MiMeDB: Showing metabocard for 17-hydroxylupanine (MMDBc0055185)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:45:43 UTC

Update Date

2022-08-12 20:09:16 UTC

Metabolite ID

MMDBc0055185

Metabolite Identification

Common Name

17-hydroxylupanine

Description

17-hydroxylupanine(1+) belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. Based on a literature review very few articles have been published on 17-hydroxylupanine(1+).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221452D          

 24 27  0  0  1  0            999 V2000
    6.3404   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3404   -1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908   -1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053   -1.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4908   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -1.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1646   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    0.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281    0.1990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5031   -1.7928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9114   -0.3844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9197   -1.2094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2053    0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3281   -1.7928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9114   -1.2094    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.9197   -0.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2053    0.8531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438   -2.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6438    0.9612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -2.5550    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6259   -0.7969    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6819   -0.8937    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1372   -1.9537    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  2  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15 11  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 10 20  1  6  0  0  0
 11 21  1  6  0  0  0
 12 22  1  1  0  0  0
 13 23  1  6  0  0  0
 24 15  1  0  0  0  0
M  CHG  1  16   1
M  END
> <DATABASE_ID>
MMDBc0055185

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C1(O)[NH+]2CCCC[C@@]2([H])[C@]2([H])CN3C(=O)CCC[C@]3([H])[C@@]1([H])C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O2/c18-14-6-3-5-13-11-8-10(9-17(13)14)12-4-1-2-7-16(12)15(11)19/h10-13,15,19H,1-9H2/p+1/t10-,11+,12-,13+,15?/m0/s1

> <INCHI_KEY>
LCORZQTZVFOPGT-IZADBBIGSA-O

> <FORMULA>
C15H25N2O2

> <MOLECULAR_WEIGHT>
265.376

> <EXACT_MASS>
265.191054473

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.569115206397214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,9R,10R)-8-hydroxy-14-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-7-ium

> <JCHEM_LOGP>
0.8168750613333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.290162461516964

> <JCHEM_PKA_STRONGEST_BASIC>
8.407727205761654

> <JCHEM_POLAR_SURFACE_AREA>
44.980000000000004

> <JCHEM_REFRACTIVITY>
83.2885

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,9R,10R)-8-hydroxy-14-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-7-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      11.835  -0.718   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.835  -2.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.783  -2.258   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.502   0.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.116  -3.028   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.783  -0.718   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.502  -3.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.774  -1.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.539   0.371   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.079   0.371   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.539  -3.346   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.168  -0.718   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.450  -2.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.116   0.052   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.079  -3.346   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       9.168  -2.258   0.000  0.00  0.00           N+1
HETATM   17  N   UNK     0       5.450  -0.718   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       4.116   1.592   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.668  -4.769   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       8.668   1.794   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.950  -4.769   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      10.502  -1.488   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.873  -1.668   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       9.590  -3.647   0.000  0.00  0.00           H+0
CONECT    1    2    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1   12                                                       
CONECT    5    3   13                                                       
CONECT    6    3   14                                                       
CONECT    7    2   16                                                       
CONECT    8   10   11                                                       
CONECT    9   10   17                                                       
CONECT   10    8    9   12   20                                             
CONECT   11    8   13   15   21                                             
CONECT   12    4   10   16   22                                             
CONECT   13    5   11   17   23                                             
CONECT   14    6   17   18                                                  
CONECT   15   11   16   19   24                                             
CONECT   16    7   12   15                                                  
CONECT   17    9   13   14                                                  
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   12                                                            
CONECT   23   13                                                            
CONECT   24   15                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

Synonyms

Value	Source
17-Hydroxylupanine	ChEBI
17-Hydroxylupaninium	ChEBI

Molecular Formula

C₁₅H₂₅N₂O₂

Average Mass

265.376

Monoisotopic Mass

265.191054473

IUPAC Name

(1S,2S,9R,10R)-8-hydroxy-14-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-7-ium

Traditional Name

(1S,2S,9R,10R)-8-hydroxy-14-oxo-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-7-ium

CAS Registry Number

Not Available

SMILES

[H]C1(O)[NH+]2CCCC[C@@]2([H])[C@]2([H])CN3C(=O)CCC[C@]3([H])[C@@]1([H])C2

InChI Identifier

InChI=1S/C15H24N2O2/c18-14-6-3-5-13-11-8-10(9-17(13)14)12-4-1-2-7-16(12)15(11)19/h10-13,15,19H,1-9H2/p+1/t10-,11+,12-,13+,15?/m0/s1

InChI Key

LCORZQTZVFOPGT-IZADBBIGSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidinone
Quinolizidine
Delta-lactam
Piperidinone
Piperidine
Tertiary carboxylic acid amide
Carboxamide group
Hemiaminal
Lactam
Alkanolamine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic cation
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

ammonium ion (CHEBI:64262 )
organic cation (CHEBI:64262 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.82	ChemAxon
pKa (Strongest Acidic)	13.29	ChemAxon
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.98 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.29 m³·mol⁻¹	ChemAxon
Polarizability	29.57 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

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human feces; Human

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

27471431

KEGG Compound ID

Not Available

BioCyc ID

CPD-13928

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56927954

PDB ID

Not Available

ChEBI ID

64262

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 17-hydroxylupanine (MMDBc0055185)

MOL for #<Metabolite:0x00007fecd0e92ce8>

3D MOL for #<Metabolite:0x00007fecd0e92ce8>

3D SDF for #<Metabolite:0x00007fecd0e92ce8>

3D-SDF for #<Metabolite:0x00007fecd0e92ce8>

PDB for #<Metabolite:0x00007fecd0e92ce8>

3D PDB for #<Metabolite:0x00007fecd0e92ce8>

SMILES for #<Metabolite:0x00007fecd0e92ce8>

INCHI for #<Metabolite:0x00007fecd0e92ce8>

Structure for #<Metabolite:0x00007fecd0e92ce8>

3D Structure for #<Metabolite:0x00007fecd0e92ce8>