NP-MRD: Showing NP-Card for 1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one (NP0208980)

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Record Information

Version

2.0

Created at

2022-09-05 06:12:31 UTC

Updated at

2022-09-05 06:12:32 UTC

NP-MRD ID

NP0208980

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one

Description

Aspidoalbine 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. 1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one is found in Aspidosperma desmanthum and Aspidosperma megalocarpon. 1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one was first documented in 2013 (PMID: 24131444). Based on a literature review very few articles have been published on Aspidoalbine (PMID: 32756456).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052208122D          

 31 36  0  0  1  0            999 V2000
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    2.1412    2.6782    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


  Mrv1652309052208122D          

 31 36  0  0  1  0            999 V2000
    2.0579    4.1048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0208980

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)N1[C@@H]2CC[C@]34CCO[C@@]33N(CC[C@@]23C2=C1C(O)=C(OC)C(OC)=C2)CCC4

> <INCHI_IDENTIFIER>
InChI=1S/C24H32N2O5/c1-4-18(27)26-17-6-8-22-7-5-11-25-12-9-23(17,24(22,25)31-13-10-22)15-14-16(29-2)21(30-3)20(28)19(15)26/h14,17,28H,4-13H2,1-3H3/t17-,22-,23-,24+/m1/s1

> <INCHI_KEY>
BJYVZJQGRUSSBS-BMZZKGLRSA-N

> <FORMULA>
C24H32N2O5

> <MOLECULAR_WEIGHT>
428.529

> <EXACT_MASS>
428.231122138

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.06626267865221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1R,4R,12R,16S)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9-trien-5-yl]propan-1-one

> <JCHEM_LOGP>
2.5577742323333315

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.157984715077799

> <JCHEM_PKA_STRONGEST_BASIC>
7.077895521548311

> <JCHEM_POLAR_SURFACE_AREA>
71.47

> <JCHEM_REFRACTIVITY>
115.22869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1R,4R,12R,16S)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9-trien-5-yl]propan-1-one

> <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       3.841   7.662   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.150   6.286   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.997   4.999   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.534   5.089   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       3.306   3.623   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.013   2.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.931   1.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.338  -0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.828  -0.715   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.235  -2.200   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.725  -2.590   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.910   0.380   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.400  -0.009   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.483   1.086   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.503   1.865   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.585   2.961   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.554   1.851   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.531   0.660   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.700  -0.637   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       0.105  -0.208   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -1.546  -0.793   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.749   0.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.541   1.908   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.083   2.252   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.369   1.406   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.962  -0.079   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.423  -0.151   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.120   1.290   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.851   3.775   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.584   4.335   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.786   3.373   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   31                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    6   16                                                  
CONECT   16   15                                                            
CONECT   17    7   18   28   31                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28   29                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   20   24   17                                             
CONECT   29   24   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    5   17                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂N₂O₅

Average Mass

428.5290 Da

Monoisotopic Mass

428.23112 Da

IUPAC Name

1-[(1R,4R,12R,16S)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9-trien-5-yl]propan-1-one

Traditional Name

1-[(1R,4R,12R,16S)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0^{1,16}.0^{4,12}.0^{6,11}.0^{12,16}]docosa-6(11),7,9-trien-5-yl]propan-1-one

CAS Registry Number

Not Available

SMILES

CCC(=O)N1[C@@H]2CC[C@]34CCO[C@@]33N(CC[C@@]23C2=C1C(O)=C(OC)C(OC)=C2)CCC4

InChI Identifier

InChI=1S/C24H32N2O5/c1-4-18(27)26-17-6-8-22-7-5-11-25-12-9-23(17,24(22,25)31-13-10-22)15-14-16(29-2)21(30-3)20(28)19(15)26/h14,17,28H,4-13H2,1-3H3/t17-,22-,23-,24+/m1/s1

InChI Key

BJYVZJQGRUSSBS-BMZZKGLRSA-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
Aspidosperma desmanthum	LOTUS Database	35616633
Aspidosperma megalocarpon Muell.Arg.	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
Quinolidine
Indolizidine
Anisole
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Piperidine
Benzenoid
N-alkylpyrrolidine
Tetrahydrofuran
Tertiary carboxylic acid amide
Pyrrolidine
Carboxamide group
Hemiaminal
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbazoles (CHEBI:2885 )

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	ChemAxon
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	7.08	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	115.23 m³·mol⁻¹	ChemAxon
Polarizability	46.07 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

390549

KEGG Compound ID

C09038

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Morales-Jadan D, Blanco-Salas J, Ruiz-Tellez T, Centeno F: Three Alkaloids from an Apocynaceae Species, Aspidosperma spruceanum as Antileishmaniasis Agents by In Silico Demo-case Studies. Plants (Basel). 2020 Aug 3;9(8). pii: plants9080983. doi: 10.3390/plants9080983. [PubMed:32756456 ]
Zhang SX, Shen XL, Li ZQ, Zou LW, Wang FQ, Zhang HB, Shao ZH: Enantioselective total synthesis of (-)-limaspermidine and formal synthesis of (-)-1-acetylaspidoalbidine. J Org Chem. 2013 Nov 15;78(22):11444-9. doi: 10.1021/jo402004f. Epub 2013 Oct 29. [PubMed:24131444 ]
LOTUS database [Link]

Showing NP-Card for 1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one (NP0208980)

MOL for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

3D MOL for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

3D SDF for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

3D-SDF for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

PDB for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

3D PDB for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

SMILES for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

INCHI for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

Structure for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)

3D Structure for NP0208980 (1-[(1r,4r,12r,16s)-7-hydroxy-8,9-dimethoxy-17-oxa-5,15-diazahexacyclo[13.4.3.0¹,¹⁶.0⁴,¹².0⁶,¹¹.0¹²,¹⁶]docosa-6(11),7,9-trien-5-yl]propan-1-one)