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3beta-angeloyloxy-10beta-hydroxy-8beta-methoxyeremophilenolide

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

Canonical Smiles	C/C=C(\C(=O)O[C@H]1CC[C@]2([C@]([C@H]1C)(C)CC1=C(C)C(=O)O[C@@]1(C2)OC)O)/C
InChI	InChI=1S/C21H30O6/c1-7-12(2)17(22)26-16-8-9-20(24)11-21(25-6)15(13(3)18(23)27-21)10-19(20,5)14(16)4/h7,14,16,24H,8-11H2,1-6H3/b12-7-/t14-,16-,19+,20-,21+/m0/s1
InChIKey	JEEFDVONXYYLJM-PTVDUSQZSA-N
Formula	C₂₁H₃₀O₆
HBA	6
HBD	1
MW	378.47
Rotatable Bonds	3
TPSA	82.06
LogP	3.04
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.71
Exact Mass	378.2
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hertia cheirifolia	Asteraceae-Compositae	Plantae	430993

Showing of synonyms

Aclinou P, Benkouider A, et al. (1991). Eremophilenolides from Hertia cheirifolia. Phytochemistry,1991,30(6),2083-2084. [View]

Pubchem: 14633025

Zinc: ZINC000238765115

Nmrshiftdb2: 70023814

No compound-protein relationship available.

SMILES: C1C(=O)OC(C=12)CC3C(C2)CCCC3

Level: 0

Mol. Weight: 192.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.43
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.69
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.47
Plasma Protein Binding: 63.92
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.16
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.11
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.72
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.0
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -10.36
Rat (Acute): 3.11
Rat (Chronic Oral): 1.61
Fathead Minnow: 3.92
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 363.23
Hydration Free Energy: -4.97
Log(D) at pH=7.4: 2.89
Log(P): 3.26
Log S: -3.5
Log(Vapor Pressure): -6.18
Melting Point: 124.95
pKa Acid: 8.27
pKa Basic: 4.82

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.9441
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.9441
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9268
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9268
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.9248
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.9248
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8401
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8401
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7876
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7876
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7848
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7848
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7812
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7812
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7723
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7723
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7722
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7722
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7716
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7716
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7715
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7715
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7649
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7649
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7504
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7504
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7323
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7323
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	4	0.7290
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	4	0.7290
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7226
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7226
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7102
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7102
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7006
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7006
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7001
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7001

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