NP-MRD: Showing NP-Card for (-)-Axinisothiocyanate M (NP0076218)

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Record Information

Version

2.0

Created at

2022-04-28 21:22:27 UTC

Updated at

2022-04-28 21:22:27 UTC

NP-MRD ID

NP0076218

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Axinisothiocyanate M

Description

Axinisothionate M belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (-)-Axinisothiocyanate M is found in Axinyssa isabela. Based on a literature review very few articles have been published on Axinisothionate M.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
    4.2147   -0.5140    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2255    0.2370    0.4925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    1.6568    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -0.2614    0.6317 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4860   -0.2249    1.9981 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7439   -1.6711    0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -2.1764    0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6647   -1.2249   -0.3756 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3993   -1.1651   -1.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -1.7805   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491   -0.8786   -0.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7846    0.5557   -0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547    1.0277    0.1410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1121    2.3175   -0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    1.4714    1.4303 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    2.0777    1.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8280    2.7232    1.4125 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5386    0.0815    0.3327 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8213    0.6456   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -0.0957   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -1.5373   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4362    2.2648   -0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888    1.7154    1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678    1.9968    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803    0.7185    2.2333 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175   -1.8268   -0.8616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728   -2.2993    0.8323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0773   -2.0998    1.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948   -3.2040    0.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5221   -0.1554   -2.2785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809   -1.5335   -2.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511   -1.8069   -2.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1133   -2.7294   -0.7154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1231   -2.0873    0.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9875   -1.0210    0.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5969   -1.2228   -1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6488    0.8391   -1.7830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7048    1.1485   -0.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9685    2.9700   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205    2.1114   -1.3137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6330    2.8905    0.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4487   -0.1394    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174    0.5521   -1.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9895    1.6544    0.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  2  0
 16 17  2  0
 13 18  1  0
 18 19  1  0
 19  4  1  0
 18  8  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  1 20  1  0
  1 21  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 14 39  1  0
 14 40  1  0
 14 41  1  0
 18 42  1  1
 19 43  1  0
 19 44  1  0
M  END


  Mrv1652304282223222D          

 19 20  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9160   -3.7777    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -1.2663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7643   -2.6656    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  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  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  2  0  0  0  0
  5 15  1  6  0  0  0
  2 16  1  1  0  0  0
  2 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076218

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NOS/c1-12(2)16(18)9-8-14(3)6-5-7-15(4,17-11-19)13(14)10-16/h13,18H,1,5-10H2,2-4H3/t13-,14-,15-,16+/m1/s1

> <INCHI_KEY>
KKOPPOVHLGSDFF-FPCVCCKLSA-N

> <FORMULA>
C16H25NOS

> <MOLECULAR_WEIGHT>
279.44

> <EXACT_MASS>
279.165685603

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.34535678736342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4aR,8R,8aR)-8-isothiocyanato-4a,8-dimethyl-2-(prop-1-en-2-yl)-decahydronaphthalen-2-ol

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
4.038609005666666

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.219300999814674

> <JCHEM_PKA_STRONGEST_BASIC>
-3.140277742681061

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
82.8804

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
axinisothiocyanate M

> <JCHEM_VEBER_RULE>
1

$$$$

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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.944  -4.440   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       3.577  -7.052   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.873  -2.364   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.150  -3.616   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.427  -4.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.689  -3.562   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   15                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    5                                                            
CONECT   16    2                                                            
CONECT   17    2   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Axinisothionic acid m	Generator

Chemical Formula

C₁₆H₂₅NOS

Average Mass

279.4400 Da

Monoisotopic Mass

279.16569 Da

IUPAC Name

(2S,4aR,8R,8aR)-8-isothiocyanato-4a,8-dimethyl-2-(prop-1-en-2-yl)-decahydronaphthalen-2-ol

Traditional Name

axinisothiocyanate M

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H25NOS/c1-12(2)16(18)9-8-14(3)6-5-7-15(4,17-11-19)13(14)10-16/h13,18H,1,5-10H2,2-4H3/t13-,14-,15-,16+/m1/s1

InChI Key

KKOPPOVHLGSDFF-FPCVCCKLSA-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
Axinyssa isabela	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Isothiocyanate
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
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	4.25	ALOGPS
logP	4.04	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.22	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.88 m³·mol⁻¹	ChemAxon
Polarizability	32.35 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

Chemspider ID

24691139

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25179335

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Axinisothiocyanate M (NP0076218)

MOL for NP0076218 ((-)-Axinisothiocyanate M)

3D MOL for NP0076218 ((-)-Axinisothiocyanate M)

3D SDF for NP0076218 ((-)-Axinisothiocyanate M)

3D-SDF for NP0076218 ((-)-Axinisothiocyanate M)

PDB for NP0076218 ((-)-Axinisothiocyanate M)

3D PDB for NP0076218 ((-)-Axinisothiocyanate M)

SMILES for NP0076218 ((-)-Axinisothiocyanate M)

INCHI for NP0076218 ((-)-Axinisothiocyanate M)

Structure for NP0076218 ((-)-Axinisothiocyanate M)

3D Structure for NP0076218 ((-)-Axinisothiocyanate M)