NP-MRD: Showing NP-Card for (-)-12-Methoxyechitamidine (NP0077838)

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Record Information

Version

2.0

Created at

2022-04-28 22:59:28 UTC

Updated at

2022-04-28 22:59:28 UTC

NP-MRD ID

NP0077838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-12-Methoxyechitamidine

Description

Methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]Octadeca-2(7),3,5,9-tetraene-10-carboxylate belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. (-)-12-Methoxyechitamidine is found in Alstonia rostrata and Winchia calophylla. Based on a literature review very few articles have been published on methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]Octadeca-2(7),3,5,9-tetraene-10-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292200592D          

 27 31  0  0  1  0            999 V2000
    2.7182    1.0454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6418    0.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336    0.1640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4286    0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    1.2509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5206    1.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    2.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763    1.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    0.8548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3624    0.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9214    1.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -0.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -1.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -2.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4017   -0.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5948    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0262    1.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8509    1.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8128    0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2061   -0.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308   -0.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  1  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
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv1652304292200592D          

 27 31  0  0  1  0            999 V2000
    2.7182    1.0454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6418    0.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380   -0.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336    0.1640    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4286    0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9361    1.2509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5206    1.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    2.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9129    1.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763    1.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4426    0.8548    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3624    0.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9214    1.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6082   -0.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8364   -1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1212   -1.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -2.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4017   -0.1957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9881    0.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5948    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0262    1.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8509    1.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8128    0.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2061   -0.3593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0308   -0.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  5  1  6  0  0  0
  1  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
  1  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=C(C=CC=C3OC)[C@]22CCN3C[C@@H]([C@H](C)O)[C@@H]1C[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O4/c1-11(24)13-10-23-8-7-21-14-5-4-6-15(26-2)18(14)22-19(21)17(20(25)27-3)12(13)9-16(21)23/h4-6,11-13,16,22,24H,7-10H2,1-3H3/t11-,12-,13-,16-,21-/m0/s1

> <INCHI_KEY>
FNDWOLJMJUSGOB-NKWDSHEASA-N

> <FORMULA>
C21H26N2O4

> <MOLECULAR_WEIGHT>
370.449

> <EXACT_MASS>
370.189257325

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
58.9441508154882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,9-tetraene-10-carboxylate

> <ALOGPS_LOGP>
2.38

> <JCHEM_LOGP>
0.6774944583333344

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.232728459407298

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.311269276663726

> <JCHEM_PKA_STRONGEST_BASIC>
9.581547760401577

> <JCHEM_POLAR_SURFACE_AREA>
71.03

> <JCHEM_REFRACTIVITY>
103.94560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,9-tetraene-10-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.074   1.951   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.931   0.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.431  -0.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.929   0.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.185   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.614   2.335   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.838   3.600   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.162   4.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.437   3.581   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.262   3.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.826   1.596   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.676   1.258   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.720   2.391   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.135  -0.212   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.428  -2.017   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.093  -2.785   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.760  -2.790   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.757  -4.330   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       6.350  -0.365   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       7.444   0.724   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.710   2.078   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.516   3.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.055   3.350   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.789   1.996   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.984   0.683   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.718  -0.671   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.257  -0.712   0.000  0.00  0.00           C+0
CONECT    1    2    6    9   21                                             
CONECT    2    1    3   19                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    7   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    3   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20    1   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0,.0,.0,]octadeca-2(7),3,5,9-tetraene-10-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₆N₂O₄

Average Mass

370.4490 Da

Monoisotopic Mass

370.18926 Da

IUPAC Name

methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,9-tetraene-10-carboxylate

Traditional Name

methyl (1S,11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-6-methoxy-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2(7),3,5,9-tetraene-10-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=C(C=CC=C3OC)[C@]22CCN3C[C@@H]([C@H](C)O)[C@@H]1C[C@@H]23

InChI Identifier

InChI=1S/C21H26N2O4/c1-11(24)13-10-23-8-7-21-14-5-4-6-15(26-2)18(14)22-19(21)17(20(25)27-3)12(13)9-16(21)23/h4-6,11-13,16,22,24H,7-10H2,1-3H3/t11-,12-,13-,16-,21-/m0/s1

InChI Key

FNDWOLJMJUSGOB-NKWDSHEASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia rostrata	LOTUS Database	35616633
Winchia calophylla	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Indolizidine
Dihydroindole
Indole or derivatives
Anisole
Aralkylamine
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Vinylogous amide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Ether
Enamine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	2.38	ALOGPS
logP	0.68	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.31	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.95 m³·mol⁻¹	ChemAxon
Polarizability	58.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163011074

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-12-Methoxyechitamidine (NP0077838)

MOL for NP0077838 ((-)-12-Methoxyechitamidine)

3D MOL for NP0077838 ((-)-12-Methoxyechitamidine)

3D SDF for NP0077838 ((-)-12-Methoxyechitamidine)

3D-SDF for NP0077838 ((-)-12-Methoxyechitamidine)

PDB for NP0077838 ((-)-12-Methoxyechitamidine)

3D PDB for NP0077838 ((-)-12-Methoxyechitamidine)

SMILES for NP0077838 ((-)-12-Methoxyechitamidine)

INCHI for NP0077838 ((-)-12-Methoxyechitamidine)

Structure for NP0077838 ((-)-12-Methoxyechitamidine)

3D Structure for NP0077838 ((-)-12-Methoxyechitamidine)