NP-MRD: Showing NP-Card for (4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione (NP0255001)

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Record Information

Version

2.0

Created at

2022-09-07 19:20:17 UTC

Updated at

2022-09-07 19:20:17 UTC

NP-MRD ID

NP0255001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione

Description

Arthropsolide A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione is found in Arthropsis truncata. (4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione was first documented in 2020 (PMID: 32712094). Based on a literature review very few articles have been published on Arthropsolide A (PMID: 33853446).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.5491   -1.0604   -3.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7075   -0.8703   -1.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6755   -0.1222   -1.2889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982   -0.4522    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7179   -0.4551    0.8150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2758   -0.7704    0.3824 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5070    0.4124    0.8279 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0564    1.2545   -0.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7552    2.5333   -0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3613    3.3612   -1.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859    1.1010    1.8705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255    0.3348    2.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8609   -1.1224    2.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3049   -1.8141    3.6292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -1.7821    1.5093 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9360   -2.9473    1.1609 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1472   -1.4371   -0.8734 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4616   -1.4369   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050   -0.6203   -3.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2539   -1.6718   -3.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.0109    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559    0.8452   -0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0793    3.0597    0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112    4.1726   -0.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5420    3.7487   -2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0737    2.7736   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839    2.1651    1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5218    0.7699    3.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8040   -1.9996    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -3.6481    1.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1767   -2.5182   -0.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947   -1.7923   -0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15  6  1  0
  6 17  1  0
 17 18  1  0
 17  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  7  1  0
  6  4  1  6
 10 24  1  0
 10 25  1  0
 10 26  1  0
  9 23  1  0
  8 22  1  0
  7 21  1  1
 11 27  1  0
 12 28  1  0
 15 29  1  1
 16 30  1  0
 17 31  1  1
 18 32  1  0
  1 19  1  0
  1 20  1  0
M  END


  Mrv1652309072221202D          

 18 19  0  0  1  0            999 V2000
   -0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846    1.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  7 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
  6 15  1  0  0  0  0
 15 16  1  1  0  0  0
  6 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0255001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\[C@H]1C=CC(=O)[C@@H](O)[C@]11[C@H](O)C(=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O5/c1-3-4-8-5-6-9(14)11(16)13(8)10(15)7(2)18-12(13)17/h3-6,8,10-11,15-16H,2H2,1H3/b4-3+/t8-,10+,11+,13+/m0/s1

> <INCHI_KEY>
ROOGVCKSAVTPSZ-KMSURZFUSA-N

> <FORMULA>
C13H14O5

> <MOLECULAR_WEIGHT>
250.25

> <EXACT_MASS>
250.084123551

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.469751038830942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5R,6S,10S)-4,6-dihydroxy-3-methylidene-10-[(1E)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione

> <JCHEM_LOGP>
0.3374237266666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.579676960908081

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.70185819895501

> <JCHEM_PKA_STRONGEST_BASIC>
-3.642851435202039

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
65.2947

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,6S,10S)-4,6-dihydroxy-3-methylidene-10-[(1E)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.465   3.556   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.370   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.140   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.450  -1.897   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.370  -1.897   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.465  -2.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15   17                                             
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    6    2   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
(4S,5R,6S,10S)-4,6-Dihydroxy-3-methylidene-10-((e)-prop-1-enyl)-2-oxaspiro(4.5)dec-8-ene-1,7-dione	MeSH

Chemical Formula

C₁₃H₁₄O₅

Average Mass

250.2500 Da

Monoisotopic Mass

250.08412 Da

IUPAC Name

(4S,5R,6S,10S)-4,6-dihydroxy-3-methylidene-10-[(1E)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione

Traditional Name

(4S,5R,6S,10S)-4,6-dihydroxy-3-methylidene-10-[(1E)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione

CAS Registry Number

Not Available

SMILES

C\C=C\[C@H]1C=CC(=O)[C@@H](O)[C@]11[C@H](O)C(=C)OC1=O

InChI Identifier

InChI=1S/C13H14O5/c1-3-4-8-5-6-9(14)11(16)13(8)10(15)7(2)18-12(13)17/h3-6,8,10-11,15-16H,2H2,1H3/b4-3+/t8-,10+,11+,13+/m0/s1

InChI Key

ROOGVCKSAVTPSZ-KMSURZFUSA-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
Arthropsis truncata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Tetrahydrofuran
Enol ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
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	0.34	ChemAxon
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.29 m³·mol⁻¹	ChemAxon
Polarizability	24.47 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

Not Available

Chemspider ID

4578819

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5467970

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sommart U, Rukachaisirikul V, Saithong S, Phongpaichit S, Sakayaroj J, Preedanon S, Chainok K, Khunrong T: 2-Oxaspiro[4.5]decane and alpha-pyrenocine derivatives from the endophytic fungus Roussoella sp. PSU-H51. Nat Prod Res. 2021 Apr 14:1-10. doi: 10.1080/14786419.2021.1910692. [PubMed:33853446 ]
Akrimajirachoote N, Satitsri S, Sommart U, Rukachaisirikul V, Muanprasat C: Inhibition of CFTR-mediated intestinal chloride secretion by a fungus-derived arthropsolide A: Mechanism of action and anti-diarrheal efficacy. Eur J Pharmacol. 2020 Oct 15;885:173393. doi: 10.1016/j.ejphar.2020.173393. Epub 2020 Jul 23. [PubMed:32712094 ]
LOTUS database [Link]

Showing NP-Card for (4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione (NP0255001)

MOL for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

3D MOL for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

3D SDF for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

3D-SDF for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

PDB for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

3D PDB for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

SMILES for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

INCHI for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

Structure for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)

3D Structure for NP0255001 ((4s,5r,6s,10s)-4,6-dihydroxy-3-methylidene-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,7-dione)