NP-MRD: Showing NP-Card for (2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one (NP0279458)

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Record Information

Version

2.0

Created at

2022-09-09 04:51:30 UTC

Updated at

2022-09-09 04:51:30 UTC

NP-MRD ID

NP0279458

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one

Description

12-Chloroillifunone C belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one was first documented in 2021 (PMID: 34478990). Based on a literature review very few articles have been published on 12-Chloroillifunone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    4.8825    1.2060    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    0.1677   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6971   -0.8999    0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -1.0564   -0.1219 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4902    0.2249    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1599   -0.0118   -0.6132 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2479   -0.1335   -1.9866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8784    1.0521   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043    0.3275   -0.7861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3859    0.8771   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4644    0.8367    1.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5141    0.0313   -0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6135    2.5431   -0.7933 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8834   -0.9908   -0.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386   -1.2003   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1252   -2.1810    0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5681   -2.1141    0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214   -2.9207    1.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392    1.2786    1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4058    1.9830   -0.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    0.0923   -1.4252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6343   -0.6526    1.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2468   -1.8512    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2827   -1.3169   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0104    1.0106   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847    0.4891    1.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0305    0.7249   -2.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8624    1.1994    0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6921    1.9967   -0.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1421    0.3736   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5033    1.1545    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -0.1821    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920    1.5973    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1399   -0.8902   -1.3031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2150   -0.2996   -0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0566    0.5978   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480   -3.0630    0.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 10 13  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  6
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  4 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14  9  1  0
 15  6  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
  9 30  1  6
  8 28  1  0
  8 29  1  0
  7 27  1  0
  5 25  1  0
  5 26  1  0
  4 24  1  6
  3 22  1  0
  3 23  1  0
  2 21  1  0
  1 19  1  0
  1 20  1  0
 16 37  1  0
M  END


  Mrv1652309092206512D          

 18 19  0  0  1  0            999 V2000
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5549    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.6979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0279458

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(Cl)[C@H]1C[C@@]2(O)C[C@@H](CC=C)C(=O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H19ClO3/c1-4-5-9-7-14(17)8-12(13(2,3)15)18-11(14)6-10(9)16/h4,6,9,12,17H,1,5,7-8H2,2-3H3/t9-,12-,14+/m1/s1

> <INCHI_KEY>
FTJNIFKKCTWGTJ-IUPBHXKESA-N

> <FORMULA>
C14H19ClO3

> <MOLECULAR_WEIGHT>
270.75

> <EXACT_MASS>
270.1022722

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.018351354993115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3aS,5R)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,3a,4,5,6-hexahydro-1-benzofuran-6-one

> <JCHEM_LOGP>
2.058934916

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.878385419373277

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.396244080717207

> <JCHEM_PKA_STRONGEST_BASIC>
-3.500278746000875

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
72.17679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3aS,5R)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.036   0.541   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.253   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.713   4.383   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      -2.713   1.303   0.000  0.00  0.00          Cl+0
HETATM   14  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    9   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    4   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₉ClO₃

Average Mass

270.7500 Da

Monoisotopic Mass

270.10227 Da

IUPAC Name

(2R,3aS,5R)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,3a,4,5,6-hexahydro-1-benzofuran-6-one

Traditional Name

(2R,3aS,5R)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one

CAS Registry Number

Not Available

SMILES

CC(C)(Cl)[C@H]1C[C@@]2(O)C[C@@H](CC=C)C(=O)C=C2O1

InChI Identifier

InChI=1S/C14H19ClO3/c1-4-5-9-7-14(17)8-12(13(2,3)15)18-11(14)6-10(9)16/h4,6,9,12,17H,1,5,7-8H2,2-3H3/t9-,12-,14+/m1/s1

InChI Key

FTJNIFKKCTWGTJ-IUPBHXKESA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Cyclohexenone
Oxolane
Tertiary alcohol
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Alkyl chloride
Alcohol
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Organic oxygen compound
Alkyl halide
Hydrocarbon derivative
Organic oxide
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	2.06	ChemAxon
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-3.5	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	3	ChemAxon
Refractivity	72.18 m³·mol⁻¹	ChemAxon
Polarizability	28.02 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

74051911

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101672253

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang JP, Li WR, Wu S, Wang XJ, Wang RB, Li M, Su GZ, Wang HQ, Yong JY, Yang J, Li L, Li YH, Ma SG: Prenylated C6-C3 derivatives from the stems and branches of Illicium ternstroemioides A. C. Smith with antiviral activity. Phytochemistry. 2021 Sep 1;192:112935. doi: 10.1016/j.phytochem.2021.112935. [PubMed:34478990 ]
LOTUS database [Link]

Showing NP-Card for (2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one (NP0279458)

MOL for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

3D MOL for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

3D SDF for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

3D-SDF for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

PDB for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

3D PDB for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

SMILES for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

INCHI for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

Structure for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)

3D Structure for NP0279458 ((2r,3as,5r)-2-(2-chloropropan-2-yl)-3a-hydroxy-5-(prop-2-en-1-yl)-2,3,4,5-tetrahydro-1-benzofuran-6-one)