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Amabiline

Family: Plantae - Boraginaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid

Canonical Smiles	O[C@@H]1CC[C@@H]2[C@]3([C@@H]1O)CCN2Cc1c3cc2OCOc2c1
InChI	InChI=1S/C16H19NO4/c18-11-1-2-14-16(15(11)19)3-4-17(14)7-9-5-12-13(6-10(9)16)21-8-20-12/h5-6,11,14-15,18-19H,1-4,7-8H2/t11-,14-,15-,16+/m1/s1
InChIKey	DLYIURZCCWSUKD-MPESAESLSA-N
Formula	C₁₆H₁₉NO₄
HBA	5
HBD	2
MW	289.33
Rotatable Bonds	0
TPSA	62.16
LogP	0.76
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	289.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Lappula spinocarpos	Boraginaceae	Plantae	1245804

Showing of synonyms

El-Shazly A, El-Domiaty M, et al. (1998). Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt). Biochemical Systematics and Ecology,1998,26(6),619-636. [View]

Pubchem: 399199

Cas: 151204-56-7

Nmrshiftdb2: 60075746

Chembl: CHEMBL456315

Comptox: DTXSID90327990

No compound-protein relationship available.

SMILES: O1COc(c2)c1cc3c2CN(CC4)C(C345)CCCC5

Level: 0

Mol. Weight: 289.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.1
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.51
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.51
Plasma Protein Binding: 33.38
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: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 13.21
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.03
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.59
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.0
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: 0.17
Rat (Acute): 2.31
Rat (Chronic Oral): 1.62
Fathead Minnow: 3.85
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: 398.6
Hydration Free Energy: -9.99
Log(D) at pH=7.4: 1.2
Log(P): 0.43
Log S: -1.83
Log(Vapor Pressure): -9.24
Melting Point: 229.43
pKa Acid: 10.42
pKa Basic: 8.43

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8768
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8768
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8725
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8725
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8477
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8477
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8308
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8308
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8239
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8239
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.8218
Odorant binding protein ASP1	Q8WRW5	Q8WRW5_APIME	Apis mellifera	3	0.8218
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8108
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8108
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7983
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7983
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7944
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7944
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7868
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7868
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7600
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7600
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7596
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7596
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7465
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7465
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7411
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7411
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7282
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7282
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7265
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7265
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7229
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7229
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7200
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7200
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7194
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7194
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7187
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7187
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7176
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7176
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7155
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7155
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7142
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7142
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	3	0.7058
Vitamin D3 receptor A	Q9PTN2	VDRA_DANRE	Danio rerio	3	0.7058
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7045
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7045
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7030
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7030
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	3	0.7005
Matrix metalloproteinase-20	O60882	MMP20_HUMAN	Homo sapiens	3	0.7005

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