Heliotridine - Compound Card

Heliotridine

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Heliotridine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles OCC1=CCN2C1[C@@H](O)CC2
InChI InChI=1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8?/m0/s1
InChIKey HJSJELVDQOXCHO-JAMMHHFISA-N
Formula C8H13NO2
HBA 3
HBD 2
MW 155.2
Rotatable Bonds 1
TPSA 43.7
LogP -0.65
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 11
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 155.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Paracaryum intermedium Boraginaceae Plantae 1288217
2 Anchusa milleri Boraginaceae Plantae 256477

Showing of synonyms

  • El-Shazly A, El-Domiaty M, et al. (1998). Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt). Biochemical Systematics and Ecology,1998,26(6),619-636. [View]
Pubchem: 72612
Nmrshiftdb2: 60077939
CPRiL: 11471
Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 155.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.28
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.05
Plasma Protein Binding
14.89
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
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.75
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.32
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.38
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
-0.27
Rat (Acute)
2.19
Rat (Chronic Oral)
1.65
Fathead Minnow
2.71
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
307.11
Hydration Free Energy
-10.45
Log(D) at pH=7.4
-1.46
Log(P)
-0.93
Log S
0.47
Log(Vapor Pressure)
-4.58
Melting Point
117.37
pKa Acid
10.41
pKa Basic
9.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-glucosidase 1 P48825 BGL1_ASPAC Aspergillus aculeatus 3 0.7765
Beta-glucosidase 1 P48825 BGL1_ASPAC Aspergillus aculeatus 3 0.7765
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7395
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7395
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7176
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7176
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7050
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7050

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