NP-MRD: Showing NP-Card for methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate (NP0154843)

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Record Information

Version

2.0

Created at

2022-09-02 11:48:57 UTC

Updated at

2022-09-02 11:48:57 UTC

NP-MRD ID

NP0154843

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate

Description

Methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]Nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate is found in Alstonia scholaris. Based on a literature review very few articles have been published on methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]Nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022213482D          

 27 31  0  0  1  0            999 V2000
    7.0200    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6701    1.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    2.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8650    2.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1150    3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4445    3.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    4.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1512    4.7283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7801    2.9972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    3.3672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2337    2.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8871    1.2170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1497    1.5869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5257    1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6812    0.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    1.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    2.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2597    3.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6727    3.6870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400    3.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679    3.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300    3.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741    2.4938    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 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
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END


  Mrv1652309022213482D          

 27 31  0  0  1  0            999 V2000
    7.0200    1.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098    0.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6701    1.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400    2.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8650    2.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1150    3.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4445    3.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393    4.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1512    4.7283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7801    2.9972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    3.3672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2337    2.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8871    1.2170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1497    1.5869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5257    1.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6812    0.2369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7463    1.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224    0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898    2.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2597    3.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6727    3.6870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9400    3.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1679    3.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5300    3.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    2.2614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4363    1.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0741    2.4938    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 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
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154843

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H]1[C@@H]2C[C@@H](N3C(C=O)=CC=C3\C2=C/C)C2=C1C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C22H20N2O3/c1-3-13-15-10-18(24-12(11-25)8-9-17(13)24)21-19(20(15)22(26)27-2)14-6-4-5-7-16(14)23-21/h3-9,11,15,18,20,23H,10H2,1-2H3/b13-3-/t15-,18-,20-/m1/s1

> <INCHI_KEY>
LMQWGENTCNSYQP-WHFMRHSRSA-N

> <FORMULA>
C22H20N2O3

> <MOLECULAR_WEIGHT>
360.413

> <EXACT_MASS>
360.147392512

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.74669805216597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0^{2,10}.0^{4,9}.0^{14,18}]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
3.286865827333333

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.383702009033225

> <JCHEM_PKA_STRONGEST_BASIC>
-6.974283714827121

> <JCHEM_POLAR_SURFACE_AREA>
64.09

> <JCHEM_REFRACTIVITY>
104.00610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0^{2,10}.0^{4,9}.0^{14,18}]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      13.104   1.882   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592   1.592   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.584   2.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.275   4.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.815   4.143   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.281   5.611   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.030   6.508   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.020   8.048   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.349   8.826   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      10.790   5.595   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.413   6.285   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.770   4.242   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.123   2.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.746   2.962   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.581   1.955   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.871   0.442   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.126   2.460   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.962   1.452   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.261   4.424   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.951   5.800   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       6.856   6.882   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       5.488   6.175   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.047   6.717   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.856   5.741   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.107   4.221   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.548   3.678   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.738   4.655   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    4   11                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20   27                                                  
CONECT   20   19   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   22                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylic acid	Generator

Chemical Formula

C₂₂H₂₀N₂O₃

Average Mass

360.4130 Da

Monoisotopic Mass

360.14739 Da

IUPAC Name

methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0^{2,10}.0^{4,9}.0^{14,18}]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate

Traditional Name

methyl (1R,11R,12S,13Z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0^{2,10}.0^{4,9}.0^{14,18}]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H]1[C@@H]2C[C@@H](N3C(C=O)=CC=C3\C2=C/C)C2=C1C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C22H20N2O3/c1-3-13-15-10-18(24-12(11-25)8-9-17(13)24)21-19(20(15)22(26)27-2)14-6-4-5-7-16(14)23-21/h3-9,11,15,18,20,23H,10H2,1-2H3/b13-3-/t15-,18-,20-/m1/s1

InChI Key

LMQWGENTCNSYQP-WHFMRHSRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia Alstonia scholaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
3-alkylindole
Indole
Aryl-aldehyde
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Aldehyde
Carbonyl group
Organic nitrogen compound
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	3.89	ALOGPS
logP	3.29	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.38	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.01 m³·mol⁻¹	ChemAxon
Polarizability	38.75 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

163193290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate (NP0154843)

MOL for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

3D MOL for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

3D SDF for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

3D-SDF for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

PDB for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

3D PDB for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

SMILES for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

INCHI for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

Structure for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)

3D Structure for NP0154843 (methyl (1r,11r,12s,13z)-13-ethylidene-17-formyl-3,18-diazapentacyclo[10.6.1.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁸]nonadeca-2(10),4,6,8,14,16-hexaene-11-carboxylate)