NP-MRD: Showing NP-Card for Hypaconine (NP0138828)

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Record Information

Version

1.0

Created at

2022-06-29 19:18:58 UTC

Updated at

2022-06-29 19:18:58 UTC

NP-MRD ID

NP0138828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hypaconine

Description

Hypaconine belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. It was first documented in 2012 (PMID: 22816290). Based on a literature review a significant number of articles have been published on Hypaconine (PMID: 29787993) (PMID: 33418305) (PMID: 34171738) (PMID: 28985284) (PMID: 27019554) (PMID: 26390658).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221192D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292221192D          

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M  END
> <DATABASE_ID>
NP0138828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC12CCC(OC)C34C5CC6(O)C(O)C5C(O)(C(C(OC)C13)C4N(C)C2)C(O)C6OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H39NO8/c1-25-9-21(10-30-2)7-6-12(31-3)23-11-8-22(28)18(26)13(11)24(29,19(27)20(22)33-5)14(17(23)25)15(32-4)16(21)23/h11-20,26-29H,6-10H2,1-5H3

> <INCHI_KEY>
BQTYHFZQSAKNQU-UHFFFAOYSA-N

> <FORMULA>
C24H39NO8

> <MOLECULAR_WEIGHT>
469.575

> <EXACT_MASS>
469.26756722

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.06993372780696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,5,7,8-tetrol

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-2.5328485276666686

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.075610909203938

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.440849572035933

> <JCHEM_PKA_STRONGEST_BASIC>
9.591365433656325

> <JCHEM_POLAR_SURFACE_AREA>
121.08000000000003

> <JCHEM_REFRACTIVITY>
116.61069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,16,18-trimethoxy-13-(methoxymethyl)-11-methyl-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecane-4,5,7,8-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -0.891   1.596   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.123  -0.151   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.233  -1.434   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.594  -2.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.199  -4.461   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.290  -4.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.373  -3.785   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.022  -2.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.790  -2.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.604  -0.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530  -0.038   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.459  -0.318   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.288  -0.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -1.915   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.616  -2.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.100  -3.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.617  -2.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.779  -3.225   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.877  -4.524   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.054  -1.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.829  -0.025   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.369   1.492   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.575  -0.460   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.368   0.912   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.185  -3.165   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.037   1.198   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.759   0.528   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.398   0.655   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.563  -5.541   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.102  -7.097   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.063  -3.764   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.833  -5.184   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.027  -6.496   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9   31                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9   12   15                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    8    2                                                  
CONECT   13   11   14   21   26                                             
CONECT   14   13   15   18                                                  
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20   25                                             
CONECT   18   17   14   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21   23                                                  
CONECT   21   20   13   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
CONECT   25   17                                                            
CONECT   26   13                                                            
CONECT   27   10   28                                                       
CONECT   28   27                                                            
CONECT   29    7   30                                                       
CONECT   30   29                                                            
CONECT   31    4   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₉NO₈

Average Mass

469.5750 Da

Monoisotopic Mass

469.26757 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

63238-68-6

SMILES

COCC12CCC(OC)C34C5CC6(O)C(O)C5C(O)(C(C(OC)C13)C4N(C)C2)C(O)C6OC

InChI Identifier

InChI=1S/C24H39NO8/c1-25-9-21(10-30-2)7-6-12(31-3)23-11-8-22(28)18(26)13(11)24(29,19(27)20(22)33-5)14(17(23)25)15(32-4)16(21)23/h11-20,26-29H,6-10H2,1-5H3

InChI Key

BQTYHFZQSAKNQU-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Quinolidine
Alkaloid or derivatives
Azepane
Piperidine
Cyclic alcohol
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Dialkyl ether
Polyol
Ether
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Amine
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

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

76189740

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yun WJ, Yao ZH, Fan CL, Qin ZF, Tang XY, Gao MX, Dai Y, Yao XS: Systematic screening and characterization of Qi-Li-Qiang-Xin capsule-related xenobiotics in rats by ultra-performance liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jul 15;1090:56-64. doi: 10.1016/j.jchromb.2018.05.014. Epub 2018 May 12. [PubMed:29787993 ]
Xu X, Xie X, Zhang H, Wang P, Li G, Chen J, Chen G, Cao X, Xiong L, Peng F, Peng C: Water-soluble alkaloids extracted from Aconiti Radix lateralis praeparata protect against chronic heart failure in rats via a calcium signaling pathway. Biomed Pharmacother. 2021 Mar;135:111184. doi: 10.1016/j.biopha.2020.111184. Epub 2021 Jan 5. [PubMed:33418305 ]
Shen BQ, Qu C, Mi L, Wang HY, Yang H: Simultaneous quantification of twenty-eight components of Shenfu Injection in rat plasma by UHPLC-QQQ MS and its application to a pharmacokinetic study. J Pharm Biomed Anal. 2021 Sep 5;203:114211. doi: 10.1016/j.jpba.2021.114211. Epub 2021 Jun 16. [PubMed:34171738 ]
Huang D, Zhao X, Liu X, Chao R: Determination of Five Aminoalcohol-diterpenoid Alkaloids in the Lateral Root of Aconitum carmichaeli by HPLC-ELSD with SPE. J Chromatogr Sci. 2017 Oct 1;55(9):940-945. doi: 10.1093/chromsci/bmx059. [PubMed:28985284 ]
Wang B, Ji J, Zhao S, Dong J, Tan P, Na S, Liu Y: An Efficient High-performance Liquid Chromatography Combined with Electrospray Ionization Tandem Mass Spectrometry Method to Elaborate the Changes of Components Between the Raw and Processed Radix Aconitum kusnezoffii. Pharmacogn Mag. 2016 Jan-Mar;12(45):4-8. doi: 10.4103/0973-1296.175989. [PubMed:27019554 ]
Tang F, Liang SY, Chen FL, Tang QF, Tan XM: [Study on material basis of Mahuang Fuzi Xixin decoction for anti-inflammation and immune suppression based on combined method of serum pharmacochemistry and serum pharmacology]. Zhongguo Zhong Yao Za Zhi. 2015 May;40(10):1971-6. [PubMed:26390658 ]
Yang CL, Huang ZF, Zhang YH, Liu YH, Liu YH, Chen Y, Yi JH: [Effects of steaming and baking on content of alkaloids in Aconite Lateralis Radix (Fuzi)]. Zhongguo Zhong Yao Za Zhi. 2014 Dec;39(24):4798-803. [PubMed:25898581 ]
Dai P, Zhu L, Yang X, Zhao M, Shi J, Wang Y, Lu L, Liu Z: Multidrug resistance-associated protein 2 is involved in the efflux of Aconitum alkaloids determined by MRP2-MDCKII cells. Life Sci. 2015 Apr 15;127:66-72. doi: 10.1016/j.lfs.2015.02.011. Epub 2015 Mar 2. [PubMed:25744397 ]
Liu X, Wang XL, Wu L, Li H, Qin KM, Cai H, Pei K, Liu T, Cai BC: Investigation on the spectrum-effect relationships of Da-Huang-Fu-Zi-Tang in rats by UHPLC-ESI-Q-TOF-MS method. J Ethnopharmacol. 2014 Jul 3;154(3):606-12. doi: 10.1016/j.jep.2014.04.027. Epub 2014 Apr 24. [PubMed:24768806 ]
Jian XX, Tang P, Liu XX, Chao RB, Chen QH, She XK, Chen DL, Wang FP: Structure-cardiac activity relationship of C19-diterpenoid alkaloids. Nat Prod Commun. 2012 Jun;7(6):713-20. [PubMed:22816290 ]

Showing NP-Card for Hypaconine (NP0138828)

MOL for NP0138828 (Hypaconine)

3D MOL for NP0138828 (Hypaconine)

3D SDF for NP0138828 (Hypaconine)

3D-SDF for NP0138828 (Hypaconine)

PDB for NP0138828 (Hypaconine)

3D PDB for NP0138828 (Hypaconine)

SMILES for NP0138828 (Hypaconine)

INCHI for NP0138828 (Hypaconine)

Structure for NP0138828 (Hypaconine)

3D Structure for NP0138828 (Hypaconine)