NP-MRD: Showing NP-Card for 13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate (NP0330503)

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Record Information

Version

1.0

Created at

2022-09-12 15:55:24 UTC

Updated at

2022-09-12 15:55:24 UTC

NP-MRD ID

NP0330503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate

Description

13,24-Dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]Tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate belongs to the class of organic compounds known as hexahydrobenzophenanthridine alkaloids. These are alkaloids containing a hexahydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a hexahydrophenanthridine moiety. 13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate is found in Corydalis bulleyana, Corydalis conspersa and Corydalis taliensis. 13,24-Dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]Tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516392D          

 34 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241516392D          

 34 39  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0330503

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(CC(C)=O)C2=C3OCOC3=CC=C2C2(C)C(CC3=CC4=C(OCO4)C=C3C12)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H27NO7/c1-13(28)7-18-23-17(5-6-19-24(23)33-12-30-19)26(3)22(34-14(2)29)9-15-8-20-21(32-11-31-20)10-16(15)25(26)27(18)4/h5-6,8,10,18,22,25H,7,9,11-12H2,1-4H3

> <INCHI_KEY>
QNWHWSOSMRYOOT-UHFFFAOYSA-N

> <FORMULA>
C26H27NO7

> <MOLECULAR_WEIGHT>
465.502

> <EXACT_MASS>
465.178752213

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.10651754710169

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14,16,21-hexaen-12-yl acetate

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
3.0926103556666673

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.31046358450544

> <JCHEM_PKA_STRONGEST_BASIC>
4.9586588701851175

> <JCHEM_POLAR_SURFACE_AREA>
83.53

> <JCHEM_REFRACTIVITY>
120.50789999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14,16,21-hexaen-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      15.277  -5.926   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      14.354  -4.694   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      12.825  -4.878   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.220  -6.294   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.144  -7.526   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.672  -7.342   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.538  -8.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.901  -3.646   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.372  -3.830   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.485  -5.090   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.014  -4.636   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.991  -3.096   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.448  -2.598   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.053  -1.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.582  -0.998   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.506  -2.230   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.035  -2.046   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.111  -0.814   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.640  -0.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.169  -0.446   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.093  -1.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.622  -1.493   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.545  -2.726   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.079  -2.863   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      21.422  -4.365   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      20.100  -5.155   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      18.940  -4.142   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.411  -4.326   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.488  -3.094   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.959  -3.278   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.716   0.602   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.321   2.019   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.850   2.203   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.397   3.251   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    3    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   17                                                  
CONECT   17   16   18   19   30                                             
CONECT   18   17                                                            
CONECT   19   17   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29    2   17                                                  
CONECT   31   19   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
13,24-Dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0,.0,.0,.0,]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetic acid	Generator
13,24-Dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetic acid	Generator

Chemical Formula

C₂₆H₂₇NO₇

Average Mass

465.5020 Da

Monoisotopic Mass

465.17875 Da

IUPAC Name

13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14,16,21-hexaen-12-yl acetate

Traditional Name

13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14,16,21-hexaen-12-yl acetate

CAS Registry Number

Not Available

SMILES

CN1C(CC(C)=O)C2=C3OCOC3=CC=C2C2(C)C(CC3=CC4=C(OCO4)C=C3C12)OC(C)=O

InChI Identifier

InChI=1S/C26H27NO7/c1-13(28)7-18-23-17(5-6-19-24(23)33-12-30-19)26(3)22(34-14(2)29)9-15-8-20-21(32-11-31-20)10-16(15)25(26)27(18)4/h5-6,8,10,18,22,25H,7,9,11-12H2,1-4H3

InChI Key

QNWHWSOSMRYOOT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Corydalis bulleyana	LOTUS Database	35616633
Corydalis conspersa	LOTUS Database	35616633
Corydalis taliensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexahydrobenzophenanthridine alkaloids. These are alkaloids containing a hexahydrobenzophenanthridine skeleton, which is a tetracyclic compound containing a benzene fused to a hexahydrophenanthridine moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Benzophenanthridine alkaloids

Sub Class

Hexahydrobenzophenanthridine alkaloids

Direct Parent

Hexahydrobenzophenanthridine alkaloids

Alternative Parents

Substituents

Hexahydrobenzophenanthridine alkaloid skeleton
Benzoquinoline
Phenanthridine
Tetralin
Tetrahydroisoquinoline
Quinoline
Benzodioxole
Aralkylamine
Beta-aminoketone
Benzenoid
Amino acid or derivatives
Carboxylic acid ester
Ketone
Tertiary aliphatic amine
Tertiary amine
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen 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	2.56	ALOGPS
logP	3.09	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	18.31	ChemAxon
pKa (Strongest Basic)	4.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	120.51 m³·mol⁻¹	ChemAxon
Polarizability	49.11 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate (NP0330503)

MOL for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

3D MOL for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

3D SDF for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

3D-SDF for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

PDB for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

3D PDB for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

SMILES for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

INCHI for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

Structure for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)

3D Structure for NP0330503 (13,24-dimethyl-23-(2-oxopropyl)-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0²,¹⁰.0⁴,⁸.0¹⁴,²².0¹⁷,²¹]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-yl acetate)