Dihydroxytriangularine - Compound Card

Dihydroxytriangularine

Select a section from the left sidebar

Dihydroxytriangularine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles C/C=C(\C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C(C(O)C)(CO)O)/C
InChI InChI=1S/C18H27NO7/c1-4-11(2)16(22)26-14-6-8-19-7-5-13(15(14)19)9-25-17(23)18(24,10-20)12(3)21/h4-5,12,14-15,20-21,24H,6-10H2,1-3H3/b11-4-/t12?,14-,15?,18?/m1/s1
InChIKey IMZYUCHNYPUYBN-FCIKVUCCSA-N
Formula C18H27NO7
HBA 8
HBD 3
MW 369.41
Rotatable Bonds 7
TPSA 116.53
LogP -0.47
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 369.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Alkanna orientalis Boraginaceae Plantae 543563

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: 91747359
Nmrshiftdb2: 60077952

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 369.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.51

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
26.8
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
3.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.28
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.35
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
-5.85
Rat (Acute)
4.05
Rat (Chronic Oral)
2.33
Fathead Minnow
4.03
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
396.46
Hydration Free Energy
-12.29
Log(D) at pH=7.4
0.6
Log(P)
0.14
Log S
-1.25
Log(Vapor Pressure)
-8.74
Melting Point
134.73
pKa Acid
6.8
pKa Basic
7.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8741
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8741
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8697
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8697
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8498
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8498
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8497
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8497
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8415
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8415
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7974
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7974
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7760
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7760
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7698
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7698
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7398
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7398
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7396
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7396
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7391
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7391
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7271
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7271
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7234
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7234
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7167
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7167
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7154
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7154
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7120
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7120
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7028
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7028

Download SDF