NP-MRD: Showing NP-Card for Xeranthemolide (NP0073777)

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Record Information

Version

2.0

Created at

2022-04-28 19:00:28 UTC

Updated at

2022-04-28 19:00:28 UTC

NP-MRD ID

NP0073777

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xeranthemolide

Description

(1'S,2'R,3S,3aR,5'S,7aS,8S,9'S,9aS,10'S,11'S)-2'-hydroxy-2',5,8-trimethyl-6'-methylidene-3a,4,6,7,7a,8,9,9a-octahydro-2H-8'-oxaspiro[azuleno[6,5-b]furan-3,13'-tetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]Pentadecan]-14'-ene-2,6,7'-trione belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Xeranthemolide is found in Anthemis austriaca and Cota austriaca. Based on a literature review very few articles have been published on (1'S,2'R,3S,3aR,5'S,7aS,8S,9'S,9aS,10'S,11'S)-2'-hydroxy-2',5,8-trimethyl-6'-methylidene-3a,4,6,7,7a,8,9,9a-octahydro-2H-8'-oxaspiro[azuleno[6,5-b]furan-3,13'-tetracyclo[9.2.2.0¹,¹⁰.0⁵,⁹]Pentadecan]-14'-ene-2,6,7'-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221002D          

 35 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282221002D          

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 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 21 27  1  1  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 20 31  1  6  0  0  0
 19 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 18 34  1  1  0  0  0
 32 35  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073777

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2OC(=O)[C@@]3(C[C@H]4C=C[C@]33[C@H]4[C@H]4OC(=O)C(=C)[C@@H]4CC[C@@]3(C)O)[C@H]2CC2=C(C)C(=O)C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O6/c1-13-9-22-20(10-19-14(2)21(30)11-18(13)19)28(26(32)34-22)12-16-5-8-29(28)23(16)24-17(6-7-27(29,4)33)15(3)25(31)35-24/h5,8,13,16-18,20,22-24,33H,3,6-7,9-12H2,1-2,4H3/t13-,16+,17-,18-,20-,22-,23+,24-,27+,28+,29+/m0/s1

> <INCHI_KEY>
JFHBPWUSUGCOPS-KSVBRIKOSA-N

> <FORMULA>
C29H34O6

> <MOLECULAR_WEIGHT>
478.585

> <EXACT_MASS>
478.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.725560265911696

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2'R,3S,3aR,5'S,7aS,8S,9'S,9aS,10'S,11'S)-2'-hydroxy-2',5,8-trimethyl-6'-methylidene-3a,4,6,7,7a,8,9,9a-octahydro-2H-8'-oxaspiro[azuleno[6,5-b]furan-3,13'-tetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadecan]-14'-ene-2,6,7'-trione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.200693046999999

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.455618514592008

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0369124617174545

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
128.6734

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2'R,3S,3aR,5'S,7aS,8S,9'S,9aS,10'S,11'S)-2'-hydroxy-2',5,8-trimethyl-6'-methylidene-4,7,7a,8,9,9a-hexahydro-3aH-8'-oxaspiro[azuleno[6,5-b]furan-3,13'-tetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadecan]-14'-ene-2,6,7'-trione

> <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       5.350   0.876   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.886   2.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.140   3.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.378   2.324   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.847   2.787   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.890   0.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.153   4.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.449   2.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.121   2.120   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.901   0.596   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.955  -0.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.490  -0.401   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.269  -1.730   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.185   0.242   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.137   1.787   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.859   1.916   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.739   2.800   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.922   3.786   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.391   3.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.602   2.660   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.514   1.328   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.794   0.514   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.245   1.030   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.747   2.485   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.192   1.951   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.029   3.340   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.913   0.685   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.215  -0.825   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.957   1.817   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.487   1.637   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.203   3.159   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.968   4.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.215   5.835   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.660   5.303   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.706   3.332   0.000  0.00  0.00           C+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    1                                                       
CONECT    7    3                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    1   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    9   18   35                                             
CONECT   18   17   19   24   34                                             
CONECT   19   18   20   32                                                  
CONECT   20   19   21   31                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25   26                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   20                                                       
CONECT   32   19   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   18                                                       
CONECT   35   32   17                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₆

Average Mass

478.5850 Da

Monoisotopic Mass

478.23554 Da

IUPAC Name

Traditional Name

(1'S,2'R,3S,3aR,5'S,7aS,8S,9'S,9aS,10'S,11'S)-2'-hydroxy-2',5,8-trimethyl-6'-methylidene-4,7,7a,8,9,9a-hexahydro-3aH-8'-oxaspiro[azuleno[6,5-b]furan-3,13'-tetracyclo[9.2.2.0^{1,10}.0^{5,9}]pentadecan]-14'-ene-2,6,7'-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2OC(=O)[C@@]3(C[C@H]4C=C[C@]33[C@H]4[C@H]4OC(=O)C(=C)[C@@H]4CC[C@@]3(C)O)[C@H]2CC2=C(C)C(=O)C[C@@H]12

InChI Identifier

InChI=1S/C29H34O6/c1-13-9-22-20(10-19-14(2)21(30)11-18(13)19)28(26(32)34-22)12-16-5-8-29(28)23(16)24-17(6-7-27(29,4)33)15(3)25(31)35-24/h5,8,13,16-18,20,22-24,33H,3,6-7,9-12H2,1-2,4H3/t13-,16+,17-,18-,20-,22-,23+,24-,27+,28+,29+/m0/s1

InChI Key

JFHBPWUSUGCOPS-KSVBRIKOSA-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
Anthemis austriaca	Plant	KNApSAcK
Cota austriaca	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Guaiane sesquiterpenoid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Lactone
Ketone
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	2.71	ALOGPS
logP	3.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.46	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	128.67 m³·mol⁻¹	ChemAxon
Polarizability	51.73 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163104547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Xeranthemolide (NP0073777)

MOL for NP0073777 (Xeranthemolide)

3D MOL for NP0073777 (Xeranthemolide)

3D SDF for NP0073777 (Xeranthemolide)

3D-SDF for NP0073777 (Xeranthemolide)

PDB for NP0073777 (Xeranthemolide)

3D PDB for NP0073777 (Xeranthemolide)

SMILES for NP0073777 (Xeranthemolide)

INCHI for NP0073777 (Xeranthemolide)

Structure for NP0073777 (Xeranthemolide)

3D Structure for NP0073777 (Xeranthemolide)