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Darcyribeirine

Family: Plantae - 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

Zinc: ZINC000238742623

Nmrshiftdb2: 70108932

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 410.47 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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