NP-MRD: Showing NP-Card for 20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol (NP0175896)

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Record Information

Version

2.0

Created at

2022-09-03 13:28:14 UTC

Updated at

2022-09-03 13:28:14 UTC

NP-MRD ID

NP0175896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol

Description

20-(Hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]Tetracos-4-en-7-ol belongs to the class of organic compounds known as solanidines and derivatives. These are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system. 20-(Hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]Tetracos-4-en-7-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652310081715092D          

 30 35  0  0  0  0            999 V2000
    5.3933    1.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652310081715092D          

 30 35  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0175896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC(CO)CN2C2CC3C4CC=C5CC(O)CCC5(C)C4CCC3(C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO2/c1-16-23-7-4-17(15-29)14-28(23)24-13-22-20-6-5-18-12-19(30)8-10-26(18,2)21(20)9-11-27(22,3)25(16)24/h5,16-17,19-25,29-30H,4,6-15H2,1-3H3

> <INCHI_KEY>
PHPBOUSFBOILOX-UHFFFAOYSA-N

> <FORMULA>
C27H43NO2

> <MOLECULAR_WEIGHT>
413.646

> <EXACT_MASS>
413.329379629

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.40301827257363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracos-4-en-7-ol

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.4874133319999987

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.20428950550382

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.431680345864109

> <JCHEM_PKA_STRONGEST_BASIC>
12.06694641398964

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
122.6873

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracos-4-en-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-17         0                                  
HETATM    1  C   UNK     0      10.068   3.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.920   1.284   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.240   2.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.325  -0.174   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.891  -2.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.381  -2.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.342   0.983   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.940   0.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.410   1.586   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.430   0.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.900   1.888   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.418  -1.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.142  -1.648   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.329  -1.935   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.803  -2.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.086   1.602   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.819  -1.633   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.908  -1.633   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.434  -0.778   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.887  -1.030   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.904   0.127   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.377  -0.728   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.852   0.681   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.886  -0.759   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.343   0.712   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.414  -0.174   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.883   0.731   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       9.346  -0.778   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0       4.293  -2.488   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      21.944  -1.079   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   26                                                            
CONECT    3   27                                                            
CONECT    4    7   17                                                       
CONECT    5    6   18                                                       
CONECT    6    5   20                                                       
CONECT    7    4   23                                                       
CONECT    8   10   19                                                       
CONECT    9   11   21                                                       
CONECT   10    8   26                                                       
CONECT   11    9   27                                                       
CONECT   12   18   19                                                       
CONECT   13   22   24                                                       
CONECT   14   17   28                                                       
CONECT   15   17   29                                                       
CONECT   16    1   23   25                                                  
CONECT   17    4   14   15                                                  
CONECT   18    5   12   26                                                  
CONECT   19    8   12   30                                                  
CONECT   20    6   21   22                                                  
CONECT   21    9   20   26                                                  
CONECT   22   13   20   27                                                  
CONECT   23    7   16   28                                                  
CONECT   24   13   25   28                                                  
CONECT   25   16   24   27                                                  
CONECT   26    2   10   18   21                                             
CONECT   27    3   11   22   25                                             
CONECT   28   14   23   24                                                  
CONECT   29   15                                                            
CONECT   30   19                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₃NO₂

Average Mass

413.6460 Da

Monoisotopic Mass

413.32938 Da

IUPAC Name

20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracos-4-en-7-ol

Traditional Name

20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{17,22}]tetracos-4-en-7-ol

CAS Registry Number

Not Available

SMILES

CC1C2CCC(CO)CN2C2CC3C4CC=C5CC(O)CCC5(C)C4CCC3(C)C12

InChI Identifier

InChI=1S/C27H43NO2/c1-16-23-7-4-17(15-29)14-28(23)24-13-22-20-6-5-18-12-19(30)8-10-26(18,2)21(20)9-11-27(22,3)25(16)24/h5,16-17,19-25,29-30H,4,6-15H2,1-3H3

InChI Key

PHPBOUSFBOILOX-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 solanidines and derivatives. These are steroids with a structure based on the solanidane skeleton. Solanidane arises from the conversion of a cholestane side-chain into a bicyclic system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Solanidines and derivatives

Alternative Parents

Substituents

Solanidane skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
Azasteroid
Delta-5-steroid
Alkaloid or derivatives
Indolizidine
N-alkylpyrrolidine
Piperidine
1,3-aminoalcohol
Cyclic alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Primary alcohol
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen 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	3.9	ALOGPS
logP	3.49	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	15.43	ChemAxon
pKa (Strongest Basic)	12.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.69 m³·mol⁻¹	ChemAxon
Polarizability	51.4 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

HMDB0165182

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

73796895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol (NP0175896)

MOL for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

3D MOL for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

3D SDF for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

3D-SDF for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

PDB for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

3D PDB for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

SMILES for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

INCHI for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

Structure for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)

3D Structure for NP0175896 (20-(hydroxymethyl)-10,14,16-trimethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-ol)