NP-MRD: Showing NP-Card for Epitulipinolide (NP0140438)

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Record Information

Version

2.0

Created at

2022-06-29 21:34:19 UTC

Updated at

2022-06-29 21:34:19 UTC

NP-MRD ID

NP0140438

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epitulipinolide

Description

Epi-tulipinolide, also known as eupatolide acetate, 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. Epitulipinolide is found in Cassinia aculeata and Liriodendron tulipifera. Based on a literature review very few articles have been published on epi-tulipinolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
    1.6735   -2.2937   -2.6265 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1774   -2.3434   -1.4116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2510   -3.3933   -0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083   -4.6111   -0.6750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928   -2.7941    0.8027 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1523   -1.6665    0.6417 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2718   -2.0187    0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2134   -1.1714    1.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6259   -1.6162    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901    0.3154    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2465    1.0269    0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2883    2.1472   -0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180    2.1683   -0.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6885    3.3748   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843    1.0031   -1.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880    0.0647   -0.9030 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4003    0.6487    0.3485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700    0.9425    0.7634 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9193    1.5514    2.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    0.6936    0.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3910   -1.2505   -0.7925 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5381   -1.4344   -3.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2491   -3.1046   -3.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5105   -0.8322    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5249   -3.0793    0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8695   -2.5487    0.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846   -1.6817    2.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3558   -0.8343    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650    0.4980    1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6763    0.7381    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083    0.3435   -0.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2747    1.5003    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5158    3.0567    0.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7500    3.0855   -0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4273    4.1306   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417    3.8324   -1.9541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361    0.5114   -2.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297    1.3116   -2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0545   -0.0934   -1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.1443    2.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9572    1.3040    2.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8414    2.6456    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6088   -1.2711   -1.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  2  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 21  1  0
 21 16  1  0
 21  6  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 16 39  1  6
 15 37  1  0
 15 38  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 12 33  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  0
 10 30  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  7 25  1  0
  6 24  1  1
  1 22  1  0
  1 23  1  0
 21 43  1  6
M  END


  Mrv1652306292223342D          

 21 22  0  0  1  0            999 V2000
    1.3328   -2.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8556   -1.7889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5643   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502   -0.8834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4589   -0.1115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9817    0.5267    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7958    0.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012   -0.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -1.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6697   -1.9226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -1.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132    1.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    2.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    1.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3652   -0.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8808    0.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5832   -0.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3551   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061   -1.3990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
  6 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  4 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140438

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6+,11-9+/t14-,15-,16-/m1/s1

> <INCHI_KEY>
UPNVKIZABMRHNR-PWCAFIOLSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
30.940597276626466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,11aR)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
2.9121302570000003

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.637506961514727

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
80.6686

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epi-tulipinolide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       2.488  -4.531   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.464  -3.339   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.920  -1.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.400  -1.649   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.857  -0.208   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.832   0.983   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.352   0.734   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.896  -0.707   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.416  -0.957   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.959  -2.397   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.983  -3.589   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.807  -2.245   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.289   2.424   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.265   3.615   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.721   5.056   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.784   3.366   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.682  -0.280   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.644   0.922   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.089  -1.765   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.529  -2.309   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.198  -2.611   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    8                                                            
CONECT   13    6   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    4                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
Epitulipinolide	ChEBI
Eupatolide acetate	ChEBI
Eupatolide acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Mass

290.3590 Da

Monoisotopic Mass

290.15181 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6+,11-9+/t14-,15-,16-/m1/s1

InChI Key

UPNVKIZABMRHNR-PWCAFIOLSA-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
Cassinia aculeata	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633

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
Germacrane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Germacrenes (C09566 )

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

C00003379

Chemspider ID

4444839

KEGG Compound ID

C09566

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281505

PDB ID

Not Available

ChEBI ID

10552

Good Scents ID

rw1443681

References

General References

Showing NP-Card for Epitulipinolide (NP0140438)

MOL for NP0140438 (Epitulipinolide)

3D MOL for NP0140438 (Epitulipinolide)

3D SDF for NP0140438 (Epitulipinolide)

3D-SDF for NP0140438 (Epitulipinolide)

PDB for NP0140438 (Epitulipinolide)

3D PDB for NP0140438 (Epitulipinolide)

SMILES for NP0140438 (Epitulipinolide)

INCHI for NP0140438 (Epitulipinolide)

Structure for NP0140438 (Epitulipinolide)

3D Structure for NP0140438 (Epitulipinolide)