NP-MRD: Showing NP-Card for (1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene (NP0196131)

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Record Information

Version

2.0

Created at

2022-09-04 14:08:43 UTC

Updated at

2022-09-04 14:08:43 UTC

NP-MRD ID

NP0196131

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene

Description

126622-61-5 Belongs to the class of organic compounds known as biflorane and serrulatane diterpenoids. These are diterpenoids with a structure based either on the biflorane or the serrulatane skeleton. (1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene is found in Acanthella cavernosa and Acanthella pulcherrima. Based on a literature review very few articles have been published on 126622-61-5.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042216082D          

 25 27  0  0  1  0            999 V2000
    5.0059   -3.6570    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.1989   -3.4855    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.3920   -3.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204   -4.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850   -3.1424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9719   -3.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6085   -2.3888    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
    0.7145   -1.2375    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4895    1.2640    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2494   -2.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  3  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 24 23  1  1  0  0  0
 18 24  1  0  0  0  0
 11 24  1  0  0  0  0
  9 25  1  0  0  0  0
  6 25  1  0  0  0  0
M  CHG  4   1  -1   2   1  16   1  17  -1
M  END


  Mrv1652309042216082D          

 25 27  0  0  1  0            999 V2000
    5.0059   -3.6570    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.1989   -3.4855    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.3920   -3.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2204   -4.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850   -3.1424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9719   -3.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6085   -2.3888    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
    0.7145   -1.2375    0.0000 C   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
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4895    1.2640    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2494   -2.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  1  0  0  0
 16 17  3  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 24 23  1  1  0  0  0
 18 24  1  0  0  0  0
 11 24  1  0  0  0  0
  9 25  1  0  0  0  0
  6 25  1  0  0  0  0
M  CHG  4   1  -1   2   1  16   1  17  -1
M  END
> <DATABASE_ID>
NP0196131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@H]2[C@@H](CC[C@@](C)([N+]#[C-])[C@H]2CC1)[C@]1(C)CC[C@@H](O1)C(C)(C)[N+]#[C-]

> <INCHI_IDENTIFIER>
InChI=1S/C22H32N2O/c1-15-8-9-17-16(14-15)18(10-12-21(17,4)24-7)22(5)13-11-19(25-22)20(2,3)23-6/h14,16-19H,8-13H2,1-5H3/t16-,17+,18-,19-,21-,22+/m1/s1

> <INCHI_KEY>
WSPJFMZOFNQTAT-NBIPDHRESA-N

> <FORMULA>
C22H32N2O

> <MOLECULAR_WEIGHT>
340.511

> <EXACT_MASS>
340.251463658

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.582348433671555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,4aS,8aR)-4-isocyano-1-[(2S,5R)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene

> <JCHEM_LOGP>
0.024827896581440967

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.42055744247885

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.818484056553594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.234903513216178

> <JCHEM_POLAR_SURFACE_AREA>
17.950000000000003

> <JCHEM_REFRACTIVITY>
120.25330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,4aR,8aS)-1-isocyano-4-[(2S,5R)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       9.344  -6.826   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       7.838  -6.506   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       6.332  -6.186   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.652  -4.680   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.011  -7.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.825  -5.866   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.681  -6.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.347  -6.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.136  -4.459   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       3.657   1.180   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0       4.647   2.359   0.000  0.00  0.00           C-1
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.199  -4.459   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   25                                             
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   18                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   14   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18   11                                                  
CONECT   25    9    6                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂N₂O

Average Mass

340.5110 Da

Monoisotopic Mass

340.25146 Da

IUPAC Name

(1R,4R,4aS,8aR)-4-isocyano-1-[(2S,5R)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene

Traditional Name

(1R,4R,4aR,8aS)-1-isocyano-4-[(2S,5R)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalene

CAS Registry Number

Not Available

SMILES

CC1=C[C@H]2[C@@H](CC[C@@](C)([N+]#[C-])[C@H]2CC1)[C@]1(C)CC[C@@H](O1)C(C)(C)[N+]#[C-]

InChI Identifier

InChI=1S/C22H32N2O/c1-15-8-9-17-16(14-15)18(10-12-21(17,4)24-7)22(5)13-11-19(25-22)20(2,3)23-6/h14,16-19H,8-13H2,1-5H3/t16-,17+,18-,19-,21-,22+/m1/s1

InChI Key

WSPJFMZOFNQTAT-NBIPDHRESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthella cavernosa	LOTUS Database	35616633
Acanthella pulcherrima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflorane and serrulatane diterpenoids. These are diterpenoids with a structure based either on the biflorane or the serrulatane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Biflorane and serrulatane diterpenoids

Alternative Parents

Substituents

Biflorane diterpenoid
Tetrahydrofuran
Oxacycle
Organoheterocyclic compound
Organic isocyanide
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	0.025	ChemAxon
pKa (Strongest Acidic)	15.82	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.95 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	120.25 m³·mol⁻¹	ChemAxon
Polarizability	39.58 Å³	ChemAxon
Number of Rings	3	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

157019

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

180440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene (NP0196131)

MOL for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

3D MOL for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

3D SDF for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

3D-SDF for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

PDB for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

3D PDB for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

SMILES for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

INCHI for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

Structure for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)

3D Structure for NP0196131 ((1r,4r,4ar,8as)-1-isocyano-4-[(2s,5r)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene)