NP-MRD: Showing NP-Card for (1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one (NP0271488)

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Record Information

Version

2.0

Created at

2022-09-08 17:47:48 UTC

Updated at

2022-09-08 17:47:48 UTC

NP-MRD ID

NP0271488

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one

Description

Ottelione A belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one is found in Ottelia alismoides. (1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one was first documented in 2007 (PMID: 17879247). Based on a literature review a small amount of articles have been published on ottelione A (PMID: 24900431) (PMID: 23131608) (PMID: 20222742) (PMID: 18341348).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -2.9017    2.5188    2.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    1.9863    1.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2371    0.5079    1.4039 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8179    0.2274    0.9371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932    0.6815   -0.5050 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1473   -0.1676   -1.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.1542   -0.8266 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4692    0.7733   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704    0.7407   -0.8184 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286   -0.2137    0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5566   -0.2270    0.4988 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4482    0.7388    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3101   -1.1443    0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7569   -2.1097    1.3946 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9809   -1.1119    0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    0.6469   -0.9549 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4740   -0.0340   -2.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554    0.3855   -3.2792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3330   -1.2023   -2.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7085   -1.8761   -1.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095   -1.3814    0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9594   -2.2569    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0318    0.0724    0.1990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2312    1.8585    3.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0307    3.5652    2.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    2.6729    0.7589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    0.0503    2.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6544   -0.8610    1.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1367    0.7580    1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4642    1.7620   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276   -1.2292   -1.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1571    0.0542   -2.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1582    1.5212   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4628    1.4869   -1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3376    1.7034    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4182    0.9214   -1.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4834    0.3842    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1683   -2.8311    1.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3648   -1.9055    0.4703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6421    1.6881   -1.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7035   -1.5674   -3.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3535   -2.7572   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -1.9009    1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1028   -3.3157    0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267    0.5415    0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 23  1  0
 23 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  3
  7 15  1  0
 15 13  2  0
 13 14  1  0
 13 10  1  0
 16  5  1  0
 21 23  1  0
 12 35  1  0
 12 36  1  0
 12 37  1  0
  9 34  1  0
  8 33  1  0
  6 31  1  0
  6 32  1  0
  5 30  1  1
  4 28  1  0
  4 29  1  0
  3 27  1  1
  2 26  1  0
  1 24  1  0
  1 25  1  0
 23 45  1  1
 16 40  1  6
 19 41  1  0
 20 42  1  0
 22 43  1  0
 22 44  1  0
 15 39  1  0
 14 38  1  0
M  END


  Mrv1652309082219472D          

 23 25  0  0  1  0            999 V2000
    1.4358   -2.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    2.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399    2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919    3.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370    3.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948    1.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6018    1.6373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428    1.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 23 21  1  1  0  0  0
  3 23  1  0  0  0  0
 16 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@@H]2C[C@@H](C=C)[C@H]3[C@@H]2C(=O)C=CC3=C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O3/c1-4-14-11-15(20-16(21)7-5-12(2)19(14)20)9-13-6-8-18(23-3)17(22)10-13/h4-8,10,14-15,19-20,22H,1-2,9,11H2,3H3/t14-,15-,19+,20+/m1/s1

> <INCHI_KEY>
ODHHTIYRUDURPW-IPZZXCBHSA-N

> <FORMULA>
C20H22O3

> <MOLECULAR_WEIGHT>
310.393

> <EXACT_MASS>
310.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.130227834596894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,3aR,7aS)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,4,7,7a-hexahydro-1H-inden-4-one

> <JCHEM_LOGP>
4.067994098333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.903825951823753

> <JCHEM_PKA_STRONGEST_BASIC>
-4.515203727077329

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
92.47109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,3aR,7aS)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1H-inden-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.235   5.161   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.741   4.841   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.772   5.985   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.296   7.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.217   3.376   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.723   3.056   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.187   2.232   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16    5   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    3   16                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₃

Average Mass

310.3930 Da

Monoisotopic Mass

310.15689 Da

IUPAC Name

(1S,3S,3aR,7aS)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,4,7,7a-hexahydro-1H-inden-4-one

Traditional Name

(1S,3S,3aR,7aS)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1H-inden-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@@H]2C[C@@H](C=C)[C@H]3[C@@H]2C(=O)C=CC3=C)C=C1O

InChI Identifier

InChI=1S/C20H22O3/c1-4-14-11-15(20-16(21)7-5-12(2)19(14)20)9-13-6-8-18(23-3)17(22)10-13/h4-8,10,14-15,19-20,22H,1-2,9,11H2,3H3/t14-,15-,19+,20+/m1/s1

InChI Key

ODHHTIYRUDURPW-IPZZXCBHSA-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
Ottelia alismoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Bicyclic monoterpenoid
11-noriridane monoterpenoid
Methoxyphenol
Aromatic monoterpenoid
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Cyclohexenone
Benzenoid
Monocyclic benzene moiety
Ketone
Ether
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.07	ChemAxon
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.47 m³·mol⁻¹	ChemAxon
Polarizability	34.13 Å³	ChemAxon
Number of Rings	3	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

9122062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10946837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chang TY, Tu YP, Wei WY, Chen HY, Chen CS, Lee YS, Huang JJ, Sha CK: Synthesis and antiproliferative activities of ottelione a analogues. ACS Med Chem Lett. 2012 Oct 30;3(12):1075-80. doi: 10.1021/ml300283f. eCollection 2012 Dec 13. [PubMed:24900431 ]
El-Missiry MA, Othman AI, Amer MA, Mohamed E: Ottelione A inhibited proliferation of Ehrlich ascites carcinoma cells in mice. Chem Biol Interact. 2012 Dec 5;200(2-3):119-27. doi: 10.1016/j.cbi.2012.10.013. Epub 2012 Nov 3. [PubMed:23131608 ]
Chen CH, Chen YK, Sha CK: Enantioselective total synthesis of otteliones A and B. Org Lett. 2010 Apr 2;12(7):1377-9. doi: 10.1021/ol902776d. [PubMed:20222742 ]
Clive DL, Liu D: Synthesis of the potent anticancer agents ottelione A and ottelione B in both racemic and natural optically pure forms. J Org Chem. 2008 Apr 18;73(8):3078-87. doi: 10.1021/jo702635t. Epub 2008 Mar 15. [PubMed:18341348 ]
Araki H, Inoue M, Suzuki T, Yamori T, Kohno M, Watanabe K, Abe H, Katoh T: Enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, (+)-3-epi-ottelione A and preliminary evaluation of their antitumor activity. Chemistry. 2007;13(35):9866-81. doi: 10.1002/chem.200700789. [PubMed:17879247 ]
LOTUS database [Link]

Showing NP-Card for (1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one (NP0271488)

MOL for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

3D MOL for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

3D SDF for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

3D-SDF for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

PDB for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

3D PDB for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

SMILES for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

INCHI for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

Structure for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)

3D Structure for NP0271488 ((1s,3s,3ar,7as)-1-ethenyl-3-[(3-hydroxy-4-methoxyphenyl)methyl]-7-methylidene-2,3,3a,7a-tetrahydro-1h-inden-4-one)