Darcyribeirine - Compound Card

Darcyribeirine

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Darcyribeirine

Structure
Zoomed Structure
  • Family: Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC(=O)C1=COC(=C)[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c1[nH]c1c2cc(c(c1)OC)OC
InChI InChI=1S/C23H26N2O5/c1-12-16-10-25-6-5-13-15-8-20(27-2)21(28-3)9-18(15)24-22(13)19(25)7-14(16)17(11-30-12)23(26)29-4/h8-9,11,14,16,19,24H,1,5-7,10H2,2-4H3/t14-,16-,19+/m0/s1
InChIKey RMQMNQMSKODSEY-URLQWDBASA-N
Formula C23H26N2O5
HBA 6
HBD 1
MW 410.47
Rotatable Bonds 3
TPSA 73.02
LogP 3.32
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.43
Exact Mass 410.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Rauvolfia caffra Apocynaceae Plantae 947877

Showing of synonyms

  • Bitombo AN, Zintchem AAA, et al. (2022). Antimicrobial and cytotoxic activities of indole alkaloids and other constituents from the stem barks of Rauvolfia caffra Sond (Apocynaceae). Natural product research,2022, 36(6), 1467-1475. [View] [PubMed]
Pubchem: 15907469
Nmrshiftdb2: 70108932

No compound-protein relationship available.

Structure

SMILES: C=C1OC=CC(C2)C1CN(CC3)C2c(c3c45)[nH]c4cccc5

Level: 0

Mol. Weight: 292.38 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.880
Plasma Protein Binding
41.96
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
12.540
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.530
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.750
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
10.280
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
-64.450
Rat (Acute)
2.600
Rat (Chronic Oral)
1.750
Fathead Minnow
4.430
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
463.650
Hydration Free Energy
-3.340
Log(D) at pH=7.4
3.640
Log(P)
2.49
Log S
-3.45
Log(Vapor Pressure)
-9.49
Melting Point
213.74
pKa Acid
9.77
pKa Basic
7.42
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9629
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9500
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9442
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.9106
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9003
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8943
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8918
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8820
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8809
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.8595
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8587
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8569
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8555
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8536
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8479
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8476
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8463
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8409
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8381
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8335
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8301
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8101
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8082
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8003
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7959
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7917
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7900
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7887
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7850
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7824
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7789
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7751
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7737
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7679
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7660
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7641
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7634
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7618
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7564
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7555
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7529
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7496
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7494
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7471
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7460
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7441
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7426
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7426
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7403
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7399
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7391
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7375
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7372
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7366
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7364
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7290
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7252
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7235
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7235
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7199
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7159
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7136
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7113
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7111
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7109
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7096
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7054
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7025
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7012

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