Table 1.

Computed Physicochemical Properties of Swertiamarin

Property	Result/value
Common name	Swertiamarin
Synonyms	Swertiamarine; Swertiamaroside; Swertiamari; Wertiamarin
Category	Iridoid/Seco-iridoid
IUPAC name	(3S,4R,4aR)-4-ethenyl-4a-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,5,6-tetrahydropyrano[3,4-c]pyran-8-one
Other name(s)	(4aR,5R,6S)-5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-1H,3H-pyrano[3,4-c]pyran-1-one; 4,4a,5,6-tetrahydro-4aa-hydroxy-1-oxo-5b-vinyl-1H,3H-pyrano[3,4-c]pyran-6-yl b-D-glucopyranoside; 4,4a,5,6-tetrahydro-4a-hydroxy-6-(tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)-5-vinylpyrano[3,4-c]pyran-(3H)-one
Canonical SMILES	C=CC1C(OC=C2C1(CCOC2=O)O)OC3C(C(C(C(O3)CO)O)O)O
Isomeric SMILES	C=C[C@H]1[C@@H](OC=C2[C@]1(CCOC2=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Molecular formula	C16H22O10
Molecular weight	374.34 g/mol
Hydrogen bond donors	5
Hydrogen bond acceptors	10
Rotatable bonds	4
Log P (partition coefficient value)	0.64 (Predicted)
Molar refractivity	82.12 cm3
Topological polar surface area	155 Å2
Percent composition	C = 51.34%, H = 5.92%, O = 42.74%
Optical rotation	[α]D20 −127° (c=1 in 96% ethanol)
XLogP3-AA	−2
Molar mass	374.121297 Da
Monoisotopic mass	374.121297 Da
Heavy atom count	26
Formal charge	0
Complexity	592
Isotope atom count	0
Atom stereocenter count	8
Bond stereocenter count	0
Covalently-bonded unit count	1
Canonicalized	Yes
Melting point	113–114 °C
Boiling point	649.3±55.0 °C (Predicted)
Appearance	Slightly pale yellow crystals
Solubility	Soluble in DMSO, formation of yellow solution in methanol
Density	1.57±0.1 g/cm3 (Predicted)
pKa	11.56±0.60 (Predicted)
Molar volume	278.51
Molecular polar surface area	155.14
Molecular 3D-polar SASA	264.008
Molecular SASA	523.67
Molar refraction	82.12