NP-MRD: Showing NP-Card for 8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one (NP0319970)

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Record Information

Version

2.0

Created at

2022-09-11 21:16:58 UTC

Updated at

2022-09-11 21:16:58 UTC

NP-MRD ID

NP0319970

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one

Description

8,20-Dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]Pentacosan-17-one 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. 8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one is found in Fritillaria imperialis. 8,20-Dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]Pentacosan-17-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161514112D          

 31 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161514112D          

 31 36  0  0  0  0            999 V2000
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 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
  2 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319970

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CN2CC3C4CC5C(CC(=O)C6CC(O)CCC56C)C4CCC3CC2C(C)(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO3/c1-15-12-27(3,31)25-8-16-4-5-18-19(21(16)14-28(25)13-15)10-22-20(18)11-24(30)23-9-17(29)6-7-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3

> <INCHI_KEY>
OVHUAFPHYGFWPY-UHFFFAOYSA-N

> <FORMULA>
C27H43NO3

> <MOLECULAR_WEIGHT>
429.645

> <EXACT_MASS>
429.324294249

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
50.95541723560021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.142576281333334

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.297070459049817

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.36331348710453

> <JCHEM_PKA_STRONGEST_BASIC>
9.859230921841002

> <JCHEM_POLAR_SURFACE_AREA>
60.77000000000001

> <JCHEM_REFRACTIVITY>
122.5355

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      10.442  -3.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.156  -2.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.695  -2.078   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      13.409  -0.714   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      14.948  -0.651   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.663   0.714   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.839   2.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.553   3.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.092   3.442   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.916   2.141   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.201   0.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.278  -0.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.658   0.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.434   1.883   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.642   2.838   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.073   2.270   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      23.281   3.226   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      22.297   0.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.728   0.179   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.952  -1.345   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      25.384  -1.913   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      22.744  -2.301   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.313  -1.733   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.089  -0.209   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.882  -1.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.300   1.951   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.585   0.587   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.047   0.524   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.252   2.050   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.579   0.991   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.332  -0.840   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   13   18   25                                             
CONECT   25   24                                                            
CONECT   26    7   27                                                       
CONECT   27   26    4   28                                                  
CONECT   28   27   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₃NO₃

Average Mass

429.6450 Da

Monoisotopic Mass

429.32429 Da

IUPAC Name

8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one

Traditional Name

8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one

CAS Registry Number

Not Available

SMILES

CC1CN2CC3C4CC5C(CC(=O)C6CC(O)CCC56C)C4CCC3CC2C(C)(O)C1

InChI Identifier

InChI=1S/C27H43NO3/c1-15-12-27(3,31)25-8-16-4-5-18-19(21(16)14-28(25)13-15)10-22-20(18)11-24(30)23-9-17(29)6-7-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3

InChI Key

OVHUAFPHYGFWPY-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

Species Name	Source	Reference
Fritillaria imperialis	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
Piperidine
Cyclic alcohol
Tertiary alcohol
Ketone
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen 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	3.3	ALOGPS
logP	3.14	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.36	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	122.54 m³·mol⁻¹	ChemAxon
Polarizability	50.96 Å³	ChemAxon
Number of Rings	6	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one (NP0319970)

MOL for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

3D MOL for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

3D SDF for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

3D-SDF for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

PDB for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

3D PDB for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

SMILES for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

INCHI for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

Structure for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)

3D Structure for NP0319970 (8,20-dihydroxy-6,8,23-trimethyl-4-azahexacyclo[12.11.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁴.0¹⁸,²³]pentacosan-17-one)