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Aristolactam BII

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

Canonical Smiles	COc1c(OC)cc2c3c1c1ccccc1cc3[nH]c2=O
InChI	InChI=1S/C17H13NO3/c1-20-13-8-11-14-12(18-17(11)19)7-9-5-3-4-6-10(9)15(14)16(13)21-2/h3-8H,1-2H3,(H,18,19)
InChIKey	YHQIYHDLBZXUON-UHFFFAOYSA-N
Formula	C₁₇H₁₃NO₃
HBA	3
HBD	1
MW	279.3
Rotatable Bonds	2
TPSA	47.56
LogP	3.58
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.12
Exact Mass	279.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Anonidium mannii	Annonaceae	Plantae	2109291

Showing of synonyms

Matchi JLT, Noungoue DT, et al. (2021). Manniindole, an indole derivative from the roots of Anonidium mannii and combined antischistosomal and enzymatic activities. Natural product research,2021, 35(24), 5665-5673. [View] [PubMed]

Pubchem: 162739

Cas: 53948-09-7

Zinc: ZINC000006017925

Nmrshiftdb2: 60021876

Chembl: CHEMBL226772

CPRiL: 270303

SMILES: c12c3cccc2c4c(cc1NC3=O)cccc4

Level: 0

Mol. Weight: 279.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.450
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.600
Plasma Protein Binding: 74.84
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.610
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.780
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.420
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.390
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.550
Rat (Acute): 2.180
Rat (Chronic Oral): 2.090
Fathead Minnow: 4.860
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 465.120
Hydration Free Energy: -10.380
Log(D) at pH=7.4: 3.050
Log(P): 3.25
Log S: -5.27
Log(Vapor Pressure): -7.91
Melting Point: 214.85
pKa Acid: 10.12
pKa Basic: 4.22

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.9655
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.9563
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9442
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9418
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9410
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.9367
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9315
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9254
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.9252
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9192
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9019
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.9001
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8999
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8978
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8904
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8853
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8851
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8766
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8729
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8721
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8710
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8678
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8661
Mucosa-associated lymphoid tissue lymphoma translocation protein 1	Q9UDY8	MALT1_HUMAN	Homo sapiens	3	0.8619
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.8612
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8607
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.8569
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8557
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.8541
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8504
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8499
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8443
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8388
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.8370
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8348
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.8293
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8287
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.8281
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8266
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8262
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8260
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.8255
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8191
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.8177
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8176
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.8164
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.8160
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8155
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8113
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8085
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8041
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8011
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8009
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7998
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7930
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7909
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7907
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7842
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7810
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7799
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7797
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7795
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	4	0.7791
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7787
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7781
Exotoxin A	P11439	TOXA_PSEAE	Pseudomonas aeruginosa	3	0.7775
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7769
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7756
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7756
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7755
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7755
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7739
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7729
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7727
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7723
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7699
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7692
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	3	0.7687
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7680
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7674
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7659
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7648
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7646
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7646
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7645
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7626
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7595
Prostaglandin G/H synthase 2	Q05769	PGH2_MOUSE	Mus musculus	3	0.7568
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7565
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7552
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7549
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	3	0.7540
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7535
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7519
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7515
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7510
Glutamate receptor 3	P19492	GRIA3_RAT	Rattus norvegicus	3	0.7474
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7473
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7472
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7469
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7464
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7459
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7450
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7447
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7432
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7430
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7426
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7411
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7392
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7357
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7355
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7332
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7316
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7303
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7302
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7288
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7265
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7261
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7249
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7249
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7239
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7238
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7232
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7232
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7228
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7220
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7217
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7215
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7206
NmrA-like family domain-containing protein 1	Q9HBL8	NMRL1_HUMAN	Homo sapiens	2	0.7205
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7204
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7198
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7194
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7179
Serine/threonine-protein kinase VRK1	Q99986	VRK1_HUMAN	Homo sapiens	3	0.7176
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7175
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7169
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7169
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7160
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7148
Calmodulin-2	P0DP24	CALM2_HUMAN	Homo sapiens	3	0.7147
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7138
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7131
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7129
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7117
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7106
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7103
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7087
dTDP-4-dehydro-6-deoxyglucose 3-epimerase	Q5SFD1	CHMJ_STRBI	Streptomyces bikiniensis	3	0.7083
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7077
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7075
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7066
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	3	0.7059
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7055
Aklanonic acid methyl ester cyclase AcmA	O52646	DNRD_STRGJ	Streptomyces galilaeus	3	0.7051
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7051
Aurora kinase B-A	Q6DE08	AUKBA_XENLA	Xenopus laevis	3	0.7051
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7050
Mitogen-activated protein kinase 1	P63086	MK01_RAT	Rattus norvegicus	3	0.7033
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7032
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7028
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7027
Renin	P00797	RENI_HUMAN	Homo sapiens	2	0.7025
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7022
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7019
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7019
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7012
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7009

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