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Dioncophylline B

Family: Plantae - Dioncophyllaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	COc1cc(C)cc2c1c(O)c(cc2)c1ccc2c(c1O)[C@@H](C)N[C@@H](C2)C
InChI	InChI=1S/C23H25NO3/c1-12-9-15-5-7-18(23(26)21(15)19(10-12)27-4)17-8-6-16-11-13(2)24-14(3)20(16)22(17)25/h5-10,13-14,24-26H,11H2,1-4H3/t13-,14-/m1/s1
InChIKey	UOMMAZXPQFOUSU-ZIAGYGMSSA-N
Formula	C₂₃H₂₅NO₃
HBA	4
HBD	3
MW	363.46
Rotatable Bonds	2
TPSA	61.72
LogP	4.83
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	363.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Triphyophyllum peltatum	Dioncophyllaceae	Plantae	63090

Showing of synonyms

François G, Bringmann G, et al. (1995). Activities of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and Ancistrocladus barteri against Plasmodium berghei (Anka strain) in vitro. Journal of Ethnopharmacology, 1995, 46(2), 115-120. [View]

Pubchem: 178558

Cas: 140367-82-4

Zinc: ZINC000005849399

Chebi: 66273

Nmrshiftdb2: 60073073

Metabolights: MTBLC66273

Chembl: CHEMBL3827456

No compound-protein relationship available.

SMILES: c1cccc(c12)ccc(c2)-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 363.46 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 363.46 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 363.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.900
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.4

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.010
Plasma Protein Binding: 89.78
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.340
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.910
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.720
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.240
Micronucleos: Toxic
NR-AhR: Toxic
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: -7.400
Rat (Acute): 2.540
Rat (Chronic Oral): 2.190
Fathead Minnow: 4.800
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: 456.280
Hydration Free Energy: -9.210
Log(D) at pH=7.4: 4.120
Log(P): 3.88
Log S: -4.61
Log(Vapor Pressure): -8.43
Melting Point: 184.23
pKa Acid: 8.43
pKa Basic: 8.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9322
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.9267
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.9241
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.9188
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9176
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.9090
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9082
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8946
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8918
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.8911
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.8875
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8764
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8717
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8660
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	3	0.8626
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8616
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.8612
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial	Q33862	Q33862_ASCSU	Ascaris suum	3	0.8558
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8516
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.8465
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8457
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.8428
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8370
AGAP001556-PA	Q7PXT9	Q7PXT9_ANOGA	Anopheles gambiae	3	0.8308
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.8279
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.8271
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8266
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8205
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8152
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8144
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8004
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	3	0.7956
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7940
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7887
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7874
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7856
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7851
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7850
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7843
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7837
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7833
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7802
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7801
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	3	0.7797
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7785
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7755
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7744
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7730
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7726
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7711
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7639
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7636
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7630
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7614
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7612
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7611
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7603
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7589
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7577
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7577
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7576
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7575
Tyrosine-protein kinase ABL1	P00519	ABL1_HUMAN	Homo sapiens	4	0.7573
Cytochrome P450 130	P9WPN5	CP130_MYCTU	Mycobacterium tuberculosis	3	0.7553
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7526
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	4	0.7517
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7508
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7499
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7492
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7486
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.7467
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7462
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7455
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	4	0.7450
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7449
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7446
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	3	0.7438
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7434
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7388
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7370
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7344
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7336
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7313
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7309
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7308
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7307
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7291
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic	P80030	FABI_BRANA	Brassica napus	4	0.7289
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7281
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7265
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7265
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7264
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7249
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7241
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7238
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7232
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7224
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7222
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7201
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7184
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7179
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7160
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7160
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7155
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7154
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7133
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7124
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	3	0.7124
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7116
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7108
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7107
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7090
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7086
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7083
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7079
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7066
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7064
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7062
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7053
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7049
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7048
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7033
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7029
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7026
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	4	0.7016
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7016
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7009
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7005
Fructose-1,6-bisphosphatase 1	P00636	F16P1_PIG	Sus scrofa	3	0.7002
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7001

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