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N-acetylanonaine

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid

Canonical Smiles	CC(=O)N1CCc2c3[C@H]1Cc1ccccc1c3c1c(c2)OCO1
InChI	InChI=1S/C19H17NO3/c1-11(21)20-7-6-13-9-16-19(23-10-22-16)18-14-5-3-2-4-12(14)8-15(20)17(13)18/h2-5,9,15H,6-8,10H2,1H3/t15-/m1/s1
InChIKey	XVIHBNVDAPQBRH-OAHLLOKOSA-N
Formula	C₁₉H₁₇NO₃
HBA	3
HBD	0
MW	307.35
Rotatable Bonds	0
TPSA	38.77
LogP	3.08
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	307.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Monanthotaxis discolor	Annonaceae	Plantae	2231809

Showing of synonyms

Sumary DP, Mgina CA, et al. (2020). Isolation and antimicrobial activities of a novel discolornolide and other compounds from Monanthotaxis discolor. Natural product research,2020, 34(22), 3163-3168. [View] [PubMed]

Pubchem: 6453733

Cas: 5894-74-6

Gnps: CCMSLIB00009919217

Chebi: 169298

Nmrshiftdb2: 60021984

Chembl: CHEMBL454847

Comptox: DTXSID90207682

No compound-protein relationship available.

SMILES: O1COc(c12)cc3c4c2c5c(cccc5)CC4NCC3

Level: 0

Mol. Weight: 307.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.29
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.17
Plasma Protein Binding: 75.59
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 12.55
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.17
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.78
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.69
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: 0.88
Rat (Acute): 2.19
Rat (Chronic Oral): 1.7
Fathead Minnow: 4.49
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 422.75
Hydration Free Energy: -8.55
Log(D) at pH=7.4: 2.63
Log(P): 3.4
Log S: -4.01
Log(Vapor Pressure): -8.52
Melting Point: 172.85
pKa Acid: 11.1
pKa Basic: 5.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9530
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9441
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.9412
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9362
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9302
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.9205
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.9178
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.9086
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8993
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8989
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8930
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8889
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.8886
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8791
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8788
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8780
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8775
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.8770
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8690
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.8682
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8644
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8633
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8584
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8569
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8546
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8514
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8513
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8442
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8418
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8344
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8296
E3 ubiquitin-protein ligase Mdm2	Q00987	MDM2_HUMAN	Homo sapiens	3	0.8294
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8291
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8271
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8223
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.8199
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8185
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	4	0.8161
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8132
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.8087
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8082
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.8072
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8013
Calmodulin-2	P0DP24	CALM2_HUMAN	Homo sapiens	3	0.7981
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7972
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7935
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7921
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7911
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7911
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7894
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7878
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	4	0.7872
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7872
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7868
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7860
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7855
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7848
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7837
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7813
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7794
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7778
Abscisic acid receptor PYL1	Q8VZS8	PYL1_ARATH	Arabidopsis thaliana	3	0.7773
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7771
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7741
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7721
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7720
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7719
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7706
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7698
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7693
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7687
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7684
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7683
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7680
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7675
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7651
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7635
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7633
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7623
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7619
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7606
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7603
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7594
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7578
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7576
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7564
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7549
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7541
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7514
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	3	0.7506
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7490
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7486
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7477
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7460
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7444
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7431
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7427
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7405
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7389
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7387
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7381
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7349
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7348
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7346
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7340
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7331
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7325
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7325
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7321
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7320
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7314
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7311
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	3	0.7288
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7288
Mitogen-activated protein kinase 1	P63086	MK01_RAT	Rattus norvegicus	3	0.7283
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7279
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7278
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7273
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7264
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7257
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7246
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7245
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7238
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7236
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7234
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7233
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7229
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7229
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7226
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	2	0.7226
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7225
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7223
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7214
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7213
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7207
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7189
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7179
Kynurenine 3-monooxygenase	P38169	KMO_YEAST	Saccharomyces cerevisiae	2	0.7176
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7159
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7142
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7135
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7126
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7123
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7119
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7109
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7102
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7100
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7092
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7091
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7083
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7083
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7075
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7065
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7065
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7063
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7050
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7046
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7044
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7017
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7016
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7015
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7009
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7008
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7003
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7002
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7001

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