NP-MRD: Showing NP-Card for Thiacremonone (NP0014590)

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Record Information

Version

2.0

Created at

2021-01-05 23:43:01 UTC

Updated at

2021-08-19 23:59:52 UTC

NP-MRD ID

NP0014590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiacremonone

Provided By

NPAtlas

Description

Thiacremonone belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. Thiacremonone is found in Acremonium sp. Thiacremonone was first documented in 2009 (PMID: 19788760). Based on a literature review a significant number of articles have been published on Thiacremonone (PMID: 32068926) (PMID: 30034986) (PMID: 27409674) (PMID: 27069909) (PMID: 26008621) (PMID: 25791937).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120043D          

 18 18  0  0  0  0            999 V2000
    2.7313   -0.5078    0.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -0.2665    0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519    0.6220   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747    1.5344   -1.2691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6571    0.6165   -0.6524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658    1.5321   -1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3456   -0.5502   -0.0620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4349   -0.0654    0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7998   -1.4599   -0.9766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0158   -1.2610    0.9492 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2546   -1.0000   -0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8751   -1.0881    1.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1947    0.5099    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949    2.5227   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3557   -0.6492    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0971   -0.0492    1.9306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    1.0109    0.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440   -1.4512   -1.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10  2  1  0  0  0  0
  1 11  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  4 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  9 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(S[C@](O[H])(C1=O)C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O3S/c1-3-4(7)5(8)6(2,9)10-3/h7,9H,1-2H3/t6-/m0/s1

> <INCHI_KEY>
JYMIRUWYSKOKRU-UHFFFAOYSA-N

> <FORMULA>
C6H8O3S

> <MOLECULAR_WEIGHT>
160.191

> <EXACT_MASS>
160.019414812

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
15.207547219858832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2,4-dihydroxy-2,5-dimethyl-2,3-dihydrothiophen-3-one

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
0.30457795166666646

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.433992792101602

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.517699019072126

> <JCHEM_PKA_STRONGEST_BASIC>
-4.155539051682163

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.1751

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,4-dihydroxy-2,5-dimethylthiophen-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       2.731  -0.508   0.506  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.301  -0.267   0.211  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.752   0.622  -0.564  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.575   1.534  -1.269  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.657   0.617  -0.652  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.366   1.532  -1.196  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.346  -0.550  -0.062  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.435  -0.065   0.869  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.800  -1.460  -0.977  0.00  0.00           O+0
HETATM   10  S   UNK     0      -0.016  -1.261   0.949  0.00  0.00           S+0
HETATM   11  H   UNK     0       3.255  -1.000  -0.358  0.00  0.00           H+0
HETATM   12  H   UNK     0       2.875  -1.088   1.413  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.195   0.510   0.651  0.00  0.00           H+0
HETATM   14  H   UNK     0       1.395   2.523  -1.040  0.00  0.00           H+0
HETATM   15  H   UNK     0      -3.356  -0.649   0.815  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.097  -0.049   1.931  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.663   1.011   0.624  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.344  -1.451  -1.849  0.00  0.00           H+0
CONECT    1    2   11   12   13                                             
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   14                                                       
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7   15   16   17                                             
CONECT    9    7   18                                                       
CONECT   10    7    2                                                       
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    4                                                            
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,4-Dihydroxy-2,5-dimethyl-3(2H)-thiophenone, 9ci	HMDB
Thiacremonone	MeSH

Chemical Formula

C₆H₈O₃S

Average Mass

160.1910 Da

Monoisotopic Mass

160.01941 Da

IUPAC Name

(2S)-2,4-dihydroxy-2,5-dimethyl-2,3-dihydrothiophen-3-one

Traditional Name

(2S)-2,4-dihydroxy-2,5-dimethylthiophen-3-one

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(=O)C(C)(O)S1

InChI Identifier

InChI=1S/C6H8O3S/c1-3-4(7)5(8)6(2,9)10-3/h7,9H,1-2H3

InChI Key

JYMIRUWYSKOKRU-UHFFFAOYSA-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
Acremonium sp.	NPAtlas	26281194

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteromonocyclic 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	1786 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.29	ALOGPS
logP	0.3	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	7.52	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.18 m³·mol⁻¹	ChemAxon
Polarizability	15.21 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA006708

HMDB ID

HMDB0035901

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014686

KNApSAcK ID

Not Available

Chemspider ID

469524

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

539170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1852391

References

General References

Dorrigiv M, Zareiyan A, Hosseinzadeh H: Garlic (Allium sativum) as an antidote or a protective agent against natural or chemical toxicities: A comprehensive update review. Phytother Res. 2020 Aug;34(8):1770-1797. doi: 10.1002/ptr.6645. Epub 2020 Feb 18. [PubMed:32068926 ]
Jamil SZMR, Rohani ER, Baharum SN, Noor NM: Metabolite profiles of callus and cell suspension cultures of mangosteen. 3 Biotech. 2018 Aug;8(8):322. doi: 10.1007/s13205-018-1336-6. Epub 2018 Jul 17. [PubMed:30034986 ]
Hwang CJ, Lee HP, Choi DY, Jeong HS, Kim TH, Lee TH, Kim YM, Moon DB, Park SS, Kim SY, Oh KW, Hwang DY, Han SB, Lee HJ, Hong JT: Inhibitory effect of thiacremonone on MPTP-induced dopaminergic neurodegeneration through inhibition of p38 activation. Oncotarget. 2016 Jul 26;7(30):46943-46958. doi: 10.18632/oncotarget.10504. [PubMed:27409674 ]
Woo KS, Hwang IG, Kim HY, Lee SH, Jeong HS: Physiological Activities of Thiacremonone Produced in High Temperature and High Pressure Treated Garlic. Prev Nutr Food Sci. 2016 Mar;21(1):68-72. doi: 10.3746/pnf.2016.21.1.68. Epub 2016 Mar 31. [PubMed:27069909 ]
Yun HM, Jin P, Park KR, Hwang J, Jeong HS, Kim EC, Jung JK, Oh KW, Hwang BY, Han SB, Hong JT: Thiacremonone Potentiates Anti-Oxidant Effects to Improve Memory Dysfunction in an APP/PS1 Transgenic Mice Model. Mol Neurobiol. 2016 May;53(4):2409-20. doi: 10.1007/s12035-015-9208-0. Epub 2015 May 26. [PubMed:26008621 ]
Ban JO, Hwang CJ, Park MH, Hwang IK, Jeong HS, Lee HP, Hyun BK, Kim JY, Youn HS, Ham YW, Yoon DY, Han SB, Song MJ, Hong JT: Enhanced cell growth inhibition by thiacremonone in paclitaxel-treated lung cancer cells. Arch Pharm Res. 2015 Jul;38(7):1351-62. doi: 10.1007/s12272-015-0589-4. Epub 2015 Mar 20. [PubMed:25791937 ]
Jo M, Yun HM, Park KR, Park MH, Lee DH, Cho SH, Yoo HS, Lee YM, Jeong HS, Kim Y, Jung JK, Hwang BY, Lee MK, Kim ND, Han SB, Hong JT: Anti-cancer effect of thiacremonone through down regulation of peroxiredoxin 6. PLoS One. 2014 Mar 11;9(3):e91508. doi: 10.1371/journal.pone.0091508. eCollection 2014. [PubMed:24618722 ]
Kim YR, Lee NJ, Ban JO, Yoo HS, Lee YM, Yoon YP, Eum SY, Jeong HS, Yoon DY, Han SB, Hong JT: Curative Effects of Thiacremonone against Acetaminophen-Induced Acute Hepatic Failure via Inhibition of Proinflammatory Cytokines Production and Infiltration of Cytotoxic Immune Cells and Kupffer Cells. Evid Based Complement Alternat Med. 2013;2013:974794. doi: 10.1155/2013/974794. Epub 2013 Jul 11. [PubMed:23935693 ]
Kim EJ, Lee DH, Kim HJ, Lee SJ, Ban JO, Cho MC, Jeong HS, Yang Y, Hong JT, Yoon DY: Thiacremonone, a sulfur compound isolated from garlic, attenuates lipid accumulation partially mediated via AMPK activation in 3T3-L1 adipocytes. J Nutr Biochem. 2012 Dec;23(12):1552-8. doi: 10.1016/j.jnutbio.2011.10.008. Epub 2012 Mar 8. [PubMed:22405697 ]
Lin GH, Lee YJ, Choi DY, Han SB, Jung JK, Hwang BY, Moon DC, Kim Y, Lee MK, Oh KW, Jeong HS, Leem JY, Shin HK, Lee JH, Hong JT: Anti-amyloidogenic effect of thiacremonone through anti-inflamation in vitro and in vivo models. J Alzheimers Dis. 2012;29(3):659-76. doi: 10.3233/JAD-2012-111709. [PubMed:22297647 ]
Ban JO, Lee DH, Kim EJ, Kang JW, Kim MS, Cho MC, Jeong HS, Kim JW, Yang Y, Hong JT, Yoon DY: Antiobesity effects of a sulfur compound thiacremonone mediated via down-regulation of serum triglyceride and glucose levels and lipid accumulation in the liver of db/db mice. Phytother Res. 2012 Sep;26(9):1265-71. doi: 10.1002/ptr.3729. Epub 2012 Jan 6. [PubMed:22228551 ]
Ban JO, Oh JH, Kim TM, Kim DJ, Jeong HS, Han SB, Hong JT: Anti-inflammatory and arthritic effects of thiacremonone, a novel sulfur compound isolated from garlic via inhibition of NF-kappaB. Arthritis Res Ther. 2009;11(5):R145. doi: 10.1186/ar2819. Epub 2009 Sep 30. [PubMed:19788760 ]

Showing NP-Card for Thiacremonone (NP0014590)

MOL for NP0014590 (Thiacremonone)

3D MOL for NP0014590 (Thiacremonone)

3D SDF for NP0014590 (Thiacremonone)

3D-SDF for NP0014590 (Thiacremonone)

PDB for NP0014590 (Thiacremonone)

3D PDB for NP0014590 (Thiacremonone)

SMILES for NP0014590 (Thiacremonone)

INCHI for NP0014590 (Thiacremonone)

Structure for NP0014590 (Thiacremonone)

3D Structure for NP0014590 (Thiacremonone)