NP-MRD: Showing NP-Card for (+)-Axiplyn B (NP0081952)

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Record Information

Version

2.0

Created at

2022-04-29 03:00:45 UTC

Updated at

2022-04-29 03:00:45 UTC

NP-MRD ID

NP0081952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Axiplyn B

Description

(1R,2S,5S,6S,9R,11S)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-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. (+)-Axiplyn B is found in Axinyssa aplysinoides. Based on a literature review very few articles have been published on (1R,2S,5S,6S,9R,11S)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]Dodecan-11-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292205002D          

 22 24  0  0  1  0            999 V2000
    1.6210   -0.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7663   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.7355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1751    1.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    2.0371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6210    1.4802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0353    0.6960    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.6193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3422    1.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    2.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727    2.1350    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8624    2.8995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520    3.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0980    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6268    3.2098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230    0.1203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2836    0.4397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0443    0.7591    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    1.0660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    2.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.4510    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
  6  7  1  0  0  0  0
  7  1  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  8 16  1  1  0  0  0
  8 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  2  0  0  0  0
  6 20  1  1  0  0  0
  3 20  1  0  0  0  0
  5 21  1  6  0  0  0
  3 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1CC[C@](C)(N=C=S)[C@@H]2CC[C@@]3(C)O[C@H](O)[C@]12O3

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO4S/c1-13(2,19)10-5-7-14(3,17-9-22)11-6-8-15(4)20-12(18)16(10,11)21-15/h10-12,18-19H,5-8H2,1-4H3/t10-,11-,12-,14-,15-,16-/m0/s1

> <INCHI_KEY>
WAWKSTXGMZGGDY-DNHGYJIUSA-N

> <FORMULA>
C16H25NO4S

> <MOLECULAR_WEIGHT>
327.44

> <EXACT_MASS>
327.150429463

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
97.49731228167812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5S,6S,9R,11S)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-11-ol

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.1367568459999986

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.974756003417092

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.156332015952934

> <JCHEM_PKA_STRONGEST_BASIC>
-2.81284640389714

> <JCHEM_POLAR_SURFACE_AREA>
71.28

> <JCHEM_REFRACTIVITY>
85.86670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6S,9R,11S)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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       3.026  -0.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.430  -0.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.675   1.373   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.327   2.948   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.709   3.803   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.026   2.763   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.799   1.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.350   1.156   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.239   2.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.604   3.831   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.056   3.985   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.476   5.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.897   6.839   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.050   4.833   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.903   5.992   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.263  -0.381   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.576   0.225   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       7.996   0.821   0.000  0.00  0.00           C+0
HETATM   19  S   UNK     0       9.416   1.417   0.000  0.00  0.00           S+0
HETATM   20  O   UNK     0       1.906   1.990   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.797   5.340   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.770   0.842   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   20   22                                             
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   11   20                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9   16   17                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16    8                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    6    3                                                       
CONECT   21    5                                                            
CONECT   22    3                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₅NO₄S

Average Mass

327.4400 Da

Monoisotopic Mass

327.15043 Da

IUPAC Name

(1R,2S,5S,6S,9R,11S)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-11-ol

Traditional Name

(1R,2S,5S,6S,9R,11S)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0^{1,6}]dodecan-11-ol

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1CC[C@](C)(N=C=S)[C@@H]2CC[C@@]3(C)O[C@H](O)[C@]12O3

InChI Identifier

InChI=1S/C16H25NO4S/c1-13(2,19)10-5-7-14(3,17-9-22)11-6-8-15(4)20-12(18)16(10,11)21-15/h10-12,18-19H,5-8H2,1-4H3/t10-,11-,12-,14-,15-,16-/m0/s1

InChI Key

WAWKSTXGMZGGDY-DNHGYJIUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Axinyssa aplysinoides	Animalia	KNApSAcK

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
Tertiary alcohol
Meta-dioxolane
Isothiocyanate
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
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	2.5	ALOGPS
logP	2.14	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.16	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	71.28 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.87 m³·mol⁻¹	ChemAxon
Polarizability	97.5 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

162849941

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Axiplyn B (NP0081952)

MOL for NP0081952 ((+)-Axiplyn B)

3D MOL for NP0081952 ((+)-Axiplyn B)

3D SDF for NP0081952 ((+)-Axiplyn B)

3D-SDF for NP0081952 ((+)-Axiplyn B)

PDB for NP0081952 ((+)-Axiplyn B)

3D PDB for NP0081952 ((+)-Axiplyn B)

SMILES for NP0081952 ((+)-Axiplyn B)

INCHI for NP0081952 ((+)-Axiplyn B)

Structure for NP0081952 ((+)-Axiplyn B)

3D Structure for NP0081952 ((+)-Axiplyn B)