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Neopulchellin

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

Canonical Smiles	CC1C[C@H]2OC(=O)C(=C)[C@H]2C[C@]2(C1C(O)CC2O)C
InChI	InChI=1S/C15H22O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-13,16-17H,2,4-6H2,1,3H3/t7?,9-,10?,11-,12?,13?,15-/m1/s1
InChIKey	BPUNWVGCTMEMKQ-PFQOCRRASA-N
Formula	C₁₅H₂₂O₄
HBA	4
HBD	2
MW	266.34
Rotatable Bonds	0
TPSA	66.76
LogP	1.26
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	19
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	266.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Gaillardia aristata	Asteraceae	Plantae	55624

Showing of synonyms

Salama MM, Kandil ZA and Islam WT. (2012). Cytotoxic compounds from the leaves of Gaillardia aristata Pursh. growing in Egypt. Natural Product Research,2012,26(22),2057-2062. [View] [PubMed]

Pubchem: 366039

No compound-protein relationship available.

SMILES: C=C1C(=O)OC(C12)CCC3C(C2)CCC3

Level: 0

Mol. Weight: 266.34 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.77
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.46
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.5
Plasma Protein Binding: 32.52
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: 9.33
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.1
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.99
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.41
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: 2.17
Rat (Acute): 3.14
Rat (Chronic Oral): 1.86
Fathead Minnow: 3.84
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 347.15
Hydration Free Energy: -8.75
Log(D) at pH=7.4: 0.96
Log(P): 0.62
Log S: -2.03
Log(Vapor Pressure): -6.33
Melting Point: 147.83
pKa Acid: 8.53
pKa Basic: 6.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8641
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8641
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8494
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8494
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8355
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8355
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8164
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8164
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8044
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8044
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8044
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8044
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8012
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8012
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8009
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8009
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7965
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7965
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7915
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7915
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7896
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7896
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7860
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7860
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7770
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7770
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7735
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7735
Corticosteroid-binding globulin	P31211	CBG_RAT	Rattus norvegicus	3	0.7712
Corticosteroid-binding globulin	P31211	CBG_RAT	Rattus norvegicus	3	0.7712
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7706
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7706
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7682
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7682
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7653
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7653
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7495
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7495
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7451
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7451
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7334
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7334
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7299
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7299
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7274
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7274
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7267
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7267
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7234
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7234
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7199
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7199
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7171
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7171
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7151
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7151
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7110
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7110
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7110
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7110
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7092
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7092
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7075
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7075
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7072
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7072
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7055
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7055
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7047
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7047
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7014
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7014
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7006
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7006

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