Decursivine - Compound Card

Decursivine

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Decursivine

Structure
Zoomed Structure
  • Family: Plantae - Onagraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles O=C1NCCc2c3c4[C@@H]1[C@@H](Oc4ccc3[nH]c2)c1ccc2c(c1)OCO2
InChI InChI=1S/C20H16N2O4/c23-20-18-17-14(4-2-12-16(17)11(8-22-12)5-6-21-20)26-19(18)10-1-3-13-15(7-10)25-9-24-13/h1-4,7-8,18-19,22H,5-6,9H2,(H,21,23)/t18-,19+/m1/s1
InChIKey WBLUYASSOGHQQA-MOPGFXCFSA-N
Formula C20H16N2O4
HBA 4
HBD 2
MW 348.36
Rotatable Bonds 1
TPSA 72.58
LogP 2.79
Number Rings 6
Number Aromatic Rings 3
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 348.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Campylospermum calanthum Ochnaceae Plantae 1321790
2 Campylospermum densiflorum Onagraceae Plantae 1321789

Showing of synonyms

  • Bikobo DSN, Nkot JL, et al. (2011). Acylsteryl glycosides and other constituents from Campylospermum densiflorum (Ochnaceae).. RASAYAN J. Chem. 2011, 4(4),753-763. [View]
  • 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: 71560220
Nmrshiftdb2: 70104517

No compound-protein relationship available.

Structure

SMILES: c12c3c4ccc2[nH]cc1CCNC(=O)C3C(O4)c(c5)ccc(c56)OCO6

Level: 1

Mol. Weight: 348.36 g/mol

Structure

SMILES: c12c3c4ccc2[nH]cc1CCNC(=O)C3CO4

Level: 0

Mol. Weight: 348.36 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 348.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.99
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.12
Plasma Protein Binding
80.93
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
Non-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
13.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.13
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.18
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
-13.55
Rat (Acute)
2.0
Rat (Chronic Oral)
1.62
Fathead Minnow
4.43
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
490.85
Hydration Free Energy
-6.06
Log(D) at pH=7.4
2.51
Log(P)
2.56
Log S
-4.98
Log(Vapor Pressure)
-12.64
Melting Point
259.56
pKa Acid
9.96
pKa Basic
6.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.9115
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8957
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.8864
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8820
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8790
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8779
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8766
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8762
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.8646
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8615
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8496
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8397
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.8392
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8372
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8365
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8307
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8261
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.8232
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8176
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8119
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8035
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.8022
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7988
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7981
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7929
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7908
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7878
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7866
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7858
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7836
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7753
Probable flavin-dependent thymidylate synthase O41156 THYX_PBCV1 Paramecium bursaria Chlorella virus 1 4 0.7738
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7720
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7705
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7702
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7693
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7678
Aldehyde dehydrogenase, dimeric NADP-preferring P30838 AL3A1_HUMAN Homo sapiens 3 0.7658
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7631
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7621
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7620
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7610
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7600
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7572
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7556
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7535
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7513
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7507
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7473
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7431
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7429
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.7421
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7421
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7402
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7386
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7379
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7369
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7368
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7358
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7341
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7328
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7327
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7321
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7317
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7302
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7267
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7259
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7257
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7250
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7239
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7236
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7222
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7201
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7199
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7198
Cytochrome P450 2D6 P10635 CP2D6_HUMAN Homo sapiens 3 0.7184
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7170
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7154
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 3 0.7153
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7146
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7122
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7115
Alpha-1-acid glycoprotein 2 P19652 A1AG2_HUMAN Homo sapiens 3 0.7102
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7094
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7090
[LysW]-aminoadipate kinase O50147 LYSZ_THET2 Thermus thermophilus 3 0.7063
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7060
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7054
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 2 0.7016
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7012

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