Isoreserpiline - Compound Card

Isoreserpiline

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Isoreserpiline

Structure
Zoomed Structure
  • 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-HAHWVIBASA-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: 161345
Nmrshiftdb2: 60063043

No compound-protein relationship available.

Structure

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)
-4.76
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
-1.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.690
Plasma Protein Binding
41.82
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
10.610
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.480
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
7.900
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-63.250
Rat (Acute)
2.660
Rat (Chronic Oral)
1.950
Fathead Minnow
4.170
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
452.200
Hydration Free Energy
-2.940
Log(D) at pH=7.4
3.370
Log(P)
2.63
Log S
-3.65
Log(Vapor Pressure)
-8.55
Melting Point
208.94
pKa Acid
9.81
pKa Basic
7.82
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9497
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9138
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9012
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8802
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8607
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8421
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8412
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.8405
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8355
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8345
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8325
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8322
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8283
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8220
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8195
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8145
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8010
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7998
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7919
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7883
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7790
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7752
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7744
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7721
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.7660
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7649
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7615
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7600
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7584
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7540
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7475
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7448
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7444
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7410
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7361
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7343
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7323
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7284
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7241
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7178
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7175
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7143
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7053
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7038
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7021

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