Calanthumindole - Compound Card

Calanthumindole

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Calanthumindole

Structure
Zoomed Structure
  • Family: Plantae - Ochnaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COc1cc(ccc1O)c1oc2c3c1C(=O)NCC(=O)c1c3c(cc2)[nH]c1
InChI InChI=1S/C20H14N2O5/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/h2-7,21,23H,8H2,1H3,(H,22,25)
InChIKey ORXXENZSODPNSX-UHFFFAOYSA-N
Formula C20H14N2O5
HBA 5
HBD 3
MW 362.34
Rotatable Bonds 2
TPSA 104.56
LogP 3.22
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.1
Exact Mass 362.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Campylospermum calanthum Ochnaceae Plantae 1321790

Showing of synonyms

  • 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: 162885525

No compound-protein relationship available.

Structure

SMILES: c12c3c4c[nH]c3ccc2oc(c1C(=O)NCC4=O)-c5ccccc5

Level: 1

Mol. Weight: 362.34 g/mol

Structure

SMILES: c12c3c4coc3ccc2[nH]cc1C(=O)CNC4=O

Level: 0

Mol. Weight: 362.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 362.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.05
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.040
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.180
Plasma Protein Binding
76.72
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
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.640
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.080
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.670
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.760
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-12.400
Rat (Acute)
2.440
Rat (Chronic Oral)
2.730
Fathead Minnow
4.950
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
541.040
Hydration Free Energy
-7.620
Log(D) at pH=7.4
3.240
Log(P)
2.06
Log S
-6.37
Log(Vapor Pressure)
-12.2
Melting Point
356.98
pKa Acid
7.44
pKa Basic
3.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9603
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.9581
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.9409
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9355
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.9253
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.9240
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9187
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9136
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.9105
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9096
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9071
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9020
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8951
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8916
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8914
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8810
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8774
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8722
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8644
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8609
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.8600
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.8568
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8542
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8495
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8480
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8453
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 4 0.8438
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8413
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8383
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8379
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic Q1XH05 HGL1B_WHEAT Triticum aestivum 4 0.8349
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8344
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 3 0.8331
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8325
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 3 0.8308
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8230
Exotoxin A P11439 TOXA_PSEAE Pseudomonas aeruginosa 4 0.8215
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.8212
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8189
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8188
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8095
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8062
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.8012
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8011
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7968
Putative mitogen-activated protein kinase Q4QHJ8 Q4QHJ8_LEIMA Leishmania major 3 0.7943
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7938
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7933
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7906
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7873
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7843
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7838
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7835
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7820
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.7819
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7811
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7809
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.7799
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7748
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 4 0.7740
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7727
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7715
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7695
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7685
Gag-Pol polyprotein O12158 POL_HV192 Human immunodeficiency virus type 1 group M subtype C 3 0.7676
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7665
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7664
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7656
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7631
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7614
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7610
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7585
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7572
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7556
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7536
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7535
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7532
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7528
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 4 0.7518
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7517
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7481
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7478
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7458
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7447
Genome polyprotein A0EKU1 A0EKU1_9FLAV Meaban virus 3 0.7446
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7446
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7445
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7440
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7431
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7424
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7420
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7414
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7401
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7396
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7394
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7391
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7389
Kelch-like ECH-associated protein 1 Q14145 KEAP1_HUMAN Homo sapiens 3 0.7363
Genome polyprotein P29991 POLG_DEN27 Dengue virus type 2 3 0.7351
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7349
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7337
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7333
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7325
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7315
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7314
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7305
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7281
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7269
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7260
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7259
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7258
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7241
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7241
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7238
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7238
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7237
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7233
Metallo-beta-lactamase L1 type 3 P52700 BLA1_STEMA Stenotrophomonas maltophilia 3 0.7215
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7214
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7206
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7204
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7202
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7198
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7197
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7191
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7175
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7164
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7163
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7160
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7155
Putative FAD-monooxygenase Q8KI25 Q8KI25_LENAE Lentzea aerocolonigenes 4 0.7152
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7150
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7150
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7130
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7124
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7119
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 3 0.7118
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7105
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7104
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7103
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7102
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7102
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7099
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7097
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7096
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7086
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7075
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7060
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7057
Genome polyprotein P12823 POLG_DEN2P Dengue virus type 2 3 0.7044
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7031
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7028
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7026
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7023
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7015
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7014
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7006
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform P42336 PK3CA_HUMAN Homo sapiens 4 0.7003

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