NP-MRD: Showing NP-Card for (3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione (NP0268787)

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Record Information

Version

2.0

Created at

2022-09-08 14:01:36 UTC

Updated at

2022-09-08 14:01:36 UTC

NP-MRD ID

NP0268787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione

Description

Monocillin II 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. (3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione is found in Monocillium nordinii and Pochonia chlamydosporia. (3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione was first documented in 2013 (PMID: 23659286). Based on a literature review a small amount of articles have been published on Monocillin II (PMID: 34655796) (PMID: 31244199) (PMID: 29048170) (PMID: 23312946).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    0.0235    2.6754    1.2626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210    2.0687    0.1167 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0656    1.4678    0.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288    1.3153   -0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520    0.2613   -0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7587   -1.0879    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3546   -1.5471    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0330   -2.8077   -0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875   -2.9928   -1.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209   -2.0682   -0.8328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0106   -1.8004   -1.8864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -1.4124    0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0685   -0.7287    0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1179   -1.3559    0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.8434    0.8236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5758    0.2986    0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5170    0.9358   -0.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8070    2.0954   -1.2323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122    0.4278   -0.4763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1462    1.1452   -1.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5810    1.6308   -2.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1137    1.2817   -0.7315 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    3.2651    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124    3.4292    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4449    1.9250    1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261    2.9630   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4316    2.2965    1.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8602    0.6418    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3257    2.2474   -0.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255    0.3132   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1768   -1.0437    1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3942   -1.8407   -0.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824   -0.7790   -0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0155   -1.6652    1.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8117   -3.5303   -0.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6033   -3.9565   -1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713   -2.1506    1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925   -0.6117    0.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9586   -2.2627    1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1806   -1.3710    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5868    0.7023    0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7262    2.4687   -1.2809 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
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22  2  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  6
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
M  END


  Mrv1652309082216012D          

 22 23  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  1  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
    3.6923   -1.3970    0.0000 C   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  1  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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0268787

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O4/c1-13-8-5-3-2-4-6-10-15(19)12-14-9-7-11-16(20)17(14)18(21)22-13/h3,5-7,9-11,13,20H,2,4,8,12H2,1H3/b5-3+,10-6+/t13-/m0/s1

> <INCHI_KEY>
LSIFWWADIGESKN-UIWFPMPVSA-N

> <FORMULA>
C18H20O4

> <MOLECULAR_WEIGHT>
300.354

> <EXACT_MASS>
300.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.446982192452786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-16-hydroxy-3-methyl-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecine-1,11-dione

> <JCHEM_LOGP>
4.592854417

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.393384215832867

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.638576827111365

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2962554407316

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
87.45189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3H-2-benzoxacyclotetradecine-1,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-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  C   UNK     0       6.892  -2.608   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.522  -1.113   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.632  -0.045   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.262   1.450   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.112  -0.472   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.221   0.596   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.852   2.091   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.701   0.168   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
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   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₄

Average Mass

300.3540 Da

Monoisotopic Mass

300.13616 Da

IUPAC Name

(3S)-16-hydroxy-3-methyl-3,4,7,8,11,12-hexahydro-1H-2-benzoxacyclotetradecine-1,11-dione

Traditional Name

(3S)-16-hydroxy-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=CC=CC(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C18H20O4/c1-13-8-5-3-2-4-6-10-15(19)12-14-9-7-11-16(20)17(14)18(21)22-13/h3,5-7,9-11,13,20H,2,4,8,12H2,1H3/b5-3+,10-6+/t13-/m0/s1

InChI Key

LSIFWWADIGESKN-UIWFPMPVSA-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
Monocillium nordinii	LOTUS Database	35616633
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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	4.59	ChemAxon
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.45 m³·mol⁻¹	ChemAxon
Polarizability	31.45 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

C00038292

Chemspider ID

23339515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

6478915

PDB ID

Not Available

ChEBI ID

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Good Scents ID

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References

General References

Gao J, Radwan MM, Leon F, Dale OR, Husni AS, Wu Y, Lupien S, Wang X, Manly SP, Hill RA, Dugan FM, Cutler HG, Cutler SJ: Neocosmospora sp.-derived resorcylic acid lactones with in vitro binding affinity for human opioid and cannabinoid receptors. J Nat Prod. 2013 May 24;76(5):824-8. doi: 10.1021/np300653d. Epub 2013 May 9. [PubMed:23659286 ]
Kuttikrishnan S, Prabhu KS, Al Sharie AH, Al Zu'bi YO, Alali FQ, Oberlies NH, Ahmad A, El-Elimat T, Uddin S: Natural resorcylic acid lactones: A chemical biology approach for anticancer activity. Drug Discov Today. 2022 Feb;27(2):547-557. doi: 10.1016/j.drudis.2021.10.001. Epub 2021 Oct 13. [PubMed:34655796 ]
Qin F, Li Y, Lin R, Zhang X, Mao Z, Ling J, Yang Y, Zhuang X, Du S, Cheng X, Xie B: Antibacterial Radicicol Analogues from Pochonia chlamydosporia and Their Biosynthetic Gene Cluster. J Agric Food Chem. 2019 Jul 3;67(26):7266-7273. doi: 10.1021/acs.jafc.9b01977. Epub 2019 Jun 24. [PubMed:31244199 ]
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 ]
Zeng J, Lytle AK, Gage D, Johnson SJ, Zhan J: Specific chlorination of isoquinolines by a fungal flavin-dependent halogenase. Bioorg Med Chem Lett. 2013 Feb 15;23(4):1001-3. doi: 10.1016/j.bmcl.2012.12.038. Epub 2012 Dec 21. [PubMed:23312946 ]
LOTUS database [Link]

Showing NP-Card for (3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione (NP0268787)

MOL for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D MOL for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D SDF for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D-SDF for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

PDB for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D PDB for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

SMILES for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

INCHI for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

Structure for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)

3D Structure for NP0268787 ((3s,5e,9e)-16-hydroxy-3-methyl-4,7,8,12-tetrahydro-3h-2-benzoxacyclotetradecine-1,11-dione)