NP-MRD: Showing NP-Card for (1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one (NP0252331)

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Record Information

Version

2.0

Created at

2022-09-07 15:48:14 UTC

Updated at

2022-09-07 15:48:15 UTC

NP-MRD ID

NP0252331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one

Description

Calamensesquiterpenone belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group. (1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one is found in Acorus calamus. Based on a literature review very few articles have been published on calamensesquiterpenone.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072217482D          

 17 19  0  0  1  0            999 V2000
    1.8384   -2.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7231   -1.4504    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9765   -1.0819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0906   -0.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9095   -0.1079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3035    0.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5199    0.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393    1.4806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1584    0.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5821    1.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5750   -0.0984    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3385    0.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8074   -0.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765   -1.4094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0559   -2.2342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3504   -0.8786    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9259   -0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  2 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  6  0  0  0
 11 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2[C@]11C[C@](C)(C[C@H]1O)C(=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9-5-6-10-13(2,3)12(17)14(4)7-11(16)15(9,10)8-14/h9-11,16H,5-8H2,1-4H3/t9-,10-,11+,14-,15-/m0/s1

> <INCHI_KEY>
DDUWSZBURGHFEW-VHKOSHJNSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.286656154801964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,8R,10R)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0^{1,5}]undecan-7-one

> <JCHEM_LOGP>
3.1336056269999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.649428316063194

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9521400545539596

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
67.0314

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,8R,10R)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0^{1,5}]undecan-7-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.432  -4.232   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.216  -2.707   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.823  -2.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.036  -0.487   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.564  -0.201   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.300   1.245   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.837   1.726   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.553   2.764   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.896   1.225   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.687   2.546   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.673  -0.184   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.098   0.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.107  -1.735   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.743  -2.631   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.704  -4.170   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.387  -1.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.462  -0.866   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   17                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2    5   17                                             
CONECT   17   16   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

(1S,2S,5R,8R,10R)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0^{1,5}]undecan-7-one

Traditional Name

(1S,2S,5R,8R,10R)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0^{1,5}]undecan-7-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2[C@]11C[C@](C)(C[C@H]1O)C(=O)C2(C)C

InChI Identifier

InChI=1S/C15H24O2/c1-9-5-6-10-13(2,3)12(17)14(4)7-11(16)15(9,10)8-14/h9-11,16H,5-8H2,1-4H3/t9-,10-,11+,14-,15-/m0/s1

InChI Key

DDUWSZBURGHFEW-VHKOSHJNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acorus calamus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.13	ChemAxon
pKa (Strongest Acidic)	14.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.03 m³·mol⁻¹	ChemAxon
Polarizability	27.29 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

25035682

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46906791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one (NP0252331)

MOL for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

3D MOL for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

3D SDF for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

3D-SDF for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

PDB for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

3D PDB for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

SMILES for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

INCHI for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

Structure for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)

3D Structure for NP0252331 ((1s,2s,5r,8r,10r)-10-hydroxy-2,6,6,8-tetramethyltricyclo[6.2.1.0¹,⁵]undecan-7-one)