NP-MRD: Showing NP-Card for [(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol (NP0318320)

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Record Information

Version

2.0

Created at

2022-09-11 18:44:29 UTC

Updated at

2022-09-11 18:44:30 UTC

NP-MRD ID

NP0318320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

Description

[(15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol 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. [(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol is found in Alstonia angustifolia and Alstonia macrophylla. [(15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]Octadeca-2(10),4(9),5,7-tetraen-13-yl]methanol is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121514252D          

 25 29  0  0  0  0            999 V2000
    5.4688    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    1.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1860    0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6183    0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -0.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    0.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6157   -0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0109   -1.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672   -1.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414    0.4109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5745    0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914    0.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2165    0.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039   -0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -1.1371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272   -1.9967    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
  9 23  2  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END


  Mrv0541 04121514252D          

 25 29  0  0  0  0            999 V2000
    5.4688    1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    1.7110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1860    0.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6183    0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013   -0.5088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690    0.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613    0.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1671   -0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6157   -0.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2297    0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9997   -0.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0109   -1.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231   -0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672   -1.0565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0572   -0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414    0.4109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2175    0.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5745    0.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914    0.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2165    0.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039   -0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666   -1.1371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1272   -1.9967    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
  9 23  2  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0318320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2N(C)C3=C(CC4C(CO)C5CC3N4C\C5=C\C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O2/c1-4-12-10-23-19-9-16-15-7-13(25-3)5-6-18(15)22(2)21(16)20(23)8-14(12)17(19)11-24/h4-7,14,17,19-20,24H,8-11H2,1-3H3/b12-4-

> <INCHI_KEY>
QWVWSERSLAJTNG-QCDXTXTGSA-N

> <FORMULA>
C21H26N2O2

> <MOLECULAR_WEIGHT>
338.451

> <EXACT_MASS>
338.199428085

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
39.44413776215048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.2744521676666665

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.402354370569924

> <JCHEM_PKA_STRONGEST_BASIC>
6.79424325492843

> <JCHEM_POLAR_SURFACE_AREA>
37.63

> <JCHEM_REFRACTIVITY>
100.6807

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      10.208   3.533   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.639   3.194   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.814   1.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.621   0.448   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.888  -0.907   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.349  -0.950   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.542   0.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.274   1.716   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.045  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.016  -1.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.559  -0.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.429   0.093   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.866  -1.181   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.887  -2.870   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.790  -0.931   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.499  -1.972   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.973  -1.272   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.757   0.767   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.406   1.851   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.072   0.952   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.597   1.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.137   1.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.927  -1.536   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       5.351  -2.123   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       5.837  -3.727   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17    9   24                                                  
CONECT   24   23    6   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

C₂₁H₂₆N₂O₂

Average Mass

338.4510 Da

Monoisotopic Mass

338.19943 Da

IUPAC Name

[(15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

Traditional Name

[(15E)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2N(C)C3=C(CC4C(CO)C5CC3N4C\C5=C\C)C2=C1

InChI Identifier

InChI=1S/C21H26N2O2/c1-4-12-10-23-19-9-16-15-7-13(25-3)5-6-18(15)22(2)21(16)20(23)8-14(12)17(19)11-24/h4-7,14,17,19-20,24H,8-11H2,1-3H3/b12-4-

InChI Key

QWVWSERSLAJTNG-QCDXTXTGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia angustifolia	LOTUS Database	35616633
Alstonia macrophylla	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
Pyridoindole
Beta-carboline
3-alkylindole
N-alkylindole
Indole
Indole or derivatives
Anisole
Quinuclidine
Aralkylamine
Alkyl aryl ether
N-methylpyrrole
Benzenoid
Piperidine
Substituted pyrrole
1,3-aminoalcohol
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Ether
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Primary alcohol
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	2.81	ALOGPS
logP	2.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.4	ChemAxon
pKa (Strongest Basic)	6.79	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.68 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

14707289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol (NP0318320)

MOL for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D MOL for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D SDF for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D-SDF for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

PDB for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D PDB for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

SMILES for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

INCHI for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

Structure for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)

3D Structure for NP0318320 ([(15e)-15-ethylidene-7-methoxy-3-methyl-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraen-13-yl]methanol)