NP-MRD: Showing NP-Card for Ephedrannin A (NP0056424)

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Record Information

Version

2.0

Created at

2022-04-28 02:12:45 UTC

Updated at

2022-04-28 02:12:45 UTC

NP-MRD ID

NP0056424

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ephedrannin A

Description

TG(10:0/10:0/10:0), Also known as caprin or glycerol tridecanoate, belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Thus, TG(10:0/10:0/10:0) Is considered to be a triradylglycerol lipid molecule. TG(10:0/10:0/10:0) Is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. TG(10:0/10:0/10:0) Exists in all eukaryotes, ranging from yeast to humans. In humans, TG(10:0/10:0/10:0) Is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway. Ephedrannin A is found in Daphniphyllum angustifolium, Ephedra sinica , Ephedra sp., Prunus armeniaca and Prunus prostrata. Ephedrannin A was first documented in 1970 (PMID: 5485729). A TG(10:0/10:0/10:0) Obtained by formal acylation of the three hydroxy groups of glycerol by capric (decanoic) acid (PMID: 21858376) (PMID: 11556330) (PMID: 10917917) (PMID: 12099290).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652302282012312D          

 41 47  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652302282012312D          

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 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 18 22  1  0  0  0  0
 27 22  2  0  0  0  0
 23 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 29  1  0  0  0  0
 21 32  1  0  0  0  0
 16 21  2  0  0  0  0
 31 16  1  0  0  0  0
 30 31  2  0  0  0  0
 32 33  2  0  0  0  0
 30 33  1  0  0  0  0
 20 34  2  0  0  0  0
 32 35  1  0  0  0  0
 30 40  1  0  0  0  0
  4 37  1  0  0  0  0
  2 38  1  0  0  0  0
  8 39  1  1  0  0  0
  9 40  1  6  0  0  0
 15 41  1  0  0  0  0
 36 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0056424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/s1

> <INCHI_KEY>
GPBSBBVDERLESN-QZFRTWIZSA-N

> <FORMULA>
C30H20O11

> <MOLECULAR_WEIGHT>
556.4732

> <EXACT_MASS>
556.100561482

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
54.54784110938584

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
4.558855188666667

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.299883314368577

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.165066351673676

> <JCHEM_PKA_STRONGEST_BASIC>
-3.883854989685802

> <JCHEM_POLAR_SURFACE_AREA>
186.36999999999998

> <JCHEM_REFRACTIVITY>
143.09700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-FEB-20         0                                  
HETATM    1  C   UNK     0     -10.487   5.647   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.820   4.877   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.820   3.337   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.487   2.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.153   3.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.153   4.877   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.819   5.647   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.486   3.337   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.486   4.877   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.152   5.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.818   7.957   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.152   7.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.818   4.877   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.485   5.647   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.485   7.187   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.693  -0.744   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.027  -1.514   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.027  -3.054   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.693  -3.824   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.360  -3.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.360  -1.514   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.361  -3.824   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.694  -3.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.028  -3.824   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.028  -5.364   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.694  -6.134   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.361  -5.364   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.362  -6.134   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.693  -5.364   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.360   1.566   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.693   0.796   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.026  -0.744   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.026   0.796   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.026  -3.824   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.692  -1.514   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -7.819   2.567   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0     -10.487   1.027   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -13.154   5.647   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -5.152   2.567   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.360   3.106   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.151   7.957   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   38                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   37                                                  
CONECT    5    4    6   36                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6    9                                                       
CONECT    8   36    9   39                                                  
CONECT    9    8    7   10   40                                             
CONECT   10    9   12   13                                                  
CONECT   11   12   15                                                       
CONECT   12   10   11                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   41                                                  
CONECT   16   17   21   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   34                                                  
CONECT   21   20   32   16                                                  
CONECT   22   18   27   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   22   26                                                       
CONECT   28   25                                                            
CONECT   29   19                                                            
CONECT   30   31   33   40                                                  
CONECT   31   16   30   36                                                  
CONECT   32   21   33   35                                                  
CONECT   33   32   30                                                       
CONECT   34   20                                                            
CONECT   35   32                                                            
CONECT   36    5    8   31                                                  
CONECT   37    4                                                            
CONECT   38    2                                                            
CONECT   39    8                                                            
CONECT   40   30    9                                                       
CONECT   41   15                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Value	Source
1,2,3-Propanol tridecanoate	ChEBI
1,2,3-Tridecanoylglycerol	ChEBI
Capric acid triglyceride	ChEBI
Capric triglyceride	ChEBI
Caprin	ChEBI
Decanoic acid, 1,2,3-propanetriyl ester	ChEBI
Glycerin tridecanoate	ChEBI
Glycerol tricaprate	ChEBI
Glycerol tridecanoate	ChEBI
Glyceryl tricaprate	ChEBI
Glyceryl tridecanoate	ChEBI
TG 10:0/10:0/10:0	ChEBI
Tri-N-caprin	ChEBI
Tricapric glyceride	ChEBI
Tridecanoin	ChEBI
Tridecanoylglycerol	ChEBI
1,2,3-Propanol tridecanoic acid	Generator
Caprate triglyceride	Generator
Decanoate, 1,2,3-propanetriyl ester	Generator
Glycerin tridecanoic acid	Generator
Glycerol tricapric acid	Generator
Glycerol tridecanoic acid	Generator
Glyceryl tricapric acid	Generator
Glyceryl tridecanoic acid	Generator
1-Animal fats-2-animal fats-3-animal fats-glycerol	HMDB
1-Decanoic acid-2-decanoic acid-3-decanoic acid-glycerol	HMDB
TAG(10:0/10:0/10:0)	HMDB
Triacylglycerol	HMDB
Tracylglycerol(30:0)	HMDB
Triglyceride	HMDB
Tracylglycerol(10:0/10:0/10:0)	HMDB
TAG(30:0)	HMDB
TG(30:0)	HMDB
1,2, 3-Propanetriyl-decanoate	HMDB
1,2, 3-Propanetriyl-decanoic acid	HMDB
2,3-Bis(decanoyloxy)propyl decanoate	HMDB
2,3-Bis(decanoyloxy)propyl decanoate (acd/name 4.0)	HMDB
2,3-Bis(decanoyloxy)propyl decanoic acid	HMDB
Glycerol tricaprin	HMDB
Tri-decanoin	HMDB
Tricaprin	HMDB
3,4',5,7-Tetrahydroxyflavan(2->7,4->8)-3,4',5,7-tetrahydroxyflavone	HMDB
3,5,11,13,15-Pentahydroxy-2,8-bis(4-hydroxyphenyl)-8,14-methano-4H,14H-1-benzopyrano[7,8-D][1,3]benzodioxocin-4-one, 9ci	HMDB
ent-Epiafzelechin(2a->o-7,4a->8)kaempferol	HMDB
Ephedrannin a	MeSH

Chemical Formula

C₃₀H₂₀O₁₁

Average Mass

556.4732 Da

Monoisotopic Mass

556.10056 Da

IUPAC Name

(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

Traditional Name

(1S,13R,21S)-6,9,17,19,21-pentahydroxy-5,13-bis(4-hydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0^{2,11}.0^{3,8}.0^{15,20}]henicosa-2(11),3(8),5,9,15(20),16,18-heptaen-7-one

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H]2C3=C(O[C@@]1(OC1=C2C2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1)C=C(O)C=C3O

InChI Identifier

InChI=1S/C30H20O11/c31-14-5-1-12(2-6-14)27-26(37)25(36)22-18(35)11-20-23(28(22)39-27)24-21-17(34)9-16(33)10-19(21)40-30(41-20,29(24)38)13-3-7-15(32)8-4-13/h1-11,24,29,31-35,37-38H/t24-,29-,30+/m0/s1

InChI Key

GPBSBBVDERLESN-QZFRTWIZSA-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
Daphniphyllum angustifolium	LOTUS Database	35616633
Ephedra sinica	Plant	KNApSAcK
Ephedra sp.	Plant	KNApSAcK
Prunus armeniaca	Plant	KNApSAcK
Prunus prostrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

Alternative Parents

Substituents

Triacyl-sn-glycerol
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

triglyceride (CHEBI:77388 )
Triacylglycerols (LMGL03012617 )

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	3.31	ALOGPS
logP	4.56	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.17	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	186.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	143.1 m³·mol⁻¹	ChemAxon
Polarizability	54.55 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000548

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003134

KNApSAcK ID

Not Available

Chemspider ID

62521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5532

PubChem Compound

69310

PDB ID

Not Available

ChEBI ID

77388

Good Scents ID

Not Available

References

General References

Troller JA, Bozeman MA: Isolation and characterization of a staphylococcal lipase. Appl Microbiol. 1970 Sep;20(3):480-4. [PubMed:5485729 ]
Brasiello A, Crescitelli S, Milano G: Development of a coarse-grained model for simulations of tridecanoin liquid-solid phase transitions. Phys Chem Chem Phys. 2011 Oct 6;13(37):16618-28. doi: 10.1039/c1cp20604d. Epub 2011 Aug 22. [PubMed:21858376 ]
Mottram HR, Evershed RP: Elucidation of the composition of bovine milk fat triacylglycerols using high-performance liquid chromatography-atmospheric pressure chemical ionisation mass spectrometry. J Chromatogr A. 2001 Aug 17;926(2):239-53. doi: 10.1016/s0021-9673(01)01048-2. [PubMed:11556330 ]
Fontagne S, Corraze G, Bergot P: Tricaproin, tricaprin and trilaurin are utilized more efficiently than tricaprylin by carp (Cyprinus carpio L.) larvae. J Nutr. 2000 Aug;130(8):2009-15. doi: 10.1093/jn/130.8.2009. [PubMed:10917917 ]
Schaefer MJ, Singh J: Effect of tricaprin on the physical characteristics and in vitro release of etoposide from PLGA microspheres. Biomaterials. 2002 Aug;23(16):3465-71. doi: 10.1016/s0142-9612(02)00053-4. [PubMed:12099290 ]

Showing NP-Card for Ephedrannin A (NP0056424)

MOL for NP0056424 (Ephedrannin A)

3D MOL for NP0056424 (Ephedrannin A)

3D SDF for NP0056424 (Ephedrannin A)

3D-SDF for NP0056424 (Ephedrannin A)

PDB for NP0056424 (Ephedrannin A)

3D PDB for NP0056424 (Ephedrannin A)

SMILES for NP0056424 (Ephedrannin A)

INCHI for NP0056424 (Ephedrannin A)

Structure for NP0056424 (Ephedrannin A)

3D Structure for NP0056424 (Ephedrannin A)