7-tigloyl-9-(hydroxypropenoyl) retronecine - Compound Card

7-tigloyl-9-(hydroxypropenoyl) retronecine

Select a section from the left sidebar

7-tigloyl-9-(hydroxypropenoyl) retronecine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles O/C=C\C(=O)OCC1=CCN2[C@H]1[C@@H](CC2)OC(=O)/C(=C/C)/C
InChI InChI=1S/C16H21NO5/c1-3-11(2)16(20)22-13-5-8-17-7-4-12(15(13)17)10-21-14(19)6-9-18/h3-4,6,9,13,15,18H,5,7-8,10H2,1-2H3/b9-6-,11-3+/t13-,15-/m1/s1
InChIKey KREIPAAFIFMOKA-QXCUTPQZSA-N
Formula C16H21NO5
HBA 6
HBD 1
MW 307.35
Rotatable Bonds 5
TPSA 76.07
LogP 1.49
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.5
Exact Mass 307.14
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: 163071287
Nmrshiftdb2: 60077941

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 307.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.660
Human Oral Bioavailability 50%
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)
0.860
Plasma Protein Binding
30.51
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
3.800
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.590
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.840
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.150
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
-0.790
Rat (Acute)
4.050
Rat (Chronic Oral)
1.850
Fathead Minnow
4.120
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
354.240
Hydration Free Energy
-9.410
Log(D) at pH=7.4
1.670
Log(P)
1.88
Log S
-1.53
Log(Vapor Pressure)
-6.65
Melting Point
110.35
pKa Acid
7.6
pKa Basic
7.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8560
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8560
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8523
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8523
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8481
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8481
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8478
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8478
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8368
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8368
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8077
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8077
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7840
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7840
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7800
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7800
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7763
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7763
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7739
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7739
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7682
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7682
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7566
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7566
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7565
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7565
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7500
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7500
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7445
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7445
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7435
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7435
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7337
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7337
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7312
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7312
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7189
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7189
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7169
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7169
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7145
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7145
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7139
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7139
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7117
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7117
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7114
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7114
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7012
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7012

Download SDF