7-acetyl-9-curassavoylheliotridine - Compound Card

7-acetyl-9-curassavoylheliotridine

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7-acetyl-9-curassavoylheliotridine

Structure
Zoomed Structure
  • Family: Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CCC([C@](C(=O)OCC1=CCN2[C@H]1[C@H](CC2)OC(=O)C)([C@H](O)C)O)C
InChI InChI=1S/C18H29NO6/c1-5-11(2)18(23,12(3)20)17(22)24-10-14-6-8-19-9-7-15(16(14)19)25-13(4)21/h6,11-12,15-16,20,23H,5,7-10H2,1-4H3/t11?,12-,15+,16-,18-/m1/s1
InChIKey NRKGCBYQDMTQRF-DLFJVTDKSA-N
Formula C18H29NO6
HBA 7
HBD 2
MW 355.43
Rotatable Bonds 7
TPSA 96.3
LogP 0.63
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 355.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anchusa milleri Boraginaceae Plantae 256477

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: 91747348
Nmrshiftdb2: 60077951

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 109.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
35.84
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
7.28
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.35
Biodegradation
Safe
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
8.95
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
-3.63
Rat (Acute)
3.65
Rat (Chronic Oral)
2.12
Fathead Minnow
3.95
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
354.27
Hydration Free Energy
-11.16
Log(D) at pH=7.4
1.12
Log(P)
1.17
Log S
-1.71
Log(Vapor Pressure)
-7.5
Melting Point
116.31
pKa Acid
7.17
pKa Basic
7.11
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 0.9155
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.9155
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8992
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8992
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8729
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.8729
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8419
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8419
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8188
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8188
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8139
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8139
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7799
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7799
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7729
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7729
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7702
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7702
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7623
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7623
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7596
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7596
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7488
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7488
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7447
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7447
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7444
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7444
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7349
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7349
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7293
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7293
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7207
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7207
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7193
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7193
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7192
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7192
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7172
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7172
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7161
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7161
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7153
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7153
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7148
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7148
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7144
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7144

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