9-hydroxyisohexenoylretronecine - Compound Card

9-hydroxyisohexenoylretronecine

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9-hydroxyisohexenoylretronecine

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O=C(OCC1=CCN2C1[C@H](O)CC2)CC=C(C)C
InChI InChI=1S/C14H21NO3/c1-10(2)3-4-13(17)18-9-11-5-7-15-8-6-12(16)14(11)15/h3,5,12,14,16H,4,6-9H2,1-2H3/t12-,14?/m1/s1
InChIKey NZTFQXQFIBMKBH-PUODRLBUSA-N
Formula C14H21NO3
HBA 4
HBD 1
MW 251.33
Rotatable Bonds 4
TPSA 49.77
LogP 1.26
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 251.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Crotalaria albicaulis Leguminosae/Fabaceae Plantae 1132156

Showing of synonyms

  • Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
Pubchem: 91749689

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 251.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.27
Plasma Protein Binding
25.34
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
6.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.19
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.13
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.89
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
-0.79
Rat (Acute)
3.28
Rat (Chronic Oral)
1.76
Fathead Minnow
4.01
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
311.55
Hydration Free Energy
-9.89
Log(D) at pH=7.4
0.92
Log(P)
1.33
Log S
-1.14
Log(Vapor Pressure)
-5.61
Melting Point
94.15
pKa Acid
8.46
pKa Basic
7.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9330
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9330
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9319
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9319
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9029
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9029
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8630
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8630
Cyclomaltodextrin glucanotransferase P05618 CDGT_BACS0 Bacillus sp 3 0.8182
Cyclomaltodextrin glucanotransferase P05618 CDGT_BACS0 Bacillus sp 3 0.8182
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8066
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8066
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7912
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7912
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7540
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7540
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7347
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7347
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7260
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7260
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7230
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7230
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7225
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7225
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7100
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 3 0.7100
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7100
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 3 0.7100
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7094
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7094
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7074
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7074
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7032
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7032

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