NP-MRD: Showing NP-Card for (1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol (NP0311479)

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Record Information

Version

2.0

Created at

2022-09-11 07:30:09 UTC

Updated at

2022-09-11 07:30:09 UTC

NP-MRD ID

NP0311479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol

Description

Anthriscifoldine B 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. (1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol is found in Delphinium anthriscifolium. Based on a literature review very few articles have been published on Anthriscifoldine B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112209302D          

 33 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112209302D          

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 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  1  6  0  0  0
 31 29  1  1  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0311479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC)CC[C@H](OC)[C@]34[C@@H]2C[C@@]2(OCO[C@@]22C[C@H](OC)[C@H]5C[C@]3(O)[C@@H]2[C@H]5O)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C25H39NO7/c1-5-26-11-21(12-29-2)7-6-17(31-4)25-16(21)10-24(20(25)26)23(32-13-33-24)9-15(30-3)14-8-22(25,28)19(23)18(14)27/h14-20,27-28H,5-13H2,1-4H3/t14-,15+,16-,17+,18+,19+,20-,21+,22+,23-,24-,25+/m1/s1

> <INCHI_KEY>
BQAIPUYVXFRLNA-NJKATMGOSA-N

> <FORMULA>
C25H39NO7

> <MOLECULAR_WEIGHT>
465.587

> <EXACT_MASS>
465.2726526

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
50.3768918838705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4S,5S,6S,8R,12R,13S,16S,19S,20R)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-2,4-diol

> <JCHEM_LOGP>
-0.7545783573333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.62739530077588

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.743751350634152

> <JCHEM_PKA_STRONGEST_BASIC>
9.531394980180727

> <JCHEM_POLAR_SURFACE_AREA>
89.85000000000001

> <JCHEM_REFRACTIVITY>
117.78949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4S,5S,6S,8R,12R,13S,16S,19S,20R)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-2,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.703   2.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.323   1.484   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.497   0.002   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -1.352  -1.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.702  -2.847   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.211  -3.584   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.749  -5.092   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.264  -5.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.225  -4.396   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.287  -4.821   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.250  -3.609   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.289  -5.291   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.051  -6.752   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.854  -2.007   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.271  -0.197   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.352   0.243   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.465  -0.512   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.605  -2.179   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.384   1.861   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.792   2.492   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.755   1.312   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.106  -0.155   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.709   0.048   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.868  -1.029   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.497  -0.910   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.723  -1.913   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.312  -2.572   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.738  -3.827   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.370  -2.759   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.678  -4.466   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.265  -1.749   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.462  -3.145   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.839  -4.099   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   18   29                                             
CONECT   15   14    3   16                                                  
CONECT   16   15   17   19   22                                             
CONECT   17   16   18                                                       
CONECT   18   17    5   14                                                  
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   16   23   31                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   14   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31   27   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₉NO₇

Average Mass

465.5870 Da

Monoisotopic Mass

465.27265 Da

IUPAC Name

(1R,2S,3S,4S,5S,6S,8R,12R,13S,16S,19S,20R)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-2,4-diol

Traditional Name

(1R,2S,3S,4S,5S,6S,8R,12R,13S,16S,19S,20R)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1^{2,5}.0^{1,13}.0^{3,8}.0^{8,12}.0^{16,20}]docosane-2,4-diol

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC)CC[C@H](OC)[C@]34[C@@H]2C[C@@]2(OCO[C@@]22C[C@H](OC)[C@H]5C[C@]3(O)[C@@H]2[C@H]5O)[C@@H]14

InChI Identifier

InChI=1S/C25H39NO7/c1-5-26-11-21(12-29-2)7-6-17(31-4)25-16(21)10-24(20(25)26)23(32-13-33-24)9-15(30-3)14-8-22(25,28)19(23)18(14)27/h14-20,27-28H,5-13H2,1-4H3/t14-,15+,16-,17+,18+,19+,20-,21+,22+,23-,24-,25+/m1/s1

InChI Key

BQAIPUYVXFRLNA-NJKATMGOSA-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
Delphinium anthriscifolium	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
Meta-dioxolane
Cyclic alcohol
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Acetal
Dialkyl ether
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
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
logP	-0.75	ChemAxon
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.85 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.79 m³·mol⁻¹	ChemAxon
Polarizability	50.38 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

102032665

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol (NP0311479)

MOL for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

3D MOL for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

3D SDF for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

3D-SDF for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

PDB for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

3D PDB for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

SMILES for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

INCHI for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

Structure for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)

3D Structure for NP0311479 ((1r,2s,3s,4s,5s,6s,8r,12r,13s,16s,19s,20r)-14-ethyl-6,19-dimethoxy-16-(methoxymethyl)-9,11-dioxa-14-azaheptacyclo[10.7.2.1²,⁵.0¹,¹³.0³,⁸.0⁸,¹².0¹⁶,²⁰]docosane-2,4-diol)