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Supinine

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

Canonical Smiles	CC([C@@](C(=O)OCC1=CCN2[C@H]1CCC2)([C@H](O)C)O)C
InChI	InChI=1S/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13+,15+/m1/s1
InChIKey	DRVWTOSBCBKXOR-ZLDLUXBVSA-N
Formula	C₁₅H₂₅NO₄
HBA	5
HBD	2
MW	283.37
Rotatable Bonds	5
TPSA	70.0
LogP	0.7
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	283.18
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Paracaryum intermedium	Boraginaceae	Plantae	1288217
2	Anchusa milleri	Boraginaceae	Plantae	256477
3	Anchusa hispida	Boraginaceae	Plantae	170551
4	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: 108053

Cas: 551-58-6

Kegg Ligand: C10403

Chebi: 9361

Nmrshiftdb2: 60026153

Comptox: DTXSID70203622

No compound-protein relationship available.

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 283.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.03
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.26
Plasma Protein Binding: 28.37
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: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.2
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.39
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.93
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: -2.16
Rat (Acute): 3.31
Rat (Chronic Oral): 1.88
Fathead Minnow: 3.84
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 313.68
Hydration Free Energy: -11.18
Log(D) at pH=7.4: 0.82
Log(P): 0.74
Log S: -1.12
Log(Vapor Pressure): -6.19
Melting Point: 122.68
pKa Acid: 7.06
pKa Basic: 7.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.9322
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.9322
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8980
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.8980
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8955
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.8955
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8837
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8837
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8798
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8798
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8590
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8590
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8571
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8571
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8528
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.8528
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8168
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8168
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8134
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.8134
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8018
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8018
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7946
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.7946
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7936
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7936
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7858
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7858
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7793
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7793
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7772
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7772
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7761
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7761
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7750
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7750
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7669
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7669
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7663
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7663
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7587
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7587
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7578
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7578
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7577
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7577
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7549
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7549
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7472
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7472
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7470
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7470
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7406
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7406
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7400
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7400
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7398
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7398
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7389
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7389
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7360
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7360
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7357
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7357
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7346
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7346
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7318
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7318
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7317
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7317
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7310
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7310
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7309
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7309
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7304
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7304
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7285
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7285
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7257
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7257
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7254
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7254
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7218
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7218
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7216
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7216
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7212
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7212
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.7177
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.7177
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.7177
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	3	0.7177
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7132
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7132
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7094
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7094
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7074
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7074
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7073
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7073
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7073
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7073
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7069
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7069
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7053
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.7053
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7028
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7028
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7026
Predicted acetyltransferase	Q97ML2	Q97ML2_CLOAB	Clostridium acetobutylicum	3	0.7026
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7011
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7011
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7002
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7002

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