NP-MRD: Showing NP-Card for Slaframine (NP0051150)

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Record Information

Version

2.0

Created at

2022-04-27 22:33:45 UTC

Updated at

2022-04-27 22:33:45 UTC

NP-MRD ID

NP0051150

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Slaframine

Description

Slaframine belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Slaframine is found in Rhizoctonia leguminicola and Trifolium repens . Slaframine was first documented in 2002 (PMID: 12521266). Based on a literature review a significant number of articles have been published on Slaframine (PMID: 26777309) (PMID: 30830325) (PMID: 28932984) (PMID: 26858953) (PMID: 25585493) (PMID: 14620842).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
    4.6689    0.9238   -0.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5644    0.1028   -0.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7535   -1.0992    0.0566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.5809    0.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3131   -0.1789    0.5713 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6550    0.2536    1.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -0.4879    1.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338   -1.1483    0.5136 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369   -1.3954    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4174   -0.5537   -1.1788 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8580   -0.6115   -1.3092 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    0.8614   -0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.9533   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -0.3586   -0.3594 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5638    1.0394   -1.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6374    1.9400   -0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6236    0.4519   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6916   -1.2284    0.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653   -0.0774    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4199    1.3175    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -1.2109    2.6410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5372    0.1881    1.9188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0687   -2.4664   -0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8493   -1.3328    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9104   -0.9539   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026   -0.5758   -0.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1519    0.1998   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2912    1.5021   -1.7822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5249    1.2512   -0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3247    1.7626   -0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0399    1.3012   -1.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.9501   -1.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14  5  1  0
 14  8  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  6
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  6
M  END


  Mrv1652304282200332D          

 14 15  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    2.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 N   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  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  2 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051150

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CCN2C[C@@H](N)CC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C10H18N2O2/c1-7(13)14-10-4-5-12-6-8(11)2-3-9(10)12/h8-10H,2-6,11H2,1H3/t8-,9-,10-/m0/s1

> <INCHI_KEY>
YYIUHLPAZILPSG-GUBZILKMSA-N

> <FORMULA>
C10H18N2O2

> <MOLECULAR_WEIGHT>
198.266

> <EXACT_MASS>
198.136827828

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
21.66390847640838

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6S,8aS)-6-amino-octahydroindolizin-1-yl acetate

> <ALOGPS_LOGP>
-0.07

> <JCHEM_LOGP>
-0.3822574723333332

> <ALOGPS_LOGS>
0.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
9.716546125306191

> <JCHEM_POLAR_SURFACE_AREA>
55.56

> <JCHEM_REFRACTIVITY>
52.8297

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
slaframine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.590   2.073   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.143   5.874   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.333   7.338   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.887   4.729   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       7.591   1.303   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
(1S,6S,8AS)-1-acetoxy-6-aminooctahydroindolizine	MeSH
Slaframine citrate salt (1:2)	MeSH

Chemical Formula

C₁₀H₁₈N₂O₂

Average Mass

198.2660 Da

Monoisotopic Mass

198.13683 Da

IUPAC Name

(1S,6S,8aS)-6-amino-octahydroindolizin-1-yl acetate

Traditional Name

slaframine

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CCN2C[C@@H](N)CC[C@@H]12

InChI Identifier

InChI=1S/C10H18N2O2/c1-7(13)14-10-4-5-12-6-8(11)2-3-9(10)12/h8-10H,2-6,11H2,1H3/t8-,9-,10-/m0/s1

InChI Key

YYIUHLPAZILPSG-GUBZILKMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Rhizoctonia leguminicola	Fungi	KNApSAcK
Trifolium repens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indolizidine
3-aminopiperidine
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organic oxide
Primary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
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
logP	-0.07	ALOGPS
logP	-0.38	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Basic)	9.72	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.83 m³·mol⁻¹	ChemAxon
Polarizability	21.66 Å³	ChemAxon
Number of Rings	2	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

C00002073

Chemspider ID

79717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Slaframine

METLIN ID

Not Available

PubChem Compound

88363

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Michael JP: Simple Indolizidine and Quinolizidine Alkaloids. Alkaloids Chem Biol. 2016;75:1-498. doi: 10.1016/bs.alkal.2014.12.001. Epub 2015 Mar 30. [PubMed:26777309 ]
Jousse C, Dalle C, Canet I, Lagree M, Traikia M, Lyan B, Mendes C, Sancelme M, Amato P, Delort AM: Metabolomic study of the response to cold shock in a strain of Pseudomonas syringae isolated from cloud water. Metabolomics. 2017 Dec 4;14(1):11. doi: 10.1007/s11306-017-1295-7. [PubMed:30830325 ]
Alhawatema MS, Gebril S, Cook D, Creamer R: RNAi-mediated down-regulation of a melanin polyketide synthase (pks1) gene in the fungus Slafractonia leguminicola. World J Microbiol Biotechnol. 2017 Sep 20;33(10):179. doi: 10.1007/s11274-017-2346-y. [PubMed:28932984 ]
Kagan IA: Blackpatch of Clover, Cause of Slobbers Syndrome: A Review of the Disease and the Pathogen, Rhizoctonia leguminicola. Front Vet Sci. 2016 Jan 27;3:3. doi: 10.3389/fvets.2016.00003. eCollection 2016. [PubMed:26858953 ]
Alhawatema MS, Sanogo S, Baucom DL, Creamer R: A search for the phylogenetic relationship of the ascomycete Rhizoctonia leguminicola using genetic analysis. Mycopathologia. 2015 Jun;179(5-6):381-9. doi: 10.1007/s11046-015-9860-y. Epub 2015 Jan 14. [PubMed:25585493 ]
Michael JP: Indolizidine and quinolizidine alkaloids. Nat Prod Rep. 2003 Oct;20(5):458-75. doi: 10.1039/b208137g. [PubMed:14620842 ]
Riet-Correa F, Rivero R, Odriozola E, Adrien Mde L, Medeiros RM, Schild AL: Mycotoxicoses of ruminants and horses. J Vet Diagn Invest. 2013 Nov;25(6):692-708. doi: 10.1177/1040638713504572. Epub 2013 Oct 3. [PubMed:24091682 ]
Cossy J: Selective methodologies for the synthesis of biologically active piperidinic compounds. Chem Rec. 2005;5(2):70-80. doi: 10.1002/tcr.20035. [PubMed:15825169 ]
Naranjo L, Martin de Valmaseda E, Casqueiro J, Ullan RV, Lamas-Maceiras M, Banuelos O, Martin JF: Inactivation of the lys7 gene, encoding saccharopine reductase in Penicillium chrysogenum, leads to accumulation of the secondary metabolite precursors piperideine-6-carboxylic acid and pipecolic acid from alpha-aminoadipic acid. Appl Environ Microbiol. 2004 Feb;70(2):1031-9. doi: 10.1128/AEM.70.2.1031-1039.2004. [PubMed:14766586 ]
Michael JP: Indolizidine and quinolizidine alkaloids. Nat Prod Rep. 2002 Dec;19(6):719-41. doi: 10.1039/b104969k. [PubMed:12521266 ]

Showing NP-Card for Slaframine (NP0051150)

MOL for NP0051150 (Slaframine)

3D MOL for NP0051150 (Slaframine)

3D SDF for NP0051150 (Slaframine)

3D-SDF for NP0051150 (Slaframine)

PDB for NP0051150 (Slaframine)

3D PDB for NP0051150 (Slaframine)

SMILES for NP0051150 (Slaframine)

INCHI for NP0051150 (Slaframine)

Structure for NP0051150 (Slaframine)

3D Structure for NP0051150 (Slaframine)