7-(2-methylbutyryl)-9-(2,3-dihydroxybutyryl) retronecine - Compound Card

7-(2-methylbutyryl)-9-(2,3-dihydroxybutyryl) retronecine

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7-(2-methylbutyryl)-9-(2,3-dihydroxybutyryl) retronecine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC(C(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C(C(O)C)O)C
InChI InChI=1S/C17H27NO6/c1-4-10(2)16(21)24-13-6-8-18-7-5-12(14(13)18)9-23-17(22)15(20)11(3)19/h5,10-11,13-15,19-20H,4,6-9H2,1-3H3/t10?,11?,13-,14?,15?/m1/s1
InChIKey URBUCYRYSVLIOW-WAMZBAIXSA-N
Formula C17H27NO6
HBA 7
HBD 2
MW 341.4
Rotatable Bonds 7
TPSA 96.3
LogP 0.24
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 341.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Echium humile Boraginaceae Plantae 161689

Showing of synonyms

  • El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile. Phytochemistry,1996,42(1),225-230. [View]
Pubchem: 6431048

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 341.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.82
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.32
Plasma Protein Binding
21.13
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
6.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.6
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.49
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.74
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
-0.51
Rat (Acute)
3.66
Rat (Chronic Oral)
2.15
Fathead Minnow
3.89
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
357.92
Hydration Free Energy
-11.62
Log(D) at pH=7.4
0.65
Log(P)
0.76
Log S
-1.4
Log(Vapor Pressure)
-7.22
Melting Point
111.72
pKa Acid
7.29
pKa Basic
7.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8938
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8938
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8809
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8809
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8593
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8593
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.8593
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8593
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8571
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8571
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8431
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8431
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8396
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8396
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8392
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8392
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8242
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8242
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8168
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8168
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8139
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8139
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7960
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7960
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7959
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7959
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.7792
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.7792
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7753
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7753
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7730
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7730
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7726
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7726
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7714
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7714
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7702
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7702
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7697
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7697
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7544
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7544
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 4 0.7521
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 4 0.7521
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7508
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7508
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7416
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7416
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7386
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7386
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7344
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7344
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7328
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7328
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7327
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7327
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7264
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7264
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7233
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7233
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7195
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7195
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7185
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7185
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 4 0.7135
Vitamin D3 receptor P11473 VDR_HUMAN Homo sapiens 4 0.7135
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7133
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7133
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7116
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7116
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7071
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7071
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7058
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7058
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7006
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7006

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