NP-MRD: Showing NP-Card for Isophorene (NP0074261)

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Record Information

Version

2.0

Created at

2022-04-28 19:24:59 UTC

Updated at

2022-04-28 19:24:59 UTC

NP-MRD ID

NP0074261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isophorene

Description

N'-methyl-N-{[(1S,5R)-1,3,3-trimethyl-5-{[methylthio(carbonoimidyl)]amino}cyclohexyl]methyl}carbamimidothioic acid belongs to the class of organic compounds known as thioureas. These are organic compounds containing the thiourea functional group, a derivative of urea with the general structure (R1(N)R2C(=S)(R3)R4, R1-R4=H, alkyl, aryl), obtained by replacing the carbonyl group of urea with a thiocarbonyl group. Isophorene is found in Mentha pulegium L. . Based on a literature review very few articles have been published on N'-methyl-N-{[(1S,5R)-1,3,3-trimethyl-5-{[methylthio(carbonoimidyl)]amino}cyclohexyl]methyl}carbamimidothioic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 48  0  0  0  0  0  0  0  0999 V2000
    5.0401    2.9183    1.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2002    1.7446    1.9332 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806    1.1228    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1649    1.8104   -0.6680 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8741   -0.0102    0.8710 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2028   -0.8224   -0.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -0.3093   -0.7123 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2112    0.9428   -1.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076    0.1301    0.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3911    0.0428   -0.2474 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3558    0.8317    0.4503 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    0.9429   -0.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1157    0.2031   -1.4492 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6732    1.7191    0.6040 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4051    2.4165    1.8222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -1.4573   -0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7658   -2.1483   -1.0528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6012   -2.6977   -2.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2146   -3.3831   -0.3258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3420   -1.3483   -1.6024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542    3.7544    2.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1415    3.3152    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0626    2.6448    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9634    1.3358    2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330   -0.3255    1.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859   -1.8261    0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9730   -1.0886   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984    0.8033   -2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866    1.8557   -0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847    1.1480   -2.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2381    1.1552    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1225   -0.6156    1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    0.2418   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132    1.3233    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6425    1.7946    0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5531    1.7334    2.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3828    2.8190    1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1570    3.2236    1.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7676   -1.5960   -0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301   -1.7813    0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6318   -2.3075   -2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891   -3.7978   -2.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1835   -2.3660   -3.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0538   -4.1296   -0.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -3.8555   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334   -3.1858    0.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696   -2.0498   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0229   -0.8712   -2.5520 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 17 20  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 20  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  6
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 11 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
M  END


  Mrv1652304282221252D          

 20 20  0  0  1  0            999 V2000
    0.0499    0.7386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3873    1.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8245    2.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2617    1.4958    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8744    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9762    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906    1.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    2.7333    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.1196    1.4958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8340    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    1.1342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575    2.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    0.0102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0997   -0.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242   -0.6607    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876   -1.4179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -2.1175    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 13  1  1  0  0  0
  3 14  1  0  0  0  0
  3 15  1  0  0  0  0
  1 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(=S)NC[C@]1(C)C[C@@H](CC(C)(C)C1)NC(=S)NC

> <INCHI_IDENTIFIER>
InChI=1S/C14H28N4S2/c1-13(2)6-10(18-12(20)16-5)7-14(3,8-13)9-17-11(19)15-4/h10H,6-9H2,1-5H3,(H2,15,17,19)(H2,16,18,20)/t10-,14-/m1/s1

> <INCHI_KEY>
KEJFAGMNOBNFJR-QMTHXVAHSA-N

> <FORMULA>
C14H28N4S2

> <MOLECULAR_WEIGHT>
316.53

> <EXACT_MASS>
316.175539266

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.03108105917219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-1-{[(1S,5R)-1,3,3-trimethyl-5-[(methylcarbamothioyl)amino]cyclohexyl]methyl}thiourea

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.1579845843333327

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.679605600722478

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.07448199937319

> <JCHEM_POLAR_SURFACE_AREA>
48.12

> <JCHEM_REFRACTIVITY>
94.4288

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-1-{[(1S,5R)-1,3,3-trimethyl-5-[(methylcarbamothioyl)amino]cyclohexyl]methyl}thiourea

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.093   1.379   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.723   2.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   4.044   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.539   4.098   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.355   2.792   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.632   1.433   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.689   3.562   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.022   2.792   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.356   3.562   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       6.356   5.102   0.000  0.00  0.00           S+0
HETATM   11  N   UNK     0       7.690   2.792   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.024   3.562   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.739   2.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   4.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.107   5.581   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.630   0.019   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.186  -1.287   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0       1.725  -1.233   0.000  0.00  0.00           S+0
HETATM   19  N   UNK     0      -0.537  -2.647   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.279  -3.953   0.000  0.00  0.00           C+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   14   15                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    5                                                            
CONECT   14    3                                                            
CONECT   15    3                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
N'-methyl-N-{[(1S,5R)-1,3,3-trimethyl-5-{[methylthio(carbonoimidyl)]amino}cyclohexyl]methyl}carbamimidothioate	Generator

Chemical Formula

C₁₄H₂₈N₄S₂

Average Mass

316.5300 Da

Monoisotopic Mass

316.17554 Da

IUPAC Name

3-methyl-1-{[(1S,5R)-1,3,3-trimethyl-5-[(methylcarbamothioyl)amino]cyclohexyl]methyl}thiourea

Traditional Name

3-methyl-1-{[(1S,5R)-1,3,3-trimethyl-5-[(methylcarbamothioyl)amino]cyclohexyl]methyl}thiourea

CAS Registry Number

Not Available

SMILES

CNC(=S)NC[C@]1(C)C[C@@H](CC(C)(C)C1)NC(=S)NC

InChI Identifier

InChI=1S/C14H28N4S2/c1-13(2)6-10(18-12(20)16-5)7-14(3,8-13)9-17-11(19)15-4/h10H,6-9H2,1-5H3,(H2,15,17,19)(H2,16,18,20)/t10-,14-/m1/s1

InChI Key

KEJFAGMNOBNFJR-QMTHXVAHSA-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
Mentha pulegium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thioureas. These are organic compounds containing the thiourea functional group, a derivative of urea with the general structure (R1(N)R2C(=S)(R3)R4, R1-R4=H, alkyl, aryl), obtained by replacing the carbonyl group of urea with a thiocarbonyl group.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioureas

Sub Class

Not Available

Direct Parent

Thioureas

Alternative Parents

Substituents

Thiourea
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	2.28	ALOGPS
logP	2.16	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	48.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.43 m³·mol⁻¹	ChemAxon
Polarizability	36.03 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

62665528

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

154496788

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

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References

General References

Not Available

Showing NP-Card for Isophorene (NP0074261)

MOL for NP0074261 (Isophorene)

3D MOL for NP0074261 (Isophorene)

3D SDF for NP0074261 (Isophorene)

3D-SDF for NP0074261 (Isophorene)

PDB for NP0074261 (Isophorene)

3D PDB for NP0074261 (Isophorene)

SMILES for NP0074261 (Isophorene)

INCHI for NP0074261 (Isophorene)

Structure for NP0074261 (Isophorene)

3D Structure for NP0074261 (Isophorene)