Pycnanthine - Compound Card

Pycnanthine

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Pycnanthine

Structure
Zoomed Structure
  • Family: Plantae - Boraginaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles OC/C(=C/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)COC(=O)[C@@]([C@@H](O)C)(C(C)C)O)/C
InChI InChI=1S/C20H31NO7/c1-12(2)20(26,14(4)23)19(25)27-11-15-5-7-21-8-6-16(18(15)21)28-17(24)9-13(3)10-22/h5,9,12,14,16,18,22-23,26H,6-8,10-11H2,1-4H3/b13-9+/t14-,16+,18+,20-/m0/s1
InChIKey UKPSUWZPUAENNH-IOOTXOJLSA-N
Formula C20H31NO7
HBA 8
HBD 3
MW 397.47
Rotatable Bonds 8
TPSA 116.53
LogP 0.16
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 397.21
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: 91748009
Nmrshiftdb2: 70003066

No compound-protein relationship available.

Structure

SMILES: C1=CCN(C12)CCC2

Level: 0

Mol. Weight: 397.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.420
Plasma Protein Binding
43.6
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
7.650
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.950
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.010
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-7.760
Rat (Acute)
3.270
Rat (Chronic Oral)
2.220
Fathead Minnow
4.020
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
397.300
Hydration Free Energy
-8.830
Log(D) at pH=7.4
0.730
Log(P)
1.02
Log S
-1.47
Log(Vapor Pressure)
-8.29
Melting Point
138.88
pKa Acid
6.83
pKa Basic
7.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8593
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8593
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8529
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8529
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8237
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8237
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7821
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7821
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7722
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7722
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7687
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7687
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7552
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7552
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7497
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7497
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7477
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7477
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7455
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7455
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7439
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7439
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7420
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7420
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7407
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7407
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7323
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7323
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7306
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7306
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7281
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7281
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7273
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7273
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7214
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7214
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7163
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7163
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7137
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7137
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7046
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7046
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7039
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7039
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7023
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7023

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