6alpha,8alpha,15-trihydroxyelema-1,3,11(13)-trien-12-olide methyl ester - Compound Card

6alpha,8alpha,15-trihydroxyelema-1,3,11(13)-trien-12-olide methyl ester

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6alpha,8alpha,15-trihydroxyelema-1,3,11(13)-trien-12-olide methyl ester

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene

Canonical Smiles	COC(=O)C(=C)C1[C@@H](O)C[C@@](C([C@H]1O)C(=C)CO)(C)C=C
InChI	InChI=1S/C16H24O5/c1-6-16(4)7-11(18)12(10(3)15(20)21-5)14(19)13(16)9(2)8-17/h6,11-14,17-19H,1-3,7-8H2,4-5H3/t11-,12?,13?,14-,16+/m0/s1
InChIKey	ZAUMFTVHLHASMN-PSRQBXPCSA-N
Formula	C₁₆H₂₄O₅
HBA	5
HBD	3
MW	296.36
Rotatable Bonds	5
TPSA	86.99
LogP	0.81
Number Rings	1
Number Aromatic Rings	0
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.56
Exact Mass	296.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Centaurea papposa	Asteraceae	Plantae	1006337

Showing of synonyms

Grafakou M.E, Barda C, et al. (2022). In vitro cytotoxic and anti-inflammatory activities of sesquiterpene lactones from Centaurea papposa (Coss.) Greuter. Natural product research, 2022, 36(12), 3211-3215. [View] [PubMed]

No compound-protein relationship available.

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 296.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.89
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.370
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.420
Plasma Protein Binding: 39.89
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.390
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 340.250
Hydration Free Energy: -13.510
Log(D) at pH=7.4: 0.600
Log(P): 1.55
Log S: -1.93
Log(Vapor Pressure): -6.71
Melting Point: 100.51
pKa Acid: 6.92
pKa Basic: 4.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.9472
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.8493
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8311
Iota toxin component Ia	Q46220	Q46220_CLOPF	Clostridium perfringens	3	0.8293
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8084
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8063
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7761
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7661
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7522
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7473
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7447
Alpha/beta hydrolase fold protein	D2J2T6	D2J2T6_9RHIZ	Ochrobactrum sp. T63	3	0.7310
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7025
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7009