ANPDB

Select a section from the left sidebar

Reserpiline

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@H]1N(C2)CCc2c1[nH]c1c2cc(c(c1)OC)OC)C
InChI	InChI=1S/C23H28N2O5/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/h8-9,11-12,14,16,19,24H,5-7,10H2,1-4H3/t12-,14-,16-,19+/m0/s1
InChIKey	FGWJRZQNNZVCHR-BCRCDCHUSA-N
Formula	C₂₃H₂₈N₂O₅
HBA	6
HBD	1
MW	412.49
Rotatable Bonds	3
TPSA	73.02
LogP	3.2
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.52
Exact Mass	412.2
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: 67228

Cas: 131-02-2

Gnps: CCMSLIB00004680048

Zinc: ZINC000072266283

Chebi: 135667

Nmrshiftdb2: 60061976

Metabolights: MTBLC135667

No compound-protein relationship available.

SMILES: c1cccc2[nH]c(c3c12)C4N(CC3)CC5C(C4)C=COC5

Level: 0

Mol. Weight: 412.49 g/mol

Antimicrobial

Cytotoxic

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.050
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.690
Plasma Protein Binding: 41.3
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: 10.630
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.410
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.550
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.890
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: -63.450
Rat (Acute): 2.660
Rat (Chronic Oral): 1.950
Fathead Minnow: 4.150
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 452.520
Hydration Free Energy: -2.960
Log(D) at pH=7.4: 3.440
Log(P): 2.65
Log S: -3.64
Log(Vapor Pressure): -8.55
Melting Point: 204.35
pKa Acid: 9.78
pKa Basic: 7.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.9284
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9275
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9038
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9005
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8959
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8904
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8696
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.8683
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8683
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8622
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8587
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8551
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8515
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8511
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8448
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8329
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8300
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8154
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8103
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.8103
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8065
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7995
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7991
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7922
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7880
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7824
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7820
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7811
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7766
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7728
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7694
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7642
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7622
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7618
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7581
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7580
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7551
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7540
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7516
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7479
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7467
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7459
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7425
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7408
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7401
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7384
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7357
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7353
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7343
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7335
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7308
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7304
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7292
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7286
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7268
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7237
DNA double-strand break repair protein Mre11	Q9X1X0	Q9X1X0_THEMA	Thermotoga maritima MSB8	3	0.7235
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7212
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7191
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7169
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.7124
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7074
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7070
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7052
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7026
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase	P12995	BIOA_ECOLI	Escherichia coli	2	0.7024
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7017

Download SDF