Flavumindole - Compound Card

Flavumindole

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Flavumindole

Structure
Zoomed Structure
  • Family: Plantae - Ochnaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC1=C(C=CC(=C1)C2C3C4=C(O2)C=CC5=C4C(=CN5)C(=O)CNC3=O)O
InChI InChI=1S/C20H16N2O5/c1-26-15-6-9(2-4-12(15)23)19-18-17-14(27-19)5-3-11-16(17)10(7-21-11)13(24)8-22-20(18)25/h2-7,18-19,21,23H,8H2,1H3,(H,22,25)
InChIKey BATKVFDLIDCNEK-UHFFFAOYSA-N
Formula C20H16N2O5
HBA 5
HBD 3
MW 364.36
Rotatable Bonds 2
TPSA 100.65
LogP 2.41
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 364.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Campylospermum calanthum Ochnaceae Plantae 1321790
2 Campylospermum flavum Ochnaceae Plantae 1321791

Showing of synonyms

  • Ndongo JT, Shaaban M, et al. (2010). Phenolic dimers and an indole alkaloid from Campylospermum flavum (Ochnaceae).. Phytochemistry,2010, 71(16), 1872-1878. [View] [PubMed]
  • Njock GBB, Bartholomeusz TA, et al. (2013). Structure and Dynamic of Three Indole Alkaloids from the Campylospermum Genus (Ochnaceae). HCA, 2013, 96, 1298-1304. [View]
Pubchem: 75287601

No compound-protein relationship available.

Structure

SMILES: c12c3c4ccc2[nH]cc1C(=O)CNC(=O)C3C(O4)c5ccccc5

Level: 1

Mol. Weight: 364.36 g/mol

Structure

SMILES: c12c3c4ccc2[nH]cc1C(=O)CNC(=O)C3CO4

Level: 0

Mol. Weight: 364.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 364.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.96
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.890
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.120
Plasma Protein Binding
51.76
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.000
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.770
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.430
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.480
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
Safe
T. Pyriformis
-11.920
Rat (Acute)
2.400
Rat (Chronic Oral)
2.550
Fathead Minnow
4.590
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
507.560
Hydration Free Energy
-7.980
Log(D) at pH=7.4
2.240
Log(P)
1.46
Log S
-5.55
Log(Vapor Pressure)
-10.44
Melting Point
268.14
pKa Acid
7.28
pKa Basic
4.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9659
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9433
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9335
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.9156
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9076
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9050
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9018
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8978
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8915
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8874
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8822
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8774
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8760
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8721
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8673
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 4 0.8646
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8552
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 3 0.8531
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8494
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8488
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8461
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8365
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8365
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8343
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8290
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8227
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8179
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8160
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8089
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8024
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8008
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7986
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7964
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7923
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7893
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7889
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7888
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7858
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7794
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.7792
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7792
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7733
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7733
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7723
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7711
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7707
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7696
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7666
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7625
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7580
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7576
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7543
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7534
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7519
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7504
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7467
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7448
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7431
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 4 0.7416
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7412
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7410
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7410
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7388
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7388
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7348
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7322
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7307
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7261
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7245
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7228
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7224
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7207
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7201
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7189
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7186
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7177
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7141
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7138
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7126
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7125
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7103
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7048
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7035
Uroporphyrinogen-III C-methyltransferase P21631 SUMT_SINSX Sinorhizobium sp 4 0.7031
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7018
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7011
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7007
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7007
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7005
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7000

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