7-(2-methylbutyryl)-9-echimidinylretronecine - Compound Card

7-(2-methylbutyryl)-9-echimidinylretronecine

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7-(2-methylbutyryl)-9-echimidinylretronecine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC(C(=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/C20H33NO7/c1-6-12(2)17(23)28-15-8-10-21-9-7-14(16(15)21)11-27-18(24)20(26,13(3)22)19(4,5)25/h7,12-13,15-16,22,25-26H,6,8-11H2,1-5H3/t12?,13-,15+,16+,20-/m0/s1
InChIKey CJYGEJQKEOQHSM-FGSQLUFMSA-N
Formula C20H33NO7
HBA 8
HBD 3
MW 399.48
Rotatable Bonds 8
TPSA 116.53
LogP 0.38
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 399.23
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: 15286360

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 399.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.11

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.39
Plasma Protein Binding
47.27
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
5.64
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.92
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
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
8.15
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
-6.41
Rat (Acute)
3.92
Rat (Chronic Oral)
2.15
Fathead Minnow
3.98
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
386.58
Hydration Free Energy
-9.97
Log(D) at pH=7.4
1.12
Log(P)
1.08
Log S
-1.78
Log(Vapor Pressure)
-8.43
Melting Point
139.45
pKa Acid
7.24
pKa Basic
7.43
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9267
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9267
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8561
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8561
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8197
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8197
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8186
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8186
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7981
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7981
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7897
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7897
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7859
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7859
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7851
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7851
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7757
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7757
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7724
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7724
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7610
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7610
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7552
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7552
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7490
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7490
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7461
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7461
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7426
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7426
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7422
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7422
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7399
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7399
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7303
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7303
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7250
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7250
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7212
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7212
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7166
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7166
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7162
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7162
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7154
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7154
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7025
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7025
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7001
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7001

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