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Savinin

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Benzodioxole

Canonical Smiles	O=C1OC[C@@H](/C/1=C\c1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2
InChI	InChI=1S/C20H16O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,6-8,14H,5,9-11H2/b15-6+/t14-/m0/s1
InChIKey	CMJGAYUQSLJSCR-ULIPXBITSA-N
Formula	C₂₀H₁₆O₆
HBA	6
HBD	0
MW	352.34
Rotatable Bonds	3
TPSA	63.22
LogP	2.94
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	352.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fagara heitzii	Rutaceae	Plantae	—

Showing of synonyms

Mbaze LM, Lado JA, et al. (2009). Oxidative burst inhibitory and cytotoxic amides and lignans from the stem bark of Fagara heitzii (Rutaceae).. Phytochemistry,2009, 70(11-12), 1442-1447. [View] [PubMed]

Pubchem: 5281867

Cas: 493-95-8

Zinc: ZINC000100059302

Kegg Ligand: C10880

Chebi: 9044

Nmrshiftdb2: 60032287

Metabolights: MTBLC9044

Chembl: CHEMBL395263

Bindingdb: 429472

CPRiL: 281168

SMILES: O1COc(c12)ccc(c2)C=C3C(=O)OCC3Cc(c4)ccc(c45)OCO5

Level: 2

Mol. Weight: 352.34 g/mol

SMILES: C=C1C(=O)OCC1Cc(c2)ccc(c23)OCO3

Level: 1

Mol. Weight: 352.34 g/mol

SMILES: C1COC(=O)C1=Cc(c2)ccc(c23)OCO3

Level: 1

Mol. Weight: 352.34 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 352.34 g/mol

SMILES: C=C1C(=O)OCC1

Level: 0

Mol. Weight: 352.34 g/mol

Suppressive on phagocytosis response upon activation with serum

Absorption

Caco-2 (logPapp): -5.04
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.78
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.44
Plasma Protein Binding: 84.76
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.86
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.51
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.31
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: Toxic
T. Pyriformis: -9.01
Rat (Acute): 2.15
Rat (Chronic Oral): 1.23
Fathead Minnow: 5.27
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 475.07
Hydration Free Energy: -5.85
Log(D) at pH=7.4: 3.54
Log(P): 3.29
Log S: -5.03
Log(Vapor Pressure): -9.19
Melting Point: 133.55
pKa Acid: 9.44
pKa Basic: 3.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9584
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9466
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9153
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9138
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.9092
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8991
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8903
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8902
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8781
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8779
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8778
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8759
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8747
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8657
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8619
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8581
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8574
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8552
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8535
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8456
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8443
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8442
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.8426
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8352
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8299
Pyruvate kinase PKM	P14618	KPYM_HUMAN	Homo sapiens	3	0.8171
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8124
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8110
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8102
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8014
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.8013
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8010
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7933
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7927
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7911
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7816
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7799
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7795
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7786
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7733
Macrophage colony-stimulating factor 1 receptor	P07333	CSF1R_HUMAN	Homo sapiens	3	0.7719
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7713
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7683
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7651
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7650
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7641
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7639
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7627
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7623
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7608
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7607
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7604
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7597
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7587
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7575
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7565
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7562
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7550
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7535
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7533
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7532
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7525
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7509
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7494
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7488
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7487
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7481
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7472
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7466
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7456
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7434
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7431
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7415
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7410
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7408
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7405
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7396
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7394
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7387
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7383
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7358
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7339
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7333
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	2	0.7333
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7324
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7320
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7312
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7310
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7298
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7298
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7295
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7279
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7270
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7250
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7250
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7242
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7237
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7214
Flavin reductase like domain-containing protein	Q4UKE8	Q4UKE8_RICFE	Rickettsia felis	3	0.7205
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7194
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7194
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7179
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7164
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7161
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7154
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	2	0.7153
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7153
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	4	0.7148
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7143
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7140
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7139
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7136
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7135
Nucleoside diphosphate kinase	Q5UQL3	NDK_MIMIV	Acanthamoeba polyphaga mimivirus	2	0.7132
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7128
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	2	0.7115
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7099
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7095
High affinity nerve growth factor receptor	P04629	NTRK1_HUMAN	Homo sapiens	3	0.7093
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7093
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7086
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7085
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7082
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7078
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7072
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7072
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7071
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7067
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7062
Cyclin-dependent kinase 8	P49336	CDK8_HUMAN	Homo sapiens	3	0.7060
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7053
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7050
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7048
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7041
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7040
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7033
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7006

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