  -2.200   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       6.576  -1.294   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.083  -1.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.113  -0.468   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.636   0.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.129   1.316   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.099   0.171   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.507  -1.808   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.609  -2.487   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.084  -0.690   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.974  -0.520   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   22                                                  
CONECT    9    8   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   14                                                  
CONECT   20   12   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21    8    3                                                  
CONECT   23   20    9    2                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂N₂O₂

Average Mass

310.3970 Da

Monoisotopic Mass

310.16813 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2COC(O)C3[C@@H]2C[C@@H]2N1[C@H]3CC1=C2NC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H22N2O2/c1-9-13-8-23-19(22)17-11(13)6-16-18-12(7-15(17)21(9)16)10-4-2-3-5-14(10)20-18/h2-5,9,11,13,15-17,19-20,22H,6-8H2,1H3/t9-,11+,13+,15-,16-,17?,19?/m0/s1

InChI Key

LVOPRJWLXUCHRL-RDKYAOAVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rauvolfia caffra	LOTUS Database	35616633
Rauvolfia mannii	LOTUS Database	35616633
Rauvolfia sumatrana	LOTUS Database	35616633
Rauvolfia volkensii	LOTUS Database	35616633

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
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Oxane
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Hemiacetal
Tertiary aliphatic amine
Tertiary amine
Azacycle
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen 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

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

34966905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102004388

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol (NP0179321)

MOL for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

3D MOL for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

3D SDF for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

3D-SDF for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

PDB for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

3D PDB for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

SMILES for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

INCHI for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

Structure for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)

3D Structure for NP0179321 ((2s,13s,15r,20s,21s)-21-methyl-18-oxa-1,11-diazahexacyclo[11.8.0.0²,¹⁶.0⁴,¹².0⁵,¹⁰.0¹⁵,²⁰]henicosa-4(12),5,7,9-tetraen-17-ol)