Echihumiline - Compound Card

Echihumiline

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Echihumiline

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CC(=CC(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@](C(O)(C)C)([C@@H](O)C)O)C
InChI InChI=1S/C20H31NO7/c1-12(2)10-16(23)28-15-7-9-21-8-6-14(17(15)21)11-27-18(24)20(26,13(3)22)19(4,5)25/h6,10,13,15,17,22,25-26H,7-9,11H2,1-5H3/t13-,15+,17+,20-/m0/s1
InChIKey XQRINBJLKOBTMI-XEQBAVFLSA-N
Formula C20H31NO7
HBA 8
HBD 3
MW 397.47
Rotatable Bonds 7
TPSA 116.53
LogP 0.3
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 397.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Echium setosum Boraginaceae Plantae 2650424
2 Echium humile Boraginaceae Plantae 161689

Showing of synonyms

  • El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine alkaloids from Echium setosum and Echium vulgare. Journal of Natural Products,1996,59(3),310-313. [View]
  • El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile. Phytochemistry,1996,42(1),225-230. [View]
Pubchem: 15286355
Nmrshiftdb2: 70003064

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 397.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.85
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
43.42
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
5.19
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.86
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.28
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
-5.69
Rat (Acute)
3.96
Rat (Chronic Oral)
2.18
Fathead Minnow
4.02
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
390.96
Hydration Free Energy
-10.51
Log(D) at pH=7.4
1.15
Log(P)
0.69
Log S
-1.79
Log(Vapor Pressure)
-8.51
Melting Point
150.43
pKa Acid
6.95
pKa Basic
7.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8337
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8337
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7920
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7920
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7906
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7906
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7733
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7733
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7638
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7638
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7636
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7636
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7444
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7444
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7432
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7432
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7323
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7323
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7311
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7311
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7245
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7245
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7161
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7161
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052

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