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Ancistrotanzanine C

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

Canonical Smiles	COc1c2c(C[C@@H](N([C@@H]2C)C)C)cc(c1c1c(C)cc2c(c1O)c(OC)ccc2)O
InChI	InChI=1S/C25H29NO4/c1-13-10-16-8-7-9-19(29-5)22(16)24(28)20(13)23-18(27)12-17-11-14(2)26(4)15(3)21(17)25(23)30-6/h7-10,12,14-15,27-28H,11H2,1-6H3/t14-,15+/m0/s1
InChIKey	UKOYLRKCEGOLOJ-LSDHHAIUSA-N
Formula	C₂₅H₂₉NO₄
HBA	5
HBD	2
MW	407.51
Rotatable Bonds	3
TPSA	62.16
LogP	5.18
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.36
Exact Mass	407.21
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ancistrocladus tanzaniensis	Ancistrocladaceae	Plantae	714107

Showing of synonyms

Bringmann G, Dreyer M, et al. (2004). Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. Journal of Natural Products,2004,67(5),743-748. [View] [PubMed]

Pubchem: 11350305

Cas: 692755-31-0

Zinc: ZINC000040874580

Nmrshiftdb2: 70030610

Chembl: CHEMBL465753

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 407.51 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 407.51 g/mol

Antiprotozoal

Absorption

Caco-2 (logPapp): -4.94
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.87
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.12
Plasma Protein Binding: 79.55
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.0
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.88
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.59
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.2
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: -31.36
Rat (Acute): 2.47
Rat (Chronic Oral): 2.09
Fathead Minnow: 4.88
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: 469.61
Hydration Free Energy: -7.16
Log(D) at pH=7.4: 3.76
Log(P): 4.34
Log S: -4.57
Log(Vapor Pressure): -8.63
Melting Point: 146.44
pKa Acid: 8.58
pKa Basic: 8.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8925
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8925
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8574
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8574
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8574
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8574
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8391
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8391
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8386
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.8386
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	4	0.8345
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	4	0.8345
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8249
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8249
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8231
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8231
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.8221
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.8221
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8062
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8062
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7987
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7987
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7981
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7981
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7957
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7957
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7874
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7874
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7829
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7829
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7782
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7782
Serine hydroxymethyltransferase	Q7SIB6	Q7SIB6_GEOSE	Geobacillus stearothermophilus	3	0.7776
Serine hydroxymethyltransferase	Q7SIB6	Q7SIB6_GEOSE	Geobacillus stearothermophilus	3	0.7776
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7720
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7720
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7710
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7710
Adenylate cyclase 2	A0A2U2H3Y1	A0A384LKY8_YERPE	Yersinia pestis	3	0.7673
Adenylate cyclase 2	A0A2U2H3Y1	A0A384LKY8_YERPE	Yersinia pestis	3	0.7673
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7649
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7649
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7617
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7617
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7614
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7614
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	3	0.7610
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	3	0.7610
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7601
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7601
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7599
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7599
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7590
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7590
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7576
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7576
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7575
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7575
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7574
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7574
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic	P80030	FABI_BRANA	Brassica napus	4	0.7507
Enoyl-[acyl-carrier-protein] reductase [NADH], chloroplastic	P80030	FABI_BRANA	Brassica napus	4	0.7507
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	4	0.7459
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	4	0.7459
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7445
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7445
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7432
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7432
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7423
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7423
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7419
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7419
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7368
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7368
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7269
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	4	0.7269
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7248
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7248
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	5	0.7240
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	5	0.7240
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7212
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7212
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7198
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7198
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7176
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7176
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7165
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7165
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7150
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7150
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7143
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7143
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7137
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7137
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7116
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7116
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7115
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7115
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7091
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7091
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7071
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7071
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7060
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7060
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7051
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7051
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7044
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7044
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7040
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7040
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7027
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7027
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7019
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7019
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7007
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7007

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