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name Structure Reference Source Properties Activities Metabolism

Rauwolfia Serpentina

AlkaPlorer ID: AK000647

Synonym: None

IUPAC Name: methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

Structure

SMILES: COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCC4=C(NC5=CC=CC=C45)[C@@H]3C[C@H]12

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InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1

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InChIKey: GRTOGORTSDXSFK-XJTZBENFSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Stemonoporus canaliculatus Stemonoporus Dipterocarpaceae Malvales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Artemisia spicigera Artemisia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Anthyllis onobrychoides Anthyllis Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Knautia montana Knautia Caprifoliaceae Dipsacales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ixeris chinensis Ixeris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euphorbia pannonica Euphorbia Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Uncaria africana Uncaria Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mitragyna speciosa Mitragyna Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sarcococca saligna Sarcococca Buxaceae Buxales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Picris conyzoides Picris Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cryptocarya lividula Cryptocarya Lauraceae Laurales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rauvolfia verticillata Rauvolfia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Bulnesia retama Bulnesia Zygophyllaceae Zygophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Uncaria elliptica Uncaria Rubiaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Penstemon gentianoides Penstemon Plantaginaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Atropa belladonna Atropa Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phyllanthus acuminatus Phyllanthus Phyllanthaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rauvolfia nitida Rauvolfia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Delphinium ternatum Delphinium Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rauvolfia yunnanensis Rauvolfia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Catharanthus roseus Catharanthus Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rauvolfia serpentina Rauvolfia Apocynaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Tetrapleura tetraptera Tetrapleura Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 352.434

TPSA？: 54.56

MolLogP？: 3.1788000000000016

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Enterococcus faecalis Enterococcus faecalis MIC 71000.0 nM 10.1021/acs.jnatprod.6b00011
Escherichia coli Escherichia coli MIC 142000.0 nM 10.1021/acs.jnatprod.6b00011
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 5610.1 nM None
Homo sapiens Alpha-2a adrenergic receptor Ki 8.2 nM 10.1021/jm00019a001
Homo sapiens Alpha-2b adrenergic receptor Ki 14.5 nM 10.1021/jm00019a001
Homo sapiens Alpha-2c adrenergic receptor Ki 5.0 nM 10.1021/jm00019a001
Homo sapiens Cytochrome P450 1A2 AC50 3981.07 nM None
Homo sapiens Cytochrome P450 1A2 AC50 7943.28 nM None
Homo sapiens Cytochrome P450 2C19 AC50 12589.25 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 Potency 12589.3 nM None
Homo sapiens Cytochrome P450 2C9 AC50 10000.0 nM None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 Potency 10000.0 nM None
Homo sapiens Cytochrome P450 2D6 AC50 1.995 nM None
Homo sapiens Cytochrome P450 2D6 AC50 7.943 nM None
Homo sapiens Cytochrome P450 2D6 Ki 3.3 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Ki 3.5 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Ki 4.6 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Ki 5.7 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Ki 13.0 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Ki 14.0 nM 10.1021/jm00061a004
Homo sapiens Cytochrome P450 2D6 Potency 2.0 nM None
Homo sapiens Cytochrome P450 2D6 Potency 7.9 nM None
Homo sapiens Cytochrome P450 3A4 AC50 10000.0 nM None
Homo sapiens Cytochrome P450 3A4 Potency 10000.0 nM None
Homo sapiens Hemoglobin beta chain Potency 12589.3 nM None
Homo sapiens Histone acetyltransferase GCN5 Potency 15848.9 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 7943.3 nM None
Homo sapiens Hypoxia-inducible factor 1 alpha Potency 5011.9 nM None
Homo sapiens Lysine-specific demethylase 4D-like Potency 12589.3 nM None
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 14125.4 nM None
Homo sapiens Prelamin-A/C Potency 7.1 nM None
Homo sapiens Prelamin-A/C Potency 70.8 nM None
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 31622.8 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Klebsiella pneumoniae Klebsiella pneumoniae MIC 150000.0 nM 10.1021/acs.jnatprod.6b00011
Pseudomonas aeruginosa Pseudomonas aeruginosa MIC 4000.0 nM 10.1021/acs.jnatprod.6b00011
Rattus norvegicus Voltage-gated L-type calcium channel alpha-1C subunit Ki 289.0 nM 10.1021/jm00019a001
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Staphylococcus aureus Staphylococcus aureus MIC 150000.0 nM 10.1021/acs.jnatprod.6b00011
None ADMET Drug metabolism nan None 10.1021/acsmedchemlett.1c00694
None Unchecked Potency 14125.4 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010992 COC(=O)C1=CO[C@@H](C)C2=CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12 R05847
AKRT010997 COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@H]2C[N+]3=CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12 58212
AKRT010998 COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@H]2C[n+]3ccc4c([n-]c5ccccc54)c3C[C@H]12 R05849
AKRT010999 COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12>>COC(=O)C1=CO[C@@H](C)[C@H]2C[n+]3ccc4c([nH]c5ccccc54)c3C[C@H]12 58132