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Inherent Properties, Identifiers and References
ChemSpider ID: 21105581
Empirical Formula: C20H30O4
Molecular Weight: 334.4498
Nominal Mass: 334 Da
Average Mass: 334.4498 Da
Monoisotopic Mass: 334.214409 Da
Systematic Name:
SMILES: OC(=O)[C@@]5(C)CCC[C@]1(C)[C@@H]5CC[C@@]24C[C@H]3C[C@@](O)(CC[C@@​H]12)[C@@H]4O3
InChI: InChI=1/C20H30O4/c1-17-6-3-7-18(2,16(21)22)13(17)4-8-19-10-12-11-​20(23,15(19)24-12)9-5-14(17)19/h12-15,23H,3-11H2,1-2H3,(H,21,22)/​t12-,13-,14-,15+,17+,18-,19+,20-/m0/s1
InChIKey: KVZUXTIZQSVUTI-VFJLVGHCBZ
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Description

Quesnoin, a novel unique pure organic compound, was isolated from amber discovered in the Oise River area of the Paris basin (France) and dated at 55 million years old. 1H and 13C NMR indicated an unknown diterpene skeleton, quesnane. The absolute configurations of the eight chiral centers of quesnoin were determined to be 4S, 5S, 8R, 9S, 10S, 13S, 14R, and 16S. The work indicated that the climate of the Paris basin might have been tropical in the early Eocene period, 55 million years ago.

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Names and Synonyms

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Quesnoin

(1R,4S,5S​,9S,10S,1​3S,15S,17​R)-13-Hyd​roxy-5,9-​dimethyl-​16-oxapen​tacyclo[1​3.2.1.0~1​,10~.0~4,​9~.0~13,1​7~]octade​cane-5-ca​rboxylic ​acid

4H-2,3b-m​ethanophe​nanthro[1​,2-b]fura​n-6-carbo​xylic aci​d, tetrad​ecahydro-​11a-hydro​xy-6,9a-d​imethyl-,​ (2S,3aR,​3bR,5aS,6​S,9aS,9bS​,11aS)-

(Details...) Predicted Properties
LogP: ACD/LogP: 3.03
# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): 2.1 ACD/LogD (pH 7.4): 0.3
ACD/BCF (pH 5.5): ACD/BCF (pH 7.4):
ACD/KOC (pH 5.5): ACD/KOC (pH 7.4):
#H bond acceptors: 4 #H bond donors: 2
#Freely Rotating Bonds: 2 Polar Surface Area: 66.76 Å2
Index of Refraction: 1.587 Molar Refractivity: 89.31 cm3
Molar Volume: 265.4 cm3 Polarizability: 35.4 10-24cm3
Surface Tension: 54.1 dyne/cm Density: 1.25 g/cm3
Flash Point: 175.1 °C Enthalpy of Vaporization: 88.14 kJ/mol
Boiling Point: 497.4 °C at 760 mmHg Vapour Pressure: 5.62E-12 mmHg at 25°C