NP-MRD: Showing NP-Card for Robustolide K (NP0082085)

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Record Information

Version

2.0

Created at

2022-04-29 03:08:39 UTC

Updated at

2022-04-29 03:08:40 UTC

NP-MRD ID

NP0082085

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Robustolide K

Description

(6Z)-1beta,8aalpha-Dimethyl-4beta-chloro-5-(hydroxymethyl)-8alpha,9beta,13alpha-triacetoxy-12-methylene-5beta,13abeta-epoxy-3aalpha,4,5,8,8a,9,10,11,12,12abeta,13,13a-dodecahydrobenzo[4,5]cyclodeca[1,2-b]furan-2(1H)-one belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Robustolide K is found in Ellisella robusta. Based on a literature review very few articles have been published on (6Z)-1beta,8aalpha-Dimethyl-4beta-chloro-5-(hydroxymethyl)-8alpha,9beta,13alpha-triacetoxy-12-methylene-5beta,13abeta-epoxy-3aalpha,4,5,8,8a,9,10,11,12,12abeta,13,13a-dodecahydrobenzo[4,5]cyclodeca[1,2-b]furan-2(1H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205082D          

 37 40  0  0  1  0            999 V2000
    3.5075    0.7436    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1 37  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292205082D          

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  9 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  8 24  1  6  0  0  0
  5 24  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
  7 28  1  6  0  0  0
 25 29  1  6  0  0  0
  6 30  1  6  0  0  0
  5 31  1  6  0  0  0
 31 32  1  0  0  0  0
  2 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  1 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0082085

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C(=O)O[C@H]2[C@@H](Cl)[C@@]3(CO)O[C@@]12[C@@H](OC(C)=O)[C@H]1C(=C)CC[C@H](OC(C)=O)[C@]1(C)[C@@H](OC(C)=O)\C=C/3

> <INCHI_IDENTIFIER>
InChI=1S/C26H33ClO10/c1-12-7-8-17(33-14(3)29)24(6)18(34-15(4)30)9-10-25(11-28)20(27)22-26(37-25,13(2)23(32)36-22)21(19(12)24)35-16(5)31/h9-10,13,17-22,28H,1,7-8,11H2,2-6H3/b10-9-/t13-,17-,18-,19+,20+,21-,22-,24+,25+,26+/m0/s1

> <INCHI_KEY>
ZRZXIRDSOAIGOX-MMPADBQXSA-N

> <FORMULA>
C26H33ClO10

> <MOLECULAR_WEIGHT>
540.99

> <EXACT_MASS>
540.176225

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.01347497487612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,7S,8R,9S,10E,12R,13R,14R,17R)-2,7-bis(acetyloxy)-13-chloro-12-(hydroxymethyl)-8,17-dimethyl-4-methylidene-16-oxo-15,18-dioxatetracyclo[10.5.1.0^{1,14}.0^{3,8}]octadec-10-en-9-yl acetate

> <ALOGPS_LOGP>
2.74

> <JCHEM_LOGP>
1.4840091019999986

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.26886676063792

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1185976788969736

> <JCHEM_POLAR_SURFACE_AREA>
134.66000000000003

> <JCHEM_REFRACTIVITY>
127.1195

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,7S,8R,9S,10E,12R,13R,14R,17R)-2,7-bis(acetyloxy)-13-chloro-12-(hydroxymethyl)-8,17-dimethyl-4-methylidene-16-oxo-15,18-dioxatetracyclo[10.5.1.0^{1,14}.0^{3,8}]octadec-10-en-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.547   1.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.453  -0.172   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.361  -1.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.747  -1.467   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.381  -0.609   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.891  -0.068   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.928   1.559   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.450   2.181   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.986   2.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.585   2.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.144   4.025   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.449   5.639   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.667   4.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.629   3.055   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.070   1.621   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.805   1.212   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.477   1.149   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.659   0.074   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.492   2.400   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.674   4.570   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.688   6.028   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.869   5.674   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.142   7.601   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.670   0.766   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.035   3.733   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.513   4.011   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.611   5.516   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.191   2.631   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.885   5.244   0.000  0.00  0.00           C+0
HETATM   30 Cl   UNK     0      -0.664  -0.500   0.000  0.00  0.00          Cl+0
HETATM   31  C   UNK     0       1.630  -2.125   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.724  -3.763   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.348  -1.723   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.976  -3.341   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.474  -4.064   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.368  -4.823   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.616   0.344   0.000  0.00  0.00           C+0
CONECT    1    2   10   15   37                                             
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24   31                                             
CONECT    6    5    7   30                                                  
CONECT    7    6    8   28                                                  
CONECT    8    7    9   24   25                                             
CONECT    9    8   10   20                                                  
CONECT   10    9    1   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    1   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    9   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    8    5                                                       
CONECT   25    8   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    7                                                       
CONECT   29   25                                                            
CONECT   30    6                                                            
CONECT   31    5   32                                                       
CONECT   32   31                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
(6Z)-1b,8Aalpha-dimethyl-4b-chloro-5-(hydroxymethyl)-8a,9b,13a-triacetoxy-12-methylene-5b,13abeta-epoxy-3aalpha,4,5,8,8a,9,10,11,12,12abeta,13,13a-dodecahydrobenzo[4,5]cyclodeca[1,2-b]furan-2(1H)-one	Generator
(6Z)-1Β,8aalpha-dimethyl-4β-chloro-5-(hydroxymethyl)-8α,9β,13α-triacetoxy-12-methylene-5β,13abeta-epoxy-3aalpha,4,5,8,8a,9,10,11,12,12abeta,13,13a-dodecahydrobenzo[4,5]cyclodeca[1,2-b]furan-2(1H)-one	Generator

Chemical Formula

C₂₆H₃₃ClO₁₀

Average Mass

540.9900 Da

Monoisotopic Mass

540.17622 Da

IUPAC Name

(1R,2S,3S,7S,8R,9S,10E,12R,13R,14R,17R)-2,7-bis(acetyloxy)-13-chloro-12-(hydroxymethyl)-8,17-dimethyl-4-methylidene-16-oxo-15,18-dioxatetracyclo[10.5.1.0^{1,14}.0^{3,8}]octadec-10-en-9-yl acetate

Traditional Name

(1R,2S,3S,7S,8R,9S,10E,12R,13R,14R,17R)-2,7-bis(acetyloxy)-13-chloro-12-(hydroxymethyl)-8,17-dimethyl-4-methylidene-16-oxo-15,18-dioxatetracyclo[10.5.1.0^{1,14}.0^{3,8}]octadec-10-en-9-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C(=O)O[C@H]2[C@@H](Cl)[C@@]3(CO)O[C@@]12[C@@H](OC(C)=O)[C@H]1C(=C)CC[C@H](OC(C)=O)[C@]1(C)[C@@H](OC(C)=O)\C=C/3

InChI Identifier

InChI=1S/C26H33ClO10/c1-12-7-8-17(33-14(3)29)24(6)18(34-15(4)30)9-10-25(11-28)20(27)22-26(37-25,13(2)23(32)36-22)21(19(12)24)35-16(5)31/h9-10,13,17-22,28H,1,7-8,11H2,2-6H3/b10-9-/t13-,17-,18-,19+,20+,21-,22-,24+,25+,26+/m0/s1

InChI Key

ZRZXIRDSOAIGOX-MMPADBQXSA-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
Ellisella robusta	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Briarane diterpenoid
Tetracarboxylic acid or derivatives
Furofuran
Gamma butyrolactone
Monosaccharide
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Organoheterocyclic compound
Ether
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organohalogen compound
Alcohol
Organochloride
Carbonyl group
Alkyl halide
Alkyl chloride
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	2.74	ALOGPS
logP	1.48	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.27	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	127.12 m³·mol⁻¹	ChemAxon
Polarizability	53.01 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

25194849

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Robustolide K (NP0082085)

MOL for NP0082085 (Robustolide K)

3D MOL for NP0082085 (Robustolide K)

3D SDF for NP0082085 (Robustolide K)

3D-SDF for NP0082085 (Robustolide K)

PDB for NP0082085 (Robustolide K)

3D PDB for NP0082085 (Robustolide K)

SMILES for NP0082085 (Robustolide K)

INCHI for NP0082085 (Robustolide K)

Structure for NP0082085 (Robustolide K)

3D Structure for NP0082085 (Robustolide K)