NP-MRD: Showing NP-Card for (1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate (NP0289505)

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Record Information

Version

2.0

Created at

2022-09-09 19:43:14 UTC

Updated at

2022-09-09 19:43:14 UTC

NP-MRD ID

NP0289505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate

Description

CONDELPHINE 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. (1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate is found in Aconitum balfourii, Aconitum sanyoense, Delphinium bicolor, Delphinium denudatum, Delphinium nuttallianum and Delphinium pyramidale. (1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate was first documented in 2016 (PMID: 27514662). Based on a literature review a small amount of articles have been published on CONDELPHINE (PMID: 32566879) (PMID: 29698893) (PMID: 35620478) (PMID: 35518334).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092221432D          

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M  END

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  Mrv1652309092221432D          

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 27 26  1  1  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0289505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@@]2(COC)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6[C@H](OC(C)=O)[C@@H]5[C@@](O)(C[C@@H]6OC)[C@H](C[C@H]23)[C@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO6/c1-5-26-11-23(12-30-3)7-6-19(28)25-15-8-14-17(31-4)10-24(29,16(22(25)26)9-18(23)25)20(15)21(14)32-13(2)27/h14-22,28-29H,5-12H2,1-4H3/t14-,15+,16+,17-,18+,19-,20+,21-,22-,23+,24+,25+/m0/s1

> <INCHI_KEY>
ZEBMMHUDQRRILP-WUEGJSKSSA-N

> <FORMULA>
C25H39NO6

> <MOLECULAR_WEIGHT>
449.588

> <EXACT_MASS>
449.27773798

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
19.695131992967816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4S,5S,6S,8R,9R,10S,13R,16S,17R)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl acetate

> <JCHEM_LOGP>
-0.4721000010000011

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.752661453550434

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.00798355132332

> <JCHEM_PKA_STRONGEST_BASIC>
9.842202932618891

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000001

> <JCHEM_REFRACTIVITY>
117.43769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S,5S,6S,8R,9R,10S,13R,16S,17R)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.615   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.078   1.214   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.386  -0.162   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.220  -1.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.543  -2.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.987  -3.527   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.243  -5.046   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.686  -5.583   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.108  -4.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.394  -4.958   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.375  -3.764   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.877  -4.105   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.981  -2.157   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.398  -0.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.473   0.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.591  -0.598   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.762  -2.285   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.167  -0.394   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.170   1.146   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.687  -0.011   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.842  -1.104   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.335  -0.724   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.752   0.758   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.329  -2.683   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.801  -4.005   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.442  -2.953   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.324  -1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.528  -3.329   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.393  -4.863   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.654  -5.747   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.050  -5.097   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.519  -7.281   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   17                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17   26                                             
CONECT   14   13    3   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   13    5                                                  
CONECT   18   15   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   13   27                                                  
CONECT   27   26   18   28                                                  
CONECT   28   27   24   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₉NO₆

Average Mass

449.5880 Da

Monoisotopic Mass

449.27774 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCN1C[C@@]2(COC)CC[C@H](O)[C@@]34[C@@H]5C[C@@H]6[C@H](OC(C)=O)[C@@H]5[C@@](O)(C[C@@H]6OC)[C@H](C[C@H]23)[C@H]14

InChI Identifier

InChI=1S/C25H39NO6/c1-5-26-11-23(12-30-3)7-6-19(28)25-15-8-14-17(31-4)10-24(29,16(22(25)26)9-18(23)25)20(15)21(14)32-13(2)27/h14-22,28-29H,5-12H2,1-4H3/t14-,15+,16+,17-,18+,19-,20+,21-,22-,23+,24+,25+/m0/s1

InChI Key

ZEBMMHUDQRRILP-WUEGJSKSSA-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
Aconitum balfourii	LOTUS Database	35616633
Aconitum sanyoense	LOTUS Database	35616633
Delphinium bicolor	LOTUS Database	35616633
Delphinium denudatum	LOTUS Database	35616633
Delphinium nuttallianum	LOTUS Database	35616633
Delphinium pyramidale	LOTUS Database	35616633

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
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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

C00001627

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

134688067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zeng Z, Qasem AMA, Woodman TJ, Rowan MG, Blagbrough IS: Impacts of Steric Compression, Protonation, and Intramolecular Hydrogen Bonding on the (15)N NMR Spectroscopy of Norditerpenoid Alkaloids and Their Piperidine-Ring Analogues. ACS Omega. 2020 Jun 8;5(23):14116-14122. doi: 10.1021/acsomega.0c01648. eCollection 2020 Jun 16. [PubMed:32566879 ]
Ahmad H, Ahmad S, Ali M, Latif A, Shah SAA, Naz H, Ur Rahman N, Shaheen F, Wadood A, Khan HU, Ahmad M: Norditerpenoid alkaloids of Delphinium denudatum as cholinesterase inhibitors. Bioorg Chem. 2018 Aug;78:427-435. doi: 10.1016/j.bioorg.2018.04.008. Epub 2018 Apr 17. [PubMed:29698893 ]
Salgado VL: Antagonist pharmacology of desensitizing and non-desensitizing nicotinic acetylcholine receptors in cockroach neurons. Neurotoxicology. 2016 Sep;56:188-195. doi: 10.1016/j.neuro.2016.08.003. Epub 2016 Aug 8. [PubMed:27514662 ]
Kumar A, Sharma M, Richardson CD, Kelvin DJ: Potential of Natural Alkaloids From Jadwar (Delphinium denudatum) as Inhibitors Against Main Protease of COVID-19: A Molecular Modeling Approach. Front Mol Biosci. 2022 May 10;9:898874. doi: 10.3389/fmolb.2022.898874. eCollection 2022. [PubMed:35620478 ]
Zeng Z, Qasem AMA, Kociok-Kohn G, Rowan MG, Blagbrough IS: The 1alpha-hydroxy-A-rings of norditerpenoid alkaloids are twisted-boat conformers. RSC Adv. 2020 May 18;10(32):18797-18805. doi: 10.1039/d0ra03811c. eCollection 2020 May 14. [PubMed:35518334 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate (NP0289505)

MOL for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D MOL for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D SDF for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D-SDF for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

PDB for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D PDB for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

SMILES for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

INCHI for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

Structure for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)

3D Structure for NP0289505 ((1s,2r,3r,4s,5s,6s,8r,9r,10s,13r,16s,17r)-11-ethyl-8,16-dihydroxy-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]nonadecan-4-yl acetate)