NP-MRD: Showing NP-Card for 2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol (NP0227063)

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Record Information

Version

2.0

Created at

2022-09-06 06:17:09 UTC

Updated at

2022-09-06 06:17:10 UTC

NP-MRD ID

NP0227063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol

Description

5-Isothiocyanato-5,9-dimethyl-2-(propan-2-yl)-10,12-dioxatricyclo[7.2.1.0¹,⁶]Dodecan-11-ol belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. 5-Isothiocyanato-5,9-dimethyl-2-(propan-2-yl)-10,12-dioxatricyclo[7.2.1.0¹,⁶]Dodecan-11-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191523332D          

 21 23  0  0  0  0            999 V2000
    1.8238    2.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6419    2.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1432    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9588    1.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7894    1.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332    0.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6590    0.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4455   -0.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4069   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793   -1.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5516   -1.9456    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281    0.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117   -0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1508    0.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -0.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9575    1.0058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7079    1.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154    0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101    0.5007    0.0000 O   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
  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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0227063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC(C)(N=C=S)C2CCC3(C)OC(O)C12O3

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO3S/c1-10(2)11-5-7-14(3,17-9-21)12-6-8-15(4)19-13(18)16(11,12)20-15/h10-13,18H,5-8H2,1-4H3

> <INCHI_KEY>
LJLZJJKLXWEJAB-UHFFFAOYSA-N

> <FORMULA>
C16H25NO3S

> <MOLECULAR_WEIGHT>
311.44

> <EXACT_MASS>
311.155514843

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.95141460076313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-isothiocyanato-5,9-dimethyl-2-(propan-2-yl)-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
3.5663148039999992

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.161002053491499

> <JCHEM_PKA_STRONGEST_BASIC>
-3.864366513381015

> <JCHEM_POLAR_SURFACE_AREA>
51.05

> <JCHEM_REFRACTIVITY>
84.1294

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       3.404   4.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.932   4.327   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.867   5.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.523   2.905   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.074   2.762   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.715   1.354   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.830   0.086   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.432  -1.401   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.226  -0.564   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.361  -2.098   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       8.496  -3.632   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       5.279   0.223   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.502  -1.201   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.907  -1.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.148   0.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.705  -0.235   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.787   1.878   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.188   2.714   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.806   4.206   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.509   1.678   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.379   0.935   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    4   12   21                                             
CONECT   21   20   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₅NO₃S

Average Mass

311.4400 Da

Monoisotopic Mass

311.15551 Da

IUPAC Name

5-isothiocyanato-5,9-dimethyl-2-(propan-2-yl)-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol

Traditional Name

2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC(C)(N=C=S)C2CCC3(C)OC(O)C12O3

InChI Identifier

InChI=1S/C16H25NO3S/c1-10(2)11-5-7-14(3,17-9-21)12-6-8-15(4)19-13(18)16(11,12)20-15/h10-13,18H,5-8H2,1-4H3

InChI Key

LJLZJJKLXWEJAB-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Ketal
Oxepane
Oxane
Meta-dioxolane
Hemiacetal
Isothiocyanate
Acetal
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen 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
logP	3.42	ALOGPS
logP	3.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.16	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.13 m³·mol⁻¹	ChemAxon
Polarizability	33.95 Å³	ChemAxon
Number of Rings	3	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

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

74335184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol (NP0227063)

MOL for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

3D MOL for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

3D SDF for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

3D-SDF for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

PDB for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

3D PDB for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

SMILES for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

INCHI for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

Structure for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)

3D Structure for NP0227063 (2-isopropyl-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol)