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Caranine

Family: Plantae - Amaryllidaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	O[C@@H]1CC=C2[C@@H]3[C@@H]1c1cc4OCOc4cc1CN3CC2
InChI	InChI=1S/C16H17NO3/c18-12-2-1-9-3-4-17-7-10-5-13-14(20-8-19-13)6-11(10)15(12)16(9)17/h1,5-6,12,15-16,18H,2-4,7-8H2/t12-,15-,16-/m1/s1
InChIKey	XKYSLILSDJBMCU-DAXOMENPSA-N
Formula	C₁₆H₁₇NO₃
HBA	4
HBD	1
MW	271.32
Rotatable Bonds	0
TPSA	41.93
LogP	1.78
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	271.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Zephyranthes candida	Amaryllidaceae	Plantae	82257

Showing of synonyms

Shawky E, El Sohafy S.M, et al. (2021). Profiling of acetylcholinesterase inhibitory alkaloids from some Crinum, Habranthus and Zephyranthes species by GC–MS combined with multivariate analyses and in silico studies.. Nat Prod Res, 2021, 35(5), 807-814.. [View] [PubMed]

Pubchem: 441589

Cas: 477-12-3

Zinc: ZINC000004097642

Kegg Ligand: C08521

Chebi: 3383

Nmrshiftdb2: 60071408

Metabolights: MTBLC3383

Chembl: CHEMBL575125

Comptox: DTXSID50331598

CPRiL: 412011

SMILES: O1COc(c12)cc3c(c2)C4C5C(=CCC4)CCN5C3

Level: 0

Mol. Weight: 271.32 g/mol

Ache-inhibitor

Absorption

Caco-2 (logPapp): -4.78
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.4
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.67
Plasma Protein Binding: 43.14
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 13.53
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.71
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.28
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.87
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: 1.61
Rat (Acute): 2.38
Rat (Chronic Oral): 1.39
Fathead Minnow: 3.9
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: 392.88
Hydration Free Energy: -8.67
Log(D) at pH=7.4: 2.03
Log(P): 1.79
Log S: -1.79
Log(Vapor Pressure): -8.36
Melting Point: 186.56
pKa Acid: 11.07
pKa Basic: 7.98

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8836
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8818
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8791
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8478
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8101
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8091
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8067
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7901
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7864
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7847
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7804
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7788
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7662
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7538
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7515
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7439
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7353
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7289
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7235
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7212
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7182
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7172
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7163
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	2	0.7157
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7096
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7092
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	4	0.7088

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