NP-MRD: Showing NP-Card for 2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol (NP0312554)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 09:26:10 UTC

Updated at

2022-09-11 09:26:11 UTC

NP-MRD ID

NP0312554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol

Description

2,10-Dioxatricyclo[5.3.1.0⁴,¹¹]Undecane-4,5-diol belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. 2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol is found in Cistanche tubulosa. 2,10-Dioxatricyclo[5.3.1.0⁴,¹¹]Undecane-4,5-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261502562D          

 13 15  0  0  0  0            999 V2000
   -0.0609    0.6592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605    1.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2257    1.5498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0044    1.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6297    1.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4764    0.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6977    0.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5569   -0.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3673    0.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623   -0.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    0.7392    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  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
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
  8 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0312554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CC2CCOC3OCC1(O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O4/c10-6-3-5-1-2-12-8-7(5)9(6,11)4-13-8/h5-8,10-11H,1-4H2

> <INCHI_KEY>
JEOPUSJCPYFSMM-UHFFFAOYSA-N

> <FORMULA>
C9H14O4

> <MOLECULAR_WEIGHT>
186.207

> <EXACT_MASS>
186.089208931

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.524050551252365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol

> <ALOGPS_LOGP>
-0.71

> <JCHEM_LOGP>
-0.6759971320000002

> <ALOGPS_LOGS>
0.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.718395680192845

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.69357240730561

> <JCHEM_PKA_STRONGEST_BASIC>
-3.278176102467521

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
43.40059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0      -0.114   1.231   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.385   1.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.980   3.005   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.155   2.893   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.608   3.402   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.776   2.397   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.489   0.884   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.036   0.375   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.441  -1.045   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.906  -0.919   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.552   0.580   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.236  -0.220   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.868   1.380   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2   12   13                                             
CONECT   12   11                                                            
CONECT   13   11    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₄O₄

Average Mass

186.2070 Da

Monoisotopic Mass

186.08921 Da

IUPAC Name

2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol

Traditional Name

2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol

CAS Registry Number

Not Available

SMILES

OC1CC2CCOC3OCC1(O)C23

InChI Identifier

InChI=1S/C9H14O4/c10-6-3-5-1-2-12-8-7(5)9(6,11)4-13-8/h5-8,10-11H,1-4H2

InChI Key

JEOPUSJCPYFSMM-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

Species Name	Source	Reference
Cistanche tubulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Furopyran
Oxane
Pyran
Cyclic alcohol
Furan
Tertiary alcohol
Tetrahydrofuran
1,2-diol
Secondary alcohol
Oxacycle
Acetal
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen 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	-0.71	ALOGPS
logP	-0.68	ChemAxon
logS	0.37	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.4 m³·mol⁻¹	ChemAxon
Polarizability	18.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

74951122

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol (NP0312554)

MOL for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

3D MOL for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

3D SDF for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

3D-SDF for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

PDB for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

3D PDB for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

SMILES for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

INCHI for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

Structure for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)

3D Structure for NP0312554 (2,10-dioxatricyclo[5.3.1.0⁴,¹¹]undecane-4,5-diol)