Lettowianthine - Compound Card

Lettowianthine

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Lettowianthine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Telisatin-Type Aporphinoid Alkaloid
Canonical Smiles O=C1C(=O)c2c3N1CCc1c3c(c3c2cccc3)c2c(c1)OCO2
InChI InChI=1S/C19H11NO4/c21-17-15-11-4-2-1-3-10(11)14-13-9(7-12-18(14)24-8-23-12)5-6-20(16(13)15)19(17)22/h1-4,7H,5-6,8H2
InChIKey FMLHJJVSHOCVAU-UHFFFAOYSA-N
Formula C19H11NO4
HBA 4
HBD 0
MW 317.3
Rotatable Bonds 0
TPSA 55.84
LogP 2.81
Number Rings 6
Number Aromatic Rings 3
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.16
Exact Mass 317.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lettowianthus stellatus Annonaceae Plantae 489335

Showing of synonyms

  • Nkunya MH, Jonker SA, et al. (2000). Aporphinoid alkaloids and other constituents from Lettowianthus stellatus. Phytochemistry,2000,53(8),1067-1073. [View] [PubMed]
Pubchem: 21593830
Chebi: 179640
Nmrshiftdb2: 60077870

No compound-protein relationship available.

Structure

SMILES: c1cccc2c1c(c3c4c25)c6c(OCO6)cc3CCN4C(=O)C5=O

Level: 0

Mol. Weight: 317.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.71
Plasma Protein Binding
71.69
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.93
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.28
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.44
Micronucleos
Toxic
NR-AhR
Toxic
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
Toxic
T. Pyriformis
0.15
Rat (Acute)
2.22
Rat (Chronic Oral)
1.68
Fathead Minnow
5.07
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
523.99
Hydration Free Energy
-7.61
Log(D) at pH=7.4
2.76
Log(P)
2.74
Log S
-5.66
Log(Vapor Pressure)
-10.79
Melting Point
308.73
pKa Acid
8.78
pKa Basic
5.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9384
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9384
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9305
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9305
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9268
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9268
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9152
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.9152
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9086
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9086
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8930
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8930
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8919
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8919
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8818
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8818
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8803
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8803
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8758
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8758
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8683
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 3 0.8683
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8658
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8658
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8600
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8600
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8569
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8569
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8548
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8548
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8498
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8498
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8488
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8488
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8298
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.8298
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8069
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.8069
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7949
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7949
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7931
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7931
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7917
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7917
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7892
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7892
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7878
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7878
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7876
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7876
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7871
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7871
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7814
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7814
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7794
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7794
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7738
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7738
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7701
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7701
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7700
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7700
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7677
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7677
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7676
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7676
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7630
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7630
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7626
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7626
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7604
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7604
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7573
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7573
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7571
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7571
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7543
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7543
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7543
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7543
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7528
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7528
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7435
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7435
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7422
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7422
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7413
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7413
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7391
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7391
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7390
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7390
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7360
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7360
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7360
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7360
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7334
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7334
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7333
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7333
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7310
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7310
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7307
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7307
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7303
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7303
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7292
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7292
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7271
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7271
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7229
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7229
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7229
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7229
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7227
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7227
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7217
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7217
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7192
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7192
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7179
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7179
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7174
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7174
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7172
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.7172
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7159
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7159
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7150
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7150
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7142
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 4 0.7142
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7133
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7133
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7114
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7114
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7092
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7092
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7087
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7087
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7085
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7085
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 2 0.7072
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 2 0.7072
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7070
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7070
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7048
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7048
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7030
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7030
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7025
Caspase-7 P55210 CASP7_HUMAN Homo sapiens 3 0.7025
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7024
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7024
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7019
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7019

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