NP-MRD: Showing NP-Card for (4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate (NP0208922)

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Record Information

Version

2.0

Created at

2022-09-05 06:08:11 UTC

Updated at

2022-09-05 06:08:12 UTC

NP-MRD ID

NP0208922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate

Description

(4R,12S,13R,14S,19R,21S)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]Docosa-5(10),6,8,17-tetraen-14-yl acetate 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. (4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate is found in Strychnos staudtii. Based on a literature review very few articles have been published on (4R,12S,13R,14S,19R,21S)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]Docosa-5(10),6,8,17-tetraen-14-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052208082D          

 32 37  0  0  1  0            999 V2000
    4.7620    0.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1237   -0.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3519   -0.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2183    0.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4465    0.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8082    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7137   -0.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052208082D          

 32 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0208922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(N([C@H]3[C@H]4[C@H]5C[C@@H]6N(CC[C@]236)CC5=CCO[C@H]4OC(C)=O)C(C)=O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O6/c1-12(27)26-20-16(4-5-17(30-3)21(20)29)24-7-8-25-11-14-6-9-31-23(32-13(2)28)19(22(24)26)15(14)10-18(24)25/h4-6,15,18-19,22-23,29H,7-11H2,1-3H3/t15-,18-,19+,22-,23-,24+/m0/s1

> <INCHI_KEY>
WUSIMBJXHMBCII-ZKHBPZIFSA-N

> <FORMULA>
C24H28N2O6

> <MOLECULAR_WEIGHT>
440.496

> <EXACT_MASS>
440.19473663

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
45.676532887679826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,12S,13R,14S,19R,21S)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0^{4,12}.0^{4,21}.0^{5,10}.0^{13,19}]docosa-5,7,9,17-tetraen-14-yl acetate

> <JCHEM_LOGP>
0.23023884362906363

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.312345846503394

> <JCHEM_PKA_STRONGEST_BASIC>
8.61382525471824

> <JCHEM_POLAR_SURFACE_AREA>
88.53999999999999

> <JCHEM_REFRACTIVITY>
115.11589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R,12S,13R,14S,19R,21S)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0^{4,12}.0^{4,21}.0^{5,10}.0^{13,19}]docosa-5,7,9,17-tetraen-14-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       8.889   0.086   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.698  -0.890   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.257  -0.346   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.007   1.174   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.567   1.718   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.375   0.742   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.625  -0.778   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.066  -1.322   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.315  -2.841   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.216  -1.419   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.977  -2.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.539  -3.494   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.174  -3.908   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.037  -0.344   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.719  -0.466   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.983  -1.446   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.554  -2.925   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.621  -4.035   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.192  -5.515   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.116  -3.667   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.557  -1.295   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.393   0.043   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.831   1.512   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.363   2.147   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.440   3.596   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0       0.256   3.553   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       1.850   3.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.717   2.543   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.818   1.162   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.682   2.139   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.484   1.506   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.442   0.892   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   29                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   29                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   14   30                                             
CONECT   30   29   26   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   24   15                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
(4R,12S,13R,14S,19R,21S)-11-Acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0,.0,.0,.0,]docosa-5(10),6,8,17-tetraen-14-yl acetic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₆

Average Mass

440.4960 Da

Monoisotopic Mass

440.19474 Da

IUPAC Name

(4R,12S,13R,14S,19R,21S)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0^{4,12}.0^{4,21}.0^{5,10}.0^{13,19}]docosa-5,7,9,17-tetraen-14-yl acetate

Traditional Name

(4R,12S,13R,14S,19R,21S)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0^{4,12}.0^{4,21}.0^{5,10}.0^{13,19}]docosa-5,7,9,17-tetraen-14-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(N([C@H]3[C@H]4[C@H]5C[C@@H]6N(CC[C@]236)CC5=CCO[C@H]4OC(C)=O)C(C)=O)=C1O

InChI Identifier

InChI=1S/C24H28N2O6/c1-12(27)26-20-16(4-5-17(30-3)21(20)29)24-7-8-25-11-14-6-9-31-23(32-13(2)28)19(22(24)26)15(14)10-18(24)25/h4-6,15,18-19,22-23,29H,7-11H2,1-3H3/t15-,18-,19+,22-,23-,24+/m0/s1

InChI Key

WUSIMBJXHMBCII-ZKHBPZIFSA-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
Strychnos staudtii	LOTUS Database	35616633

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
Indole or derivatives
Indolizidine
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Acetamide
Tertiary carboxylic acid amide
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxamide group
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Organopnictogen compound
Amine
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	0.23	ChemAxon
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	8.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.12 m³·mol⁻¹	ChemAxon
Polarizability	45.68 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

13994708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate (NP0208922)

MOL for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

3D MOL for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

3D SDF for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

3D-SDF for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

PDB for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

3D PDB for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

SMILES for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

INCHI for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

Structure for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)

3D Structure for NP0208922 ((4r,12s,13r,14s,19r,21s)-11-acetyl-9-hydroxy-8-methoxy-15-oxa-1,11-diazahexacyclo[16.3.1.0⁴,¹².0⁴,²¹.0⁵,¹⁰.0¹³,¹⁹]docosa-5,7,9,17-tetraen-14-yl acetate)