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Polygamain

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	O=C1OC[C@H]2[C@H]1[C@H](c1ccc3c(c1)OCO3)c1c(C2)cc2c(c1)OCO2
InChI	InChI=1S/C20H16O6/c21-20-19-12(7-22-20)3-11-5-16-17(26-9-25-16)6-13(11)18(19)10-1-2-14-15(4-10)24-8-23-14/h1-2,4-6,12,18-19H,3,7-9H2/t12-,18+,19-/m0/s1
InChIKey	SCTKDFCQZSBHEE-RQUSPXKASA-N
Formula	C₂₀H₁₆O₆
HBA	6
HBD	0
MW	352.34
Rotatable Bonds	1
TPSA	63.22
LogP	2.62
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	352.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Haplophyllum tuberculatum	Rutaceae	Plantae	452784

Showing of synonyms

M. Sheriha G, Abouamer K, et al. (1987). Quinoline alkaloids and cytotoxic lignans from Haplophyllum tuberculatum. Phytochemistry, 1987, 26(12), 3339-3341. [View]

Pubchem: 156202

Cas: 71640-49-8

Zinc: ZINC000001647415

Nmrshiftdb2: 70055840

Chembl: CHEMBL465763

No compound-protein relationship available.

SMILES: O1COc(c12)cc3c(c2)C(C4C(C3)COC4=O)c(c5)ccc(c56)OCO6

Level: 1

Mol. Weight: 352.34 g/mol

SMILES: O1COc(c12)cc3c(c2)CC4C(C3)COC4=O

Level: 0

Mol. Weight: 352.34 g/mol

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 352.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.16
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.8
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.55

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.49
Plasma Protein Binding: 78.47
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: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 14.85
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.33
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.53
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.46
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: -12.82
Rat (Acute): 2.17
Rat (Chronic Oral): 1.41
Fathead Minnow: 4.76
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 488.92
Hydration Free Energy: -5.95
Log(D) at pH=7.4: 2.88
Log(P): 3.05
Log S: -4.73
Log(Vapor Pressure): -9.71
Melting Point: 197.5
pKa Acid: 9.48
pKa Basic: 3.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.9667
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9597
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9582
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9482
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9471
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9392
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9215
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.9014
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8955
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8927
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8829
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8757
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8659
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8394
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8283
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8254
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8214
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8182
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8169
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7967
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7923
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7901
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7694
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7691
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7653
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7641
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7587
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7571
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7552
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7529
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7526
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7515
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7477
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7475
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7464
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7459
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7459
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7446
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7439
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7374
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7330
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7321
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7315
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7314
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7303
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7297
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7291
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7286
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7273
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	2	0.7266
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7252
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7251
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7245
Rifampin ADP-ribosyl transferase	A0QRS5	A0QRS5_MYCS2	Mycolicibacterium smegmatis155)	3	0.7229
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7213
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7206
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7189
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7181
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7164
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7155
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7141
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7128
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7093
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7092
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.7091
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7081
Actin, alpha skeletal muscle	P68135	ACTS_RABIT	Oryctolagus cuniculus	3	0.7062
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7062
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7045
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7012
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7002
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7000

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