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Korupensamine C

Family: Plantae - Ancistrocladaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Naphthylisoquinoline Alkaloid

Canonical Smiles	COc1ccc(c2c1c(OC)cc(c2)C)c1c(O)cc(c2c1C[C@@H](C)N[C@@H]2C)O
InChI	InChI=1S/C24H27NO4/c1-12-8-16-15(6-7-20(28-4)24(16)21(9-12)29-5)23-17-10-13(2)25-14(3)22(17)18(26)11-19(23)27/h6-9,11,13-14,25-27H,10H2,1-5H3/t13-,14-/m1/s1
InChIKey	PLLKZICNVDBVIE-ZIAGYGMSSA-N
Formula	C₂₄H₂₇NO₄
HBA	5
HBD	3
MW	393.48
Rotatable Bonds	3
TPSA	70.95
LogP	4.84
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	393.19
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus korupensis	Ancistrocladaceae	Plantae	63089

Showing of synonyms

Hallock YF, Manfredi KP, et al. (1994). Korupensamines A-D, Novel Antimalarial Alkaloids from Ancistrocladus korupensis. J. Org. Chem. 1994, 59, 21, 6349–6355. [View]

Pubchem: 392422

Zinc: ZINC000003811681

Nmrshiftdb2: 70077123

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c3cccc(c34)CNCC4

Level: 1

Mol. Weight: 393.48 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 393.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.18
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.910
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.09

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.110
Plasma Protein Binding: 80.07
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.510
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.430
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.500
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.000
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -19.180
Rat (Acute): 2.250
Rat (Chronic Oral): 2.190
Fathead Minnow: 4.910
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: 460.250
Hydration Free Energy: -7.740
Log(D) at pH=7.4: 3.870
Log(P): 4.22
Log S: -4.66
Log(Vapor Pressure): -8.81
Melting Point: 180.36
pKa Acid: 9.31
pKa Basic: 9.52

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9372
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9372
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9346
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9346
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9238
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9238
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9006
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9006
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8999
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8999
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8799
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8799
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8610
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8610
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8512
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8512
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8197
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8197
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8146
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8146
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8018
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8018
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7937
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7937
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7907
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7907
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7797
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7797
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7766
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7766
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7712
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7712
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.7581
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.7581
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7554
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7554
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7554
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7554
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7536
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7536
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7535
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7535
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7413
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7413
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7398
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7398
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7293
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7293
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7287
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7287
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7269
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7269
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7239
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7239
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7234
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7234
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7179
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7179
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7121
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7121
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7119
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7119
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7079
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7079
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7075
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7075
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7057
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7057
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7055
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7055
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7044
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7044
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7019
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7019

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