NP-MRD: Showing NP-Card for (1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid (NP0229701)

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Record Information

Version

2.0

Created at

2022-09-06 09:52:46 UTC

Updated at

2022-09-06 09:52:46 UTC

NP-MRD ID

NP0229701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid

Description

Echinosporin belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. (1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid was first documented in 2007 (PMID: 17376609). Based on a literature review a small amount of articles have been published on Echinosporin (PMID: 27354061) (PMID: 30117099) (PMID: 23605638) (PMID: 22646909).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062211522D          

 16 18  0  0  1  0            999 V2000
    3.2075    1.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4075    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1822    2.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8329    1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130    0.6530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9493   -0.2810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1823   -0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1198    0.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707    0.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2992    1.5274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6227    1.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4584   -0.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453   -0.4834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0523    0.2645    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=N)C1=C[C@H]2[C@H]3C=C[C@@]2(O)C(=O)O[C@@H]3O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)/t4-,5+,8+,10+/m1/s1

> <INCHI_KEY>
OXSZHYWOGQJUST-YYZSKVJKSA-N

> <FORMULA>
C10H9NO5

> <MOLECULAR_WEIGHT>
223.184

> <EXACT_MASS>
223.048072394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
50.76809316863137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,7R,8S)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0^{4,8}]undeca-5,9-diene-10-carboximidic acid

> <JCHEM_LOGP>
-1.6125000486670444

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.69435113221918

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.067232050841527

> <JCHEM_PKA_STRONGEST_BASIC>
6.364019222795059

> <JCHEM_POLAR_SURFACE_AREA>
99.84

> <JCHEM_REFRACTIVITY>
63.40310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,7R,8S)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0^{4,8}]undeca-5,9-diene-10-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  N   UNK     0       5.987   2.920   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.494   3.297   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.073   4.778   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.421   2.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.953   2.500   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.144   1.219   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.772  -0.525   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.340  -0.827   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.224   0.762   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.185   1.330   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.425   2.851   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.031   1.392   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.896   2.666   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.589  -0.162   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.258  -0.902   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.831   0.494   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₉NO₅

Average Mass

223.1840 Da

Monoisotopic Mass

223.04807 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC(=N)C1=C[C@H]2[C@H]3C=C[C@@]2(O)C(=O)O[C@@H]3O1

InChI Identifier

InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)/t4-,5+,8+,10+/m1/s1

InChI Key

OXSZHYWOGQJUST-YYZSKVJKSA-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 delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta valerolactone
Delta_valerolactone
Oxane
Tertiary alcohol
Carboxamide group
Carboxylic acid ester
Primary carboxylic acid amide
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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

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

65440

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72542

PDB ID

Not Available

ChEBI ID

189178

Good Scents ID

Not Available

References

General References

Cui CB, Liu HB, Gu JY, Gu QQ, Cai B, Zhang DY, Zhu TJ: Echinosporins as new cell cycle inhibitors and apoptosis inducers from marine-derived Streptomyces albogriseolus. Fitoterapia. 2007 Apr;78(3):238-40. doi: 10.1016/j.fitote.2006.11.017. Epub 2007 Feb 6. [PubMed:17376609 ]
Dame ZT, Islam MT, Helmke E, von Tiedemann A, Laatsch H: Oligomycins and pamamycin homologs impair motility and induce lysis of zoospores of the grapevine downy mildew pathogen, Plasmopara viticola. FEMS Microbiol Lett. 2016 Aug;363(16):fnw167. doi: 10.1093/femsle/fnw167. Epub 2016 Jun 27. [PubMed:27354061 ]
Xu X, Han L, Zhao L, Chen X, Miao C, Hu L, Huang X, Chen Y, Li Y: Echinosporin antibiotics isolated from Amycolatopsis strain and their antifungal activity against root-rot pathogens of the Panax notoginseng. Folia Microbiol (Praha). 2019 Mar;64(2):171-175. doi: 10.1007/s12223-018-0642-z. Epub 2018 Aug 16. [PubMed:30117099 ]
Lankapalli AR, Kannabiran K: Interaction of marine Streptomyces compounds with selected cancer drug target proteins by in silico molecular docking studies. Interdiscip Sci. 2013 Mar;5(1):37-44. doi: 10.1007/s12539-013-0146-0. Epub 2013 Apr 19. [PubMed:23605638 ]
Flasz JT, Hale KJ: A new stereocontrolled synthetic route to (-)-echinosporin from D-glucose via Padwa allenylsulfone [3 + 2]-anionic cycloadditive elimination. Org Lett. 2012 Jun 15;14(12):3024-7. doi: 10.1021/ol301090v. Epub 2012 May 30. [PubMed:22646909 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid (NP0229701)

MOL for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D MOL for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D SDF for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D-SDF for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

PDB for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D PDB for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

SMILES for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

INCHI for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

Structure for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)

3D Structure for NP0229701 ((1s,4s,7r,8s)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.0⁴,⁸]undeca-5,9-diene-10-carboximidic acid)