NP-MRD: Showing NP-Card for 3,12-Cyathadiene (NP0085028)

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Record Information

Version

2.0

Created at

2022-04-29 05:36:37 UTC

Updated at

2022-04-29 05:36:38 UTC

NP-MRD ID

NP0085028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,12-Cyathadiene

Description

(-)-Cyatha-3,12-diene belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3,12-Cyathadiene is found in Hericium erinaceum . 3,12-Cyathadiene was first documented in 2009 (PMID: 20161213). Based on a literature review very few articles have been published on (-)-cyatha-3,12-diene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    4.3188    2.0733   -0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0732    1.3309   -0.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312    0.2046   -1.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2642   -0.7918   -1.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -1.1170   -0.4526 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2173   -1.3611    0.7487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7030   -2.4700   -0.7444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099   -2.7685    0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423   -1.8555    0.1505 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2357   -2.1967   -1.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802   -1.7927    1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813   -0.6119    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1165    0.3319    0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4236    1.7550    0.2210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5955    2.6805   -0.5559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8372    2.3534    1.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360   -0.4054    0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3358   -0.0003   -0.2793 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9550    0.9682    0.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203    1.9848    0.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7298    1.7634    0.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1059    1.7833   -0.9563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1861    3.1727   -0.2673 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2772   -0.0459   -1.4139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6291   -0.3223   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7392   -1.6944   -2.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0549   -0.6789    0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6621   -1.5252    1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7111   -2.3640    0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5295   -3.2117   -0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2621   -2.5789   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6697   -3.8134    0.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1160   -2.7942    1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2216   -2.6690   -0.8565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4756   -1.2617   -1.6585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6897   -2.9384   -1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0916   -1.4840    2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1217   -2.6751    1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9182   -0.1595    1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8579   -0.8811   -0.2265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511    1.7931   -0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2757    2.2599   -1.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8163    3.2250    0.0184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711    3.5439   -0.8837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7371    1.8012    1.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0143    2.3459    2.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1953    3.3957    1.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2974    0.5280   -1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1529    1.4724    1.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.4590    1.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2623    2.4602   -0.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0633    2.7822    0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  2  0
  5 18  1  0
 17  9  1  0
 17 18  1  0
 18 48  1  6
 19 49  1  0
 19 50  1  0
 20 51  1  0
 20 52  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 14 41  1  6
 15 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
M  END


  Mrv1652304292207362D          

 21 23  0  0  1  0            999 V2000
   -0.7304   -0.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069   -0.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    0.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6298    1.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4370    1.1654    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8905    1.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7141    1.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842    1.0692    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6073    1.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6307    0.3800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1461   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278   -1.0599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5076   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1296   -1.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    0.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8798    0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1231    1.9284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    0.4281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9823    0.4146    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4615   -0.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6603   -0.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
  5 17  1  1  0  0  0
  5 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085028

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CCC(C)=CC[C@]1(C)CC[C@@]1(C)CCC(C(C)C)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C20H32/c1-14(2)16-9-11-20(5)13-12-19(4)10-8-15(3)6-7-17(19)18(16)20/h8,14,17H,6-7,9-13H2,1-5H3/t17-,19-,20-/m1/s1

> <INCHI_KEY>
HYUVPCPBEOBIGN-MISYRCLQSA-N

> <FORMULA>
C20H32

> <MOLECULAR_WEIGHT>
272.476

> <EXACT_MASS>
272.25040103

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
34.680949207550064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,5aS,10aS)-3a,5a,8-trimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]indene

> <ALOGPS_LOGP>
7.22

> <JCHEM_LOGP>
5.717214636666666

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
89.23039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,5aS,10aS)-1-isopropyl-3a,5a,8-trimethyl-2H,3H,4H,5H,6H,9H,10H,10aH-cyclohepta[e]indene

> <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      -1.363  -0.717   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.013  -0.026   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.012   1.514   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.176   2.493   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.682   2.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.529   3.462   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.066   3.372   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.757   1.996   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.734   3.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.911   0.709   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.873  -0.493   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.465  -1.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.548  -3.074   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.975  -2.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.314   0.050   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.242   1.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.096   3.600   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.373   0.799   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       1.834   0.774   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       2.728  -0.599   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.232  -0.966   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17   18                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11   18                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16                                                       
CONECT   16   15    8                                                       
CONECT   17    5                                                            
CONECT   18    5   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂

Average Mass

272.4760 Da

Monoisotopic Mass

272.25040 Da

IUPAC Name

(3aS,5aS,10aS)-3a,5a,8-trimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,9H,10H,10aH-cyclohepta[e]indene

Traditional Name

(3aS,5aS,10aS)-1-isopropyl-3a,5a,8-trimethyl-2H,3H,4H,5H,6H,9H,10H,10aH-cyclohepta[e]indene

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC(C)=CC[C@]1(C)CC[C@@]1(C)CCC(C(C)C)=C21

InChI Identifier

InChI=1S/C20H32/c1-14(2)16-9-11-20(5)13-12-19(4)10-8-15(3)6-7-17(19)18(16)20/h8,14,17H,6-7,9-13H2,1-5H3/t17-,19-,20-/m1/s1

InChI Key

HYUVPCPBEOBIGN-MISYRCLQSA-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
Hericium erinaceus	Fungi	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
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
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	7.22	ALOGPS
logP	5.72	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.23 m³·mol⁻¹	ChemAxon
Polarizability	34.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00054717

Chemspider ID

78436544

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15519950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sparling BA, Simpson GL, Jamison TF: Strategic use of nickel(0)-catalyzed enyne-epoxide reductive coupling towards the synthesis of (-)-cyatha-3,12-diene. Tetrahedron. 2009 Apr 18;65(16):3270-3280. doi: 10.1016/j.tet.2008.11.086. [PubMed:20161213 ]

Showing NP-Card for 3,12-Cyathadiene (NP0085028)

MOL for NP0085028 (3,12-Cyathadiene)

3D MOL for NP0085028 (3,12-Cyathadiene)

3D SDF for NP0085028 (3,12-Cyathadiene)

3D-SDF for NP0085028 (3,12-Cyathadiene)

PDB for NP0085028 (3,12-Cyathadiene)

3D PDB for NP0085028 (3,12-Cyathadiene)

SMILES for NP0085028 (3,12-Cyathadiene)

INCHI for NP0085028 (3,12-Cyathadiene)

Structure for NP0085028 (3,12-Cyathadiene)

3D Structure for NP0085028 (3,12-Cyathadiene)