NP-MRD: Showing NP-Card for (3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one (NP0144961)

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Record Information

Version

2.0

Created at

2022-09-02 00:03:33 UTC

Updated at

2022-09-02 00:03:33 UTC

NP-MRD ID

NP0144961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one

Description

(3R,3aR,6aR,9aR,9bR)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophene]-5-yl]ethyl}-dodecahydroazuleno[4,5-b]furan-2-one belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one is found in Arctium lappa. Based on a literature review very few articles have been published on (3R,3aR,6aR,9aR,9bR)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophene]-5-yl]ethyl}-dodecahydroazuleno[4,5-b]furan-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202032D          

 33 37  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.3294    0.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6007    0.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5302    1.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1578    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7429    3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4769    2.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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   10.6218    1.3854    0.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022202032D          

 33 37  0  0  1  0            999 V2000
    1.8651    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.1204   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0144961

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)C[C@@]1(O)[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O4S2/c1-4-5-17-8-11-22(32-17)23-13-12-21(33-23)20(28)14-27(30)19-10-7-15(2)18-9-6-16(3)24(18)25(19)31-26(27)29/h8,11-13,18-19,24-25,30H,2-3,6-7,9-10,14H2,1H3/t18-,19+,24-,25-,27+/m0/s1

> <INCHI_KEY>
WKQBNYGTPIGLMV-JCIMOPRDSA-N

> <FORMULA>
C27H26O4S2

> <MOLECULAR_WEIGHT>
478.62

> <EXACT_MASS>
478.127251665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
52.74743101838288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,6aR,9aR,9bR)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophene]-5-yl]ethyl}-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
5.559963731333333

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.640441372676271

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.99010446981489

> <JCHEM_PKA_STRONGEST_BASIC>
-4.159365909377262

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
126.71

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,6aR,9aR,9bR)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophene]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.482   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.691  -1.610   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.380  -2.161   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.781   0.446   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.948   1.708   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.486   1.784   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.321   0.490   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.190   3.154   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.495   4.528   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.587   5.614   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.957   4.911   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.331   5.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.577   7.126   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.098   7.363   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.793   5.988   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.314   5.743   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      20.834   5.497   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.354   5.252   0.000  0.00  0.00           C+0
HETATM   26  S   UNK     0      16.701   4.903   0.000  0.00  0.00           S+0
HETATM   27  S   UNK     0      13.711   3.391   0.000  0.00  0.00           S+0
HETATM   28  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.455  -1.610   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.996  -3.052   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    5   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   19                                                       
CONECT   27   18   15                                                       
CONECT   28    6   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    2   28                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₆O₄S₂

Average Mass

478.6200 Da

Monoisotopic Mass

478.12725 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)C[C@@]1(O)[C@@H]2CCC(=C)[C@@H]3CCC(=C)[C@@H]3[C@H]2OC1=O

InChI Identifier

InChI=1S/C27H26O4S2/c1-4-5-17-8-11-22(32-17)23-13-12-21(33-23)20(28)14-27(30)19-10-7-15(2)18-9-6-16(3)24(18)25(19)31-26(27)29/h8,11-13,18-19,24-25,30H,2-3,6-7,9-10,14H2,1H3/t18-,19+,24-,25-,27+/m0/s1

InChI Key

WKQBNYGTPIGLMV-JCIMOPRDSA-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
Arctium lappa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
Guaiane sesquiterpenoid
Bithiophene
Aryl alkyl ketone
Aryl ketone
2,5-disubstituted thiophene
Gamma butyrolactone
Beta-hydroxy ketone
Heteroaromatic compound
Thiophene
Tetrahydrofuran
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

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

163061788

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one (NP0144961)

MOL for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

3D MOL for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

3D SDF for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

3D-SDF for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

PDB for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

3D PDB for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

SMILES for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

INCHI for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

Structure for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)

3D Structure for NP0144961 ((3r,3ar,6ar,9ar,9br)-3-hydroxy-6,9-dimethylidene-3-{2-oxo-2-[5'-(prop-1-yn-1-yl)-[2,2'-bithiophen]-5-yl]ethyl}-octahydroazuleno[4,5-b]furan-2-one)