NP-MRD: Showing NP-Card for (4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one (NP0329950)

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Record Information

Version

2.0

Created at

2022-09-12 14:50:23 UTC

Updated at

2022-09-12 14:50:23 UTC

NP-MRD ID

NP0329950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

Description

Glaziovina belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. (4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one is found in Cissampelos capensis, Croton bonplandianus, Hypserpa nitida, Liriodendron tulipifera, Neostenanthera gabonensis, Pachygone ovata, Stephania cephalantha and Xylopia parviflora. Based on a literature review very few articles have been published on Glaziovina.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122216502D          

 22 25  0  0  1  0            999 V2000
    2.1488    3.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7665    2.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6017    1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192    1.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6544    0.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721    0.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0545    0.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2193    1.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0018    1.3763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7765    0.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1950   -0.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0199   -0.3363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7884   -1.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0657   -1.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2789   -0.7800    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5679   -1.1984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5748   -2.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8501   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    0.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 10 17  1  0  0  0  0
 18 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3[C@H](CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3-4,6-7,9,13,21H,5,8,10H2,1-2H3/t13-/m0/s1

> <INCHI_KEY>
PNJUPRNTSWJWAX-ZDUSSCGKSA-N

> <FORMULA>
C18H19NO3

> <MOLECULAR_WEIGHT>
297.354

> <EXACT_MASS>
297.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.19568457373473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4'S)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <JCHEM_LOGP>
2.3109943059999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.840613452854564

> <JCHEM_PKA_STRONGEST_BASIC>
7.45769475933462

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
87.78769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4'S)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.011   5.632   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.164   4.611   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.856   3.102   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.396   2.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.088   1.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.241   0.084   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.702   0.572   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.009   2.081   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.470   2.569   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.617  -0.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.376   0.674   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.916   0.687   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.697  -0.641   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.237  -0.628   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.938  -1.981   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.398  -1.993   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.723  -1.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.254  -1.456   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.927  -2.237   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.940  -3.777   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.587  -1.478   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.574   0.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   16   17                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10                                                       
CONECT   17   10   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    5                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO₃

Average Mass

297.3540 Da

Monoisotopic Mass

297.13649 Da

IUPAC Name

(4'S)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

Traditional Name

(4'S)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0^{4,12}]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=C3[C@H](CC4(C=CC(=O)C=C4)C3=C1O)N(C)CC2

InChI Identifier

InChI=1S/C18H19NO3/c1-19-8-5-11-9-14(22-2)17(21)16-15(11)13(19)10-18(16)6-3-12(20)4-7-18/h3-4,6-7,9,13,21H,5,8,10H2,1-2H3/t13-/m0/s1

InChI Key

PNJUPRNTSWJWAX-ZDUSSCGKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cissampelos capensis	LOTUS Database	35616633
Croton bonplandianus	LOTUS Database	35616633
Hypserpa nitida	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Neostenanthera gabonensis	LOTUS Database	35616633
Pachygone ovata	LOTUS Database	35616633
Stephania cephalantha	LOTUS Database	35616633
Xylopia parviflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Proaporphines

Sub Class

Not Available

Direct Parent

Proaporphines

Alternative Parents

Substituents

Proaporphine
Tetrahydroisoquinoline
Indane
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Ketone
Tertiary amine
Cyclic ketone
Tertiary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.31	ChemAxon
pKa (Strongest Acidic)	9.84	ChemAxon
pKa (Strongest Basic)	7.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.79 m³·mol⁻¹	ChemAxon
Polarizability	32.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

66138

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one (NP0329950)

MOL for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D MOL for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D SDF for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D-SDF for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

PDB for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D PDB for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

SMILES for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

INCHI for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

Structure for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)

3D Structure for NP0329950 ((4's)-11'-hydroxy-10'-methoxy-5'-methyl-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(11'),2,5,8'(12'),9'-pentaen-4-one)