NP-MRD: Showing NP-Card for (-)-Phlegmarine (NP0051056)

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Record Information

Version

2.0

Created at

2022-04-27 22:30:02 UTC

Updated at

2022-04-27 22:30:02 UTC

NP-MRD ID

NP0051056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Phlegmarine

Description

Phlegmarine belongs to the class of organic compounds known as quinolidines. These are organic compounds containing a quinolidine or decahydroquinoline moiety, which is a bicyclic skeleton consisting of a piperidine fused to a cyclohexane ring. (-)-Phlegmarine is found in Huperzia serrata , Lycopodiastrum casuarinoides, Palhinhaea cernua, Lycopodium phlegmaria and Lycopodium annotinum. (-)-Phlegmarine was first documented in 2016 (PMID: 26871307). Based on a literature review a small amount of articles have been published on Phlegmarine (PMID: 30928888) (PMID: 31181922) (PMID: 29947225) (PMID: 28322567).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
   -1.8455   -1.2981    2.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7536   -1.8237    1.1818 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4083   -1.3955    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3531    0.0801    0.6589 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9231    0.7558    0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1174    0.4243    1.1479 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3078    1.2382    0.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    0.7537   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098   -0.7236   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9198   -1.4414   -0.1465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3988   -0.9897    1.1041 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4573    0.6552   -0.2314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8303    1.2379   -1.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9631    1.6916   -2.4025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805    1.6441   -1.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122    0.3341   -1.2144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455   -0.3662   -0.6776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9224   -1.3018    0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4258   -2.0415    3.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396   -1.1729    3.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4313   -0.3567    2.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774   -2.9331    1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3375   -1.9736    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4515   -1.7709   -0.4875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340    0.3505    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2093    0.6879   -0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    1.8663    0.4833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9483    0.7102    2.2057 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9354    2.2759    0.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834    1.2112    1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1515    0.8858   -1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8068    1.2738   -0.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322   -0.7664    0.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5869   -1.0890   -1.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1506   -2.5093   -0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2155   -1.2964   -0.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691   -1.3619    1.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9518    1.4926    0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022    2.1046   -1.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053    0.4188   -2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164    2.7588   -2.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514    1.0835   -3.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.9039   -2.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3472    2.4128   -0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3524    0.3344   -0.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370   -1.0034   -1.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4399   -2.1474   -0.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6884   -0.8238    1.0551 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 11  6  1  0
 17 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  1
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  5 27  1  0
  6 28  1  1
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 17 46  1  6
 18 47  1  0
 18 48  1  0
M  END


  Mrv1652304282200302D          

 18 20  0  0  1  0            999 V2000
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    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
  1  6  1  0  0  0  0
  2  7  1  1  0  0  0
  8  7  1  1  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
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  6  0  0  0
 10 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H](C[C@@H]2CCCCN2)[C@H]2CCCN[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H30N2/c1-12-9-13(11-14-5-2-3-7-17-14)15-6-4-8-18-16(15)10-12/h12-18H,2-11H2,1H3/t12-,13+,14+,15-,16-/m1/s1

> <INCHI_KEY>
HLJWSLBSLJLQBA-LYYZXLFJSA-N

> <FORMULA>
C16H30N2

> <MOLECULAR_WEIGHT>
250.43

> <EXACT_MASS>
250.240898974

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
31.495782780858026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S,7R,8aR)-7-methyl-5-{[(2S)-piperidin-2-yl]methyl}-decahydroquinoline

> <ALOGPS_LOGP>
3.06

> <JCHEM_LOGP>
2.7601607079999995

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.939764736207414

> <JCHEM_POLAR_SURFACE_AREA>
24.06

> <JCHEM_REFRACTIVITY>
76.9198

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phlegmarine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -2.667   1.540   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   10                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₃₀N₂

Average Mass

250.4300 Da

Monoisotopic Mass

250.24090 Da

IUPAC Name

(4aR,5S,7R,8aR)-7-methyl-5-{[(2S)-piperidin-2-yl]methyl}-decahydroquinoline

Traditional Name

phlegmarine

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H](C[C@@H]2CCCCN2)[C@H]2CCCN[C@@H]2C1

InChI Identifier

InChI=1S/C16H30N2/c1-12-9-13(11-14-5-2-3-7-17-14)15-6-4-8-18-16(15)10-12/h12-18H,2-11H2,1H3/t12-,13+,14+,15-,16-/m1/s1

InChI Key

HLJWSLBSLJLQBA-LYYZXLFJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Huperzia serrata	Plant	KNApSAcK
Lycopodiastrum casuarinoides	-	KNApSAcK
Palhinhaea cernua	-	KNApSAcK
Phlegmariurus phlegmaria	Plant	KNApSAcK
Spinulum annotinum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolidines. These are organic compounds containing a quinolidine or decahydroquinoline moiety, which is a bicyclic skeleton consisting of a piperidine fused to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolidines

Sub Class

Not Available

Direct Parent

Quinolidines

Alternative Parents

Substituents

Quinolidine
Piperidine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

organic heterobicyclic compound (CHEBI:8109 )
organonitrogen heterocyclic compound (CHEBI:8109 )

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	3.06	ALOGPS
logP	2.76	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	10.94	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	24.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.92 m³·mol⁻¹	ChemAxon
Polarizability	31.5 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

C00001954

Chemspider ID

390922

KEGG Compound ID

C09892

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442494

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xiong J, Meng WJ, Zhang HY, Zou Y, Wang WX, Wang XY, Yang QL, Osman EEA, Hu JF: Lycofargesiines A-F, further Lycopodium alkaloids from the club moss Huperzia fargesii. Phytochemistry. 2019 Jun;162:183-192. doi: 10.1016/j.phytochem.2019.03.015. Epub 2019 Mar 29. [PubMed:30928888 ]
Bosch C, Bradshaw B, Bonjoch J: Decahydroquinoline Ring (13)C NMR Spectroscopic Patterns for the Stereochemical Elucidation of Phlegmarine-Type Lycopodium Alkaloids: Synthesis of (-)-Serralongamine A and Structural Reassignment and Synthesis of (-)-Huperzine K and (-)-Huperzine M (Lycoposerramine Y). J Nat Prod. 2019 Jun 28;82(6):1576-1586. doi: 10.1021/acs.jnatprod.9b00071. Epub 2019 Jun 5. [PubMed:31181922 ]
Pinto A, Picciche M, Griera R, Molins E, Bosch J, Amat M: Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline. J Org Chem. 2018 Aug 3;83(15):8364-8375. doi: 10.1021/acs.joc.8b00983. Epub 2018 Jul 10. [PubMed:29947225 ]
Pinto A, Griera R, Molins E, Fernandez I, Bosch J, Amat M: Access to Enantiopure 5-, 7-, and 5,7-Substituted cis-Decahydroquinolines: Enantioselective Synthesis of (-)-Cermizine B. Org Lett. 2017 Apr 7;19(7):1714-1717. doi: 10.1021/acs.orglett.7b00492. Epub 2017 Mar 21. [PubMed:28322567 ]
Zhang LD, Zhong LR, Xi J, Yang XL, Yao ZJ: Enantioselective Total Synthesis of Lycoposerramine-Z Using Chiral Phosphoric Acid Catalyzed Intramolecular Michael Addition. J Org Chem. 2016 Mar 4;81(5):1899-904. doi: 10.1021/acs.joc.5b02723. Epub 2016 Feb 22. [PubMed:26871307 ]

Showing NP-Card for (-)-Phlegmarine (NP0051056)

MOL for NP0051056 ((-)-Phlegmarine)

3D MOL for NP0051056 ((-)-Phlegmarine)

3D SDF for NP0051056 ((-)-Phlegmarine)

3D-SDF for NP0051056 ((-)-Phlegmarine)

PDB for NP0051056 ((-)-Phlegmarine)

3D PDB for NP0051056 ((-)-Phlegmarine)

SMILES for NP0051056 ((-)-Phlegmarine)

INCHI for NP0051056 ((-)-Phlegmarine)

Structure for NP0051056 ((-)-Phlegmarine)

3D Structure for NP0051056 ((-)-Phlegmarine)