3beta-dihydroholaphyllamine - Compound Card

3beta-dihydroholaphyllamine

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3beta-dihydroholaphyllamine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Steroid Alkaloid
Canonical Smiles N[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
InChI InChI=1S/C21H35NO/c1-13(23)17-6-7-18-16-5-4-14-12-15(22)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19H,4-12,22H2,1-3H3/t14-,15-,16-,17+,18-,19-,20-,21+/m0/s1
InChIKey POWBIOMTXFDIOP-FZCSVUEKSA-N
Formula C21H35NO
HBA 2
HBD 1
MW 317.52
Rotatable Bonds 1
TPSA 43.09
LogP 4.56
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.95
Exact Mass 317.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Holarrhena africana Apocynaceae Plantae 2708850

Showing of synonyms

  • Nnadi CO, Nwodo NJ, et al. (2017). Steroid alkaloids from Holarrhena africana with strong activity against Trypanosoma brucei rhodesiense. Molecules, 2017, 22(7), 1129. [View]
Pubchem: 57521800
Bindingdb: 50388501

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 317.52 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.290
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.210
Plasma Protein Binding
66.06
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
Substrate
CYP 2C9 Inhibitor
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
20.170
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.400
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.440
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2.250
Rat (Acute)
2.430
Rat (Chronic Oral)
1.380
Fathead Minnow
3.920
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
379.120
Hydration Free Energy
-2.740
Log(D) at pH=7.4
4.630
Log(P)
4.29
Log S
-3.87
Log(Vapor Pressure)
-6.39
Melting Point
166.94
pKa Acid
11.45
pKa Basic
8.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8967
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8633
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8016
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7860
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.7739
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7709
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7415
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7375
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7102
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7050
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7006

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