NP-MRD: Showing NP-Card for (1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol (NP0257627)

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Record Information

Version

2.0

Created at

2022-09-07 22:48:15 UTC

Updated at

2022-09-07 22:48:15 UTC

NP-MRD ID

NP0257627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol

Description

Longiborneol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol is found in Cedrus libani, Pinus densiflora and Scapania undulata. (1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol was first documented in 2022 (PMID: 35165424). Based on a literature review a small amount of articles have been published on Longiborneol (PMID: 35807365) (PMID: 35170951) (PMID: 36098550) (PMID: 36098194).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    2.8199   -1.3311    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8829   -0.2612    0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2192   -0.2354    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418    1.0965   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2604    1.6244   -1.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316    1.0891   -1.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    0.7246   -0.6316 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2075    1.7131   -0.5641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    0.7086    0.6821 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3573    0.3632    1.6321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -0.3303    0.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5598   -0.6680   -0.4037 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2308   -1.3500   -1.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572   -1.4980    0.3044 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3109   -2.6522   -0.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5518   -0.5100    0.2256 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7792   -1.3618    0.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0037   -0.9899   -1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.3030   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0209    0.7428    2.5499 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3049   -0.4281    2.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6810   -1.0681    2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033    0.9828   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3241    1.7880    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0273    2.7011   -0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475    1.8282   -2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4638    1.9747   -2.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0785    0.4062   -2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1089    1.3583   -1.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305    2.1175    0.4166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644    2.6043   -1.1764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991    1.5911    0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084    1.2742    2.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0239   -0.3050    2.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7700   -1.2542    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    0.2877    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1752   -2.4485   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2905   -1.0466   -1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7703   -1.0841   -2.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7502   -1.9077    1.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1425   -3.3584    0.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -0.5849   -0.9023 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  6
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9 16  1  0
 16 14  1  0
 14 15  1  0
 16  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
 14 12  1  0
  7 12  1  0
  7  9  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 11 35  1  0
 11 36  1  0
 10 33  1  0
 10 34  1  0
  9 32  1  1
 16 42  1  6
 14 40  1  1
 15 41  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
M  END

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.112  -2.584   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.759  -1.849   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.309  -3.322   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.799  -0.610   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.416   0.978   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.948   1.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.395   0.920   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.845   1.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.096  -0.929   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.754  -1.296   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.678  -0.202   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.547   0.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.748   2.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.224  -0.076   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.712   0.322   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.941  -1.675   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   16                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9    2                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@H]3[C@H]([C@@H]1O)C(C)(C)CCC[C@@]23C

InChI Identifier

InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)10-6-9-15(14,4)12(16)11(10)13/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14+,15+/m0/s1

InChI Key

MNNFKQAYXGEKFA-SZWZKDINSA-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
Cedrus libani	LOTUS Database	35616633
Pinus densiflora	LOTUS Database	35616633
Scapania undulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bornane monoterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038056

Chemspider ID

67031278

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304755

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lusi RF, Sennari G, Sarpong R: Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy. Nat Chem. 2022 Apr;14(4):450-456. doi: 10.1038/s41557-021-00870-4. Epub 2022 Feb 14. [PubMed:35165424 ]
Ye F, Qiao X, Gui A, Liu P, Wang S, Wang X, Teng J, Zheng L, Feng L, Han H, Zhang B, Chen X, Gao Z, Gao S, Zheng P: Characterization of Roasting Time on Sensory Quality, Color, Taste, and Nonvolatile Compounds of Yuan An Yellow Tea. Molecules. 2022 Jun 27;27(13). pii: molecules27134119. doi: 10.3390/molecules27134119. [PubMed:35807365 ]
Lusi RF, Perea MA, Sarpong R: C-C Bond Cleavage of alpha-Pinene Derivatives Prepared from Carvone as a General Strategy for Complex Molecule Synthesis. Acc Chem Res. 2022 Mar 1;55(5):746-758. doi: 10.1021/acs.accounts.1c00783. Epub 2022 Feb 16. [PubMed:35170951 ]
Lusi RF, Sennari G, Sarpong R: Strategy Evolution in a Skeletal Remodeling and C-H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids. J Am Chem Soc. 2022 Sep 21;144(37):17277-17294. doi: 10.1021/jacs.2c08136. Epub 2022 Sep 13. [PubMed:36098550 ]
E Marouf A: Efficacy of Mandarin Crust Oil, Marigold Extract and Their Nanoemulsions, on Spodoptera littoralis (Boisd.) Larvae. Pak J Biol Sci. 2022 Jan;25(8):688-697. doi: 10.3923/pjbs.2022.688.697. [PubMed:36098194 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol (NP0257627)

MOL for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

3D MOL for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

3D SDF for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

3D-SDF for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

PDB for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

3D PDB for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

SMILES for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

INCHI for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

Structure for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)

3D Structure for NP0257627 ((1s,2r,7s,8s,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-ol)