Akuammiline - Compound Card

Akuammiline

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Akuammiline

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles COC(=O)C1(COC(=O)C)[C@@H]2C[C@H]3C4=Nc5c([C@@]14CCN3C/C/2=C/C)cccc5
InChI InChI=1S/C23H26N2O4/c1-4-15-12-25-10-9-22-16-7-5-6-8-18(16)24-20(22)19(25)11-17(15)23(22,21(27)28-3)13-29-14(2)26/h4-8,17,19H,9-13H2,1-3H3/b15-4-/t17-,19+,22-,23?/m1/s1
InChIKey QBHALCZZZWCCLV-CLNIADLISA-N
Formula C23H26N2O4
HBA 6
HBD 0
MW 394.47
Rotatable Bonds 3
TPSA 68.2
LogP 2.79
Number Rings 5
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.52
Exact Mass 394.19
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: 9977936
Nmrshiftdb2: 60061979

No compound-protein relationship available.

Structure

SMILES: C1C(C2)C(=C)CN(CC3)C2C4=Nc(c5C134)cccc5

Level: 0

Mol. Weight: 394.47 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.830
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
63.1
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
Non-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
5.470
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.060
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.170
Micronucleos
Toxic
NR-AhR
Safe
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
-33.880
Rat (Acute)
3.520
Rat (Chronic Oral)
2.010
Fathead Minnow
4.710
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
434.140
Hydration Free Energy
-3.830
Log(D) at pH=7.4
2.410
Log(P)
2.3
Log S
-3.25
Log(Vapor Pressure)
-7.56
Melting Point
169.85
pKa Acid
7.67
pKa Basic
6.3
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8708
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8505
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8454
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8029
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7825
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7776
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7701
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7649
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7564
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7501
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7447
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7437
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7402
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7361
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7358
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7318
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7277
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7253
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7200
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7136
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7121
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7120
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7105
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7076
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7011
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7003

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