NP-MRD: Showing NP-Card for 3-hydroxytrichodenone C (NP0018528)

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Record Information

Version

2.0

Created at

2021-01-06 03:07:59 UTC

Updated at

2021-07-15 17:28:28 UTC

NP-MRD ID

NP0018528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-hydroxytrichodenone C

Provided By

NPAtlas

Description

(4S)-2-chloro-4-hydroxy-3-[(1R)-1-hydroxyethyl]cyclopent-2-en-1-one belongs to the class of organic compounds known as alpha-chloroketones. These are organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group. 3-hydroxytrichodenone C is found in Trichoderma. 3-hydroxytrichodenone C was first documented in 2018 (PMID: 30072624). Based on a literature review very few articles have been published on (4S)-2-chloro-4-hydroxy-3-[(1R)-1-hydroxyethyl]cyclopent-2-en-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104353D          

 20 20  0  0  0  0            999 V2000
    2.4389    0.3940   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721   -0.6259   -0.2165 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4378   -1.5549    0.8485 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0105   -0.0396   -0.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    1.2006    0.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7129    2.6171    0.2723 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7948    1.3344    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511    2.3018    0.4392 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3404    0.1001   -0.5543 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2388   -0.8708   -0.2985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4766   -1.6278    0.8357 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4248   -0.1427   -0.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4119    0.9108    0.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903    1.1470   -0.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670   -1.1562   -1.1926 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3356   -1.4777    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3201   -0.2013   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4567    0.2619   -1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670   -1.5633   -1.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5212   -1.0077    1.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10  4  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  6  0  0  0
  3 16  1  0  0  0  0
  9 17  1  0  0  0  0
  9 18  1  0  0  0  0
 10 19  1  6  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0018528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C1=C(Cl)C(=O)C([H])([H])[C@]1([H])O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C7H9ClO3/c1-3(9)6-4(10)2-5(11)7(6)8/h3-4,9-10H,2H2,1H3/t3-,4+/m1/s1

> <INCHI_KEY>
WYSSYCHKVAYMNP-DMTCNVIQSA-N

> <FORMULA>
C7H9ClO3

> <MOLECULAR_WEIGHT>
176.6

> <EXACT_MASS>
176.0240218

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
16.210437395997772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-2-chloro-4-hydroxy-3-[(1R)-1-hydroxyethyl]cyclopent-2-en-1-one

> <ALOGPS_LOGP>
-0.57

> <JCHEM_LOGP>
-0.26533706133333357

> <ALOGPS_LOGS>
-0.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.943606988245396

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.982605507952616

> <JCHEM_PKA_STRONGEST_BASIC>
-2.907353434726816

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
41.368

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-2-chloro-4-hydroxy-3-[(1R)-1-hydroxyethyl]cyclopent-2-en-1-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       2.439   0.394  -0.042  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.372  -0.626  -0.217  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.438  -1.555   0.849  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.011  -0.040  -0.150  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.335   1.201   0.036  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       0.713   2.617   0.272  0.00  0.00          Cl+0
HETATM    7  C   UNK     0      -1.795   1.334   0.030  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.451   2.302   0.439  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.340   0.100  -0.554  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.239  -0.871  -0.299  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.477  -1.628   0.836  0.00  0.00           O+0
HETATM   12  H   UNK     0       3.425  -0.143  -0.053  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.412   0.911   0.923  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.390   1.147  -0.848  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.467  -1.156  -1.193  0.00  0.00           H+0
HETATM   16  H   UNK     0       2.336  -1.478   1.263  0.00  0.00           H+0
HETATM   17  H   UNK     0      -3.320  -0.201  -0.103  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.457   0.262  -1.654  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.067  -1.563  -1.144  0.00  0.00           H+0
HETATM   20  H   UNK     0      -1.521  -1.008   1.609  0.00  0.00           H+0
CONECT    1    2   12   13   14                                             
CONECT    2    1    3    4   15                                             
CONECT    3    2   16                                                       
CONECT    4    2    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17   18                                             
CONECT   10    9   11    4   19                                             
CONECT   11   10   20                                                       
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₇H₉ClO₃

Average Mass

176.6000 Da

Monoisotopic Mass

176.02402 Da

IUPAC Name

(4S)-2-chloro-4-hydroxy-3-[(1R)-1-hydroxyethyl]cyclopent-2-en-1-one

Traditional Name

(4S)-2-chloro-4-hydroxy-3-[(1R)-1-hydroxyethyl]cyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

C[C@@H](O)C1=C(Cl)C(=O)C[C@@H]1O

InChI Identifier

InChI=1S/C7H9ClO3/c1-3(9)6-4(10)2-5(11)7(6)8/h3-4,9-10H,2H2,1H3/t3-,4+/m1/s1

InChI Key

WYSSYCHKVAYMNP-DMTCNVIQSA-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
Trichoderma	NPAtlas	30072624

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-chloroketones. These are organic compounds contaning a chlorine atom attached to the alpha carbon atom relative to C=O group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-chloroketones

Alternative Parents

Substituents

Alpha-chloroketone
Cyclic ketone
Secondary alcohol
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxide
Hydrocarbon derivative
Organochloride
Organohalogen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-0.57	ALOGPS
logP	-0.27	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	13.98	ChemAxon
pKa (Strongest Basic)	-2.9	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	1	ChemAxon
Refractivity	41.37 m³·mol⁻¹	ChemAxon
Polarizability	16.21 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA023420

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

71048399

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590701

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Song YP, Miao FP, Fang ST, Yin XL, Ji NY: Halogenated and Nonhalogenated Metabolites from the Marine-Alga-Endophytic Fungus Trichoderma asperellum cf44-2. Mar Drugs. 2018 Aug 2;16(8). pii: md16080266. doi: 10.3390/md16080266. [PubMed:30072624 ]

Showing NP-Card for 3-hydroxytrichodenone C (NP0018528)

MOL for NP0018528 (3-hydroxytrichodenone C)

3D MOL for NP0018528 (3-hydroxytrichodenone C)

3D SDF for NP0018528 (3-hydroxytrichodenone C)

3D-SDF for NP0018528 (3-hydroxytrichodenone C)

PDB for NP0018528 (3-hydroxytrichodenone C)

3D PDB for NP0018528 (3-hydroxytrichodenone C)

SMILES for NP0018528 (3-hydroxytrichodenone C)

INCHI for NP0018528 (3-hydroxytrichodenone C)

Structure for NP0018528 (3-hydroxytrichodenone C)

3D Structure for NP0018528 (3-hydroxytrichodenone C)