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8-oxo-pinoresinol

Family: Plantae - Caryophyllaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	COc1cc(ccc1O)[C@@H]1OC[C@H]2[C@@H]1C(=O)O[C@H]2c1ccc(c(c1)O)O
InChI	InChI=1S/C19H18O7/c1-24-15-7-10(3-5-13(15)21)18-16-11(8-25-18)17(26-19(16)23)9-2-4-12(20)14(22)6-9/h2-7,11,16-18,20-22H,8H2,1H3/t11-,16-,17-,18-/m0/s1
InChIKey	QCJIWHHQLRNORM-VMCJVTOISA-N
Formula	C₁₉H₁₈O₇
HBA	7
HBD	3
MW	358.35
Rotatable Bonds	3
TPSA	105.45
LogP	2.41
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	358.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pteranthus dichotomus	Caryophyllaceae	Plantae	325512

Showing of synonyms

Allaoua Z, Benkhaled M, et al. (2016). Chemical composition, antioxidant and antibacterial properties of Pteranthus dichotomus from Algerian Sahara. Natural product research, 2016, 30(6), 700-4. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(OC2=O)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 358.35 g/mol

SMILES: O=C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 358.35 g/mol

SMILES: C1OCC(C12)C(OC2=O)c3ccccc3

Level: 1

Mol. Weight: 358.35 g/mol

SMILES: O=C1OCC(C12)COC2

Level: 0

Mol. Weight: 358.35 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 358.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.31
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.910
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.060
Plasma Protein Binding: 76.81
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: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 11.300
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.550
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.170
Micronucleos: Toxic
NR-AhR: Toxic
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: -2.640
Rat (Acute): 2.280
Rat (Chronic Oral): 2.540
Fathead Minnow: 4.090
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 461.650
Hydration Free Energy: -7.910
Log(D) at pH=7.4: 2.140
Log(P): 0.7
Log S: -3.9
Log(Vapor Pressure): -8.85
Melting Point: 233.93
pKa Acid: 7.8
pKa Basic: 4.31

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	0.9266
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9211
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8658
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8631
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8599
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8575
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8504
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8470
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8410
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8410
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8149
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8148
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8145
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8098
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7989
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	4	0.7926
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7898
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7890
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7842
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7726
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7708
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7695
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7694
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7615
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7606
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7604
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7582
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7540
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7535
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7535
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.7529
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7508
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7502
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7497
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7494
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7466
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7457
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7447
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7435
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7425
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7389
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7377
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7374
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7353
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	4	0.7345
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7335
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7307
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7285
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7270
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	4	0.7229
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7225
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7221
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7122
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7086
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7081
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7076
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7072
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7045

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