Sternbergine - Compound Card

Sternbergine

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Sternbergine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CC(=O)OC1C(C=C2CCN3C2C1C4=CC(=C(C=C4C3)O)OC)O
InChI InChI=1S/C18H21NO5/c1-9(20)24-18-14(22)5-10-3-4-19-8-11-6-13(21)15(23-2)7-12(11)16(18)17(10)19/h5-7,14,16-18,21-22H,3-4,8H2,1-2H3
InChIKey JKXPUEOBLNILSU-UHFFFAOYSA-N
Formula C18H21NO5
HBA 6
HBD 2
MW 331.37
Rotatable Bonds 2
TPSA 79.23
LogP 1.3
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 331.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Zephyranthes candida Amaryllidaceae Plantae 82257

Showing of synonyms

  • 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: 178814
Nmrshiftdb2: 60071283

No compound-protein relationship available.

Structure

SMILES: C1CCC(C2C=13)c4c(cccc4)CN2CC3

Level: 0

Mol. Weight: 331.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.78
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
-4.22
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
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.86
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.21
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.1
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
-0.93
Rat (Acute)
2.75
Rat (Chronic Oral)
2.26
Fathead Minnow
4.17
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
389.4
Hydration Free Energy
-9.36
Log(D) at pH=7.4
0.74
Log(P)
0.71
Log S
-1.87
Log(Vapor Pressure)
-7.67
Melting Point
201.08
pKa Acid
7.88
pKa Basic
6.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8759
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8727
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8699
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 5 0.8445
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8358
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.8335
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8251
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8191
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8191
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8142
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8068
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7996
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7992
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7973
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7930
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7908
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7882
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7776
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7705
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 4 0.7630
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7589
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7479
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7477
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7472
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7389
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7383
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7343
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7338
Threonine synthase 1, chloroplastic Q9S7B5 THRC1_ARATH Arabidopsis thaliana 3 0.7335
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7317
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7259
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7217
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7194
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7190
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7173
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7171
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7170
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 4 0.7149
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7131
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7126
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7090
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7085
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7061
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7049
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 3 0.7032
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7018
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7003

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