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

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Inherent Properties, Identifiers and References

ChemSpider ID:	21105569
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-ZQXRTKJUBO

Std. InChI:

InChI=1S/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

Std. InChIKey:

KVZUXTIZQSVUTI-ZQXRTKJUSA-N

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Supplemental Information

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.

Links & References

[DOI: 10.1021/jo701544k]

Jossang J., Bel-Kassaoui H. , Jossang A., Seuleiman M., and Nel A.. Quesnoin, a Novel Pentacyclic ent-Diterpene from 55 Million Years Old Oise Amber, J. Org. Chem., 2008, 73 (2), 412 -417

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