Identification

PhytoHub ID
PHUB000180
Name
Obacunone
Systematic Name
Not Available
Synonyms
  • Casimirolide
CAS Number
Not Available
Average Mass
454.519
Monoisotopic Mass
454.199153306
Chemical Formula
C26H30O7
IUPAC Name
(1R,2R,4S,7S,8S,11R,12R,18R)-7-(furan-3-yl)-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-ene-5,15,20-trione
InChI Key
MAYJEFRPIKEYBL-OASIGRBWSA-N
InChI Identifier
InChI=1S/C26H30O7/c1-22(2)16-12-17(27)25(5)15(23(16,3)9-7-18(28)32-22)6-10-24(4)19(14-8-11-30-13-14)31-21(29)20-26(24,25)33-20/h7-9,11,13,15-16,19-20H,6,10,12H2,1-5H3/t15-,16+,19+,20-,23-,24+,25+,26-/m1/s1
SMILES
C[[email protected]@]12CC[[email protected]@H]3[[email protected]@]4(C)C=CC(=O)OC(C)(C)[[email protected]@H]4CC(=O)[[email protected]@]3(C)[[email protected]]11O[[email protected]@H]1C(=O)O[[email protected]]2C1=COC=C1
Structure

Calculated Properties

Solubility (ALOGPS)
2.37e-02 g/l
LogS (ALOGPS)
-4.28
LogP (ALOGPS)
3.76
Hydrogen Acceptors
4
Hydrogen Donors
0
Rotatable Bond Count
1
Polar Surface Area
95.34
Refractivity
116.18639999999999
Polarizability
47.04394128321587
Formal Charge
0
Physiological Charge
0
pKa (strongest basic)
-2.8727490624590906
pKa (strongest acidic)
19.63172958869265
Number of Rings
6
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy

Family
Terpenoids
Class
Triterpenoids
Sub-class
Limonoids

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Prenol lipids
Super-class
Lipids and lipid-like molecules
Sub-class
Triterpenoids
Direct Parent Name
Limonoids
Alternative Parent Names
["1,4-dioxepanes", "Delta valerolactones", "Dialkyl ethers", "Dicarboxylic acids and derivatives", "Enoate esters", "Epoxides", "Furans", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Ketones", "Naphthalenes", "Naphthopyrans", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Pyrans"]
External Descriptor Annotations
["Limonoids", "limonoid"]
Substituent Names
["1,4-dioxepane", "Alpha,beta-unsaturated carboxylic ester", "Aromatic heteropolycyclic compound", "Carbonyl group", "Carboxylic acid derivative", "Carboxylic acid ester", "Delta valerolactone", "Delta_valerolactone", "Dialkyl ether", "Dicarboxylic acid or derivatives", "Dioxepane", "Enoate ester", "Ether", "Furan", "Heteroaromatic compound", "Hydrocarbon derivative", "Ketone", "Lactone", "Limonoid skeleton", "Naphthalene", "Naphthopyran", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Oxirane", "Pyran"]

Spectra

No spectra information available

Food Sources

NameGroup
Sour orangeFruit, Citrus PublicationsShow

Metabolism

No metabolism information available

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