Aulicine - Compound Card

Aulicine

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Aulicine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CO[C@@H]1CC[C@@]23[C@@H](C1)N(CC2)Cc1c3c(O)c(c(c1)OC)OC
InChI InChI=1S/C18H25NO4/c1-21-12-4-5-18-6-7-19(14(18)9-12)10-11-8-13(22-2)17(23-3)16(20)15(11)18/h8,12,14,20H,4-7,9-10H2,1-3H3/t12-,14-,18+/m1/s1
InChIKey XQFCONVZHYBBOH-DFHBCGBQSA-N
Formula C18H25NO4
HBA 5
HBD 1
MW 319.4
Rotatable Bonds 3
TPSA 51.16
LogP 2.43
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 319.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Zephyranthes robusta Amaryllidaceae Plantae 1234388
2 Zephyranthes rosea Amaryllidaceae Plantae 146470

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: 72695729

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C123)N(CC2)Cc4c3cccc4

Level: 0

Mol. Weight: 319.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.370
Plasma Protein Binding
33.7
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-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
7.220
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.850
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.090
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
9.110
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
-2.320
Rat (Acute)
2.810
Rat (Chronic Oral)
1.600
Fathead Minnow
4.040
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
363.840
Hydration Free Energy
-8.000
Log(D) at pH=7.4
1.600
Log(P)
1.48
Log S
-1.07
Log(Vapor Pressure)
-6.11
Melting Point
173.43
pKa Acid
9.65
pKa Basic
8.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9341
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9322
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9205
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9169
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9143
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9008
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8954
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 4 0.8639
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8356
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8321
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8306
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8305
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8264
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8163
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8151
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8128
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7926
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7838
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7838
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7837
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7804
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7732
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7650
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7499
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7475
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7458
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7400
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7382
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7378
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7267
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7262
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7176
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7154
Acetylserotonin O-methyltransferase P46597 ASMT_HUMAN Homo sapiens 4 0.7085
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7061
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7056
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7046
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7046
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7035
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7027
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7019

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