NP-MRD: Showing NP-Card for (3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan (NP0234441)

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Record Information

Version

2.0

Created at

2022-09-06 16:28:50 UTC

Updated at

2022-09-06 16:28:50 UTC

NP-MRD ID

NP0234441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan

Description

Spongian belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. (3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan is found in Cadlina luteomarginata. (3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan was first documented in 2020 (PMID: 32586020). Based on a literature review a significant number of articles have been published on Spongian (PMID: 33467112) (PMID: 33197184) (PMID: 32374067) (PMID: 32281798) (PMID: 34348550) (PMID: 34940679).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -3.6693    0.3863    1.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895    0.4249    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4557    1.7478   -0.4904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709   -0.7282   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8853   -2.0098   -0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4871   -1.9163    0.1755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -0.6839   -0.3940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7919   -0.8194   -1.8526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138    0.4693    0.2121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8757    1.7537   -0.2223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902    1.7926    0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    0.6223   -0.0002 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8875    0.9709   -1.3074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5410    0.6077    0.9934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4705    1.7457    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7580    1.2598    0.6665 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7096   -0.0833    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -0.6050    0.8922 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8851   -1.6911    0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935   -1.8940    0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -0.6256    0.2324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9306   -0.6801    1.7657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5923    0.9633    1.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102    0.6860    2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4602    2.4851    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5372    1.6132   -0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8311    2.0611   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560   -0.8148   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -0.4556   -1.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367   -2.7026   -1.2572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4689   -2.5757    0.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4653   -1.8612    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397   -2.8396   -0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056   -1.5090   -2.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8915    0.1069   -2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1193   -1.4187   -2.1649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2768    0.3945    1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6902    1.8102   -1.3125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4331    2.6121    0.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3680    1.6591    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0078    2.7524    0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992    0.7635   -1.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8553    2.0946   -1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4560    0.5502   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0403    0.6922    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659    2.4073   -0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819    2.4014    1.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9615   -0.3848   -0.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135   -0.5602    1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -1.0342    1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -2.6462    0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677   -1.6034   -1.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1088   -2.5209   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -2.6003    0.9769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536   -0.5702    1.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  9  2  1  0
 21 12  1  0
 21  7  1  0
 18 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  1
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  1
 15 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  1
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 21 55  1  1
M  END


  Mrv1652309062218282D          

 21 24  0  0  1  0            999 V2000
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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  6  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
  7 21  1  0  0  0  0
 12 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3COC[C@@H]3CC[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-18(2)9-5-10-20(4)16(18)8-11-19(3)15-13-21-12-14(15)6-7-17(19)20/h14-17H,5-13H2,1-4H3/t14-,15+,16-,17-,19-,20-/m0/s1

> <INCHI_KEY>
SAXSHFDCJZQLLD-KCMORZRYSA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.491

> <EXACT_MASS>
290.260965715

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
35.93797407783009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,7S,10R,11R,15R)-2,6,6,10-tetramethyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane

> <JCHEM_LOGP>
4.871763677999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1268296682432695

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
87.86439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7S,10R,11R,15R)-2,6,6,10-tetramethyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.352   0.273   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.366  -1.095   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   21                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   21                                             
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7   12                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O

Average Mass

290.4910 Da

Monoisotopic Mass

290.26097 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3COC[C@@H]3CC[C@H]21

InChI Identifier

InChI=1S/C20H34O/c1-18(2)9-5-10-20(4)16(18)8-11-19(3)15-13-21-12-14(15)6-7-17(19)20/h14-17H,5-13H2,1-4H3/t14-,15+,16-,17-,19-,20-/m0/s1

InChI Key

SAXSHFDCJZQLLD-KCMORZRYSA-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
Cadlina luteomarginata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Spongiane diterpenoid
Steroid
16-oxasteroid
Oxolane
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040352

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

101333827

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tai CJ, Huang CY, Ahmed AF, Orfali RS, Alarif WM, Huang YM, Wang YH, Hwang TL, Sheu JH: An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea. Mar Drugs. 2021 Jan 16;19(1). pii: md19010038. doi: 10.3390/md19010038. [PubMed:33467112 ]
Bory A, Shilling AJ, Allen J, Azhari A, Roth A, Shaw LN, Kyle DE, Adams JH, Amsler CD, McClintock JB, Baker BJ: Bioactivity of Spongian Diterpenoid Scaffolds from the Antarctic Sponge Dendrilla antarctica. Mar Drugs. 2020 Jun 23;18(6). pii: md18060327. doi: 10.3390/md18060327. [PubMed:32586020 ]
Allred TK, Dieskau AP, Zhao P, Lackner GL, Overman LE: General Access to Concave-Substituted cis-Dioxabicyclo[3.3.0]octanones: Enantioselective Total Syntheses of Macfarlandin C and Dendrillolide A. J Org Chem. 2020 Dec 4;85(23):15532-15551. doi: 10.1021/acs.joc.0c02273. Epub 2020 Nov 16. [PubMed:33197184 ]
Qiao T, Wang Y, Zheng S, Kang H, Liang G: Total Syntheses of Norrisolide-Type Spongian Diterpenes Cheloviolene C, Seconorrisolide B, and Seconorrisolide C. Angew Chem Int Ed Engl. 2020 Aug 10;59(33):14111-14114. doi: 10.1002/anie.202005600. Epub 2020 Jun 4. [PubMed:32374067 ]
Shilling AJ, Witowski CG, Maschek JA, Azhari A, Vesely BA, Kyle DE, Amsler CD, McClintock JB, Baker BJ: Spongian Diterpenoids Derived from the Antarctic Sponge Dendrilla antarctica Are Potent Inhibitors of the Leishmania Parasite. J Nat Prod. 2020 May 22;83(5):1553-1562. doi: 10.1021/acs.jnatprod.0c00025. Epub 2020 Apr 13. [PubMed:32281798 ]
Jin T, Li P, Wang C, Tang X, Yv X, Li K, Luo L, Ou H, Li G: Two new spongian diterpene derivatives from the aquaculture sponge Spongia officinalis Linnaeus, 1759. Nat Prod Res. 2023 Jan;37(2):216-226. doi: 10.1080/14786419.2021.1961137. Epub 2021 Aug 4. [PubMed:34348550 ]
Forster LC, Clegg JK, Cheney KL, Garson MJ: Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus Goniobranchus and Evaluation of Their Anatomical Distribution. Mar Drugs. 2021 Nov 29;19(12):680. doi: 10.3390/md19120680. [PubMed:34940679 ]
Tai CJ, Ahmed AF, Chao CH, Yen CH, Hwang TL, Chang FR, Huang YM, Sheu JH: Spongenolactones A-C, Bioactive 5,5,6,6,5-Pentacyclic Spongian Diterpenes from the Red Sea Sponge Spongia sp. Mar Drugs. 2022 Aug 1;20(8):498. doi: 10.3390/md20080498. [PubMed:36005501 ]
Dyshlovoy SA, Shubina LK, Makarieva TN, Hauschild J, Strewinsky N, Guzii AG, Menshov AS, Popov RS, Grebnev BB, Busenbender T, Oh-Hohenhorst SJ, Maurer T, Tilki D, Graefen M, Bokemeyer C, Stonik VA, von Amsberg G: New diterpenes from the marine sponge Spongionella sp. overcome drug resistance in prostate cancer by inhibition of P-glycoprotein. Sci Rep. 2022 Aug 9;12(1):13570. doi: 10.1038/s41598-022-17447-x. [PubMed:35945234 ]
Allred TK, Dieskau AP, Zhao P, Lackner GL, Overman LE: Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo[3.3.0]octanone Fragment. Angew Chem Int Ed Engl. 2020 Apr 6;59(15):6268-6272. doi: 10.1002/anie.201916753. Epub 2020 Feb 19. [PubMed:31965671 ]
LOTUS database [Link]

Showing NP-Card for (3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan (NP0234441)

MOL for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

3D MOL for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

3D SDF for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

3D-SDF for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

PDB for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

3D PDB for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

SMILES for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

INCHI for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

Structure for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)

3D Structure for NP0234441 ((3ar,3br,5as,9as,9br,11ar)-3b,6,6,9a-tetramethyl-dodecahydro-1h-phenanthro[1,2-c]furan)