Holarrheline - Compound Card

Holarrheline

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Holarrheline

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Steroid Alkaloid
Canonical Smiles CN[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2C[C@@H](O)[C@]24[C@H]3CC[C@@H]4[C@@H](N(C2)C)C)C1)C
InChI InChI=1S/C23H38N2O/c1-14-18-7-8-19-17-6-5-15-11-16(24-3)9-10-22(15,2)20(17)12-21(26)23(18,19)13-25(14)4/h5,14,16-21,24,26H,6-13H2,1-4H3/t14-,16-,17-,18+,19-,20-,21+,22-,23+/m0/s1
InChIKey WOLVJLISTFAJCZ-WONNUDCJSA-N
Formula C23H38N2O
HBA 3
HBD 2
MW 358.57
Rotatable Bonds 1
TPSA 35.5
LogP 3.44
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.91
Exact Mass 358.3
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: 102093827

No compound-protein relationship available.

Structure

SMILES: C1NCC(C123)CCC2C4C(CC3)C5C(=CC4)CCCC5

Level: 0

Mol. Weight: 358.57 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.8
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
50.36
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
21.57
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.35
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.45
Micronucleos
Safe
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
-8.52
Rat (Acute)
2.83
Rat (Chronic Oral)
1.15
Fathead Minnow
3.72
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
400.53
Hydration Free Energy
-5.22
Log(D) at pH=7.4
2.4
Log(P)
3.2
Log S
-3.33
Log(Vapor Pressure)
-7.02
Melting Point
190.93
pKa Acid
10.86
pKa Basic
10.44
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8783
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8471
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7929
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7304
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7069
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7006

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