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(+)-vasicinone

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Pyrrolo-Quinolizidine

Canonical Smiles	O[C@@H]1CCn2c1nc1ccccc1c2=O
InChI	InChI=1S/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m1/s1
InChIKey	SDIVYZXRQHWCKF-SECBINFHSA-N
Formula	C₁₁H₁₀N₂O₂
HBA	4
HBD	1
MW	202.21
Rotatable Bonds	0
TPSA	55.12
LogP	0.83
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	15
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	202.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Galega lindblomi	Leguminosae/Fabaceae	Plantae	—
2	Galega battiscombei	Leguminosae/Fabaceae	Plantae	—

Showing of synonyms

Susag L, Mathenge S, et al. (2003). The alkaloids of two species of Afrogalega.. Biochemical systematics and ecology,2003,31(6),645-647. [View] [PubMed]

Pubchem: 776133

Cas: 119364-42-0

Zinc: ZINC000000265484

Nmrshiftdb2: 70129554

Chembl: CHEMBL4218004

No compound-protein relationship available.

SMILES: C1CCn(c12)c(=O)c3c(n2)cccc3

Level: 0

Mol. Weight: 202.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.65
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.07
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.58
Plasma Protein Binding: 52.4
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: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.2
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.79
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.52
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 2.77
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: 1.09
Rat (Acute): 2.4
Rat (Chronic Oral): 1.48
Fathead Minnow: 3.92
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: 362.86
Hydration Free Energy: -11.43
Log(D) at pH=7.4: 0.52
Log(P): 0.47
Log S: -1.95
Log(Vapor Pressure): -7.14
Melting Point: 201.0
pKa Acid: 11.0
pKa Basic: 4.99

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.9528
Ceramide transfer protein	Q9Y5P4	CERT_HUMAN	Homo sapiens	3	0.9466
Odorant-binding protein	P81245	OBP_PIG	Sus scrofa	3	0.9332
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.9192
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.9180
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	4	0.9168
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9093
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8949
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.8683
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8669
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8653
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.8641
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.8577
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8567
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.8322
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8237
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8174
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.8099
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.8094
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.8088
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8042
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8037
D(3) dopamine receptor	P35462	DRD3_HUMAN	Homo sapiens	3	0.8023
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8000
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7947
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7910
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7873
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	4	0.7851
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7850
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7841
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7737
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7734
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7722
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7722
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7705
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7699
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7685
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7652
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7650
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	4	0.7590
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7590
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7562
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	3	0.7558
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7551
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7551
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7542
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7513
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7509
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	2	0.7500
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7499
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7498
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7488
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7482
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7459
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7459
Fatty acid-binding protein, adipocyte	P15090	FABP4_HUMAN	Homo sapiens	2	0.7453
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7446
D-alanine--D-alanine ligase	Q5HEB7	DDL_STAAC	Staphylococcus aureus	3	0.7446
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7428
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7424
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7422
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7417
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.7414
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7408
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q02127	PYRD_HUMAN	Homo sapiens	3	0.7406
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7402
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7399
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7387
Fructose-1,6-bisphosphatase 1	P00636	F16P1_PIG	Sus scrofa	3	0.7386
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7379
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	3	0.7367
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7350
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7350
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7332
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7303
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7292
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7282
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7281
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7269
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7259
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7226
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7224
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7211
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7210
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7206
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7200
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7194
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7153
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7148
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7142
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	2	0.7136
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	4	0.7117
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7111
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7099
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7090
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7078
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7069
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7062
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7058
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7045
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7031
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7028
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7026
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7023
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7022
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7016

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