NP-MRD: Showing NP-Card for Loliolide C-3 Anomer (NP0331670)

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Record Information

Version

2.0

Created at

2023-06-01 12:00:18 UTC

Updated at

2024-09-03 04:16:27 UTC

NP-MRD ID

NP0331670

Natural Product DOI

https://doi.org/10.57994/0666

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Loliolide C-3 Anomer

Description

Isololiolide belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Loliolide C-3 Anomer was first documented in 2006 (PMID: 16872130). Based on a literature review a significant number of articles have been published on isololiolide (PMID: 24955560) (PMID: 33926330) (PMID: 33179569) (PMID: 31136901) (PMID: 27981801) (PMID: 27064014).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.4797   -0.4946    1.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0835   -0.3259   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1050   -0.9850   -1.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875    1.1450   -0.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0914    1.8961    0.0445 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0187    3.2345   -0.3955 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.2902   -0.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -0.1197    0.0531 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5742   -0.1583    1.5834 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5755   -0.8585   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474   -2.0240   -0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617   -2.9728   -1.4516 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851   -1.9901   -0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2733   -0.8963   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8505   -1.2390    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5464    0.4818    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5149   -0.9522    1.3138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -2.0296   -1.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -0.4144   -2.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1181   -1.0090   -0.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    1.2332   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0096    1.6188   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0150    1.9684    1.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7888    3.6788   -0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4232    1.3654   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143    1.8770    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8130    0.4417    2.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5690    0.2452    1.8977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5425   -1.2173    1.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645   -2.7892   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  1
  8  7  1  0
  7  5  1  0
  5  6  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 14  1  0
 14 13  2  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 14  8  1  0
 10  8  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  7 25  1  0
  7 26  1  0
  5 23  1  1
  6 24  1  0
  4 21  1  0
  4 22  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
 13 30  1  0
M  END


  Mrv1652306302200182D          

 14 15  0  0  1  0            999 V2000
    1.8371    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0251   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2505   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
  6 12  1  0  0  0  0
  6 13  1  0  0  0  0
  4 14  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0331670

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@@H](O)CC(C)(C)C1=CC(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11-/m0/s1

> <INCHI_KEY>
XEVQXKKKAVVSMW-CPCISQLKSA-N

> <FORMULA>
C11H16O3

> <MOLECULAR_WEIGHT>
196.246

> <EXACT_MASS>
196.109944375

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
20.716189866304873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S,7aS)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.1080473940000004

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.127833489157034

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7428856318427135

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
52.558800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S,7aS)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-22         0                                  
HETATM    1  C   UNK     0       3.429   0.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.126  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.647  -4.203   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.201  -4.203   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12   13                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2                                                       
CONECT   12    6                                                            
CONECT   13    6                                                            
CONECT   14    4                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₆O₃

Average Mass

196.2460 Da

Monoisotopic Mass

196.10994 Da

IUPAC Name

(6S,7aS)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

Traditional Name

(6S,7aS)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@@H](O)CC(C)(C)C1=CC(=O)O2

InChI Identifier

InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11-/m0/s1

InChI Key

XEVQXKKKAVVSMW-CPCISQLKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	fatimah2940@uitm.edu.my	Not Available	Not Available	2023-06-01	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	fatimah2940@uitm.edu.my	Not Available	Not Available	2023-06-01	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	fatimah2940@uitm.edu.my	Not Available	Not Available	2023-06-01	View Spectrum
HMQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	fatimah2940@uitm.edu.my	Not Available	Not Available	2023-06-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	fatimah2940@uitm.edu.my	Not Available	Not Available	2023-06-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	fatimah2940@uitm.edu.my	Not Available	Not Available	2023-06-01	View Spectrum

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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
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	1.66	ALOGPS
logP	1.11	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	15.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.56 m³·mol⁻¹	ChemAxon
Polarizability	20.72 Å³	ChemAxon
Number of Rings	2	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

C00019146

Chemspider ID

9194965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11019783

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao J, Evangelopoulos D, Bhakta S, Gray AI, Seidel V: Antitubercular activity of Arctium lappa and Tussilago farfara extracts and constituents. J Ethnopharmacol. 2014 Aug 8;155(1):796-800. doi: 10.1016/j.jep.2014.06.034. Epub 2014 Jun 20. [PubMed:24955560 ]
Xu W, Wang J, Ju B, Lan X, Ying X, Stien D: Seven compounds from Portulaca oleracea L. and their anticholinesterase activities. Nat Prod Res. 2022 May;36(10):2547-2553. doi: 10.1080/14786419.2021.1916928. Epub 2021 Apr 30. [PubMed:33926330 ]
Baruah VJ, Paul R, Gogoi D, Mazumder N, Chakraborty S, Das A, Mondal TK, Sarmah B: Integrated computational approach toward discovery of multi-targeted natural products from Thumbai (Leucas aspera) for attuning NKT cells. J Biomol Struct Dyn. 2022 Apr;40(7):2893-2907. doi: 10.1080/07391102.2020.1844056. Epub 2020 Nov 12. [PubMed:33179569 ]
Lima ML, Romanelli MM, Borborema SET, Johns DM, Migotto AE, Lago JHG, Tempone AG: Antitrypanosomal activity of isololiolide isolated from the marine hydroid Macrorhynchia philippina (Cnidaria, Hydrozoa). Bioorg Chem. 2019 Aug;89:103002. doi: 10.1016/j.bioorg.2019.103002. Epub 2019 May 20. [PubMed:31136901 ]
Salem AB, Di Giuseppe G, Anesi A, Hammami S, Mighri Z, Guella G: Natural Products among Brown Algae: The Case of Cystoseira schiffneri Hamel (Sargassaceae, Phaeophyceae). Chem Biodivers. 2017 Apr;14(4). doi: 10.1002/cbdv.201600333. Epub 2017 Mar 20. [PubMed:27981801 ]
Vizetto-Duarte C, Custodio L, Gangadhar KN, Lago JH, Dias C, Matos AM, Neng N, Nogueira JM, Barreira L, Albericio F, Rauter AP, Varela J: Isololiolide, a carotenoid metabolite isolated from the brown alga Cystoseira tamariscifolia, is cytotoxic and able to induce apoptosis in hepatocarcinoma cells through caspase-3 activation, decreased Bcl-2 levels, increased p53 expression and PARP cleavage. Phytomedicine. 2016 May 15;23(5):550-7. doi: 10.1016/j.phymed.2016.02.008. Epub 2016 Feb 26. [PubMed:27064014 ]
Fang HY, Chokkalingam U, Chiou SF, Hwang TL, Chen SL, Wang WL, Sheu JH: Bioactive chemical constituents from the brown alga Homoeostrichus formosana. Int J Mol Sci. 2014 Dec 30;16(1):736-46. doi: 10.3390/ijms16010736. [PubMed:25561228 ]
Pan W, Liu K, Guan Y, Tan GT, Hung NV, Cuong NM, Soejarto DD, Pezzuto JM, Fong HH, Zhang H: Bioactive compounds from Vitex leptobotrys. J Nat Prod. 2014 Mar 28;77(3):663-7. doi: 10.1021/np400779v. Epub 2014 Jan 9. [PubMed:24404757 ]
Ratnayake R, Liu Y, Paul VJ, Luesch H: Cultivated sea lettuce is a multiorgan protector from oxidative and inflammatory stress by enhancing the endogenous antioxidant defense system. Cancer Prev Res (Phila). 2013 Sep;6(9):989-99. doi: 10.1158/1940-6207.CAPR-13-0014. [PubMed:24005795 ]
Sadhu SK, Okuyama E, Fujimoto H, Ishibashi M: Diterpenes from Leucas aspera inhibiting prostaglandin-induced contractions. J Nat Prod. 2006 Jul;69(7):988-94. doi: 10.1021/np058118m. [PubMed:16872130 ]

Showing NP-Card for Loliolide C-3 Anomer (NP0331670)

MOL for NP0331670 (Loliolide C-3 Anomer)

3D MOL for NP0331670 (Loliolide C-3 Anomer)

3D SDF for NP0331670 (Loliolide C-3 Anomer)

3D-SDF for NP0331670 (Loliolide C-3 Anomer)

PDB for NP0331670 (Loliolide C-3 Anomer)

3D PDB for NP0331670 (Loliolide C-3 Anomer)

SMILES for NP0331670 (Loliolide C-3 Anomer)

INCHI for NP0331670 (Loliolide C-3 Anomer)

Structure for NP0331670 (Loliolide C-3 Anomer)

3D Structure for NP0331670 (Loliolide C-3 Anomer)