NP-MRD: Showing NP-Card for Lappaphen A (NP0046368)

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Record Information

Version

2.0

Created at

2022-03-17 19:56:53 UTC

Updated at

2022-03-17 19:56:53 UTC

NP-MRD ID

NP0046368

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lappaphen A

Description

Lappaphen A 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. Lappaphen A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223322D          

 33 37  0  0  0  0            999 V2000
    0.1643    4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565    4.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565    3.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3138    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0522    3.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775    4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643    3.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391    1.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    2.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313    2.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522    1.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418   -4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209   -3.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -4.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -4.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -3.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487   -3.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -3.4899    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    0.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9027    0.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.4517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565   -1.6830    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -0.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -1.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4 12  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 25  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  3  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 33  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 30  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END


  Mrv0541 02241223322D          

 33 37  0  0  0  0            999 V2000
    0.1643    4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565    4.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6565    3.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3138    3.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0522    3.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4775    4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565    4.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1643    3.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391    1.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    2.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313    2.4214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132    1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522    1.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6418   -4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8209   -3.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643   -4.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -4.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956   -4.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235   -3.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1487   -3.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -3.4899    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1643    0.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9027    0.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740   -0.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.4517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6565   -1.6830    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844   -0.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8061   -1.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9703   -1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -2.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  2  0  0  0  0
  4 12  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 25  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 25  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  3  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 33  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 30  1  0  0  0  0
 29 30  1  0  0  0  0
 29 33  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046368

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)CC1(O)C2CCC(=C)C3CCC(=C)C3C2OC1=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

> <INCHI_KEY>
WKQBNYGTPIGLMV-UHFFFAOYSA-N

> <FORMULA>
C27H26O4S2

> <MOLECULAR_WEIGHT>
478.623

> <EXACT_MASS>
478.1272507

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
52.85412953832203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-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>
3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.307   8.813   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.225   8.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.225   6.820   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.452   5.900   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.831   6.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.758   7.586   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.225   7.586   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.307   6.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.919   4.827   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   3.601   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.380   3.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.605   4.367   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.298   4.520   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.451   2.988   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.831   2.374   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.065  -8.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.532  -7.433   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.307  -8.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.071  -8.047   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.605  -8.200   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.217  -6.820   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.144  -5.747   0.000  0.00  0.00           C+0
HETATM   23  S   UNK     0       0.765  -6.514   0.000  0.00  0.00           S+0
HETATM   24  O   UNK     0      -0.307   1.455   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.071   2.374   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.685   0.842   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.071  -0.536   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.460  -0.843   0.000  0.00  0.00           O+0
HETATM   29  S   UNK     0       1.225  -3.142   0.000  0.00  0.00           S+0
HETATM   30  C   UNK     0       1.838  -1.762   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.371  -1.916   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.678  -3.448   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.298  -4.215   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12                                                       
CONECT   12    4   11                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   19   22                                                       
CONECT   24   25                                                            
CONECT   25   10   14   24   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27                                                            
CONECT   29   30   33                                                       
CONECT   30   27   29   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   22   29   32                                                  
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

478.6230 Da

Monoisotopic Mass

478.12725 Da

IUPAC Name

3-hydroxy-6,9-dimethylidene-3-(2-oxo-2-{5-[5-(prop-1-yn-1-yl)thiophen-2-yl]thiophen-2-yl}ethyl)-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC#CC1=CC=C(S1)C1=CC=C(S1)C(=O)CC1(O)C2CCC(=C)C3CCC(=C)C3C2OC1=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

InChI Key

WKQBNYGTPIGLMV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arctium lappa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Guaiane sesquiterpenoid
Sesquiterpenoid
Bithiophene
Aryl alkyl ketone
Aryl ketone
2,5-disubstituted thiophene
Beta-hydroxy ketone
Gamma butyrolactone
Heteroaromatic compound
Thiophene
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
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
logP	4.96	ALOGPS
logP	5.56	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.71 m³·mol⁻¹	ChemAxon
Polarizability	52.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

FDB004114

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

13856335

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lappaphen A (NP0046368)

MOL for NP0046368 (Lappaphen A)

3D MOL for NP0046368 (Lappaphen A)

3D SDF for NP0046368 (Lappaphen A)

3D-SDF for NP0046368 (Lappaphen A)

PDB for NP0046368 (Lappaphen A)

3D PDB for NP0046368 (Lappaphen A)

SMILES for NP0046368 (Lappaphen A)

INCHI for NP0046368 (Lappaphen A)

Structure for NP0046368 (Lappaphen A)

3D Structure for NP0046368 (Lappaphen A)