NP-MRD: Showing NP-Card for 6-Hydroxytremetone (NP0051398)

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Record Information

Version

2.0

Created at

2022-04-27 22:46:49 UTC

Updated at

2022-04-27 22:46:49 UTC

NP-MRD ID

NP0051398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxytremetone

Description

6-Hydroxytremetone belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure. 6-Hydroxytremetone is found in Abrotanella forsteroides, Abrotanella spp., Tagetes erecta, Austrobrickellia spp., Clibadium armanii, Encelia ventuorum, Enceliopsis nudicaulis, Eupatorium cannabinum, Eupatorium rugosum, Eupatorium urticaefolium, Flourensia heterolepis, Geraea viscida, Helianthella spp., Helianthella uniflora, Helichrysum spp., Hemizonia congesta, Ligularia intermedia, Ligularia stenocephala, Senecio glaucus, Senecio spp. , Sinacalia tangutica, Tagetes patula, Tagetes spp. and Tussilago farfara. 6-Hydroxytremetone was first documented in 2011 (PMID: 21964240). Based on a literature review a small amount of articles have been published on 6-Hydroxytremetone (PMID: 32550575) (PMID: 23831837) (PMID: 23413577) (PMID: 21398137).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -4.0940    1.2211    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5470    0.0870   -0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4034   -1.1539   -0.3129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1305   -0.0564   -0.5308 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3266    1.1863   -0.3181 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573    0.6149   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140    1.1484   -0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517    0.3683   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7591    0.9669   -0.1406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9685    0.1761    0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8210    2.1943   -0.4729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827   -0.9514    0.3453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812   -1.7644    0.5934 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0049   -1.4814    0.4581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0975   -0.7175    0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730   -1.0305    0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    2.1144    0.3588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1626    1.2040    0.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4305   -0.8025   -0.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0255   -1.7497   -1.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3586   -1.6743    0.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0210   -0.3814   -1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132    1.6950    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3765    1.8765   -1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4331    2.1950   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0088   -0.6545   -0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8699    0.8416   -0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0303   -0.2240    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2639   -2.7222    0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9344   -2.5255    0.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6 15  2  0
 15 16  1  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12  8  1  0
  8  7  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 16  4  1  0
  7  6  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  1 17  1  0
  1 18  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
 14 30  1  0
 13 29  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
M  END


  Mrv1652304282200462D          

 16 17  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   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
    1.3556   -1.5229    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
    2.7845    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    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 O   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
   -1.8659    0.0165    0.0000 C   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
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1CC2=C(O1)C=C(O)C(=C2)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O3/c1-7(2)12-5-9-4-10(8(3)14)11(15)6-13(9)16-12/h4,6,12,15H,1,5H2,2-3H3/t12-/m1/s1

> <INCHI_KEY>
FHJSLVLVJPGFRY-GFCCVEGCSA-N

> <FORMULA>
C13H14O3

> <MOLECULAR_WEIGHT>
218.252

> <EXACT_MASS>
218.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.52306328292736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2R)-6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethan-1-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.793923418666666

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.609453022488587

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.285092994515336

> <JCHEM_PKA_STRONGEST_BASIC>
-4.904086151749123

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
61.32940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxytremetone

> <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       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.198  -2.843   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.198   0.237   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.531  -0.533   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.268  -2.549   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₄O₃

Average Mass

218.2520 Da

Monoisotopic Mass

218.09429 Da

IUPAC Name

1-[(2R)-6-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran-5-yl]ethan-1-one

Traditional Name

6-hydroxytremetone

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1CC2=C(O1)C=C(O)C(=C2)C(C)=O

InChI Identifier

InChI=1S/C13H14O3/c1-7(2)12-5-9-4-10(8(3)14)11(15)6-13(9)16-12/h4,6,12,15H,1,5H2,2-3H3/t12-/m1/s1

InChI Key

FHJSLVLVJPGFRY-GFCCVEGCSA-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
Abrotanella forsteroides	LOTUS Database	35616633
Abrotanella spp.	Plant	KNApSAcK
African marigold	LOTUS Database	35616633
Austrobrickellia spp.	Plant	KNApSAcK
Clibadium armanii	Plant	KNApSAcK
Encelia ventuorum	Plant	KNApSAcK
Enceliopsis nudicaulis	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Eupatorium rugosum	Plant	KNApSAcK
Eupatorium urticaefolium	Plant	KNApSAcK
Flourensia heterolepis	Plant	KNApSAcK
Geraea viscida	LOTUS Database	35616633
Helianthella spp.	Plant	KNApSAcK
Helianthella uniflora	LOTUS Database	35616633
Helichrysum spp.	Plant	KNApSAcK
Hemizonia congesta	Plant	KNApSAcK
Ligularia intermedia	Plant	KNApSAcK
Ligularia stenocephala	Plant	KNApSAcK
Senecio glaucus	LOTUS Database	35616633
Senecio spp.	Plant	KNApSAcK
Sinacalia tangutica	LOTUS Database	35616633
Tagetes patula	LOTUS Database	35616633
Tagetes spp.	Plant	KNApSAcK
Tussilago farfara	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Acetophenones

Direct Parent

Acetophenones

Alternative Parents

Substituents

Acetophenone
Coumaran
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzofurans (CHEBI:2202 )

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	2.27	ALOGPS
logP	2.79	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.33 m³·mol⁻¹	ChemAxon
Polarizability	23.52 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

C00002399

Chemspider ID

161731

KEGG Compound ID

C08744

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

186059

PDB ID

Not Available

ChEBI ID

2202

Good Scents ID

Not Available

References

General References

Green BT, Lee ST, Davis TZ, Welch KD: Microsomal activation, and SH-SY5Y cell toxicity studies of tremetone and 6-hydroxytremetone isolated from rayless goldenrod (Isocoma pluriflora) and white snakeroot (Agertina altissima), respectively. Toxicon X. 2019 Nov 11;5:100018. doi: 10.1016/j.toxcx.2019.100018. eCollection 2020 Mar. [PubMed:32550575 ]
Davis TZ, Stegelmeier BL, Lee ST, Green BT, Hall JO: Experimental rayless goldenrod (Isocoma pluriflora) toxicosis in horses. Toxicon. 2013 Oct;73:88-95. doi: 10.1016/j.toxicon.2013.06.018. Epub 2013 Jul 4. [PubMed:23831837 ]
Gonzalez AM, Tracanna MI, Amani SM, Schuff C, Poch MJ, Bach H, Catalan CA: Chemical composition, antimicrobial and antioxidant properties of the volatile oil and methanol extract of Xenophyllum poposum. Nat Prod Commun. 2012 Dec;7(12):1663-6. [PubMed:23413577 ]
Romano E, Raschi AB, Benavente A, Brandan SA: Structural analysis, vibrational spectra and coordinated normal of 2R-(-)-6-hydroxytremetone. Spectrochim Acta A Mol Biomol Spectrosc. 2011 Dec 15;84(1):111-6. doi: 10.1016/j.saa.2011.09.011. Epub 2011 Sep 16. [PubMed:21964240 ]
Romano E, Raschi AB, Gonzalez AM, Jaime G, Fortuna MA, Hernandez LR, Bach H, Benavente AM: Phytotoxic activities of (2R)-6-hydroxytremetone. Plant Physiol Biochem. 2011 Jun;49(6):671-5. doi: 10.1016/j.plaphy.2011.02.014. Epub 2011 Feb 26. [PubMed:21398137 ]

Showing NP-Card for 6-Hydroxytremetone (NP0051398)

MOL for NP0051398 (6-Hydroxytremetone)

3D MOL for NP0051398 (6-Hydroxytremetone)

3D SDF for NP0051398 (6-Hydroxytremetone)

3D-SDF for NP0051398 (6-Hydroxytremetone)

PDB for NP0051398 (6-Hydroxytremetone)

3D PDB for NP0051398 (6-Hydroxytremetone)

SMILES for NP0051398 (6-Hydroxytremetone)

INCHI for NP0051398 (6-Hydroxytremetone)

Structure for NP0051398 (6-Hydroxytremetone)

3D Structure for NP0051398 (6-Hydroxytremetone)