NP-MRD: Showing NP-Card for (1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol (NP0279834)

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Record Information

Version

2.0

Created at

2022-09-09 05:21:58 UTC

Updated at

2022-09-09 05:21:58 UTC

NP-MRD ID

NP0279834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol

Description

(-)-Uniflorine A 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. (1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol is found in Eugenia uniflora and Myrcia multiflora. (1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol was first documented in 2004 (PMID: 15104453). Based on a literature review a significant number of articles have been published on (-)-uniflorine A (PMID: 20028000) (PMID: 25407551) (PMID: 21574569) (PMID: 19835391) (PMID: 18517213) (PMID: 16872219).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.1728    1.5230    0.2148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9848    0.9999   -0.2090 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8222    1.4303    0.6990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3065    0.7998    0.1895 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124    1.4362    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3420    0.4103   -0.7578 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6560    0.5399   -0.3945 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -0.9199   -0.3427 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5120   -1.4616    0.7016 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3835   -0.5972    0.2215 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7551   -1.1534   -0.6100 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8626   -2.5202   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0435   -0.5063   -0.1999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0821   -0.8914   -1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2087    2.4771   -0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7055    1.3103   -1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0168    1.0568    1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206    2.5064    0.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4060    2.3512   -0.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9888    1.6653    1.0062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2268    0.5235   -1.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8344    0.1738    0.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6861   -1.5963   -1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476   -2.1377    0.3767 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2402   -0.9614    1.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5726   -1.0414   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6305   -2.7311    0.2369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2949   -0.8496    0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1020   -1.8362   -1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
 10  4  1  0
  7 22  1  0
  6 21  1  6
  5 19  1  0
  5 20  1  0
  3 17  1  0
  3 18  1  0
  2 16  1  6
  1 15  1  0
 13 28  1  1
 14 29  1  0
 11 26  1  6
 12 27  1  0
 10 25  1  1
  8 23  1  6
  9 24  1  0
M  END


  Mrv1652309092207212D          

 14 15  0  0  1  0            999 V2000
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10  4  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0279834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CN2C[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO5/c10-3-1-9-2-4(11)7(13)8(14)5(9)6(3)12/h3-8,10-14H,1-2H2/t3-,4+,5-,6-,7-,8-/m1/s1

> <INCHI_KEY>
KSWHMQGAWBUNLD-XAZAIFFQSA-N

> <FORMULA>
C8H15NO5

> <MOLECULAR_WEIGHT>
205.21

> <EXACT_MASS>
205.095022587

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.612665385988173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7R,8R,8aR)-octahydroindolizine-1,2,6,7,8-pentol

> <JCHEM_LOGP>
-3.2447880609999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.390864570514982

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.757110173036196

> <JCHEM_PKA_STRONGEST_BASIC>
8.391094683258208

> <JCHEM_POLAR_SURFACE_AREA>
104.39000000000001

> <JCHEM_REFRACTIVITY>
45.532799999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7R,8R,8aR)-octahydroindolizine-1,2,6,7,8-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.197   2.073   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
Uniflorine a	MeSH

Chemical Formula

C₈H₁₅NO₅

Average Mass

205.2100 Da

Monoisotopic Mass

205.09502 Da

IUPAC Name

(1S,2R,6S,7R,8R,8aR)-octahydroindolizine-1,2,6,7,8-pentol

Traditional Name

(1S,2R,6S,7R,8R,8aR)-octahydroindolizine-1,2,6,7,8-pentol

CAS Registry Number

Not Available

SMILES

O[C@@H]1CN2C[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H]1O

InChI Identifier

InChI=1S/C8H15NO5/c10-3-1-9-2-4(11)7(13)8(14)5(9)6(3)12/h3-8,10-14H,1-2H2/t3-,4+,5-,6-,7-,8-/m1/s1

InChI Key

KSWHMQGAWBUNLD-XAZAIFFQSA-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
Eugenia uniflora	LOTUS Database	35616633
Myrcia multiflora	LOTUS Database	35616633

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
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-aminoalcohol
Azacycle
Polyol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxygen 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	-3.2	ChemAxon
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	104.39 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.53 m³·mol⁻¹	ChemAxon
Polarizability	19.61 Å³	ChemAxon
Number of Rings	2	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

7970025

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9794258

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ritthiwigrom T, Willis AC, Pyne SG: Total synthesis of uniflorine A, casuarine, australine, 3-epi-australine, and 3,7-di-epi-australine from a common precursor. J Org Chem. 2010 Feb 5;75(3):815-24. doi: 10.1021/jo902355p. [PubMed:20028000 ]
D'Adamio G, Sgambato A, Forcella M, Caccia S, Parmeggiani C, Casartelli M, Parenti P, Bini D, Cipolla L, Fusi P, Cardona F: New synthesis and biological evaluation of uniflorine A derivatives: towards specific insect trehalase inhibitors. Org Biomol Chem. 2015 Jan 21;13(3):886-92. doi: 10.1039/c4ob02016b. [PubMed:25407551 ]
Liu XK, Qiu S, Xiang YG, Ruan YP, Zheng X, Huang PQ: SmI2-mediated radical cross-couplings of alpha-hydroxylated aza-hemiacetals and N,S-acetals with alpha,beta-unsaturated compounds: asymmetric synthesis of (+)-hyacinthacine A2, (-)-uniflorine A, and (+)-7-epi-casuarine. J Org Chem. 2011 Jun 17;76(12):4952-63. doi: 10.1021/jo200600n. Epub 2011 May 26. [PubMed:21574569 ]
Parmeggiani C, Martella D, Cardona F, Goti A: Total synthesis of (-)-uniflorine A. J Nat Prod. 2009 Nov;72(11):2058-60. doi: 10.1021/np900435d. [PubMed:19835391 ]
Ritthiwigrom T, Pyne SG: Synthesis of (+)-uniflorine a: a structural reassignment and a configurational assignment. Org Lett. 2008 Jul 3;10(13):2769-71. doi: 10.1021/ol8009144. Epub 2008 Jun 3. [PubMed:18517213 ]
Karanjule NS, Markad SD, Dhavale DD: Synthesis of pentahydroxy indolizidine alkaloids using ring closing metathesis: attempts to find the correct structure of uniflorine A. J Org Chem. 2006 Aug 4;71(16):6273-6. doi: 10.1021/jo060823s. [PubMed:16872219 ]
Davis AS, Pyne SG, Skelton BW, White AH: Synthesis of putative uniflorine A. J Org Chem. 2004 Apr 30;69(9):3139-43. doi: 10.1021/jo049806y. [PubMed:15104453 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol (NP0279834)

MOL for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

3D MOL for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

3D SDF for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

3D-SDF for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

PDB for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

3D PDB for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

SMILES for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

INCHI for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

Structure for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)

3D Structure for NP0279834 ((1s,2r,6s,7r,8r,8ar)-octahydroindolizine-1,2,6,7,8-pentol)