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Ancistrobrevine H

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

Canonical Smiles	COc1cc2C[C@@H](C)N[C@@H](c2c(c1c1ccc(c2c1cc(C)cc2OC)OC)OC)C
InChI	InChI=1S/C26H31NO4/c1-14-10-19-18(8-9-20(28-4)24(19)21(11-14)29-5)25-22(30-6)13-17-12-15(2)27-16(3)23(17)26(25)31-7/h8-11,13,15-16,27H,12H2,1-7H3/t15-,16-/m1/s1
InChIKey	MWONATDKBORUOS-HZPDHXFCSA-N
Formula	C₂₆H₃₁NO₄
HBA	5
HBD	1
MW	421.54
Rotatable Bonds	5
TPSA	48.95
LogP	5.44
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 abbreviatus	Ancistrocladaceae	Plantae	122295

Showing of synonyms

Fayez S, Feineis D, et al. (2018). Ancistrobrevines E-J and related naphthylisoquinoline alkaloids from the West African liana Ancistrocladus abbreviatus with inhibitory activities against Plasmodium falciparum and PANC-1 human pancreatic cancer cells. Fitoterapia, 2018, 131, 245-259. [View]

Pubchem: 155552929

Chembl: CHEMBL4544997

No compound-protein relationship available.

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

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

Anti-plasmodial

Absorption

Caco-2 (logPapp): -5.2
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.820
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.35

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.260
Plasma Protein Binding: 72.97
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-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: 8.390
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.980
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.080
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 10.220
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: Toxic
T. Pyriformis: -56.390
Rat (Acute): 2.910
Rat (Chronic Oral): 2.010
Fathead Minnow: 5.760
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: 469.720
Hydration Free Energy: -4.550
Log(D) at pH=7.4: 3.990
Log(P): 4.96
Log S: -4.49
Log(Vapor Pressure): -8.46
Melting Point: 146.48
pKa Acid: 12.37
pKa Basic: 10.13

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	0.9524
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9405
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.9267
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9119
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8871
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.8559
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8429
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8348
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8327
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8319
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8274
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8257
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8198
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.8192
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8135
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.8096
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.8061
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.8048
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7911
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7900
Endolysin	P00720	ENLYS_BPT4	Enterobacteria phage T4	3	0.7878
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7858
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7834
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7827
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7825
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7814
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7792
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7789
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7783
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7758
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7702
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7698
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7680
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7664
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7611
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7590
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7580
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7526
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7506
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7474
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7442
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7433
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7415
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7411
Ketimine reductase mu-crystallin	O54983	CRYM_MOUSE	Mus musculus	3	0.7410
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7402
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7392
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7370
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7349
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7345
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7334
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7321
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7294
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7287
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7281
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7263
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7249
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.7249
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7245
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7240
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7235
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7221
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7219
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7218
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7205
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7174
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7133
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7128
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7113
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7105
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	4	0.7096
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7085
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7071
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7055
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	4	0.7046
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7023
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7021
Thyroxine-binding globulin	P05543	THBG_HUMAN	Homo sapiens	3	0.7007

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