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Hovetrichoside C

Family: Plantae - Cistaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Aurone Glycoside

Canonical Smiles	OCC1O[C@@H](Oc2cc(O)cc3c2C(=O)C(O3)(O)Cc2ccc(cc2)O)C([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C21H22O11/c22-8-14-16(25)17(26)18(27)20(31-14)30-12-5-11(24)6-13-15(12)19(28)21(29,32-13)7-9-1-3-10(23)4-2-9/h1-6,14,16-18,20,22-27,29H,7-8H2/t14?,16-,17+,18?,20-,21?/m1/s1
InChIKey	KJIWCKSQHHNTTL-RDBLRTHZSA-N
Formula	C₂₁H₂₂O₁₁
HBA	11
HBD	7
MW	450.4
Rotatable Bonds	5
TPSA	186.37
LogP	-1.22
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	450.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Helianthemum sessiliflorum	Cistaceae	Plantae	2650562

Showing of synonyms

Benabdelaziz I, Marcourt L, et al. (2017). Antioxidant and antibacterial activities and polyphenolic constituents of Helianthemum sessiliflorum Pers.. Natural product research, 2017, 31(6), 686-690. [View] [PubMed]

Pubchem: 42607791

Chebi: 179870

No compound-protein relationship available.

SMILES: c1ccccc1CC(C2=O)Oc(c23)cccc3OC4CCCCO4

Level: 2

Mol. Weight: 450.4 g/mol

SMILES: O=C1COc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 450.4 g/mol

SMILES: c1ccccc1CC(C2=O)Oc(c23)cccc3

Level: 1

Mol. Weight: 450.4 g/mol

SMILES: O=C1COc(c12)cccc2

Level: 0

Mol. Weight: 450.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 450.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 450.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.56
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.73
Plasma Protein Binding: 51.68
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: 10.05
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.49
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.81
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.36
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -73.46
Rat (Acute): 2.39
Rat (Chronic Oral): 4.09
Fathead Minnow: 4.08
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: 554.99
Hydration Free Energy: -4.36
Log(D) at pH=7.4: -0.25
Log(P): -0.86
Log S: -3.33
Log(Vapor Pressure): -11.25
Melting Point: 199.13
pKa Acid: 4.68
pKa Basic: 6.35

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8860
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8661
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8622
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8531
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.8410
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.8323
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8167
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7921
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7883
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7810
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7697
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7674
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7664
Mitogen-activated protein kinase 1	P63086	MK01_RAT	Rattus norvegicus	3	0.7635
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7633
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7552
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7546
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	3	0.7511
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7497
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7427
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7387
Isoflavone-7-O-methyltransferase 8	O24529	7OMT8_MEDSA	Medicago sativa	5	0.7357
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7333
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7287
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7287
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7253
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7247
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7247
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7241
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7220
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7185
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7184
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7161
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7142
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7138
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7102

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