NP-MRD: Showing NP-Card for rubrenolide (NP0297350)

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Record Information

Version

2.0

Created at

2022-09-10 07:35:56 UTC

Updated at

2022-09-10 07:35:56 UTC

NP-MRD ID

NP0297350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

rubrenolide

Description

RUBRENOLIDE belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. rubrenolide is found in Sextonia rubra. rubrenolide was first documented in 2005 (PMID: 15612067). Based on a literature review a small amount of articles have been published on RUBRENOLIDE (PMID: 32999145) (PMID: 30760744) (PMID: 29856602) (PMID: 20886871).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 51  0  0  0  0  0  0  0  0999 V2000
    5.5859   -0.2458    2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9866    0.3425    0.9369 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4571   -0.5005   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5904   -0.2512   -1.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1208   -0.6043   -1.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3582   -0.3243   -2.3431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9245   -0.5900   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9528    0.1499   -1.5694 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943    0.1397   -0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.8857    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4142    0.2989    0.2399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5486    1.1014    0.9135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6629    0.0928    0.7037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8150    0.4861    1.5667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9977   -0.4316    1.4590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0024    0.0765    2.2821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5579   -0.5079    0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9317    0.7697   -0.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.1391    1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242   -2.1879    1.6611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -0.9693    0.8187 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5946   -1.3234    2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2379    0.3396    2.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9726    1.4092    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4735   -0.1394   -0.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5272   -1.5565    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8750   -0.8736   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6127    0.8078   -1.6808 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299   -1.7288   -0.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8060   -0.1061   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5717    0.7513   -2.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8501   -0.9421   -3.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073   -0.5468   -3.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7835   -1.7109   -2.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169   -0.1759   -1.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9430    1.2540   -1.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2338   -0.8527    0.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9815    0.8066    0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559    0.9277    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0900    1.9415    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7243    0.2460   -0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    2.0517    0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135    1.1377    1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026    0.1162   -0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1438    1.5004    1.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4924    0.5934    2.6032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7229   -1.4258    1.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6326    0.6481    1.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8620   -0.9199   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4494   -1.1675    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0956    1.2584   -0.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  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
 11 21  1  0
 21 19  1  0
 19 20  2  0
 19 13  1  0
 18 51  1  0
 17 49  1  0
 17 50  1  0
 15 47  1  1
 16 48  1  0
 14 45  1  0
 14 46  1  0
 13 44  1  6
 12 42  1  0
 12 43  1  0
 11 41  1  6
 10 39  1  0
 10 40  1  0
  9 37  1  0
  9 38  1  0
  8 35  1  0
  8 36  1  0
  7 33  1  0
  7 34  1  0
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  4 27  1  0
  4 28  1  0
  3 25  1  0
  3 26  1  0
  2 24  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652309102209352D          

 21 21  0  0  1  0            999 V2000
    4.5727   -5.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2872   -4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0017   -5.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7161   -4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4306   -5.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1451   -4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8596   -5.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5740   -4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2885   -5.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0030   -4.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7174   -5.2767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4711   -4.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0232   -5.5542    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8436   -5.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1792   -4.7143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.6943   -4.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9997   -4.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3352   -3.8744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6107   -6.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9462   -7.0223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8037   -6.0971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 11 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H](O)C[C@H]1C[C@@H](CCCCCCCCC=C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H30O4/c1-2-3-4-5-6-7-8-9-10-16-12-14(17(20)21-16)11-15(19)13-18/h2,14-16,18-19H,1,3-13H2/t14-,15+,16+/m0/s1

> <INCHI_KEY>
SGQLBAQDXUEXPK-ARFHVFGLSA-N

> <FORMULA>
C17H30O4

> <MOLECULAR_WEIGHT>
298.423

> <EXACT_MASS>
298.214409446

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
35.43292360830522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,5R)-5-(dec-9-en-1-yl)-3-[(2R)-2,3-dihydroxypropyl]oxolan-2-one

> <JCHEM_LOGP>
3.261751443666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.78633495297776

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.24952698131716

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9362565422661433

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
83.16969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
rubrenolide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.536  -9.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.869  -9.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.203  -9.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.537  -9.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.870  -9.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.204  -9.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.538  -9.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.872  -9.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.205  -9.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.539  -9.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.873  -9.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.279  -9.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.310 -10.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.841 -10.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.468  -8.800   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      25.563  -7.554   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      27.999  -8.639   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      28.626  -7.232   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.540 -11.702   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      24.166 -13.108   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      22.034 -11.381   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   11                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₃₀O₄

Average Mass

298.4230 Da

Monoisotopic Mass

298.21441 Da

IUPAC Name

(3S,5R)-5-(dec-9-en-1-yl)-3-[(2R)-2,3-dihydroxypropyl]oxolan-2-one

Traditional Name

rubrenolide

CAS Registry Number

Not Available

SMILES

OC[C@H](O)C[C@H]1C[C@@H](CCCCCCCCC=C)OC1=O

InChI Identifier

InChI=1S/C17H30O4/c1-2-3-4-5-6-7-8-9-10-16-12-14(17(20)21-16)11-15(19)13-18/h2,14-16,18-19H,1,3-13H2/t14-,15+,16+/m0/s1

InChI Key

SGQLBAQDXUEXPK-ARFHVFGLSA-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
Sextonia rubra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Oxolane
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.26	ChemAxon
pKa (Strongest Acidic)	14.25	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	83.17 m³·mol⁻¹	ChemAxon
Polarizability	35.43 Å³	ChemAxon
Number of Rings	1	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

9056342

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10881073

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujioka H: Development of New Innovative Synthetic Organic Chemistry Using Lone Pairs of Oxygen Atoms. Chem Pharm Bull (Tokyo). 2020;68(10):907-945. doi: 10.1248/cpb.c20-00178. [PubMed:32999145 ]
Fu T, Houel E, Amusant N, Touboul D, Genta-Jouve G, Della-Negra S, Fisher GL, Brunelle A, Duplais C: Biosynthetic investigation of gamma-lactones in Sextonia rubra wood using in situ TOF-SIMS MS/MS imaging to localize and characterize biosynthetic intermediates. Sci Rep. 2019 Feb 13;9(1):1928. doi: 10.1038/s41598-018-37577-5. [PubMed:30760744 ]
Fu T, Touboul D, Della-Negra S, Houel E, Amusant N, Duplais C, Fisher GL, Brunelle A: Tandem Mass Spectrometry Imaging and in Situ Characterization of Bioactive Wood Metabolites in Amazonian Tree Species Sextonia rubra. Anal Chem. 2018 Jun 19;90(12):7535-7543. doi: 10.1021/acs.analchem.8b01157. Epub 2018 Jun 8. [PubMed:29856602 ]
Rodrigues AM, Theodoro PN, Eparvier V, Basset C, Silva MR, Beauchene J, Espindola LS, Stien D: Search for antifungal compounds from the wood of durable tropical trees. J Nat Prod. 2010 Oct 22;73(10):1706-7. doi: 10.1021/np1001412. Epub 2010 Oct 1. [PubMed:20886871 ]
Fujioka H, Ohba Y, Hirose H, Murai K, Kita Y: A double iodoetherification of sigma-symmetric diene acetals for installing four stereogenic centers in a single operation: short asymmetric total synthesis of rubrenolide. Angew Chem Int Ed Engl. 2005 Jan 21;44(5):734-7. doi: 10.1002/anie.200461584. [PubMed:15612067 ]
LOTUS database [Link]

Showing NP-Card for rubrenolide (NP0297350)

MOL for NP0297350 (rubrenolide)

3D MOL for NP0297350 (rubrenolide)

3D SDF for NP0297350 (rubrenolide)

3D-SDF for NP0297350 (rubrenolide)

PDB for NP0297350 (rubrenolide)

3D PDB for NP0297350 (rubrenolide)

SMILES for NP0297350 (rubrenolide)

INCHI for NP0297350 (rubrenolide)

Structure for NP0297350 (rubrenolide)

3D Structure for NP0297350 (rubrenolide)