1-formyl-5-hydroxy-N-methylindolin-1-ium - Compound Card

1-formyl-5-hydroxy-N-methylindolin-1-ium

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1-formyl-5-hydroxy-N-methylindolin-1-ium

Structure
Zoomed Structure
  • Family: Rutaceae
  • Kingdom: Plantae
  • Class: Indole Alkaloid
Canonical Smiles O=C[N+]1(C)CCc2c1ccc(c2)O
InChI InChI=1S/C10H11NO2/c1-11(7-12)5-4-8-6-9(13)2-3-10(8)11/h2-3,6-7H,4-5H2,1H3/p+1
InChIKey RRDVNWBJIHSQRZ-UHFFFAOYSA-O
Formula C10H12NO2+
HBA 2
HBD 1
MW 178.21
Rotatable Bonds 1
TPSA 37.3
LogP 1.04
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 13
Formal Charge 1
Fraction CSP3 0.3
Exact Mass 178.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Citrus x paradisi Rutaceae Plantae 37656

Showing of synonyms

  • Noulala CGT, Ouete JLN, et al. (2023). Coumarinolignoid and Indole Alkaloids from the Roots of the Hybrid Plant Citrus × paradisi Macfad (Rutaceae). Molecules. 2023, 28(3), 1078. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1C[NH2+]c(c12)cccc2

Level: 0

Mol. Weight: 120.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.07
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.13
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.15
Plasma Protein Binding
14.99
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
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
7.91
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.13
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.09
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.91
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
3.67
Rat (Acute)
2.34
Rat (Chronic Oral)
1.81
Fathead Minnow
3.79
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
296.93
Hydration Free Energy
-11.74
Log(D) at pH=7.4
0.05
Log(P)
-2.01
Log S
-0.45
Log(Vapor Pressure)
-5.86
Melting Point
234.99
pKa Acid
7.23
pKa Basic
1.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9229
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9197
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.9059
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7924
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 2 0.7750
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7528
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7489
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7469
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7430
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7425
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7413
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7409
Thiazole tautomerase P25053 TENI_BACSU Bacillus subtilis 2 0.7402
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7400
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7387
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7335
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7320
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7314
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7312
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7309
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7305
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7299
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7291
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7283
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7282
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7272
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7268
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7267
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7256
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7255
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7250
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7238
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7235
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7216
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7207
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7203
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7203
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7201
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7197
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7196
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7192
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7167
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7161
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7149
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7146
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7144
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7140
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7129
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7123
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7116
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7103
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 2 0.7098
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7067
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7064
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7061
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7060
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7055
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7050
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7050
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7049
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7045
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7039
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7036
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7023
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7021
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7018
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7015
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7004
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 2 0.7002
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7001
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 2 0.7001

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