(-)-5-hydroxyprantschimgin - Compound Card

(-)-5-hydroxyprantschimgin

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(-)-5-hydroxyprantschimgin

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles CC(=CC(=O)OC([C@H]1Oc2c(C1)c(O)c1c(c2)oc(=O)cc1)(C)C)C
InChI InChI=1S/C19H20O6/c1-10(2)7-17(21)25-19(3,4)15-8-12-14(23-15)9-13-11(18(12)22)5-6-16(20)24-13/h5-7,9,15,22H,8H2,1-4H3/t15-/m0/s1
InChIKey XGVLCRIOXLEBRU-HNNXBMFYSA-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: 71713632
Nmrshiftdb2: 70071767

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)
-4.57
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.12
Plasma Protein Binding
65.65
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
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.28
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.08
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
1.33
Rat (Acute)
2.33
Rat (Chronic Oral)
1.68
Fathead Minnow
4.57
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
422.67
Hydration Free Energy
-9.55
Log(D) at pH=7.4
2.88
Log(P)
3.31
Log S
-4.64
Log(Vapor Pressure)
-7.52
Melting Point
170.94
pKa Acid
8.33
pKa Basic
5.76
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 0.9852
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9852
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8689
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8689
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8610
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8610
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8437
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8437
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8419
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8419
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8322
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8322
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8272
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8272
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8224
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8224
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8204
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8204
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8114
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8114
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8074
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8074
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8015
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8015
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8008
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8008
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7958
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7958
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7937
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7937
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7924
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7924
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7915
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7915
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7908
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7908
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7890
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7890
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7843
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7843
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7809
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7809
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7747
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7747
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7710
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7710
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7679
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7679
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7668
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7668
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7654
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7654
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7634
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7634
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7629
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7629
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7619
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7619
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7596
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7596
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7589
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7589
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7582
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7582
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7474
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7474
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7455
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7455
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7455
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7455
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7439
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7439
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7430
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7430
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7427
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7427
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7389
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7389
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7387
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7387
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7382
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7382
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7324
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7324
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7310
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7310
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7277
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7277
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7263
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7263
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7232
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7232
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7223
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7223
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7213
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7213
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7190
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7190
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7185
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7185
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7173
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7173
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7163
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7163
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7139
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7139
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7134
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7134
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7119
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7119
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7114
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 4 0.7114
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7081
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7081
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7071
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7071
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7058
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7058
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7049
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7049
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7046
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7046
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7027
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7027
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7014
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7014

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