NP-MRD: Showing NP-Card for (1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol (NP0310337)

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Record Information

Version

2.0

Created at

2022-09-11 05:34:48 UTC

Updated at

2022-09-11 05:34:48 UTC

NP-MRD ID

NP0310337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol

Description

ZINC100060917 belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. (1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol is found in Veratrum viride. Based on a literature review very few articles have been published on ZINC100060917.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112207342D          

 36 42  0  0  1  0            999 V2000
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M  END

     RDKit          2D

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M  END


  Mrv1652309112207342D          

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    1.7916    3.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9932    2.4637    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4397    3.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3708    1.7302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1948    1.6904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2634    2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9147    2.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 12  1  1  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 33 31  1  6  0  0  0
  9 33  1  0  0  0  0
 33 34  1  0  0  0  0
  5 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0310337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2N(C1)C[C@H]1[C@@H]3C[C@@]45O[C@]6(O)[C@@H](C[C@@H](O)[C@H]4[C@]3(O)[C@@H](O)[C@H](O)[C@@H]1[C@]2(C)O)[C@]5(C)CC[C@@H]6O

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO8/c1-12-4-5-17-24(3,33)19-13(11-28(17)10-12)14-9-25-21(26(14,34)22(32)20(19)31)15(29)8-16-23(25,2)7-6-18(30)27(16,35)36-25/h12-22,29-35H,4-11H2,1-3H3/t12-,13-,14-,15+,16-,17-,18-,19+,20+,21+,22-,23-,24+,25+,26-,27+/m0/s1

> <INCHI_KEY>
RNPABQVCNAUEIY-YFHOBTAISA-N

> <FORMULA>
C27H43NO8

> <MOLECULAR_WEIGHT>
509.64

> <EXACT_MASS>
509.298867349

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
48.304171495610746

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16R,18S,19S,22S,23R,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosane-10,12,13,14,16,22,23-heptol

> <JCHEM_LOGP>
-1.5064331906666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.726108818988468

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.91199090815346

> <JCHEM_PKA_STRONGEST_BASIC>
7.971262330874552

> <JCHEM_POLAR_SURFACE_AREA>
154.08

> <JCHEM_REFRACTIVITY>
127.97840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,16R,18S,19S,22S,23R,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosane-10,12,13,14,16,22,23-heptol

> <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      10.649  -2.322   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.945  -0.952   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.778   0.342   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.073   1.712   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.535   1.786   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.702   0.491   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.406  -0.878   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.163   0.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.459   1.935   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.920   2.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.778   0.928   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.309   1.574   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.521   0.167   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.343   1.140   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.396   2.679   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.719   0.297   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.216   0.656   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.897  -1.043   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.362  -0.852   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.022   0.767   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.235  -0.123   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.063   2.191   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.996   3.725   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.461   4.169   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.766   5.679   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.662   3.168   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.216   3.378   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.389   4.677   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.049   4.673   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.344   6.042   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.587   4.599   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.421   5.894   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.292   3.230   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.830   3.155   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.958   4.690   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.174   3.907   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20   26                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16   22                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   14   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   12   27                                                  
CONECT   27   26   10   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    9   34                                                  
CONECT   34   33    5   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₃NO₈

Average Mass

509.6400 Da

Monoisotopic Mass

509.29887 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2N(C1)C[C@H]1[C@@H]3C[C@@]45O[C@]6(O)[C@@H](C[C@@H](O)[C@H]4[C@]3(O)[C@@H](O)[C@H](O)[C@@H]1[C@]2(C)O)[C@]5(C)CC[C@@H]6O

InChI Identifier

InChI=1S/C27H43NO8/c1-12-4-5-17-24(3,33)19-13(11-28(17)10-12)14-9-25-21(26(14,34)22(32)20(19)31)15(29)8-16-23(25,2)7-6-18(30)27(16,35)36-25/h12-22,29-35H,4-11H2,1-3H3/t12-,13-,14-,15+,16-,17-,18-,19+,20+,21+,22-,23-,24+,25+,26-,27+/m0/s1

InChI Key

RNPABQVCNAUEIY-YFHOBTAISA-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
Veratrum viride	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Alkaloid or derivatives
Oxepane
Piperidine
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Tertiary amine
Secondary alcohol
Tertiary aliphatic amine
1,2-aminoalcohol
Hemiacetal
Azacycle
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
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

19953392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23616919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol (NP0310337)

MOL for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

3D MOL for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

3D SDF for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

3D-SDF for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

PDB for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

3D PDB for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

SMILES for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

INCHI for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

Structure for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)

3D Structure for NP0310337 ((1s,2s,6s,9s,10s,11r,12r,13s,14s,15s,16r,18s,19s,22s,23r,25r)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosane-10,12,13,14,16,22,23-heptol)