NP-MRD: Showing NP-Card for Ambrosic acid (NP0064132)

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Record Information

Version

1.0

Created at

2022-04-28 08:24:52 UTC

Updated at

2022-04-28 08:24:52 UTC

NP-MRD ID

NP0064132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ambrosic acid

Description

Ambrosic acid, also known as ambrosate, belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Ambrosic acid is found in Ambrosia artemisiifolia and Ambrosia tenuifolia. It was first documented in 2022 (PMID: 35483916). Based on a literature review a significant number of articles have been published on Ambrosic acid (PMID: 35483915) (PMID: 35483914) (PMID: 35483913) (PMID: 35483912).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.5723    1.3095    0.9031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8349    0.2509    0.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -0.9371    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757   -1.9685   -0.1993 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9701   -0.9857    0.2303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    0.3810    0.4820 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7453    0.4178   -0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7417    0.6332   -0.6944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4089    0.3406   -2.0171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9582    2.0824   -0.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.9678   -0.8405 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1910    2.2197    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6476    0.7850    0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3789    0.0313    0.4735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5878    0.2610    1.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.5321    1.3349 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0400   -1.7552    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4670   -1.4433    0.5783 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1948   -2.1759   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1310    2.2441    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6429    1.2353    0.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5298   -0.9704   -0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1443    1.4415    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1369    1.3522   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159   -0.3976   -1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723   -0.3631   -2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -0.0163   -1.9402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520    1.2697   -2.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9963    2.7235   -0.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0064    2.7620    1.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0477    0.7385    1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4014    0.4858   -0.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -0.8075    2.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4106   -1.9168   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -2.6579    1.2645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8558   -1.7042    1.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767   -2.2583   -1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953   -3.2461   -0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131   -1.7968   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  1
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  8  1  0
  8  9  1  6
  8  7  1  0
  7  6  1  0
  6  2  1  0
  2  1  2  3
  2  3  1  0
  3  5  1  0
  3  4  2  0
 14 18  1  0
  8 14  1  0
  6 16  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
 18 36  1  1
 17 34  1  0
 17 35  1  0
 16 33  1  1
 13 31  1  0
 13 32  1  0
 12 29  1  0
 12 30  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  7 24  1  0
  7 25  1  0
  6 23  1  1
  1 20  1  0
  1 21  1  0
  5 22  1  0
M  END


  Mrv1652304282210242D          

 19 21  0  0  1  0            999 V2000
    0.8666   -0.7914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4129   -0.0379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8277    0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.7011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1253   -0.0522    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3147   -0.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5622   -1.3471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5044   -2.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4805   -0.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123    1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7104    2.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9372    1.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3602    2.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3392    0.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4111   -0.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0239    0.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5066   -1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2541   -1.3804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0841    0.6206    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
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  6  0  0  0
  5  9  1  1  0  0  0
  1  9  1  1  0  0  0
  4 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H]2O[C@]11CCC(=O)[C@@]1(C)C[C@@H]2C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-6-11-10(9(2)13(17)18)7-14(3)12(16)4-5-15(8,14)19-11/h8,10-11H,2,4-7H2,1,3H3,(H,17,18)/t8-,10+,11-,14+,15+/m0/s1

> <INCHI_KEY>
ZONXEWIGPLHXNT-ULEBWITMSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.378919117821642

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,5S,7R,8S,10S)-5,10-dimethyl-4-oxo-11-oxatricyclo[6.2.1.0^{1,5}]undecan-7-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
2.220890851

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.051828272646517

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.525342913650187

> <JCHEM_PKA_STRONGEST_BASIC>
-4.201117882732009

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
68.54630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,5S,7R,8S,10S)-5,10-dimethyl-4-oxo-11-oxatricyclo[6.2.1.0^{1,5}]undecan-7-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.618  -1.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.771  -0.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.545   1.358   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.153   1.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.967  -0.098   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.321  -1.684   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.916  -2.515   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.808  -4.051   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.764  -0.717   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.943   2.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.193   3.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.483   2.608   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.272   3.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.233   1.263   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.767  -0.413   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.911   0.618   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.946  -1.952   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.474  -2.577   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.157   1.158   0.000  0.00  0.00           C+0
CONECT    1    2    7    9   18                                             
CONECT    2    1    3   15   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5    1                                                       
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    1                                                       
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Ambrosate	Generator

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

2-[(1R,5S,7R,8S,10S)-5,10-dimethyl-4-oxo-11-oxatricyclo[6.2.1.0^{1,5}]undecan-7-yl]prop-2-enoic acid

Traditional Name

2-[(1R,5S,7R,8S,10S)-5,10-dimethyl-4-oxo-11-oxatricyclo[6.2.1.0^{1,5}]undecan-7-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H]2O[C@]11CCC(=O)[C@@]1(C)C[C@@H]2C(=C)C(O)=O

InChI Identifier

InChI=1S/C15H20O4/c1-8-6-11-10(9(2)13(17)18)7-14(3)12(16)4-5-15(8,14)19-11/h8,10-11H,2,4-7H2,1,3H3,(H,17,18)/t8-,10+,11-,14+,15+/m0/s1

InChI Key

ZONXEWIGPLHXNT-ULEBWITMSA-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
Ambrosia artemisiifolia	Plant	KNApSAcK
Ambrosia tenuifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Tetrahydrofuran
Ketone
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.12	ALOGPS
logP	2.22	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.55 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00021057

Chemspider ID

29814899

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75368818

PDB ID

Not Available

ChEBI ID

182484

Good Scents ID

Not Available

References

General References

Uchida Y, Kan H, Sakurai K, Horimoto Y, Hayashi E, Iida A, Okamura N, Oishi K, Matsukawa N: APOE varepsilon4 dose associates with increased brain iron and beta-amyloid via blood-brain barrier dysfunction. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2021-328519. doi: 10.1136/jnnp-2021-328519. [PubMed:35483916 ]
Cacciaguerra L, Pagani E, Radaelli M, Mesaros S, Martinelli V, Ivanovic J, Drulovic J, Filippi M, Rocca MA: MR T2-relaxation time as an indirect measure of brain water content and disease activity in NMOSD. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2022-328956. doi: 10.1136/jnnp-2022-328956. [PubMed:35483915 ]
Broomfield NM, West R, Barber M, Quinn TJ, Gillespie D, Walters M, House A: TEARS: a longitudinal investigation of the prevalence, psychological associations and trajectory of poststroke emotionalism. J Neurol Neurosurg Psychiatry. 2022 Apr 28. pii: jnnp-2022-329042. doi: 10.1136/jnnp-2022-329042. [PubMed:35483914 ]
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Showing NP-Card for Ambrosic acid (NP0064132)

MOL for NP0064132 (Ambrosic acid)

3D MOL for NP0064132 (Ambrosic acid)

3D SDF for NP0064132 (Ambrosic acid)

3D-SDF for NP0064132 (Ambrosic acid)

PDB for NP0064132 (Ambrosic acid)

3D PDB for NP0064132 (Ambrosic acid)

SMILES for NP0064132 (Ambrosic acid)

INCHI for NP0064132 (Ambrosic acid)

Structure for NP0064132 (Ambrosic acid)

3D Structure for NP0064132 (Ambrosic acid)