NP-MRD: Showing NP-Card for methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate (NP0241611)

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Record Information

Version

2.0

Created at

2022-09-07 01:44:24 UTC

Updated at

2022-09-07 01:44:24 UTC

NP-MRD ID

NP0241611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Repandin B belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate is found in Tetragonotheca repanda. methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate was first documented in 2007 (PMID: 17149609). Based on a literature review very few articles have been published on Repandin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203442D          

 36 37  0  0  1  0            999 V2000
    2.4237   -1.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688   -0.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168   -1.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1069    0.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    1.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4040    1.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2100    2.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 35  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072203442D          

 36 37  0  0  1  0            999 V2000
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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 34 33  1  6  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0241611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@H]1[C@@H]2[C@H](OC(=O)C2=C)[C@@H](O)C(=C)CC\C=C(/[C@@H]1OC(=O)C(\CO)=C/C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-7-13(3)23(29)36-22-18-15(5)24(30)35-21(18)19(28)14(4)10-9-11-17(26(32)33-6)20(22)34-25(31)16(8-2)12-27/h8,11,13,18-22,27-28H,4-5,7,9-10,12H2,1-3,6H3/b16-8-,17-11+/t13?,18-,19-,20-,21-,22-/m0/s1

> <INCHI_KEY>
IVQFRPZHDFKKNP-XTCMNXESSA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.548

> <EXACT_MASS>
506.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.99866800928962

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3aS,4S,5S,11S,11aS)-11-hydroxy-5-{[(2Z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_LOGP>
3.167341029999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.906892514114755

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.560299069429597

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8487204073352945

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
128.0583

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3aS,4S,5S,11S,11aS)-11-hydroxy-5-{[(2Z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3aH,4H,5H,8H,9H,11H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.524  -2.432   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.048  -0.968   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.018  -2.112   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.512  -1.792   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.036  -0.327   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.066   0.817   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.590   2.282   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.621   3.426   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.084   2.602   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.392   4.067   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.573   0.497   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.097   1.962   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.127   3.106   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.633   2.786   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.651   4.571   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.145   4.891   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.114   3.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.682   5.715   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.206   7.180   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.603   1.641   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.079   3.106   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.413   3.876   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.413   5.416   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.746   3.106   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.746   1.566   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.080   3.876   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.080   5.416   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.109   1.321   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.355   2.226   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.601   3.132   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.601   1.321   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.066   1.797   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       8.125  -0.143   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.585  -0.143   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.555  -1.288   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.031  -2.752   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18                                                            
CONECT   20   11   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   20   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   28   35                                                  
CONECT   35   34    2   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₁₀

Average Mass

506.5480 Da

Monoisotopic Mass

506.21520 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@H]1[C@@H]2[C@H](OC(=O)C2=C)[C@@H](O)C(=C)CC\C=C(/[C@@H]1OC(=O)C(\CO)=C/C)C(=O)OC

InChI Identifier

InChI=1S/C26H34O10/c1-7-13(3)23(29)36-22-18-15(5)24(30)35-21(18)19(28)14(4)10-9-11-17(26(32)33-6)20(22)34-25(31)16(8-2)12-27/h8,11,13,18-22,27-28H,4-5,7,9-10,12H2,1-3,6H3/b16-8-,17-11+/t13?,18-,19-,20-,21-,22-/m0/s1

InChI Key

IVQFRPZHDFKKNP-XTCMNXESSA-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
Tetragonotheca repanda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Tetracarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101532555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma G, Khan SI, Benavides G, Schuhly W, Fischer NH, Khan IA, Pasco DS: Inhibition of NF-kappaB-mediated transcription and induction of apoptosis by melampolides and repandolides. Cancer Chemother Pharmacol. 2007 Jun;60(1):35-43. doi: 10.1007/s00280-006-0344-0. Epub 2006 Dec 6. [PubMed:17149609 ]
LOTUS database [Link]

Showing NP-Card for methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate (NP0241611)

MOL for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0241611 (methyl (3as,4s,5s,11s,11as)-11-hydroxy-5-{[(2z)-2-(hydroxymethyl)but-2-enoyl]oxy}-4-[(2-methylbutanoyl)oxy]-3,10-dimethylidene-2-oxo-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)