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8,15-diydroxygermacra-1(10),4,11(13)-trien-(12,6)-olide-14-al 15-O-beta-D-glucopyranoside 2'-p-hydroxyphenylacetate

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

Canonical Smiles	OCC1OC(OC/C/2=C\[C@H]3OC(=O)C(=C)[C@@H]3[C@H](C/C(=C\CC2)/C=O)O)C(C(C1O)O)OC(=O)Cc1ccc(cc1)O
InChI	InChI=1S/C29H34O12/c1-15-24-20(33)9-17(12-30)3-2-4-18(10-21(24)39-28(15)37)14-38-29-27(26(36)25(35)22(13-31)40-29)41-23(34)11-16-5-7-19(32)8-6-16/h3,5-8,10,12,20-22,24-27,29,31-33,35-36H,1-2,4,9,11,13-14H2/b17-3+,18-10-/t20-,21+,22?,24+,25?,26?,27?,29?/m0/s1
InChIKey	HTXHLEQRUIDRPP-NENSKQIUSA-N
Formula	C₂₉H₃₄O₁₂
HBA	12
HBD	5
MW	574.58
Rotatable Bonds	8
TPSA	189.28
LogP	-0.0
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.48
Exact Mass	574.21
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Urospermum picroides	Asteraceae	Plantae	268113

Showing of synonyms

Balboul BAAA, Ahmed AA, et al. (1997). Sesquiterpene lactones and glycosides from Urospermum picroides. Phytochemistry,1997,45(2),369-373. [View]

Pubchem: 162816839

Nmrshiftdb2: 60046513

No compound-protein relationship available.

SMILES: c1ccccc1CC(=O)OC2C(OCCC2)OCC(=CC(C34)OC(=O)C3=C)CCC=CCC4

Level: 2

Mol. Weight: 574.58 g/mol

SMILES: C=C1C(=O)OC(C12)C=C(CCC=CCC2)COC3CCCCO3

Level: 1

Mol. Weight: 574.58 g/mol

SMILES: C1OCCCC1OC(=O)Cc2ccccc2

Level: 1

Mol. Weight: 574.58 g/mol

SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2

Level: 0

Mol. Weight: 574.58 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 574.58 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 574.58 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.95
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.85
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.66
Plasma Protein Binding: 31.14
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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.17
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.6
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.79
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 8.2
Micronucleos: Toxic
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: -5894.27
Rat (Acute): 3.82
Rat (Chronic Oral): 3.33
Fathead Minnow: 16.43
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 424.27
Hydration Free Energy: -2.93
Log(D) at pH=7.4: 1.08
Log(P): -0.14
Log S: -2.45
Log(Vapor Pressure): -10.06
Melting Point: 148.59
pKa Acid: 5.27
pKa Basic: 3.18

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9026
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9026
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7899
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7899
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7509
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7509
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7447
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7447
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7391
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7391
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7350
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7350
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7242
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7242
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7204
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7204
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7120
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7120
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7051
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7051
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7044
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7044
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7033
CCR4-NOT transcription complex subunit 6-like	Q96LI5	CNO6L_HUMAN	Homo sapiens	4	0.7033
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7029
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7029
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7026
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7026

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