Triangularine - Compound Card

Triangularine

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Triangularine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C(\C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)/C(=C\C)/CO)/C
InChI InChI=1S/C18H25NO5/c1-4-12(3)17(21)24-15-7-9-19-8-6-14(16(15)19)11-23-18(22)13(5-2)10-20/h4-6,15-16,20H,7-11H2,1-3H3/b12-4-,13-5-/t15-,16-/m1/s1
InChIKey GOENJWUGVSLZDQ-NCLHDQKXSA-N
Formula C18H25NO5
HBA 6
HBD 1
MW 335.4
Rotatable Bonds 6
TPSA 76.07
LogP 1.36
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 335.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alkanna orientalis Boraginaceae Plantae 543563
2 Alkanna orientalis Boraginaceae Plantae 543563

Showing of synonyms

  • Roeder E, Sarg T, et al. (1992). Pyrrolizidine alkaloids from Alkanna orientalis. Fitoterapia,1992,63(5),405-408. [View]
  • 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: 5281755
Kegg Ligand: C10410
Chebi: 9672
Nmrshiftdb2: 60069733

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 335.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
40.53
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.71
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.0
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5.22
Rat (Acute)
3.46
Rat (Chronic Oral)
1.94
Fathead Minnow
4.15
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
356.37
Hydration Free Energy
-8.64
Log(D) at pH=7.4
1.36
Log(P)
2.02
Log S
-1.81
Log(Vapor Pressure)
-6.77
Melting Point
100.8
pKa Acid
8.94
pKa Basic
7.28
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8784
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8784
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8679
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8679
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8394
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8394
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8354
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8354
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8205
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8205
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8198
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8198
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8018
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8018
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7964
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7964
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7923
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7923
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7887
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7887
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7864
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7864
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7792
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7792
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7789
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7789
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7616
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7616
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7575
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7575
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7509
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7509
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7454
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7454
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7424
FKBP-type peptidyl-prolyl cis-trans isomerase FkpA P45523 FKBA_ECOLI Escherichia coli 4 0.7424
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7419
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7419
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7320
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7320
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7304
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7304
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7267
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7267
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7224
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7224
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7180
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7180
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7161
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7161
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7056
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7056
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7054
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7054
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7030
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7030
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7001
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7001

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