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Ancistrocongoline D

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

Canonical Smiles	COc1c2[C@@H](C)N[C@@H](Cc2cc(c1c1c(C)cc(c2c1cccc2OC)OC)O)C
InChI	InChI=1S/C25H29NO4/c1-13-10-20(29-5)23-17(8-7-9-19(23)28-4)21(13)24-18(27)12-16-11-14(2)26-15(3)22(16)25(24)30-6/h7-10,12,14-15,26-27H,11H2,1-6H3/t14-,15-/m1/s1
InChIKey	RPYYNECGOSGRFR-HUUCEWRRSA-N
Formula	C₂₅H₂₉NO₄
HBA	5
HBD	2
MW	407.51
Rotatable Bonds	4
TPSA	59.95
LogP	5.14
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 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: 10409129

Cas: 455255-22-8

Zinc: ZINC000013359035

Nmrshiftdb2: 70128624

Chembl: CHEMBL489959

No compound-protein relationship available.

SMILES: c1cccc(c12)cccc2-c(c3)ccc(c34)CCNC4

Level: 1

Mol. Weight: 259.35 g/mol

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 133.19 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.01
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: -1.64

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.29
Plasma Protein Binding: 78.09
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: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.81
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.88
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.15
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 9.64
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: -34.23
Rat (Acute): 2.58
Rat (Chronic Oral): 2.01
Fathead Minnow: 5.35
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: 468.23
Hydration Free Energy: -5.91
Log(D) at pH=7.4: 4.03
Log(P): 4.32
Log S: -4.72
Log(Vapor Pressure): -8.76
Melting Point: 156.43
pKa Acid: 10.13
pKa Basic: 9.49

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	0.9530
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9530
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9135
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9135
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8918
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8918
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8782
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8782
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8744
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8744
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8605
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8605
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.8533
Dihydrofolate reductase type 1 from Tn4003	P13955	DYRA_STAAU	Staphylococcus aureus	4	0.8533
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8485
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.8485
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8478
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8478
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8438
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8438
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8355
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8355
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8311
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8311
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8246
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8246
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8228
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8228
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8215
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8215
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8180
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8180
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8173
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8173
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8060
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8060
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.8046
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.8046
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8019
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8019
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7979
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7979
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7932
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7932
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7878
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7878
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7840
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7840
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7825
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7825
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7809
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7809
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7787
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7787
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7748
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7748
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7747
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7747
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7722
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7722
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7705
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7705
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7705
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7705
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7689
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7689
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7658
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7658
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7642
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7642
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7637
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7637
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7576
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7576
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7540
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7540
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7536
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7536
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7521
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7521
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7492
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7492
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	4	0.7487
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7487
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	4	0.7487
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7487
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7481
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7481
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7393
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7393
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7363
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7363
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7354
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7354
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7329
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7329
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7323
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7323
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7267
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7267
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7267
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7267
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7250
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7250
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7248
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7248
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7242
Endoplasmin	P14625	ENPL_HUMAN	Homo sapiens	3	0.7242
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7237
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7237
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7235
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7235
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7200
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7200
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7195
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7195
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7181
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7181
Dihydrofolate reductase	P9WNX1	DYR_MYCTU	Mycobacterium tuberculosis	3	0.7172
Dihydrofolate reductase	P9WNX1	DYR_MYCTU	Mycobacterium tuberculosis	3	0.7172
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7171
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7171
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7150
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7150
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7138
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7138
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7087
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7087
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7076
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7076
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7066
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7066
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7038
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7038
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7014
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7014

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