NP-MRD: Showing NP-Card for (-)-Cyanthiwigin F (NP0081982)

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Record Information

Version

2.0

Created at

2022-04-29 03:02:22 UTC

Updated at

2022-04-29 03:02:23 UTC

NP-MRD ID

NP0081982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Cyanthiwigin F

Description

Cyanthiwigin F belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (-)-Cyanthiwigin F is found in Myrmekioderma rea and Myrmekioderma styx. (-)-Cyanthiwigin F was first documented in 2008 (PMID: 18580947). Based on a literature review very few articles have been published on Cyanthiwigin F.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -3.8118    2.4815   -1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8858    1.4055   -0.7403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4095    0.2098   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8806   -1.1011   -0.3596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3926   -1.2401   -0.3619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9237   -1.2446   -1.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.6613    0.1300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -2.7089    1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1386   -3.5138    1.9649 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2801   -1.8375    0.8828 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3724   -2.5206    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6981   -1.2239    2.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2723    0.1065    1.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7462    0.4882    0.6382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1158    1.7586   -0.0192 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1098    2.5636    0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7274    1.4991   -1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157   -0.5315    0.1830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6378   -0.3460    0.5475 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0288    1.0367    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    1.8275   -0.4247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1080    3.0478   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7092    2.0645   -1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866    3.2174   -1.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4685    0.1882   -0.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3424   -1.8396   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126   -1.3780    0.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1539   -2.0311   -1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -1.5443   -2.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5424   -0.3198   -2.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646   -3.0368    0.7623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0023   -3.3822   -0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2885   -2.5113    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024   -2.0613   -0.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1253   -3.5915   -0.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -1.0806    2.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4449   -1.8712    2.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994    0.6060    2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898    2.4454   -0.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0850    2.0773    0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204    3.5601    0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6590    2.7198    1.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9399    1.4480   -2.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3873    2.3620   -1.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080    0.5799   -1.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9724   -0.7391   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268   -0.8112    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2548    1.5695    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162    1.0901    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8322    1.8667   -1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5181    2.9073   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 10  1  0
 10 11  1  6
 10 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  2  0
 18 14  1  0
  5 19  1  0
  8 10  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 15 39  1  6
 17 43  1  0
 17 44  1  0
 17 45  1  0
 13 38  1  0
 12 36  1  0
 12 37  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 18 46  1  6
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
M  END


  Mrv1652304292205022D          

 21 23  0  0  1  0            999 V2000
    1.8701   -1.9938    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2402   -1.2564    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7868   -0.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9632   -0.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5097    0.0738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5930   -1.3527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0465   -2.0419    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5312   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408   -2.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2025   -1.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495   -3.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697   -4.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477   -3.6905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0700   -0.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0475   -1.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6839   -1.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -2.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0170   -2.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2158   -2.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -2.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -0.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  6  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  6  0  0  0
 17 20  1  0  0  0  0
  2 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC[C@]2(C)[C@H]1[C@H]1CCC(C)=CC[C@]1(C)CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O/c1-13(2)15-9-11-20(5)17(21)12-19(4)10-8-14(3)6-7-16(19)18(15)20/h8-9,13,16,18H,6-7,10-12H2,1-5H3/t16-,18-,19-,20+/m1/s1

> <INCHI_KEY>
YAXKUXVYYMVPCV-AFYVEPGGSA-N

> <FORMULA>
C20H30O

> <MOLECULAR_WEIGHT>
286.459

> <EXACT_MASS>
286.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.94903232037494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,5aR,10aR,10bS)-3a,5a,8-trimethyl-1-(propan-2-yl)-3H,3aH,4H,5H,5aH,6H,9H,10H,10aH,10bH-cyclohepta[e]inden-4-one

> <ALOGPS_LOGP>
5.50

> <JCHEM_LOGP>
5.0935891

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.4975491521066235

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
90.19019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,5aR,10aR,10bS)-1-isopropyl-3a,5a,8-trimethyl-3H,5H,6H,9H,10H,10aH,10bH-cyclohepta[e]inden-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.491  -3.722   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.182  -2.345   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.335  -1.059   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.798  -1.149   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.951   0.138   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.107  -2.525   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.954  -3.812   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.992  -5.014   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.449  -4.471   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.378  -2.933   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.399  -6.499   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.317  -7.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.889  -6.889   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.131  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.689  -2.027   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.877  -3.007   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.851  -4.547   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.632  -5.487   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.136  -5.120   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.228  -5.238   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.768  -0.921   0.000  0.00  0.00           C+0
CONECT    1    2    7   19                                                  
CONECT    2    1    3   15   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10   14                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1                                                       
CONECT   20   17                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(-)-Cyanthiwigin F	MeSH

Chemical Formula

C₂₀H₃₀O

Average Mass

286.4590 Da

Monoisotopic Mass

286.22967 Da

IUPAC Name

(3aR,5aR,10aR,10bS)-3a,5a,8-trimethyl-1-(propan-2-yl)-3H,3aH,4H,5H,5aH,6H,9H,10H,10aH,10bH-cyclohepta[e]inden-4-one

Traditional Name

(3aR,5aR,10aR,10bS)-1-isopropyl-3a,5a,8-trimethyl-3H,5H,6H,9H,10H,10aH,10bH-cyclohepta[e]inden-4-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC[C@]2(C)[C@H]1[C@H]1CCC(C)=CC[C@]1(C)CC2=O

InChI Identifier

InChI=1S/C20H30O/c1-13(2)15-9-11-20(5)17(21)12-19(4)10-8-14(3)6-7-16(19)18(15)20/h8-9,13,16,18H,6-7,10-12H2,1-5H3/t16-,18-,19-,20+/m1/s1

InChI Key

YAXKUXVYYMVPCV-AFYVEPGGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Myrmekioderma rea	LOTUS Database	35616633
Myrmekioderma styx	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	5.5	ALOGPS
logP	5.09	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	34.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00048672

Chemspider ID

8215220

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10039656

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Enquist JA Jr, Stoltz BM: The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation. Nature. 2008 Jun 26;453(7199):1228-31. doi: 10.1038/nature07046. [PubMed:18580947 ]

Showing NP-Card for (-)-Cyanthiwigin F (NP0081982)

MOL for NP0081982 ((-)-Cyanthiwigin F)

3D MOL for NP0081982 ((-)-Cyanthiwigin F)

3D SDF for NP0081982 ((-)-Cyanthiwigin F)

3D-SDF for NP0081982 ((-)-Cyanthiwigin F)

PDB for NP0081982 ((-)-Cyanthiwigin F)

3D PDB for NP0081982 ((-)-Cyanthiwigin F)

SMILES for NP0081982 ((-)-Cyanthiwigin F)

INCHI for NP0081982 ((-)-Cyanthiwigin F)

Structure for NP0081982 ((-)-Cyanthiwigin F)

3D Structure for NP0081982 ((-)-Cyanthiwigin F)