NP-MRD: Showing NP-Card for (7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate (NP0315548)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 14:13:55 UTC

Updated at

2022-09-11 14:13:55 UTC

NP-MRD ID

NP0315548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate

Description

Eupenicilazaphilone C 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. (7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate was first documented in 2021 (PMID: 34677428). Based on a literature review very few articles have been published on Eupenicilazaphilone C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112216132D          

 29 30  0  0  1  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3848   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 14  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
   -4.2274    1.2259   -2.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7852    0.4797   -1.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8889   -0.3961   -0.7221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1204    0.4675   -0.3817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4480   -0.9913    0.5959 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5516   -1.7957    1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2989   -1.9349    0.5183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3140   -2.7029    1.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6067   -2.9133   -0.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -1.3636    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3902   -0.4326    0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532    0.0955    0.6031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5414    1.0158    1.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8570    1.4817    0.8890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5142    2.3947    1.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032    3.0423    3.0576 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8466    2.8584    1.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141    3.9631    1.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6885    2.0606    0.2726 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0296    1.7010    0.9009 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9674    2.7640   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9738    0.7592    0.0002 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6664   -0.0565   -0.9256 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2112   -1.2709   -0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9147   -2.0324   -1.6857 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1217   -1.7357    0.5191 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5340    0.9647   -0.3498 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9513   -0.3937   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5675   -0.4361   -0.5155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4527    1.9962   -2.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1783    1.7742   -2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    0.4953   -3.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.2216   -1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3503    1.1302   -0.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1954   -1.1446   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7520    0.6110   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7600   -0.0494    0.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8148    1.4232    0.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3340   -0.2005    1.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8153   -1.5678    1.9373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3165   -1.9133    2.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4038   -3.3078    1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2291   -3.3049    1.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6645   -2.5131   -1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061   -1.7187   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8991   -0.0380    1.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284    1.4225    2.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7140    2.5701    0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8583    1.3152    1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4378    0.8375    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7589    2.2014   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9883    0.1885    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0894   -1.3860   -2.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8773   -2.4575   -1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3186   -2.9201   -2.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3566    1.7134   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -1.2056   -0.1659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571   -0.5482   -1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  6
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 27  1  0
 27 28  1  0
 28 29  1  0
 29 12  1  0
 27 14  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  6
  4 36  1  0
  4 37  1  0
  4 38  1  0
  5 39  1  1
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 13 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 22 52  1  1
 25 53  1  0
 25 54  1  0
 25 55  1  0
 27 56  1  6
 28 57  1  0
 28 58  1  0
M  END


  Mrv1652309112216132D          

 29 30  0  0  1  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1270    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3848   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
 27 14  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0315548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)[C@@H](O)[C@@](C)(O)\C=C\C1=CC2=C(Cl)C(=O)[C@](C)(O)[C@H](OC(C)=O)[C@H]2CO1

> <INCHI_IDENTIFIER>
InChI=1S/C21H29ClO7/c1-6-11(2)17(24)20(4,26)8-7-13-9-14-15(10-28-13)19(29-12(3)23)21(5,27)18(25)16(14)22/h7-9,11,15,17,19,24,26-27H,6,10H2,1-5H3/b8-7+/t11-,15-,17+,19+,20-,21-/m0/s1

> <INCHI_KEY>
BPFKUKMOOOUEPT-QTKYNUCXSA-N

> <FORMULA>
C21H29ClO7

> <MOLECULAR_WEIGHT>
428.91

> <EXACT_MASS>
428.160181

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.26188893616529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7R,8R,8aR)-5-chloro-3-[(1E,3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-6,7,8,8a-tetrahydro-1H-isochromen-8-yl acetate

> <JCHEM_LOGP>
1.1492024343333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.017905935288294

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.39981048254982

> <JCHEM_PKA_STRONGEST_BASIC>
-3.344185333464587

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
110.84419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(7R,8R,8aR)-5-chloro-3-[(1E,3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1H-isochromen-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104   0.976   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.564   3.644   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       5.335   1.540   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.195  -3.757   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   14   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   12                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₉ClO₇

Average Mass

428.9100 Da

Monoisotopic Mass

428.16018 Da

IUPAC Name

(7R,8R,8aR)-5-chloro-3-[(1E,3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-6,7,8,8a-tetrahydro-1H-isochromen-8-yl acetate

Traditional Name

(7R,8R,8aR)-5-chloro-3-[(1E,3S,4R,5S)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1H-isochromen-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)[C@@H](O)[C@@](C)(O)\C=C\C1=CC2=C(Cl)C(=O)[C@](C)(O)[C@H](OC(C)=O)[C@H]2CO1

InChI Identifier

InChI=1S/C21H29ClO7/c1-6-11(2)17(24)20(4,26)8-7-13-9-14-15(10-28-13)19(29-12(3)23)21(5,27)18(25)16(14)22/h7-9,11,15,17,19,24,26-27H,6,10H2,1-5H3/b8-7+/t11-,15-,17+,19+,20-,21-/m0/s1

InChI Key

BPFKUKMOOOUEPT-QTKYNUCXSA-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 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
Acyloin
Alpha-haloketone
Alpha-chloroketone
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organochloride
Organohalogen compound
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	1.15	ChemAxon
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.84 m³·mol⁻¹	ChemAxon
Polarizability	44.26 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

71044341

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591270

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang HC, Ke TY, Ko YC, Lin JJ, Chang JS, Cheng YB: Anti-Inflammatory Azaphilones from the Edible Alga-Derived Fungus Penicillium sclerotiorum. Mar Drugs. 2021 Sep 22;19(10). pii: md19100529. doi: 10.3390/md19100529. [PubMed:34677428 ]
LOTUS database [Link]

Showing NP-Card for (7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate (NP0315548)

MOL for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

3D MOL for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

3D SDF for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

3D-SDF for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

PDB for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

3D PDB for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

SMILES for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

INCHI for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

Structure for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)

3D Structure for NP0315548 ((7r,8r,8ar)-5-chloro-3-[(1e,3s,4r,5s)-3,4-dihydroxy-3,5-dimethylhept-1-en-1-yl]-7-hydroxy-7-methyl-6-oxo-8,8a-dihydro-1h-isochromen-8-yl acetate)