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3-epimacronine

Family: Plantae - Amaryllidaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Amaryllidaceae Alkaloid

Canonical Smiles	CO[C@@H]1C=C[C@]23[C@H](C1)N(C)C[C@@H]2OC(=O)c1c3cc2OCOc2c1
InChI	InChI=1S/C18H19NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-16H,5,8-9H2,1-2H3/t10-,15+,16+,18+/m1/s1
InChIKey	YEISBJOTHHFANE-NJVUAGGXSA-N
Formula	C₁₈H₁₉NO₅
HBA	6
HBD	0
MW	329.35
Rotatable Bonds	1
TPSA	57.23
LogP	1.48
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	329.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Narcissus tazetta	Amaryllidaceae	Plantae	54860
2	Zephyranthes candida	Amaryllidaceae	Plantae	82257

Showing of synonyms

Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]
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: 375117

Cas: 17322-73-5

Gnps: CCMSLIB00012176757

Zinc: ZINC000005845664

Kegg Ligand: C12178

Chebi: 31115

Nmrshiftdb2: 60027844

Metabolights: MTBLC31115

Chembl: CHEMBL1976572

No compound-protein relationship available.

SMILES: O1COc(c2)c1cc3c2C(=O)OC(C345)CNC4CCC=C5

Level: 0

Mol. Weight: 329.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.81
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.680
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.570
Plasma Protein Binding: 31.98
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 10.050
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.720
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.390
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 9.970
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: -5.070
Rat (Acute): 2.990
Rat (Chronic Oral): 1.270
Fathead Minnow: 3.960
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 375.400
Hydration Free Energy: -8.190
Log(D) at pH=7.4: 2.070
Log(P): 1.78
Log S: -1.95
Log(Vapor Pressure): -8.07
Melting Point: 168.79
pKa Acid: 7.08
pKa Basic: 6.95

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9592
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9592
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9519
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9519
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9272
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9272
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.8828
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	3	0.8828
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8658
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8658
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8634
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8634
Acidic mammalian chitinase	Q9BZP6	CHIA_HUMAN	Homo sapiens	3	0.8601
Acidic mammalian chitinase	Q9BZP6	CHIA_HUMAN	Homo sapiens	3	0.8601
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8424
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8424
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8337
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8337
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.8224
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.8224
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	3	0.8208
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	3	0.8208
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8141
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8141
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8014
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8014
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7990
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7990
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7847
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7847
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7754
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7754
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7702
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7702
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7679
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	3	0.7679
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7657
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7657
Mitomycin biosynthesis 6-O-methyltransferase	Q9X5T6	MMCR_STRLA	Streptomyces lavendulae	3	0.7622
Mitomycin biosynthesis 6-O-methyltransferase	Q9X5T6	MMCR_STRLA	Streptomyces lavendulae	3	0.7622
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7601
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7601
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7567
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7567
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7457
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7457
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7395
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7395
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7367
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7367
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7358
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7358
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7338
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7338
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7304
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7304
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7298
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7298
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7296
Cholesterol oxidase	P22637	CHOD_BREST	Brevibacterium sterolicum	3	0.7296
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7181
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7181
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7165
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7165
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7112
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7112
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7077
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7077
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7073
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7073
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7065
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7065
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7056
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7056
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7002
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7002

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