NP-MRD: Showing NP-Card for 13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene (NP0327837)

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Record Information

Version

2.0

Created at

2022-09-12 10:46:36 UTC

Updated at

2022-09-12 10:46:36 UTC

NP-MRD ID

NP0327837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene

Description

13-Methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]Pentacosa-2,4(8),9,15(23),16(20),21-hexaene belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom). 13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene is found in Argemone grandiflora, Delphinium glaucum, Delphinium grandiflorum, Sarcocapnos crassifolia and Sarcocapnos enneaphylla. 13-Methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]Pentacosa-2,4(8),9,15(23),16(20),21-hexaene is a strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201506402D          

 26 32  0  0  0  0            999 V2000
    5.6426    6.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619    5.7931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407    5.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471    4.8048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537    4.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7602    3.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6079    3.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8977    2.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7115    2.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2356    3.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0598    3.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2793    4.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5908    4.6286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9458    4.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    4.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    5.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7643    5.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2079    5.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830    5.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    4.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545    4.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    3.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102    3.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3684    3.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1934    3.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6131    4.5489    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  5 26  1  0  0  0  0
 18 26  1  0  0  0  0
M  END


  Mrv1533004201506402D          

 26 32  0  0  0  0            999 V2000
    5.6426    6.5689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619    5.7931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8407    5.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471    4.8048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537    4.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7602    3.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6079    3.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8977    2.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7115    2.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2356    3.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0598    3.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2793    4.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5908    4.6286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9458    4.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    4.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207    5.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7643    5.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2079    5.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3830    5.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    4.5657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545    4.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0600    3.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8102    3.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3684    3.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1934    3.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6131    4.5489    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  5 26  1  0  0  0  0
 18 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2CC3=CC4=C(OCO4)C=C3C22CC3=CC=C4OCOC4=C3C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H17NO5/c1-21-16-5-11-4-14-15(24-8-23-14)6-12(11)20(16)7-10-2-3-13-18(25-9-22-13)17(10)19(21)26-20/h2-4,6,16,19H,5,7-9H2,1H3

> <INCHI_KEY>
HJDZNSLTBDNJJW-UHFFFAOYSA-N

> <FORMULA>
C20H17NO5

> <MOLECULAR_WEIGHT>
351.358

> <EXACT_MASS>
351.110672651

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.846898101337054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
3.116040120666667

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.3548181026918265

> <JCHEM_POLAR_SURFACE_AREA>
49.39

> <JCHEM_REFRACTIVITY>
90.4084

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      10.533  12.262   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      10.009  10.814   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      10.903   9.480   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.608   8.969   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.313   8.702   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.886   7.119   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.468   6.743   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.009   5.301   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.528   5.049   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.506   6.238   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.045   6.307   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.455   7.792   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.170   8.640   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.965   7.680   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.446   7.933   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.439  10.352   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.027  10.983   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.988   9.833   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.448   9.848   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.665   8.523   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.155   8.218   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.979   6.688   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.379   6.047   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.421   7.181   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.961   7.166   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.745   8.491   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16   26                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14    3    7                                                  
CONECT   16    5    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25    5   18                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₇NO₅

Average Mass

351.3580 Da

Monoisotopic Mass

351.11067 Da

IUPAC Name

13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene

Traditional Name

13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene

CAS Registry Number

Not Available

SMILES

CN1C2CC3=CC4=C(OCO4)C=C3C22CC3=CC=C4OCOC4=C3C1O2

InChI Identifier

InChI=1S/C20H17NO5/c1-21-16-5-11-4-14-15(24-8-23-14)6-12(11)20(16)7-10-2-3-13-18(25-9-22-13)17(10)19(21)26-20/h2-4,6,16,19H,5,7-9H2,1H3

InChI Key

HJDZNSLTBDNJJW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Argemone grandiflora	LOTUS Database	35616633
Delphinium glaucum	LOTUS Database	35616633
Delphinium grandiflorum	LOTUS Database	35616633
Sarcocapnos crassifolia	LOTUS Database	35616633
Sarcocapnos enneaphylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Benzopyran
Isochromane
2-benzopyran
Benzodioxole
Indane
Azepine
Benzenoid
Oxazolidine
Acetal
Oxacycle
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen 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	2.26	ALOGPS
logP	3.12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	3.35	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.39 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.41 m³·mol⁻¹	ChemAxon
Polarizability	36.85 Å³	ChemAxon
Number of Rings	7	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

494334

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene (NP0327837)

MOL for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

3D MOL for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

3D SDF for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

3D-SDF for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

PDB for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

3D PDB for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

SMILES for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

INCHI for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

Structure for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)

3D Structure for NP0327837 (13-methyl-5,7,17,19,25-pentaoxa-13-azaheptacyclo[12.10.1.0¹,¹².0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁶,²⁰]pentacosa-2,4(8),9,15,20,22-hexaene)