Norbutsanguinine - Compound Card

Norbutsanguinine

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Norbutsanguinine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C[C@@H](CC(=O)O[C@H]1C=C[C@@]23C(C1)Oc1c3c(CNCC2)ccc1O)O
InChI InChI=1S/C19H23NO5/c1-11(21)8-16(23)24-13-4-5-19-6-7-20-10-12-2-3-14(22)18(17(12)19)25-15(19)9-13/h2-5,11,13,15,20-22H,6-10H2,1H3/t11-,13-,15?,19-/m0/s1
InChIKey TYKZEEVHXFAXJZ-YFGLXPNFSA-N
Formula C19H23NO5
HBA 6
HBD 3
MW 345.4
Rotatable Bonds 3
TPSA 88.02
LogP 1.53
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.53
Exact Mass 345.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lycoris sanguinea Amaryllidaceae Plantae 108053

Showing of synonyms

  • Abdallah OM. (1995). Minor alkaloids from Lycoris sanguinea. Phytochemistry,1995,39(2),477-478. [View]
Pubchem: 162886399

No compound-protein relationship available.

Structure

SMILES: C1=CCCC2Oc(c3C124)cccc3CNCC4

Level: 0

Mol. Weight: 345.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.08
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.43
Plasma Protein Binding
31.96
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
14.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.09
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
9.8
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.38
Rat (Acute)
2.89
Rat (Chronic Oral)
1.93
Fathead Minnow
3.98
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
399.22
Hydration Free Energy
-11.94
Log(D) at pH=7.4
1.13
Log(P)
0.89
Log S
-2.07
Log(Vapor Pressure)
-7.82
Melting Point
151.03
pKa Acid
7.75
pKa Basic
7.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8613
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8613
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8373
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8373
N-glycosylase/DNA lyase O15527 OGG1_HUMAN Homo sapiens 4 0.8139
N-glycosylase/DNA lyase O15527 OGG1_HUMAN Homo sapiens 4 0.8139
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7994
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7994
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7991
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7991
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7978
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7978
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7931
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.7931
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7894
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7894
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7792
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7792
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7659
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7659
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7599
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7599
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7563
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7563
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7493
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7493
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 4 0.7485
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 4 0.7485
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7425
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7425
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7370
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7370
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7346
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7346
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7321
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7321
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7319
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7319
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7310
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7310
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7303
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7303
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7284
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7284
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7257
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7257
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7252
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7252
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7242
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7242
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7232
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7232
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7206
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7206
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7183
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7183
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7109
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7109
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7106
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7106
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7079
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7079
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7059
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7059
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7039
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase Q9WY79 MURE_THEMA Thermotoga maritima 3 0.7039
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7008
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7008
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7007
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7007
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7002
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7002

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