(-)-5-hydroxydeltoin - Compound Card

(-)-5-hydroxydeltoin

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(-)-5-hydroxydeltoin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles C/C=C(\C(=O)OC([C@H]1Oc2c(C1)c(O)c1c(c2)oc(=O)cc1)(C)C)/C
InChI InChI=1S/C19H20O6/c1-5-10(2)18(22)25-19(3,4)15-8-12-14(23-15)9-13-11(17(12)21)6-7-16(20)24-13/h5-7,9,15,21H,8H2,1-4H3/b10-5-/t15-/m0/s1
InChIKey LKYRHPWVCQSGGQ-ANOSYLROSA-N
Formula C19H20O6
HBA 6
HBD 1
MW 344.36
Rotatable Bonds 3
TPSA 85.97
LogP 3.09
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.37
Exact Mass 344.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula lutea Apiaceae Plantae 52470

Showing of synonyms

  • Ben Salem S, Jabrane A, et al. (2013). New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire.. Bioorganic and Medicinal Chemistry Letters,2013,23(14),4248-4252. [View] [PubMed]
Pubchem: 72734402
Nmrshiftdb2: 70071766

No compound-protein relationship available.

Structure

SMILES: C1COc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 344.36 g/mol

Antioxidant
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.56
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
71.33
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
7.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.05
Micronucleos
Toxic
NR-AhR
Toxic
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
-2.03
Rat (Acute)
2.45
Rat (Chronic Oral)
1.65
Fathead Minnow
4.59
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
419.56
Hydration Free Energy
-9.29
Log(D) at pH=7.4
3.12
Log(P)
3.55
Log S
-4.64
Log(Vapor Pressure)
-7.42
Melting Point
157.32
pKa Acid
8.36
pKa Basic
5.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9840
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9840
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8592
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8592
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8416
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8416
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8310
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8310
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8289
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8289
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8256
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8256
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8151
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8151
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8113
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8113
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7972
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7972
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7855
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7855
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7826
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7826
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7796
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7796
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7795
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7795
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7718
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7718
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7717
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7717
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7695
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7695
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7660
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7660
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7658
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7658
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7614
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7614
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7609
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7609
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7603
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7603
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7596
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7596
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7590
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7590
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7587
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7587
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7581
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7581
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7564
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7564
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7502
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7502
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7469
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7469
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7455
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7455
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7424
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7424
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7418
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7418
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7411
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7411
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7402
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7402
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7359
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7359
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7347
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7347
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7300
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7300
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7291
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7291
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7234
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7234
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7169
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7169
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7128
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7128
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7127
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7127
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7124
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7124
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7100
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7100
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7095
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7095
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7087
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7087
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7073
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7073
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 4 0.7033
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 4 0.7033
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7029
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7029
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7027
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7027
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7011
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7011
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7006
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7006

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