Artabotrysine - Compound Card

Artabotrysine

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Artabotrysine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Dimeric Aporphine Alkaloid
Canonical Smiles COc1c2CCNc3c2c(c2c1OCO2)c1c(c3c2c3NCCc4c3c(c3c2cccc3)c2c(c4)OCO2)cccc1
InChI InChI=1S/C35H26N2O5/c1-38-32-22-11-13-37-31-26(19-7-3-5-9-21(19)29(27(22)31)34-35(32)42-16-41-34)25-18-6-2-4-8-20(18)28-24-17(10-12-36-30(24)25)14-23-33(28)40-15-39-23/h2-9,14,36-37H,10-13,15-16H2,1H3
InChIKey BLYZSWKPVVYANJ-UHFFFAOYSA-N
Formula C35H26N2O5
HBA 7
HBD 2
MW 554.6
Rotatable Bonds 2
TPSA 70.21
LogP 7.37
Number Rings 10
Number Aromatic Rings 6
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 554.18
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Artabotrys thomsonii Annonaceae Plantae 1636230

Showing of synonyms

  • Chimeze VWN, Bankoglu EE, et al. (2022). Cytotoxic and genotoxic properties of artathomsonine, a new oxoberberine alkaloid from Artabotrys thomsonii (annonaceae).. Natural product research,2022, 36(11), 2791-2799. [View] [PubMed]
Pubchem: 162903235

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c4c2c5c(cccc5)c(c4NCC3)-c(c6NCC7)c(cccc8)c8c9c6c7cc(c19)OCO1

Level: 1

Mol. Weight: 554.6 g/mol

Structure

SMILES: O1COc(c12)cc3c4c2c5c(cccc5)cc4NCC3

Level: 0

Mol. Weight: 554.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.4
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
67.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
2.17
Plasma Protein Binding
92.2
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.48
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.31
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-123776.66
Rat (Acute)
2.65
Rat (Chronic Oral)
1.76
Fathead Minnow
168.82
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
8985.59
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.41
Log(P)
7.2
Log S
-4.74
Log(Vapor Pressure)
-358.59
Melting Point
277.39
pKa Acid
10.96
pKa Basic
6.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.9631
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.9629
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9335
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9178
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8291
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8047
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8033
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7848
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.7842
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7805
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7767
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7706
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7620
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7559
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7539
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7517
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7509
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7471
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7457
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7382
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7370
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7327
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7218
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7189
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7166
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7128
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7120
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7087
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7072
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7071
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7071
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7038
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7024
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7008
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7002

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