NP-MRD: Showing NP-Card for (1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid (NP0285357)

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Record Information

Version

1.0

Created at

2022-09-09 13:30:11 UTC

Updated at

2022-09-09 13:30:11 UTC

NP-MRD ID

NP0285357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid

Description

Chiisanogenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid is found in Eleutherococcus senticosus. It was first documented in 2005 (PMID: 16204946). Based on a literature review a significant number of articles have been published on Chiisanogenin (PMID: 33615691) (PMID: 33188566) (PMID: 33183092) (PMID: 31460786) (PMID: 30672331) (PMID: 27324351).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215302D          

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M  END

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M  END


  Mrv1652309092215302D          

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   -1.5106    2.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659    0.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6404   -0.1256    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4315   -0.3594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246   -0.5358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7053   -0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
  4 34  1  0  0  0  0
  9 34  1  0  0  0  0
 34 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0285357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](C[C@H]4OC(=O)C[C@@H](O)[C@@]5(C)[C@@H](CC[C@]3(C)[C@H]45)C(C)=C)[C@@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-16(2)18-8-11-30(26(33)34)13-12-27(5)20(24(18)30)14-21-25-28(27,6)10-9-19(17(3)4)29(25,7)22(31)15-23(32)35-21/h18-22,24-25,31H,1,3,8-15H2,2,4-7H3,(H,33,34)/t18-,19-,20+,21+,22+,24+,25-,27+,28+,29+,30-/m0/s1

> <INCHI_KEY>
BYCBJBLIOKGBPB-YQIBJACNSA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.80022486903097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,9R,10R,12R,16R,17S,18S,21S)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0^{2,10}.0^{5,9}.0^{17,21}]henicosane-5-carboxylic acid

> <JCHEM_LOGP>
5.0917127393333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.409879770510145

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.466892650528626

> <JCHEM_PKA_STRONGEST_BASIC>
-3.05691858841928

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
133.9428

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,9R,10R,12R,16R,17S,18S,21S)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0^{2,10}.0^{5,9}.0^{17,21}]henicosane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.755  -1.354   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.759  -2.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.278  -3.979   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.244  -2.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.193  -3.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.308  -3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.757  -1.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.808  -2.684   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.294  -0.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.155   1.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.655   1.388   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.706   0.262   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.207   0.609   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.952   1.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.301   3.352   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.766   3.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.183   4.614   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.464   1.664   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.653   0.136   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.258  -0.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.421  -1.526   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.128  -3.038   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.876  -1.023   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.809  -1.989   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.308  -2.337   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.257  -1.211   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.760  -2.667   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.716   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.253   2.420   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.820   3.852   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.296   1.288   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.062  -0.234   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.539  -0.671   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.726  -1.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.183  -1.498   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   34                                                  
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13   21   24                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12    7   27                                             
CONECT   27   26                                                            
CONECT   28   10   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    4    9   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

(1R,2R,5S,8R,9R,10R,12R,16R,17S,18S,21S)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0^{2,10}.0^{5,9}.0^{17,21}]henicosane-5-carboxylic acid

Traditional Name

(1R,2R,5S,8R,9R,10R,12R,16R,17S,18S,21S)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0^{2,10}.0^{5,9}.0^{17,21}]henicosane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](C[C@H]4OC(=O)C[C@@H](O)[C@@]5(C)[C@@H](CC[C@]3(C)[C@H]45)C(C)=C)[C@@H]12)C(O)=O

InChI Identifier

InChI=1S/C30H44O5/c1-16(2)18-8-11-30(26(33)34)13-12-27(5)20(24(18)30)14-21-25-28(27,6)10-9-19(17(3)4)29(25,7)22(31)15-23(32)35-21/h18-22,24-25,31H,1,3,8-15H2,2,4-7H3,(H,33,34)/t18-,19-,20+,21+,22+,24+,25-,27+,28+,29+,30-/m0/s1

InChI Key

BYCBJBLIOKGBPB-YQIBJACNSA-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
Eleutherococcus senticosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	5.09	ChemAxon
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.94 m³·mol⁻¹	ChemAxon
Polarizability	54.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00032619

Chemspider ID

10270314

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21636080

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao Y, Wang X, Chen C, Shi K, Li J, Du R: Protective Effects of 3,4-Seco-Lupane Triterpenes from Food Raw Materials of the Leaves of Eleutherococcus Senticosus and Eleutherococcus Sessiliflorus on Arrhythmia Induced by Barium Chloride. Chem Biodivers. 2021 Apr;18(4):e2001021. doi: 10.1002/cbdv.202001021. Epub 2021 Mar 31. [PubMed:33615691 ]
Wang H, Chen C, Liu R, Wang X, Zhao Y, Yan Z, Cai E, Zhu H: Potential Myocardial Protection of 3,4-seco-Lupane Triterpenoids from Acanthopanax sessiliflorus Leaves. Chem Biodivers. 2021 Jan;18(1):e2000830. doi: 10.1002/cbdv.202000830. Epub 2020 Dec 14. [PubMed:33188566 ]
Wang H, Yu W, Zhang D, Zhao Y, Chen C, Zhu H, Cai E, Yan Z: Cytotoxic and anti-tumor effects of 3,4-seco-lupane triterpenoids from the leaves of Eleutherococcus sessiliflorus against hepatocellular carcinoma. Nat Prod Res. 2022 Feb;36(4):1062-1066. doi: 10.1080/14786419.2020.1844698. Epub 2020 Nov 13. [PubMed:33183092 ]
Zhang D, Chen C, Zhao Y, Gao Y, Cai E, Zhu H: 3,4-seco-lupane triterpene derivatives with cytotoxic activities from the leaves of Eleutherococcus sessiliflorus. Nat Prod Res. 2021 Aug;35(16):2633-2639. doi: 10.1080/14786419.2019.1656622. Epub 2019 Aug 28. [PubMed:31460786 ]
Chen C, Zhang D, Zhao Y, Cai E, Zhu H, Gao Y: A new 3,4-seco-lupane triterpenene glycosyl ester from the leaves of Eleutherococcus sessiliflorus. Nat Prod Res. 2020 Jul;34(13):1927-1930. doi: 10.1080/14786419.2018.1564292. Epub 2019 Jan 23. [PubMed:30672331 ]
Song Y, Wang Z, Feng X, Deng X, Zhu J: Simultaneous determination and pharmacokinetics of four triterpenoids by ultra high performance liquid chromatography with tandem mass spectrometry after the oral administration of Acanthopanax sessiliflorus (Rupr. et Maxim) Seem extract. J Sep Sci. 2016 Jun;39(12):2229-37. doi: 10.1002/jssc.201501350. Epub 2016 May 31. [PubMed:27324351 ]
Yang C, Yu K, Song Y, Qin F, Li F: Determination and pharmacokinetic study of chiisanogenin in rat plasma by ultra performance liquid chromatography-tandem mass spectrometry. Phytochem Anal. 2011 May-Jun;22(3):225-9. doi: 10.1002/pca.1269. Epub 2010 Nov 2. [PubMed:21046686 ]
Yang C, An Q, Song Y, Xiong Z, Li F: [Isolation and identification of chemical constituents of fruits of Acanthopanax sessiliflorus]. Zhongguo Zhong Yao Za Zhi. 2009 Mar;34(6):715-7. [PubMed:19624012 ]
Won JH, Park SY, Nam SG, Park HJ, Choi JW, Lee KT: Inhibition of lipopolysaccharide-induced expression of inducible nitric oxide and cyclooxygenase-2 by chiisanoside via suppression of nuclear factor-kappaB activation in RAW 264.7 macrophage cells. Biol Pharm Bull. 2005 Oct;28(10):1919-24. doi: 10.1248/bpb.28.1919. [PubMed:16204946 ]
Jung HJ, Nam JH, Choi J, Lee KT, Park HJ: Antiinflammatory effects of chiisanoside and chiisanogenin obtained from the leaves of Acanthopanax chiisanensis in the carrageenan- and Freund's complete adjuvant-induced rats. J Ethnopharmacol. 2005 Feb 28;97(2):359-67. doi: 10.1016/j.jep.2004.11.026. Epub 2005 Jan 18. [PubMed:15707776 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid (NP0285357)

MOL for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

3D MOL for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

3D SDF for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

3D-SDF for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

PDB for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

3D PDB for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

SMILES for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

INCHI for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

Structure for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)

3D Structure for NP0285357 ((1r,2r,5s,8r,9r,10r,12r,16r,17s,18s,21s)-16-hydroxy-1,2,17-trimethyl-14-oxo-8,18-bis(prop-1-en-2-yl)-13-oxapentacyclo[10.8.1.0²,¹⁰.0⁵,⁹.0¹⁷,²¹]henicosane-5-carboxylic acid)