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Ancistrocongoline B

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

Canonical Smiles	COc1cc(O)c2c(c1c1ccc(c3c1cc(C)cc3OC)OC)C[C@H](N([C@@H]2C)C)C
InChI	InChI=1S/C26H31NO4/c1-14-10-18-17(8-9-21(29-5)26(18)22(11-14)30-6)25-19-12-15(2)27(4)16(3)24(19)20(28)13-23(25)31-7/h8-11,13,15-16,28H,12H2,1-7H3/t15-,16-/m1/s1
InChIKey	YDUMNUIISWCVDA-HZPDHXFCSA-N
Formula	C₂₆H₃₁NO₄
HBA	5
HBD	1
MW	421.54
Rotatable Bonds	4
TPSA	51.16
LogP	5.48
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	421.23
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus congolensis	Ancistrocladaceae	Plantae	714097

Showing of synonyms

Bringmann G, Messer K, et al. (2002). Ancistrocongolines A-D, new naphthylisoquinoline alkaloids from Ancistrocladus congolensis. Journal of natural products,2002, 65(8), 1096-1101. [View] [PubMed]

Pubchem: 11742933

Cas: 455255-18-2

Zinc: ZINC000036402164

Nmrshiftdb2: 70059386

Chembl: CHEMBL489149

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 421.54 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 421.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.08
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.830
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.57

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.140
Plasma Protein Binding: 74.05
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: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 9.380
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.400
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.250
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 10.380
Micronucleos: Toxic
NR-AhR: Safe
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: Toxic
T. Pyriformis: -52.240
Rat (Acute): 2.670
Rat (Chronic Oral): 1.920
Fathead Minnow: 5.380
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: 465.480
Hydration Free Energy: -4.650
Log(D) at pH=7.4: 4.200
Log(P): 4.98
Log S: -4.73
Log(Vapor Pressure): -9.17
Melting Point: 144.66
pKa Acid: 10.04
pKa Basic: 9.64

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9442
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9442
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9362
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9362
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9155
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9155
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9016
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9016
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8793
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8793
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8603
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8603
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8602
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8602
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8343
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8343
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8280
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8280
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8204
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8204
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8176
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8176
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8084
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8084
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.8068
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.8068
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8004
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8004
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8001
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8001
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7992
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7992
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7966
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7966
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7868
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7868
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7794
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7794
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7773
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7773
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7637
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7637
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7569
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7569
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7550
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7550
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7545
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7545
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7502
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7502
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7476
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7476
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7473
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7473
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7471
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7471
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7423
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7423
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7354
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7354
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7349
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7349
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7342
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7342
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7327
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7327
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7324
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7324
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7320
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7320
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7317
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7317
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7303
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7303
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7298
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7298
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7296
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7296
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7252
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7252
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7222
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7222
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7202
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7202
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7200
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7200
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7199
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7199
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7188
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7188
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7185
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7185
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7182
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7182
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7180
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7180
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7153
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7153
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7152
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7152
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7141
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7141
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7132
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7132
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7126
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7126
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7119
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7119
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7111
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7111
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7082
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7082
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7065
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7065
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7056
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7056
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7053
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7053
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7050
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7050
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7047
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7047
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7015
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7015

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