2',3'-dihydroxyasteranthine - Compound Card

2',3'-dihydroxyasteranthine

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2',3'-dihydroxyasteranthine

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles OC(C(O)(C)C)Cc1c[nH]c2c1ccc1c2OC(C=C1)(C)C
InChI InChI=1S/C18H23NO3/c1-17(2)8-7-11-5-6-13-12(9-14(20)18(3,4)21)10-19-15(13)16(11)22-17/h5-8,10,14,19-21H,9H2,1-4H3
InChIKey QBDVBDCNSPYCRW-UHFFFAOYSA-N
Formula C18H23NO3
HBA 3
HBD 3
MW 301.39
Rotatable Bonds 3
TPSA 65.48
LogP 3.03
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 301.17
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]
Pubchem: 101379690

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 301.39 g/mol

Antimycotic

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.84
Plasma Protein Binding
18.49
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.29
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.63
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
2.08
Rat (Acute)
3.33
Rat (Chronic Oral)
2.23
Fathead Minnow
4.1
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
397.78
Hydration Free Energy
-13.65
Log(D) at pH=7.4
3.08
Log(P)
2.94
Log S
-3.27
Log(Vapor Pressure)
-8.11
Melting Point
197.42
pKa Acid
11.29
pKa Basic
6.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8787
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8787
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8680
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8680
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8531
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8531
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8412
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8412
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8326
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8326
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8295
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8295
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8248
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8248
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8221
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8221
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8187
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8187
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8181
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8181
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8123
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.8123
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8097
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8097
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8090
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8090
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7934
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7934
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7933
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7933
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7883
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7883
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7825
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7825
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7739
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7739
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7625
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7625
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7615
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7615
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7613
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7613
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7578
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7578
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7556
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7556
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7552
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7552
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7503
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7503
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7476
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.7476
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7473
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7473
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7472
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7472
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7447
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7447
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7411
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7411
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7332
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7332
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7331
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7331
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7292
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7292
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7285
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7285
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7223
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7223
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7212
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7212
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7191
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7191
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7180
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7180
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7178
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7178
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7122
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7122
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7109
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7109
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7077
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7077
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7065
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7065
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7060
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7060
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7053
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 4 0.7053
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7052
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7052
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7050
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7050
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7026
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7026
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7024
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7024
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7011
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7011
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7006
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7006

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