NP-MRD: Showing NP-Card for (1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0319515)

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Record Information

Version

2.0

Created at

2022-09-11 20:34:46 UTC

Updated at

2022-09-11 20:34:46 UTC

NP-MRD ID

NP0319515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

Description

Sordarin belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid is found in Hypoxylon croceum and Parascedosporium putredinis. (1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid was first documented in 2016 (PMID: 27072286). Based on a literature review a significant number of articles have been published on Sordarin (PMID: 28383269) (PMID: 31478377) (PMID: 35546152) (PMID: 32358585) (PMID: 35701881) (PMID: 34767248).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222342D          

 35 39  0  0  1  0            999 V2000
    1.2213   -5.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0555   -1.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112222342D          

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    1.1016    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2455   -4.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 11 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0319515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](C)O[C@@H](OC[C@@]23C[C@@H]4[C@H](C)CC[C@H]4[C@]4(CC2C=C(C(C)C)[C@@]34C(O)=O)C=O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O8/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32)/t14-,15-,16?,17-,18-,20+,21+,22-,23-,25+,26+,27+/m1/s1

> <INCHI_KEY>
OGGVRVMISBQNMQ-UQYLMRGISA-N

> <FORMULA>
C27H40O8

> <MOLECULAR_WEIGHT>
492.609

> <EXACT_MASS>
492.272318248

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.0484054436428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,5R,8R,9S)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_LOGP>
2.106303971333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.278874515867924

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.179115773290818

> <JCHEM_PKA_STRONGEST_BASIC>
-3.680400020079378

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
126.51859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,8R,9S)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <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       2.280  -9.835   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.206  -8.731   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.625  -7.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.551  -6.145   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.942  -6.523   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.970  -4.663   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.104  -3.560   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.463  -4.285   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.882  -2.804   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.808  -1.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.227  -0.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.577  -1.130   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.817  -0.188   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.356  -0.254   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.207  -1.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.894   1.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.687   2.147   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.404   1.295   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.783   0.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.211   2.359   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.707   2.727   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.785  -0.943   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.525  -0.291   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.341   0.975   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.618   2.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.257   3.658   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.372   4.719   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.221   4.093   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.967   1.564   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.781   2.871   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.261   3.297   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.056   4.230   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.537  -5.389   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.118  -6.871   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.192  -7.975   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23   29                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   22   29                                             
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   11   19   30                                             
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    8   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Sordarin b	MeSH

Chemical Formula

C₂₇H₄₀O₈

Average Mass

492.6090 Da

Monoisotopic Mass

492.27232 Da

IUPAC Name

(1R,2S,4R,5R,8R,9S)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

Traditional Name

(1R,2S,4R,5R,8R,9S)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](C)O[C@@H](OC[C@@]23C[C@@H]4[C@H](C)CC[C@H]4[C@]4(CC2C=C(C(C)C)[C@@]34C(O)=O)C=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H40O8/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32)/t14-,15-,16?,17-,18-,20+,21+,22-,23-,25+,26+,27+/m1/s1

InChI Key

OGGVRVMISBQNMQ-UQYLMRGISA-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
Hypoxylon croceum	LOTUS Database	35616633
Parascedosporium putredinis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
1,2-diol
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Aldehyde
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
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	2.11	ChemAxon
pKa (Strongest Acidic)	4.18	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.52 m³·mol⁻¹	ChemAxon
Polarizability	53.05 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00015130

Chemspider ID

426016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44582273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dewapriya P, Prasad P, Damodar R, Salim AA, Capon RJ: Talarolide A, a Cyclic Heptapeptide Hydroxamate from an Australian Marine Tunicate-Associated Fungus, Talaromyces sp. (CMB-TU011). Org Lett. 2017 Apr 21;19(8):2046-2049. doi: 10.1021/acs.orglett.7b00638. Epub 2017 Apr 6. [PubMed:28383269 ]
Zhang MQ, Xu KX, Xue Y, Cao F, Yang LJ, Hou XM, Wang CY, Shao CL: Sordarin Diterpene Glycosides with an Unusual 1,3-Dioxolan-4-one Ring from the Zoanthid-Derived Fungus Curvularia hawaiiensis TA26-15. J Nat Prod. 2019 Sep 27;82(9):2477-2482. doi: 10.1021/acs.jnatprod.9b00164. Epub 2019 Sep 3. [PubMed:31478377 ]
Sun Z, Jamieson CS, Ohashi M, Houk KN, Tang Y: Discovery and characterization of a terpene biosynthetic pathway featuring a norbornene-forming Diels-Alderase. Nat Commun. 2022 May 11;13(1):2568. doi: 10.1038/s41467-022-30288-6. [PubMed:35546152 ]
Ueno M, Kobayashi M, Fujie A, Shibata T: Cloning and heterologous expression of P450Lent4B11, a novel bacterial P450 gene, for hydroxylation of an antifungal agent sordaricin. J Antibiot (Tokyo). 2020 Sep;73(9):615-621. doi: 10.1038/s41429-020-0310-9. Epub 2020 May 1. [PubMed:32358585 ]
Kudo F, Matsuura Y, Hayashi T, Fukushima M, Eguchi T: Genome mining of the sordarin biosynthetic gene cluster from Sordaria araneosa Cain ATCC 36386: characterization of cycloaraneosene synthase and GDP-6-deoxyaltrose transferase. J Antibiot (Tokyo). 2016 Jul;69(7):541-8. doi: 10.1038/ja.2016.40. Epub 2016 Apr 13. [PubMed:27072286 ]
Liu SH, Sun JL, Hu YL, Zhang L, Zhang X, Yan ZY, Guo X, Guo ZK, Jiao RH, Zhang B, Tan RX, Ge HM: Biosynthesis of Sordarin Revealing a Diels-Alderase for the Formation of the Norbornene Skeleton. Angew Chem Int Ed Engl. 2022 Aug 15;61(33):e202205577. doi: 10.1002/anie.202205577. Epub 2022 Jul 7. [PubMed:35701881 ]
Shao Y, Molestak E, Su W, Stankevic M, Tchorzewski M: Sordarin- An anti-fungal antibiotic with a unique modus operandi. Br J Pharmacol. 2022 Mar;179(6):1125-1145. doi: 10.1111/bph.15724. Epub 2022 Jan 13. [PubMed:34767248 ]
Harms K, Milic A, Stchigel AM, Stadler M, Surup F, Marin-Felix Y: Three New Derivatives of Zopfinol from Pseudorhypophila Mangenotii gen. et comb. nov. J Fungi (Basel). 2021 Mar 3;7(3):181. doi: 10.3390/jof7030181. [PubMed:33802411 ]
Park MY, Park SJ, Kim JJ, Lee DH, Kim BS: Inhibitory Effect of Moriniafungin Produced by Setosphaeria rostrata F3736 on the Development of Rhizopus Rot. Plant Pathol J. 2020 Dec 1;36(6):570-578. doi: 10.5423/PPJ.OA.09.2020.0176. [PubMed:33312092 ]
Dorfer M, Heine D, Konig S, Gore S, Werz O, Hertweck C, Gressler M, Hoffmeister D: Melleolides impact fungal translation via elongation factor 2. Org Biomol Chem. 2019 May 15;17(19):4906-4916. doi: 10.1039/c9ob00562e. [PubMed:31042251 ]
Wu Y, Dockendorff C: Synthesis of Simplified Azasordarin Analogs as Potential Antifungal Agents. J Org Chem. 2019 May 3;84(9):5292-5304. doi: 10.1021/acs.joc.9b00296. Epub 2019 Apr 9. [PubMed:30919633 ]
Liang XR, Ma XY, Ji NY: Trichosordarin A, a norditerpene glycoside from the marine-derived fungus Trichoderma harzianum R5. Nat Prod Res. 2020 Jul;34(14):2037-2042. doi: 10.1080/14786419.2019.1574782. Epub 2019 Feb 19. [PubMed:30777455 ]
Villahermosa D, Knapp K, Fleck O: A mutated dph3 gene causes sensitivity of Schizosaccharomyces pombe cells to cytotoxic agents. Curr Genet. 2017 Dec;63(6):1081-1091. doi: 10.1007/s00294-017-0711-x. Epub 2017 May 29. [PubMed:28555368 ]
Seyedmousavi S, Rafati H, Ilkit M, Tolooe A, Hedayati MT, Verweij P: Systemic Antifungal Agents: Current Status and Projected Future Developments. Methods Mol Biol. 2017;1508:107-139. doi: 10.1007/978-1-4939-6515-1_5. [PubMed:27837500 ]
Abeyrathne PD, Koh CS, Grant T, Grigorieff N, Korostelev AA: Ensemble cryo-EM uncovers inchworm-like translocation of a viral IRES through the ribosome. Elife. 2016 May 9;5:e14874. doi: 10.7554/eLife.14874. [PubMed:27159452 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0319515)

MOL for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D MOL for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D SDF for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D-SDF for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

PDB for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D PDB for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

SMILES for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

INCHI for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

Structure for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D Structure for NP0319515 ((1r,2s,4r,5r,8r,9s)-2-({[(2r,3s,4s,5s,6r)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)