15-hydroxyvomicine - Compound Card

15-hydroxyvomicine

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15-hydroxyvomicine

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Monoindole Alkaloid
Canonical Smiles CN1CC[C@@]23C(=O)C[C@]4(C(=CCOC5=CC(=O)N([C@H]2[C@@H]45)c2c3cccc2O)C1)O
InChI InChI=1S/C22H22N2O5/c1-23-7-6-21-13-3-2-4-14(25)19(13)24-17(27)9-15-18(20(21)24)22(28,10-16(21)26)12(11-23)5-8-29-15/h2-5,9,18,20,25,28H,6-8,10-11H2,1H3/t18-,20-,21+,22+/m0/s1
InChIKey NDIBCEQFECLLFG-VXSCBNMQSA-N
Formula C22H22N2O5
HBA 6
HBD 2
MW 394.43
Rotatable Bonds 0
TPSA 90.31
LogP 0.85
Number Rings 7
Number Aromatic Rings 1
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 394.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Strychnos icaja Loganiaceae Plantae 1040889

Showing of synonyms

  • Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
Pubchem: 162866782
Nmrshiftdb2: 70048584

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)N5C2C6C(=CC5=O)OCC=C(C6CC3=O)CNCC4

Level: 0

Mol. Weight: 394.43 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.2
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
44.86
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.96
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.75
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.91
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
-30.18
Rat (Acute)
2.76
Rat (Chronic Oral)
2.21
Fathead Minnow
4.02
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
480.47
Hydration Free Energy
-4.89
Log(D) at pH=7.4
0.53
Log(P)
-0.58
Log S
-3.27
Log(Vapor Pressure)
-10.9
Melting Point
286.87
pKa Acid
6.16
pKa Basic
5.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9391
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.9212
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.8777
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8538
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8082
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7509
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7373
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7253
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7167
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7132
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7064
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7006

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