NP-MRD: Showing NP-Card for Tetraludin B (NP0058438)

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Record Information

Version

2.0

Created at

2022-04-28 03:48:35 UTC

Updated at

2022-04-28 03:48:35 UTC

NP-MRD ID

NP0058438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tetraludin B

Description

Methyl (3aR,4S,5S,11aS)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Tetraludin B is found in Tetragonotheca ludoviciana. Based on a literature review very few articles have been published on methyl (3aR,4S,5S,11aS)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205482D          

 37 38  0  0  1  0            999 V2000
   -0.3381    1.7406    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
  3 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282205482D          

 37 38  0  0  1  0            999 V2000
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 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  1 15  1  1  0  0  0
  9 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  8 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 28 32  1  1  0  0  0
  7 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058438

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C\CC\C(C)=C\[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(=O)[C@@](C)(O)[C@@H](C)O)[C@H]\1OC(=O)[C@@H](C)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O11/c1-12-9-8-10-17(24(31)34-7)20(36-22(29)13(2)15(4)27)21(37-25(32)26(6,33)16(5)28)19-14(3)23(30)35-18(19)11-12/h10-11,13,15-16,18-21,27-28,33H,3,8-9H2,1-2,4-7H3/b12-11+,17-10-/t13-,15+,16+,18-,19+,20-,21-,26-/m0/s1

> <INCHI_KEY>
OQBDEQQBLOQXJR-QTIXGZKYSA-N

> <FORMULA>
C26H36O11

> <MOLECULAR_WEIGHT>
524.563

> <EXACT_MASS>
524.225761979

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
52.37902997135482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3aR,4S,5S,11aS)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.9384526423333344

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.60953487920591

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.671274333824991

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867882565965267

> <JCHEM_POLAR_SURFACE_AREA>
165.89

> <JCHEM_REFRACTIVITY>
129.78069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3aR,4S,5S,11aS)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.631   3.249   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.631   4.451   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.503   4.759   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.013   0.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.044  -0.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.518   0.643   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.288  -0.691   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.144   2.050   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.105   1.334   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -0.000   3.080   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.498   5.251   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
CONECT    1    2   10   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   33                                                  
CONECT    8    7    9   25                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9    1   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    1                                                       
CONECT   16    9   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    8   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33    7   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3ar,4S,5S,11as)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₆O₁₁

Average Mass

524.5630 Da

Monoisotopic Mass

524.22576 Da

IUPAC Name

methyl (3aR,4S,5S,11aS)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

methyl (3aR,4S,5S,11aS)-4-{[(2S,3R)-2,3-dihydroxy-2-methylbutanoyl]oxy}-5-{[(2S,3R)-3-hydroxy-2-methylbutanoyl]oxy}-10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C\CC\C(C)=C\[C@@H]2OC(=O)C(=C)[C@H]2[C@H](OC(=O)[C@@](C)(O)[C@@H](C)O)[C@H]\1OC(=O)[C@@H](C)[C@@H](C)O

InChI Identifier

InChI=1S/C26H36O11/c1-12-9-8-10-17(24(31)34-7)20(36-22(29)13(2)15(4)27)21(37-25(32)26(6,33)16(5)28)19-14(3)23(30)35-18(19)11-12/h10-11,13,15-16,18-21,27-28,33H,3,8-9H2,1-2,4-7H3/b12-11+,17-10-/t13-,15+,16+,18-,19+,20-,21-,26-/m0/s1

InChI Key

OQBDEQQBLOQXJR-QTIXGZKYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 ludoviciana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Germacrane sesquiterpenoid
Tetracarboxylic acid or derivatives
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.41	ALOGPS
logP	1.94	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	129.78 m³·mol⁻¹	ChemAxon
Polarizability	52.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

162945610

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tetraludin B (NP0058438)

MOL for NP0058438 (Tetraludin B)

3D MOL for NP0058438 (Tetraludin B)

3D SDF for NP0058438 (Tetraludin B)

3D-SDF for NP0058438 (Tetraludin B)

PDB for NP0058438 (Tetraludin B)

3D PDB for NP0058438 (Tetraludin B)

SMILES for NP0058438 (Tetraludin B)

INCHI for NP0058438 (Tetraludin B)

Structure for NP0058438 (Tetraludin B)

3D Structure for NP0058438 (Tetraludin B)