NP-MRD: Showing NP-Card for 9,13:15,16-diepoxylabdan-15-ol (NP0043717)

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Record Information

Version

2.0

Created at

2021-06-21 01:02:55 UTC

Updated at

2021-06-30 00:19:34 UTC

NP-MRD ID

NP0043717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9,13:15,16-diepoxylabdan-15-ol

Provided By

JEOL Database JEOL Logo

Description

Tetramethyldispiro[[?]]Ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 9,13:15,16-diepoxylabdan-15-ol is found in Leucas stelligera. 9,13:15,16-diepoxylabdan-15-ol was first documented in 2013 (Kulkarni, R.R., et al.). Based on a literature review very few articles have been published on tetramethyldispiro[[?]]Ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306222119292D          

 24 27  0  0  1  0            999 V2000
    0.4230   -2.1899    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1825   -1.6296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7880   -1.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -0.2646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1825   -0.0204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3651    0.7841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880   -0.5808    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0537    0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8786    0.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228   -0.5990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7968   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4575   -0.6173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1919   -1.3983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6677   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3670   -1.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4488   -1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6055   -1.3854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4304   -1.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2110   -1.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285   -2.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -2.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3651   -2.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9462   -3.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1755   -2.2798    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
  4  5  1  0  0  0  0
  5  6  1  1  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  6  0  0  0
  7 16  1  1  0  0  0
  7 17  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@H](C)[C@]3(CC[C@]4(CO[C@H](O)C4)O3)[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O3/c1-14-6-7-15-17(2,3)8-5-9-18(15,4)20(14)11-10-19(23-20)12-16(21)22-13-19/h14-16,21H,5-13H2,1-4H3/t14-,15+,16+,18+,19+,20-/m1/s1

> <INCHI_KEY>
VOHURPICLQUNQE-XSBFNCLBSA-N

> <FORMULA>
C20H34O3

> <MOLECULAR_WEIGHT>
322.489

> <EXACT_MASS>
322.250794955

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
37.31024690489494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4aS,5'S,5''S,8aS)-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-5''-ol

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
4.331943900999999

> <ALOGPS_LOGS>
-5.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.375615556971972

> <JCHEM_PKA_STRONGEST_BASIC>
-3.946705755380459

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
89.88669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aS,5'S,5''S,8aS)-2,5,5,8a-tetramethyl-hexahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-5''-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  H   UNK     0       0.790  -4.088   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.341  -3.042   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.471  -1.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.130  -0.494   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.341  -0.038   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.681   1.464   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.471  -1.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.967   0.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.507   0.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.963  -1.118   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.221  -0.230   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.454  -1.152   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.958  -2.610   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.846  -3.868   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.418  -2.589   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.704  -2.006   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.130  -2.586   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.670  -2.607   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.261  -3.632   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.920  -5.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.449  -5.590   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.681  -4.544   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.766  -5.637   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.194  -4.256   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16   17                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15   16                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   10                                                       
CONECT   16   10    7                                                       
CONECT   17    7    2   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O₃

Average Mass

322.4890 Da

Monoisotopic Mass

322.25079 Da

IUPAC Name

(1R,2R,4aS,5'S,5''S,8aS)-2,5,5,8a-tetramethyl-octahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-5''-ol

Traditional Name

(1R,2R,4aS,5'S,5''S,8aS)-2,5,5,8a-tetramethyl-hexahydro-2H-dispiro[naphthalene-1,2':5',3''-bis(oxolane)]-5''-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])OC([H])([H])[C@@]2(O[C@]3(C([H])([H])C2([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]32C([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C20H34O3/c1-14-6-7-15-17(2,3)8-5-9-18(15,4)20(14)11-10-19(23-20)12-16(21)22-13-19/h14-16,21H,5-13H2,1-4H3/t14-,15+,16+,18+,19+,20-/m1/s1

InChI Key

VOHURPICLQUNQE-XSBFNCLBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Leucas stelligera	JEOL database	Kulkarni, R.R., et al, J. Nat. Prod. 76, 1836 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Grindelane diterpenoid
Diterpenoid
Oxolane
Hemiacetal
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen 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	3.35	ALOGPS
logP	4.33	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.89 m³·mol⁻¹	ChemAxon
Polarizability	37.31 Å³	ChemAxon
Number of Rings	4	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

30835015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72701754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kulkarni, R.R., et al. (2013). Kulkarni, R.R., et al, J. Nat. Prod. 76, 1836 (2013). J. Nat. Prod..

Showing NP-Card for 9,13:15,16-diepoxylabdan-15-ol (NP0043717)

MOL for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

3D MOL for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

3D SDF for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

3D-SDF for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

PDB for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

3D PDB for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

SMILES for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

INCHI for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

Structure for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)

3D Structure for NP0043717 (9,13:15,16-diepoxylabdan-15-ol)