NP-MRD: Showing NP-Card for [(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate (NP0299935)

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Record Information

Version

2.0

Created at

2022-09-10 12:03:32 UTC

Updated at

2022-09-10 12:03:32 UTC

NP-MRD ID

NP0299935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate

Description

CHEMBL251088 belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. [(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate is found in Ferula varia. Based on a literature review very few articles have been published on CHEMBL251088.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102214032D          

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M  END
> <DATABASE_ID>
NP0299935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OC[C@@]1(O)[C@@H]2CC[C@]3(C)[C@H](OC(=O)C(\C)=C\C)[C@@H]4O[C@@H]4C(=C)[C@H]3[C@@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O8/c1-7-12(3)21(26)30-11-25(29)15-9-10-24(6)16(18(15)32-23(25)28)14(5)17-19(31-17)20(24)33-22(27)13(4)8-2/h7-8,15-20,29H,5,9-11H2,1-4,6H3/b12-7-,13-8+/t15-,16+,17-,18-,19-,20-,24+,25-/m1/s1

> <INCHI_KEY>
KUJBZYFVSIIWFZ-ORAOACIHSA-N

> <FORMULA>
C25H32O8

> <MOLECULAR_WEIGHT>
460.523

> <EXACT_MASS>
460.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.796434785301244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,2S,5S,6R,9S,10S,11R,13R)-5-hydroxy-9-methyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0^{2,6}.0^{11,13}]tetradecan-5-yl]methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.670502015666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.327353179861607

> <JCHEM_PKA_STRONGEST_BASIC>
-4.251368475807129

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000003

> <JCHEM_REFRACTIVITY>
117.62689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,5S,6R,9S,10S,11R,13R)-5-hydroxy-9-methyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0^{2,6}.0^{11,13}]tetradecan-5-yl]methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.288  -0.802   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.757  -2.248   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.743  -3.430   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.260  -3.167   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.080  -1.864   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.574  -2.241   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.756  -1.255   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.676  -3.778   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.194  -3.515   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.096  -5.259   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.023  -6.364   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.443  -7.845   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.937  -8.222   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.370  -8.950   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.877  -8.573   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.790 -10.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.283 -10.809   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.247  -4.350   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.716  -5.796   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.198  -6.059   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.212  -4.876   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.681  -6.321   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.695  -5.139   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.164  -6.584   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.646  -6.847   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.115  -8.293   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.660  -5.664   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.142  -5.927   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.191  -4.219   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.204  -3.036   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.708  -3.956   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.722  -2.773   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.239  -2.511   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   18                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18    8    4   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    3   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
CONECT   31   23   32   33                                                  
CONECT   32   31   33                                                       
CONECT   33   32    2   31                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₈

Average Mass

460.5230 Da

Monoisotopic Mass

460.20972 Da

IUPAC Name

[(1R,2S,5S,6R,9S,10S,11R,13R)-5-hydroxy-9-methyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0^{2,6}.0^{11,13}]tetradecan-5-yl]methyl (2Z)-2-methylbut-2-enoate

Traditional Name

[(1R,2S,5S,6R,9S,10S,11R,13R)-5-hydroxy-9-methyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0^{2,6}.0^{11,13}]tetradecan-5-yl]methyl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OC[C@@]1(O)[C@@H]2CC[C@]3(C)[C@H](OC(=O)C(\C)=C\C)[C@@H]4O[C@@H]4C(=C)[C@H]3[C@@H]2OC1=O

InChI Identifier

InChI=1S/C25H32O8/c1-7-12(3)21(26)30-11-25(29)15-9-10-24(6)16(18(15)32-23(25)28)14(5)17-19(31-17)20(24)33-22(27)13(4)8-2/h7-8,15-20,29H,5,9-11H2,1-4,6H3/b12-7-,13-8+/t15-,16+,17-,18-,19-,20-,24+,25-/m1/s1

InChI Key

KUJBZYFVSIIWFZ-ORAOACIHSA-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
Ferula varia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Tricarboxylic acid or derivatives
Fatty acid ester
Oxepane
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
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	3.67	ChemAxon
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.63 m³·mol⁻¹	ChemAxon
Polarizability	48.8 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

23311269

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44445506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate (NP0299935)

MOL for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

3D MOL for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

3D SDF for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

PDB for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

3D PDB for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

SMILES for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

INCHI for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

Structure for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)

3D Structure for NP0299935 ([(1r,2s,5s,6r,9s,10s,11r,13r)-5-hydroxy-9-methyl-10-{[(2e)-2-methylbut-2-enoyl]oxy}-14-methylidene-4-oxo-3,12-dioxatetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-5-yl]methyl (2z)-2-methylbut-2-enoate)