(+)-(S)-dihydro-2',3'-epoxyasteranthine - Compound Card

(+)-(S)-dihydro-2',3'-epoxyasteranthine

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(+)-(S)-dihydro-2',3'-epoxyasteranthine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC1(C)C=Cc2c(O1)c1[nH]cc(c1cc2)C[C@@H]1OC1(C)C
InChI InChI=1S/C18H21NO2/c1-17(2)8-7-11-5-6-13-12(9-14-18(3,4)20-14)10-19-15(13)16(11)21-17/h5-8,10,14,19H,9H2,1-4H3/t14-/m0/s1
InChIKey WGCRCPAMKCMAIH-AWEZNQCLSA-N
Formula C18H21NO2
HBA 2
HBD 1
MW 283.37
Rotatable Bonds 2
TPSA 37.55
LogP 4.07
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 283.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Asteranthe asterias Annonaceae Plantae 489324

Showing of synonyms

  • Nkunya MHH, Jonker SA, et al. (1996). New diprenylated indoles from Asteranthe asterias (Annonaceae). Natural Product Letters,1996,9(1),71-78. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CC1Cc2c[nH]c(c23)c4c(cc3)C=CCO4

Level: 1

Mol. Weight: 283.37 g/mol

Structure

SMILES: c1c[nH]c(c12)c3c(cc2)C=CCO3

Level: 0

Mol. Weight: 283.37 g/mol

Structure

SMILES: C1CO1

Level: 0

Mol. Weight: 283.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.88
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.6
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.49

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.55
Plasma Protein Binding
26.7
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
17.33
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.6
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.98
Micronucleos
Toxic
NR-AhR
Toxic
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
2.7
Rat (Acute)
2.54
Rat (Chronic Oral)
1.79
Fathead Minnow
4.51
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
392.85
Hydration Free Energy
-8.86
Log(D) at pH=7.4
4.19
Log(P)
4.4
Log S
-4.45
Log(Vapor Pressure)
-6.32
Melting Point
129.38
pKa Acid
9.06
pKa Basic
4.16
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7982
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7982
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7864
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7864
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7850
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7850
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7708
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7708
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7704
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7704
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7690
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7690
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7688
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7688
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7676
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7676
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7595
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7595
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7566
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7566
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7471
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7471
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7464
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7464
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7435
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7435
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7357
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7357
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7320
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7320
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7306
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7306
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7165
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7165
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7097
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7097
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7091
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7091
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7085
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7085
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7029
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7029
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7024
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7024

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