Acetyllycopsamine - Compound Card

Acetyllycopsamine

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Acetyllycopsamine

Structure
Zoomed Structure
  • Family: Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Pyrrolizidine Alkaloid
Canonical Smiles CC(=O)O[C@@H]1CCN2C1C(=CC2)COC(=O)C([C@@H](O)C)(C(C)C)O
InChI InChI=1S/C17H27NO6/c1-10(2)17(22,11(3)19)16(21)23-9-13-5-7-18-8-6-14(15(13)18)24-12(4)20/h5,10-11,14-15,19,22H,6-9H2,1-4H3/t11-,14+,15?,17?/m0/s1
InChIKey RKDOFSJTBIDAHX-PNIKOYRFSA-N
Formula C17H27NO6
HBA 7
HBD 2
MW 341.4
Rotatable Bonds 6
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 Lappula spinocarpos Boraginaceae Plantae 1245804

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: 91747357
Nmrshiftdb2: 60077943
CPRiL: 424357
Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 109.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.84
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.29
Plasma Protein Binding
30.3
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
7.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.53
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.18
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.94
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
-1.62
Rat (Acute)
3.31
Rat (Chronic Oral)
2.03
Fathead Minnow
3.98
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
341.76
Hydration Free Energy
-11.18
Log(D) at pH=7.4
0.28
Log(P)
0.9
Log S
-1.34
Log(Vapor Pressure)
-6.88
Melting Point
127.81
pKa Acid
7.02
pKa Basic
7.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.9000
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.9000
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8800
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8800
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8601
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8601
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8309
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8309
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7969
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7969
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7854
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7854
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7776
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7776
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7700
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7700
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7687
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7687
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7650
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7650
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7633
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7633
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7517
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7517
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7375
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7375
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7361
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7361
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7251
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7251
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7213
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7213
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7207
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7207
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7189
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7189
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7149
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7149
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7125
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7125
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7108
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7108
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7102
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7102
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7089
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7089
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7046
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7046

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