NP-MRD: Showing NP-Card for Isoaltholactone (NP0140130)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-06-29 20:47:24 UTC

Updated at

2022-06-29 20:47:24 UTC

NP-MRD ID

NP0140130

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoaltholactone

Description

Isoaltholactone belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Isoaltholactone is found in Goniothalamus aruensis, Goniothalamus grandiflorus, Goniothalamus griffithii and Goniothalamus malayanus. Isoaltholactone was first documented in 2011 (PMID: 21666896). Based on a literature review a small amount of articles have been published on Isoaltholactone (PMID: 31918304) (PMID: 28529789) (PMID: 24127819) (PMID: 22002630).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -4.2653    0.9652   -2.0933 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5603    0.5893   -1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1212    1.5293   -0.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904    1.1460    0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838   -0.2542    1.0820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6078   -0.3517    1.4218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0029    0.2201    0.3028 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4467   -0.1228    0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4057    0.8339   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365    0.4727   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644   -0.8207    0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2213   -1.7717    0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8727   -1.4161    0.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7684   -0.3077   -0.9024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0542    0.7483   -1.7329 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9720   -0.9415   -0.2529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1736   -0.7536   -0.9735 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.5802   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0857    1.9183    1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5938   -0.7955    1.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1276    1.3223    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813    1.8408   -0.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4915    1.2223   -0.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091   -1.1121    0.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4978   -2.7877    0.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1232   -2.1666    0.6638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1094   -1.0690   -1.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2380    1.3056   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7720   -2.0236   -0.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 17  1  0
 17 16  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 16 14  1  0
 13  8  1  0
 16  5  1  0
 15 28  1  0
 14 27  1  6
  7 21  1  1
  5 20  1  1
  4 19  1  0
  3 18  1  0
 16 29  1  1
  9 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
M  END


  Mrv1652306292222472D          

 17 19  0  0  1  0            999 V2000
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  7  4  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  7 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  1  0  0  0
  8 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140130

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@@H](O[C@H]2C=CC(=O)O[C@@H]12)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O4/c14-10-7-6-9-13(17-10)11(15)12(16-9)8-4-2-1-3-5-8/h1-7,9,11-13,15H/t9-,11-,12-,13+/m0/s1

> <INCHI_KEY>
ZKIRVBNLJKGIEM-XYJRDEOASA-N

> <FORMULA>
C13H12O4

> <MOLECULAR_WEIGHT>
232.235

> <EXACT_MASS>
232.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.904039594869744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,3aS,7aS)-3-hydroxy-2-phenyl-2H,3H,3aH,5H,7aH-furo[3,2-b]pyran-5-one

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.591554522333333

> <ALOGPS_LOGS>
-1.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.598610469576432

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.98890632529218

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6782177838194894

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
59.9076

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,3aS,7aS)-3-hydroxy-2-phenyl-2H,3H,3aH,7aH-furo[3,2-b]pyran-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -5.793  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.023  -2.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.530  -2.843   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.744  -4.013   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    7                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    8                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₂O₄

Average Mass

232.2350 Da

Monoisotopic Mass

232.07356 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@@H](O[C@H]2C=CC(=O)O[C@@H]12)C1=CC=CC=C1

InChI Identifier

InChI=1S/C13H12O4/c14-10-7-6-9-13(17-10)11(15)12(16-9)8-4-2-1-3-5-8/h1-7,9,11-13,15H/t9-,11-,12-,13+/m0/s1

InChI Key

ZKIRVBNLJKGIEM-XYJRDEOASA-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
Goniothalamus aruensis	LOTUS Database	35616633
Goniothalamus grandiflorus	LOTUS Database	35616633
Goniothalamus griffithii	LOTUS Database	35616633
Goniothalamus malayanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Dihydropyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
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

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

8574471

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10399033

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Meesakul P, Jaidee W, Richardson C, Andersen RJ, Patrick BO, Willis AC, Muanprasat C, Wang J, Lei X, Hadsadee S, Jungsuttiwong S, Pyne SG, Laphookhieo S: Styryllactones from Goniothalamus tamirensis. Phytochemistry. 2020 Mar;171:112248. doi: 10.1016/j.phytochem.2019.112248. Epub 2020 Jan 6. [PubMed:31918304 ]
Zukerman-Schpector J, Moro AV, Dos Santos MR, Correia CRD, Jotani MM, Tiekink ERT: 3-Hy-droxy-2-phenyl-2,3,3a,7a-tetra-hydro-1H,5H-pyrano[3,2-b]pyrrol-5-one: crystal structure and Hirshfeld surface analysis. Acta Crystallogr E Crystallogr Commun. 2017 Apr 21;73(Pt 5):746-751. doi: 10.1107/S2056989017005680. eCollection 2017 May 1. [PubMed:28529789 ]
Nicolas L, Izquierdo E, Angibaud P, Stansfield I, Meerpoel L, Reymond S, Cossy J: Cobalt-catalyzed diastereoselective synthesis of C-furanosides. Total synthesis of (-)-isoaltholactone. J Org Chem. 2013 Dec 6;78(23):11807-14. doi: 10.1021/jo401845q. Epub 2013 Nov 12. [PubMed:24127819 ]
Moharam BA, Jantan I, Jalil J, Ahmad F: Inhibitory effect of compounds from Goniothalamus tapis Miq. and Goniothalamus uvaroides King on platelet-activating factor receptor binding. Phytother Res. 2012 May;26(5):687-91. doi: 10.1002/ptr.3620. Epub 2011 Oct 17. [PubMed:22002630 ]
Unsworth WP, Stevens K, Lamont SG, Robertson J: Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone. Chem Commun (Camb). 2011 Jul 21;47(27):7659-61. doi: 10.1039/c1cc11805f. Epub 2011 Jun 10. [PubMed:21666896 ]

Showing NP-Card for Isoaltholactone (NP0140130)

MOL for NP0140130 (Isoaltholactone)

3D MOL for NP0140130 (Isoaltholactone)

3D SDF for NP0140130 (Isoaltholactone)

3D-SDF for NP0140130 (Isoaltholactone)

PDB for NP0140130 (Isoaltholactone)

3D PDB for NP0140130 (Isoaltholactone)

SMILES for NP0140130 (Isoaltholactone)

INCHI for NP0140130 (Isoaltholactone)

Structure for NP0140130 (Isoaltholactone)

3D Structure for NP0140130 (Isoaltholactone)