NP-MRD: Showing NP-Card for (3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione (NP0275067)

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Record Information

Version

2.0

Created at

2022-09-08 22:41:16 UTC

Updated at

2022-09-08 22:41:16 UTC

NP-MRD ID

NP0275067

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione

Description

Pochonin D belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione is found in Pochonia chlamydosporia. (3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione was first documented in 2005 (PMID: 15884943). Based on a literature review a significant number of articles have been published on Pochonin D (PMID: 20961859) (PMID: 19821460) (PMID: 29048170) (PMID: 29715717) (PMID: 19101477).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.2772   -3.1159    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9945   -1.7893    0.5645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4617   -2.0366    0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0448   -1.2529   -0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3467    0.0347   -0.7242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1411    0.9023    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175    2.2535    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021    2.2840   -1.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7100    2.3863   -1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3538    2.4873   -0.5262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1903    3.4569   -0.6115 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6015    1.5582    0.6075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8096    0.7211    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889    1.1276    0.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0100    2.5688    1.9951 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1749    0.4679    0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3511    0.9141    1.4444 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2215   -0.6567    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -1.0904   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1129   -2.2287   -1.3858 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387   -0.4041   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -0.9455   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8906   -1.3385   -2.3231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373   -1.0050   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1847   -3.4051   -0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0283   -3.9282    0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -3.1221    1.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8722   -1.2903    1.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9967   -1.8177    1.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6183   -3.1464    0.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2428   -1.7750   -1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7793    0.5652   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331    0.4094    1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384    1.0577    0.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5051    2.9516    0.0367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098    2.6027    0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7332    2.2139   -2.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911    2.4025   -2.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    0.9113    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7758    2.2296    1.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107    1.7427    2.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1514   -1.1925   -0.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9807   -2.7084   -1.4960 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
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24  2  1  0
 21 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 12 39  1  0
 12 40  1  0
 17 41  1  0
 18 42  1  0
 20 43  1  0
M  END


  Mrv1652309092200412D          

 24 25  0  0  1  0            999 V2000
    6.6647    1.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629    0.6623    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6555    0.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8537   -0.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6463   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8445   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2500   -1.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4574   -1.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629   -2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0703   -2.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758   -2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721   -1.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795   -1.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4850   -1.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831   -2.4267    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -1.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4942   -0.5962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -0.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905    0.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813   -0.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4758    0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2776    1.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    0.0903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0275067

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C\C=C\CC\C=C\C(=O)CC2=C(Cl)C(O)=CC(O)=C2C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H19ClO5/c1-11-7-5-3-2-4-6-8-12(20)9-13-16(18(23)24-11)14(21)10-15(22)17(13)19/h3,5-6,8,10-11,21-22H,2,4,7,9H2,1H3/b5-3+,8-6+/t11-/m1/s1

> <INCHI_KEY>
FJVQHTGEXYKKBS-CJRGTMQESA-N

> <FORMULA>
C18H19ClO5

> <MOLECULAR_WEIGHT>
350.8

> <EXACT_MASS>
350.0921014

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
35.10067649857946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-13-chloro-14,16-dihydroxy-3-methyl-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecine-1,11-dione

> <JCHEM_LOGP>
4.893333771666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.842870337517638

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.022421816352043

> <JCHEM_PKA_STRONGEST_BASIC>
-4.304656899510616

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
94.23759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3H-2-benzoxacyclotetradecine-1,11-dione

> <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      12.441   2.731   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.811   1.236   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.290   0.809   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.660  -0.686   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.140  -1.113   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.510  -2.608   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.400  -3.676   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.920  -3.248   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.811  -4.316   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.331  -3.889   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.221  -4.957   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.961  -2.394   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.482  -1.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.372  -3.035   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0       8.742  -4.530   0.000  0.00  0.00          Cl+0
HETATM   16  C   UNK     0       6.892  -2.608   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.783  -3.676   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.522  -1.113   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.632  -0.045   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.262   1.450   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.112  -0.472   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.221   0.596   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.852   2.091   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.701   0.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉ClO₅

Average Mass

350.8000 Da

Monoisotopic Mass

350.09210 Da

IUPAC Name

(3R)-13-chloro-14,16-dihydroxy-3-methyl-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecine-1,11-dione

Traditional Name

(3R)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3H-2-benzoxacyclotetradecine-1,11-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C\C=C\CC\C=C\C(=O)CC2=C(Cl)C(O)=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C18H19ClO5/c1-11-7-5-3-2-4-6-8-12(20)9-13-16(18(23)24-11)14(21)10-15(22)17(13)19/h3,5-6,8,10-11,21-22H,2,4,7,9H2,1H3/b5-3+,8-6+/t11-/m1/s1

InChI Key

FJVQHTGEXYKKBS-CJRGTMQESA-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

Species Name	Source	Reference
Pochonia chlamydosporia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Dihydroxybenzoic acid
4-halophenol
2-halophenol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl chloride
Aryl halide
Benzenoid
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.89	ChemAxon
pKa (Strongest Acidic)	7.02	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.24 m³·mol⁻¹	ChemAxon
Polarizability	35.1 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

C00045020

Chemspider ID

4979979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11405422

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou H, Qiao K, Gao Z, Vederas JC, Tang Y: Insights into radicicol biosynthesis via heterologous synthesis of intermediates and analogs. J Biol Chem. 2010 Dec 31;285(53):41412-21. doi: 10.1074/jbc.M110.183574. Epub 2010 Oct 20. [PubMed:20961859 ]
Dakas PY, Jogireddy R, Valot G, Barluenga S, Winssinger N: Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin. Chemistry. 2009 Nov 2;15(43):11490-7. doi: 10.1002/chem.200901373. [PubMed:19821460 ]
Choe H, Cho H, Ko HJ, Lee J: Total Synthesis of (+)-Pochonin D and (+)-Monocillin II via Chemo- and Regioselective Intramolecular Nitrile Oxide Cycloaddition. Org Lett. 2017 Nov 3;19(21):6004-6007. doi: 10.1021/acs.orglett.7b03054. [PubMed:29048170 ]
Song JH, Shim A, Kim YJ, Ahn JH, Kwon BE, Pham TT, Lee J, Chang SY, Ko HJ: Antiviral and Anti-Inflammatory Activities of Pochonin D, a Heat Shock Protein 90 Inhibitor, against Rhinovirus Infection. Biomol Ther (Seoul). 2018 Nov 1;26(6):576-583. doi: 10.4062/biomolther.2017.233. [PubMed:29715717 ]
Wang S, Xu Y, Maine EA, Wijeratne EM, Espinosa-Artiles P, Gunatilaka AA, Molnar I: Functional characterization of the biosynthesis of radicicol, an Hsp90 inhibitor resorcylic acid lactone from Chaetomium chiversii. Chem Biol. 2008 Dec 22;15(12):1328-38. doi: 10.1016/j.chembiol.2008.10.006. [PubMed:19101477 ]
Moulin E, Zoete V, Barluenga S, Karplus M, Winssinger N: Design, synthesis, and biological evaluation of HSP90 inhibitors based on conformational analysis of radicicol and its analogues. J Am Chem Soc. 2005 May 18;127(19):6999-7004. doi: 10.1021/ja043101w. [PubMed:15884943 ]
LOTUS database [Link]

Showing NP-Card for (3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione (NP0275067)

MOL for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D MOL for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D SDF for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D-SDF for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

PDB for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D PDB for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

SMILES for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

INCHI for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

Structure for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D Structure for NP0275067 ((3r,5e,9e)-13-chloro-14,16-dihydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)