NP-MRD: Showing NP-Card for Triobolide (NP0051970)

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Record Information

Version

2.0

Created at

2022-04-27 23:10:36 UTC

Updated at

2022-04-27 23:10:36 UTC

NP-MRD ID

NP0051970

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triobolide

Description

Trilobolide belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Triobolide is found in Laser trilobum, Laserpitium siler and Thapsia transtagana. Triobolide was first documented in 2015 (PMID: 26474674). Based on a literature review a significant number of articles have been published on Trilobolide (PMID: 34355433) (PMID: 33797641) (PMID: 33291419) (PMID: 31501660) (PMID: 30731148) (PMID: 28781697).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201102D          

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 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  1  0  0  0
 16 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 27 30  1  1  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 14 34  1  6  0  0  0
 31 35  1  1  0  0  0
 31 36  1  6  0  0  0
 15 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051970

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@H]1C[C@](C)(OC(C)=O)[C@H]2C[C@@H](OC(=O)C(\C)=C/C)C(C)=C2[C@@H]2OC(=O)[C@@](C)(O)[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O10/c1-9-13(3)22(29)34-18-11-17-20(15(18)5)21-27(33,26(8,32)24(31)36-21)19(35-23(30)14(4)10-2)12-25(17,7)37-16(6)28/h9,14,17-19,21,32-33H,10-12H2,1-8H3/b13-9-/t14-,17-,18+,19-,21-,25-,26+,27+/m0/s1

> <INCHI_KEY>
FIAZIVNRHQWTPY-QAAPNFDWSA-N

> <FORMULA>
C27H38O10

> <MOLECULAR_WEIGHT>
522.591

> <EXACT_MASS>
522.246497424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.59391868667348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,3aR,4S,6S,6aS,8R,9bS)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-{[(2S)-2-methylbutanoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.596354071666667

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.498782583667722

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.135615258280229

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307568504710141

> <JCHEM_POLAR_SURFACE_AREA>
145.66

> <JCHEM_REFRACTIVITY>
130.34419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trilobolide

> <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      -0.016   0.778   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.786   2.112   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.292   1.792   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.453   0.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.046  -0.366   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.787  -0.510   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -5.120   0.260   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.120   1.800   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.454  -0.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.788   0.260   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.788   1.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.454  -2.050   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.436   2.822   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.223   3.546   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.249   4.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.521   3.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.636   1.596   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.507   0.549   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.580  -0.556   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.159  -2.038   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.231  -3.143   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.666  -2.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.244  -0.968   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.855   3.902   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.188   3.132   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.188   1.592   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.522   3.902   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.856   3.132   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.189   3.902   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.522   5.442   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.272   5.539   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.186   6.037   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.640   7.509   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.109   4.805   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.804   5.693   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.934   6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.615   4.709   0.000  0.00  0.00           O+0
CONECT    1    2    5   18                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9                                                            
CONECT   13    3                                                            
CONECT   14    2   15   34                                                  
CONECT   15   14   16   31   37                                             
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17    1   19   23                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18                                                            
CONECT   24   16   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27                                                            
CONECT   31   15   32   35   36                                             
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   14                                                       
CONECT   35   31                                                            
CONECT   36   31                                                            
CONECT   37   15                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₁₀

Average Mass

522.5910 Da

Monoisotopic Mass

522.24650 Da

IUPAC Name

(3S,3aR,4S,6S,6aS,8R,9bS)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-{[(2S)-2-methylbutanoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

Traditional Name

trilobolide

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@H]1C[C@](C)(OC(C)=O)[C@H]2C[C@@H](OC(=O)C(\C)=C/C)C(C)=C2[C@@H]2OC(=O)[C@@](C)(O)[C@@]12O

InChI Identifier

InChI=1S/C27H38O10/c1-9-13(3)22(29)34-18-11-17-20(15(18)5)21-27(33,26(8,32)24(31)36-21)19(35-23(30)14(4)10-2)12-25(17,7)37-16(6)28/h9,14,17-19,21,32-33H,10-12H2,1-8H3/b13-9-/t14-,17-,18+,19-,21-,25-,26+,27+/m0/s1

InChI Key

FIAZIVNRHQWTPY-QAAPNFDWSA-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
Laser trilobum	Plant	KNApSAcK
Laserpitium siler	LOTUS Database	35616633
Thapsia transtagana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
1,2-diol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:9724 )
Guaianolide (C09563 )

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	2.27	ALOGPS
logP	2.6	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.14	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.34 m³·mol⁻¹	ChemAxon
Polarizability	54.59 Å³	ChemAxon
Number of Rings	3	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

C00003377

Chemspider ID

4444837

KEGG Compound ID

C09563

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281503

PDB ID

Not Available

ChEBI ID

9724

Good Scents ID

Not Available

References

General References

Zhou XQ, Mao XM, Fan R, Li SY, Shang J, Zhang T, Li RH, Li HQ, Hui Y, Chen WH, Wang ZX, Shen DY: Trilobolide-6-O-isobutyrate suppresses hepatocellular carcinoma tumorigenesis through inhibition of IL-6/STAT3 signaling pathway. Phytother Res. 2021 Oct;35(10):5741-5753. doi: 10.1002/ptr.7233. Epub 2021 Aug 6. [PubMed:34355433 ]
Christensen SB, Simonsen HT, Engedal N, Nissen P, Moller JV, Denmeade SR, Isaacs JT: From Plant to Patient: Thapsigargin, a Tool for Understanding Natural Product Chemistry, Total Syntheses, Biosynthesis, Taxonomy, ATPases, Cell Death, and Drug Development. Prog Chem Org Nat Prod. 2021;115:59-114. doi: 10.1007/978-3-030-64853-4_2. [PubMed:33797641 ]
Zimmermann T, Drasar P, Rimpelova S, Christensen SB, Khripach VA, Jurasek M: Large Scale Conversion of Trilobolide into the Payload of Mipsagargin: 8-O-(12-Aminododecanoyl)-8-O-Debutanoylthapsigargin. Biomolecules. 2020 Dec 5;10(12). pii: biom10121640. doi: 10.3390/biom10121640. [PubMed:33291419 ]
Rimpelova S, Jurasek M, Peterkova L, Bejcek J, Spiwok V, Majdl M, Jirasko M, Budesinsky M, Harmatha J, Kmonickova E, Drasar P, Ruml T: Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica. Beilstein J Org Chem. 2019 Aug 13;15:1933-1944. doi: 10.3762/bjoc.15.189. eCollection 2019. [PubMed:31501660 ]
Harmatha J, Budesinsky M, Jurasek M, Zimmermann T, Drasar P, Zidek Z, Kmonickova E, Vejvodova L: Structural modification of trilobolide for upgrading its immunobiological properties and reducing its cytotoxic action. Fitoterapia. 2019 Apr;134:88-95. doi: 10.1016/j.fitote.2019.02.002. Epub 2019 Feb 4. [PubMed:30731148 ]
Skorpilova L, Rimpelova S, Jurasek M, Budesinsky M, Lokajova J, Effenberg R, Slepicka P, Ruml T, Kmonickova E, Drasar PB, Wimmer Z: BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide. Beilstein J Org Chem. 2017 Jul 4;13:1316-1324. doi: 10.3762/bjoc.13.128. eCollection 2017. [PubMed:28781697 ]
Huml L, Jurasek M, Miksatkova P, Zimmermann T, Tomanova P, Budesinsky M, Rottnerova Z, Simkova M, Harmatha J, Kmonickova E, Lapcik O, Drasar PB: Immunoassay for determination of trilobolide. Steroids. 2017 Jan;117:105-111. doi: 10.1016/j.steroids.2016.08.019. Epub 2016 Sep 4. [PubMed:27600788 ]
Jurasek M, Dzubak P, Rimpelova S, Sedlak D, Konecny P, Frydrych I, Gurska S, Hajduch M, Bogdanova K, Kolar M, Muller T, Kmonickova E, Ruml T, Harmatha J, Drasar PB: Trilobolide-steroid hybrids: Synthesis, cytotoxic and antimycobacterial activity. Steroids. 2017 Jan;117:97-104. doi: 10.1016/j.steroids.2016.08.011. Epub 2016 Aug 17. [PubMed:27543674 ]
Harmatha J, Vokac K, Budesinsky M, Zidek Z, Kmonickova E: Immunobiological properties of sesquiterpene lactones obtained by chemically transformed structural modifications of trilobolide. Fitoterapia. 2015 Dec;107:90-99. doi: 10.1016/j.fitote.2015.10.002. Epub 2015 Oct 22. [PubMed:26474674 ]
Tomanova P, Rimpelova S, Jurasek M, Budesinsky M, Vejvodova L, Ruml T, Kmonickova E, Drasar PB: Trilobolide-porphyrin conjugates: on synthesis and biological effects evaluation. Steroids. 2015 May;97:8-12. doi: 10.1016/j.steroids.2014.08.024. Epub 2014 Sep 6. [PubMed:25204594 ]

Showing NP-Card for Triobolide (NP0051970)

MOL for NP0051970 (Triobolide)

3D MOL for NP0051970 (Triobolide)

3D SDF for NP0051970 (Triobolide)

3D-SDF for NP0051970 (Triobolide)

PDB for NP0051970 (Triobolide)

3D PDB for NP0051970 (Triobolide)

SMILES for NP0051970 (Triobolide)

INCHI for NP0051970 (Triobolide)

Structure for NP0051970 (Triobolide)

3D Structure for NP0051970 (Triobolide)