NP-MRD: Showing NP-Card for (1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one (NP0187010)

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Record Information

Version

2.0

Created at

2022-09-04 03:02:26 UTC

Updated at

2022-09-04 03:02:27 UTC

NP-MRD ID

NP0187010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one

Description

82375-29-9, Also known as humantenine, belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21. (1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one is found in Gelsemium elegans. Based on a literature review very few articles have been published on 82375-29-9.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042205022D          

 26 30  0  0  1  0            999 V2000
    2.6258    0.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0602   -0.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573   -0.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0832    0.0303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370    0.3270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9120    0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    1.6148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    2.8761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982    2.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989    3.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    4.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276    2.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8521    2.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.8385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0671    1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    0.5756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0797    0.7020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2823    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359    2.2957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
M  END


  Mrv1652309042205022D          

 26 30  0  0  1  0            999 V2000
    2.6258    0.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0602   -0.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2573   -0.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5182   -0.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0832    0.0303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370    0.3270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9120    0.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    1.6148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0338    2.8761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4982    2.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989    3.5461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1063    4.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276    2.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8521    2.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2384    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8002    0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    1.8385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0671    1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7033    0.5756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0797    0.7020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2823    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3359    2.2957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 20  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 23 22  1  6  0  0  0
  3 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)[C@@]2(C[C@H]3[C@@H]4CO[C@@H]2C[C@@H]4\C(CN3C)=C/C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O3/c1-4-13-11-22(2)18-10-21(19-9-14(13)15(18)12-26-19)16-7-5-6-8-17(16)23(25-3)20(21)24/h4-8,14-15,18-19H,9-12H2,1-3H3/b13-4-/t14-,15-,18+,19-,21+/m1/s1

> <INCHI_KEY>
SJKRPUOXUNOPOP-SBKPKGBVSA-N

> <FORMULA>
C21H26N2O3

> <MOLECULAR_WEIGHT>
354.45

> <EXACT_MASS>
354.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.46163051085112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,3S,4'S,7'E,8'S,9'R)-7'-ethylidene-1-methoxy-5'-methyl-1,2-dihydro-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-2-one

> <JCHEM_LOGP>
2.018941925666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.12828620232061

> <JCHEM_POLAR_SURFACE_AREA>
42.010000000000005

> <JCHEM_REFRACTIVITY>
100.0941

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,3S,4'S,7'E,8'S,9'R)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0^{4,9}]dodecane]-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.902   0.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.846  -0.845   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.347  -0.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.967  -1.288   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       0.155   0.057   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.277   0.623   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.122   0.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.569   1.475   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.340   3.014   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.235   4.551   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.930   5.369   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       4.663   5.126   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       5.038   6.619   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.932   7.691   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.652   3.945   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.191   3.889   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.912   2.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.094   1.223   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.555   1.279   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.834   2.640   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.770   3.432   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.125   2.246   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.313   1.074   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.149   1.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.527   3.155   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.627   4.285   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20   21                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15    9                                                  
CONECT   21    9   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23    7   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
Humantenine	MeSH

Chemical Formula

C₂₁H₂₆N₂O₃

Average Mass

354.4500 Da

Monoisotopic Mass

354.19434 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CON1C(=O)[C@@]2(C[C@H]3[C@@H]4CO[C@@H]2C[C@@H]4\C(CN3C)=C/C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C21H26N2O3/c1-4-13-11-22(2)18-10-21(19-9-14(13)15(18)12-26-19)16-7-5-6-8-17(16)23(25-3)20(21)24/h4-8,14-15,18-19H,9-12H2,1-3H3/b13-4-/t14-,15-,18+,19-,21+/m1/s1

InChI Key

SJKRPUOXUNOPOP-SBKPKGBVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gelsemium elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Gelsemium alkaloids

Sub Class

Not Available

Direct Parent

Gelsemium alkaloids

Alternative Parents

Substituents

Gelsemium skeleton
Indole or derivatives
Aralkylamine
Oxepane
Benzenoid
Piperidine
Oxane
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00025092

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

129316501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one (NP0187010)

MOL for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D MOL for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D SDF for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D-SDF for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

PDB for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D PDB for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

SMILES for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

INCHI for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

Structure for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)

3D Structure for NP0187010 ((1'r,3s,4's,7'e,8's,9'r)-7'-ethylidene-1-methoxy-5'-methyl-11'-oxa-5'-azaspiro[indole-3,2'-tricyclo[6.3.1.0⁴,⁹]dodecan]-2-one)