NP-MRD: Showing NP-Card for alpha-Obscurine (NP0140904)

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Record Information

Version

2.0

Created at

2022-06-29 21:57:47 UTC

Updated at

2022-06-29 21:57:47 UTC

NP-MRD ID

NP0140904

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Obscurine

Description

Alpha-Obscurine, also known as α-obscurine, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Obscurine is found in Austrolycopodium fastigiatum, Dendrolycopodium obscurum and Diphasiastrum digitatum. alpha-Obscurine was first documented in 2015 (PMID: 25421949). Based on a literature review a small amount of articles have been published on alpha-Obscurine (PMID: 32914364) (PMID: 31109141) (PMID: 30698428) (PMID: 28744720).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -1.1847    2.9237    2.0223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6253    2.0262    0.9375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2632    2.3509   -0.3771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9133    1.3653   -1.4433 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4933    1.4457   -1.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3954    0.5792   -1.0894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141    0.0153    0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0260   -0.2495    1.0740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2129   -1.0334    0.5031 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -0.4574   -0.7774 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014   -0.6793   -1.2186 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    0.3650   -1.5362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4189   -0.3797    0.2820 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8616    0.6009    1.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633   -0.0083   -0.9170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2649   -1.0544   -1.9863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8104   -2.3299   -1.3290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7461   -2.7041   -0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033   -1.6993    0.6477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -2.0640    1.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4894    3.8880    1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0726    2.5135    2.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817    3.2045    2.7593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    2.2627    0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9680    3.3742   -0.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3774    2.2812   -0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5802    1.5331   -2.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240    1.1324   -2.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8765    2.4783   -1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    0.7119    1.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6150   -0.7474    1.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0556   -0.8918    1.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -2.1056    0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0748    0.7996   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1942    0.4723    2.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135    0.4661    1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3173    0.0695   -0.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -1.2506   -2.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952   -0.7718   -2.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9747   -3.1255   -2.0673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118   -2.0331   -0.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0906   -3.6451    0.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1875   -2.8746   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1409   -1.2902    2.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -2.5920    2.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5892   -2.8725    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 14  2  1  0
 15  4  1  0
 12  6  1  0
 13 19  1  1
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  6
  5 28  1  0
  5 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  1
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.050  -0.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.903  -0.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.189  -1.325   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.656  -1.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.025  -1.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.495   0.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.790   1.745   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.624   3.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.162   2.966   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.867   1.597   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.405   1.522   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       5.033   0.302   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.324   2.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.046   1.511   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.075   0.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.366   0.151   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.557   1.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.309   2.647   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       0.132   3.191   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       0.381   4.711   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6                                                       
CONECT   13    7   14   15   19                                             
CONECT   14   13    2                                                       
CONECT   15   13    4   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
a-Obscurine	Generator
Α-obscurine	Generator

Chemical Formula

C₁₇H₂₆N₂O

Average Mass

274.4080 Da

Monoisotopic Mass

274.20451 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2CC3=C(CCC(=O)N3)[C@@]3(C1)[C@@H]2CCCN3C

InChI Identifier

InChI=1S/C17H26N2O/c1-11-8-12-9-15-14(5-6-16(20)18-15)17(10-11)13(12)4-3-7-19(17)2/h11-13H,3-10H2,1-2H3,(H,18,20)/t11-,12+,13-,17-/m1/s1

InChI Key

HXJHQEWSHQXRPH-IPJQOSJUSA-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
Austrolycopodium fastigiatum	LOTUS Database	35616633
Dendrolycopodium obscurum	LOTUS Database	35616633
Diphasiastrum digitatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
1,7-phenanthroline
Quinolidine
Tetrahydropyridine
Piperidine
Amino acid or derivatives
Carboxamide group
Lactam
Secondary carboxylic acid amide
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:10322 )

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

C00001951

Chemspider ID

10234071

KEGG Compound ID

C09889

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5462446

PDB ID

Not Available

ChEBI ID

10322

Good Scents ID

Not Available

References

General References

Yang Z, Yin Q, Ma J, Yang C, Sheng Y, Song L, Pang T, Zhuang P, Guo H, Zhang Y: Screen the Effective Components of Lycopodii herba on Rheumatoid Arthritis with the Aid of Spectrum-Effect Relationship and Uncover its Potential Mechanism. Inflammation. 2020 Dec;43(6):2087-2097. doi: 10.1007/s10753-020-01276-z. [PubMed:32914364 ]
Ma D, Gu X, Wang X, Liu Y, Di X: Pharmacokinetic Studies of Three Alkaloids in Rats After Intragastrical Administration of Lycopodii Herba Extract by LC-MS/MS. Molecules. 2019 May 19;24(10). pii: molecules24101930. doi: 10.3390/molecules24101930. [PubMed:31109141 ]
Yeap JS, Lim KH, Yong KT, Lim SH, Kam TS, Low YY: Lycopodium Alkaloids: Lycoplatyrine A, an Unusual Lycodine-Piperidine Adduct from Lycopodium platyrhizoma and the Absolute Configurations of Lycoplanine D and Lycogladine H. J Nat Prod. 2019 Feb 22;82(2):324-329. doi: 10.1021/acs.jnatprod.8b00754. Epub 2019 Jan 30. [PubMed:30698428 ]
Liu YC, Zhang ZJ, Su J, Peng LY, Pan LT, Wu XD, Zhao QS: Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata. Nat Prod Bioprospect. 2017 Oct;7(5):405-411. doi: 10.1007/s13659-017-0140-z. Epub 2017 Jul 25. [PubMed:28744720 ]
Wu J, Wang H, Ma Y, Jiang J, Zhan R, Chen Y: Isolation of a new lycodine alkaloid from Lycopodium japonicum. Nat Prod Res. 2015;29(8):735-8. doi: 10.1080/14786419.2014.984184. Epub 2014 Nov 25. [PubMed:25421949 ]

Showing NP-Card for alpha-Obscurine (NP0140904)

MOL for NP0140904 (alpha-Obscurine)

3D MOL for NP0140904 (alpha-Obscurine)

3D SDF for NP0140904 (alpha-Obscurine)

3D-SDF for NP0140904 (alpha-Obscurine)

PDB for NP0140904 (alpha-Obscurine)

3D PDB for NP0140904 (alpha-Obscurine)

SMILES for NP0140904 (alpha-Obscurine)

INCHI for NP0140904 (alpha-Obscurine)

Structure for NP0140904 (alpha-Obscurine)

3D Structure for NP0140904 (alpha-Obscurine)