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(-)-syringaresinol

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Furanolignan

Canonical Smiles	COc1cc(cc(c1O)OC)[C@@H]1OCC2C1CO[C@H]2c1cc(OC)c(c(c1)OC)O
InChI	InChI=1S/C22H26O8/c1-25-15-5-11(6-16(26-2)19(15)23)21-13-9-30-22(14(13)10-29-21)12-7-17(27-3)20(24)18(8-12)28-4/h5-8,13-14,21-24H,9-10H2,1-4H3/t13?,14?,21-,22-/m0/s1
InChIKey	KOWMJRJXZMEZLD-ITQCSFDJSA-N
Formula	C₂₂H₂₆O₈
HBA	8
HBD	2
MW	418.44
Rotatable Bonds	6
TPSA	95.84
LogP	3.21
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	418.16
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Drypetes molunduana	Euphorbiaceae	Plantae	20145

Showing of synonyms

Wandji J, Wansi JD, et al. (2000). Sesquiterpene lactone and friedelane derivative from drypetes molunduana.. Phytochemistry,2000, 54(8), 811-815. [View] [PubMed]

Pubchem: 89843520

No compound-protein relationship available.

SMILES: c1ccccc1C(OC2)C(C23)COC3c4ccccc4

Level: 2

Mol. Weight: 418.44 g/mol

SMILES: C1OCC(C12)COC2c3ccccc3

Level: 1

Mol. Weight: 418.44 g/mol

SMILES: C1OCC(C12)COC2

Level: 0

Mol. Weight: 418.44 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 418.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.0
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.960
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.930
Plasma Protein Binding: 64.67
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: 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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.850
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.570
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.710
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.350
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: Toxic
T. Pyriformis: -48.990
Rat (Acute): 2.130
Rat (Chronic Oral): 2.320
Fathead Minnow: 4.740
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 449.040
Hydration Free Energy: -3.580
Log(D) at pH=7.4: 2.880
Log(P): 1.38
Log S: -4.2
Log(Vapor Pressure): -8.29
Melting Point: 167.91
pKa Acid: 8.37
pKa Basic: 2.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9642
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9475
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9418
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9282
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9109
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9080
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8947
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8883
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8740
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8718
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8630
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8464
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.8389
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8284
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.8203
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8144
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	4	0.8143
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8122
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.8109
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8107
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8092
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8073
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8001
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	4	0.7956
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7956
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7925
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7905
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7887
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7839
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7837
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7833
Uridine phosphorylase 2	O95045	UPP2_HUMAN	Homo sapiens	4	0.7819
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7801
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	4	0.7783
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	4	0.7767
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7676
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7676
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7659
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7620
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7619
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7592
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7565
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7526
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7506
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	4	0.7504
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7481
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7470
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7414
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7390
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.7384
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7374
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7357
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7347
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7344
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7337
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7335
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7329
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7310
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7308
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7300
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7288
Peroxidase C1A	P00433	PER1A_ARMRU	Armoracia rusticana	2	0.7269
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	4	0.7262
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.7260
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7241
Aspartokinase 1, chloroplastic	Q9LYU8	AK1_ARATH	Arabidopsis thaliana	3	0.7227
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7222
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7214
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7209
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	4	0.7199
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7189
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7172
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7172
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7167
Nucleoside phosphorylase, putative	Q57VZ2	Q57VZ2_TRYB2	Trypanosoma brucei brucei	4	0.7162
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7151
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7142
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7109
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7097
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7092
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	3	0.7089
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7074
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7054
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7053
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7044
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	4	0.7042
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7040
Histidine kinase 4	Q9C5U0	AHK4_ARATH	Arabidopsis thaliana	3	0.7037
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7036
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7035
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7022
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7017
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7016

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