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Manniindole

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

Canonical Smiles	CC(=CCc1cccc2c1[nH]cc2C1CCCN1C(=O)N)C
InChI	InChI=1S/C18H23N3O/c1-12(2)8-9-13-5-3-6-14-15(11-20-17(13)14)16-7-4-10-21(16)18(19)22/h3,5-6,8,11,16,20H,4,7,9-10H2,1-2H3,(H2,19,22)
InChIKey	NTODKAPIVYYQMO-UHFFFAOYSA-N
Formula	C₁₈H₂₃N₃O
HBA	1
HBD	2
MW	297.4
Rotatable Bonds	3
TPSA	62.12
LogP	3.89
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.39
Exact Mass	297.18
Number of Lipinski Rule Violations	0

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

Showing of synonyms

Ngangoue MO, Ndifor AR, et al. (2024). Isolation and antibacterial activity of anomanol B and other secondary metabolites from the stem bark of Anonidium mannii (Annonaceae). Natural product research,2024, 38(11), 1813-1822. [View] [PubMed]
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]

No compound-protein relationship available.

SMILES: c1cccc(c12)[nH]cc2C3CCCN3

Level: 1

Mol. Weight: 297.4 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 297.4 g/mol

SMILES: C1CCNC1

Level: 0

Mol. Weight: 297.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.7
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.86
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.54

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.06
Plasma Protein Binding: 43.12
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 5.65
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.9
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.88
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.84
Micronucleos: Toxic
NR-AhR: Safe
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: 1.75
Rat (Acute): 2.86
Rat (Chronic Oral): 2.44
Fathead Minnow: 4.2
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: 385.14
Hydration Free Energy: -11.31
Log(D) at pH=7.4: 2.68
Log(P): 3.73
Log S: -3.67
Log(Vapor Pressure): -10.52
Melting Point: 170.89
pKa Acid: 12.17
pKa Basic: 7.21

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	0.9269
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8974
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8759
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8733
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8640
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.8597
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8553
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8432
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8408
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8269
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8197
Purine nucleoside phosphorylase, putative	A2E7Y6	A2E7Y6_TRIVA	Trichomonas vaginalis	3	0.8146
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8137
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7998
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7946
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7911
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7892
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7842
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7785
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7777
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7764
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7741
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7699
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7686
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7680
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7661
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7636
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7621
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7594
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7594
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7589
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7491
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7486
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7473
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7472
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7429
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7396
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7380
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7337
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7329
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7319
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7304
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7258
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7250
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7250
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7244
Archaeal actin homolog	Q9HKL4	ACTH_THEAC	Thermoplasma acidophilum	2	0.7241
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7231
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7221
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7198
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7195
NAD-dependent protein deacetylase	Q9WYW0	NPD_THEMA	Thermotoga maritima	3	0.7188
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7163
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7139
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7129
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7128
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7119
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7105
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7104
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7100
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7098
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7090
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7081
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7067
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7067
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7066
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7063
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7048
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7047
HLA class I histocompatibility antigen, B alpha chain	P01889	HLAB_HUMAN	Homo sapiens	3	0.7036
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7032
Sodium/potassium-transporting ATPase subunit alpha	Q4H132	Q4H132_SQUAC	Squalus acanthias	2	0.7030
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7022
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7018
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7015

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