3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone - Compound Card

3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone

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3-acetoxy-7-hydroxy-5-tigloyloxycarvotacetone

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Carvotacetone Derivative

Canonical Smiles	C/C=C(/C(=O)O[C@H]1C(C(C)C)[C@H](OC(=O)C)C=C(C1=O)CO)\C
InChI	InChI=1S/C17H24O6/c1-6-10(4)17(21)23-16-14(9(2)3)13(22-11(5)19)7-12(8-18)15(16)20/h6-7,9,13-14,16,18H,8H2,1-5H3/b10-6+/t13-,14?,16+/m1/s1
InChIKey	NUENJLVLKHHYJS-XZYCGLOESA-N
Formula	C₁₇H₂₄O₆
HBA	6
HBD	1
MW	324.37
Rotatable Bonds	5
TPSA	89.9
LogP	1.57
Number Rings	1
Number Aromatic Rings	0
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.59
Exact Mass	324.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Sphaeranthus bullatus	Asteraceae	Plantae	1548657

Showing of synonyms

Machumi F, Yenesew A, et al. (2012). Antiparasitic and anticancer carvotacetone derivatives of Sphaeranthus bullatus. Natural Product Communications,2012,7(9),1123-1126. [View] [PubMed]

No compound-protein relationship available.

SMILES: O=C1C=CCCC1

Level: 0

Mol. Weight: 324.37 g/mol

Anti-leishmanial

Anti-plasmodial

Anticancer

Absorption

Caco-2 (logPapp): -4.64
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.53
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.1

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.25
Plasma Protein Binding: 51.04
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

General Properties

Boiling Point: 327.19
Hydration Free Energy: -9.38
Log(D) at pH=7.4: 1.61
Log(P): 2.06
Log S: -2.78
Log(Vapor Pressure): -5.77
Melting Point: 103.85
pKa Acid: 8.63
pKa Basic: 4.57

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8824
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8824
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8133
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8133
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7956
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7956
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7593
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7593
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7568
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7568
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7443
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7443
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7407
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7407