13-hydroxyfeselol diacetate - Compound Card

13-hydroxyfeselol diacetate

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13-hydroxyfeselol diacetate

Structure
Zoomed Structure
  • Family: Apiaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Sesquiterpene Coumarin Ester
Canonical Smiles CC(=O)OC[C@@]1(C)[C@H](CC[C@]2([C@H]1CC=C([C@@H]2COc1ccc2c(c1)oc(=O)cc2)C)C)OC(=O)C
InChI InChI=1S/C28H34O7/c1-17-6-10-24-27(4,13-12-25(34-19(3)30)28(24,5)16-33-18(2)29)22(17)15-32-21-9-7-20-8-11-26(31)35-23(20)14-21/h6-9,11,14,22,24-25H,10,12-13,15-16H2,1-5H3/t22-,24+,25-,27+,28+/m0/s1
InChIKey BYJYILQHGALOLC-FTYRIKNVSA-N
Formula C28H34O7
HBA 7
HBD 0
MW 482.57
Rotatable Bonds 6
TPSA 92.04
LogP 5.06
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.54
Exact Mass 482.23
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Ferula vesceritensis Apiaceae Plantae 1514058

Showing of synonyms

  • Ahmed AA, Hegazy MEF, et al. (2007). Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from Ferula species. Phytochemistry,2007,68(5),680-686. [View]
Pubchem: 102469380
Nmrshiftdb2: 70028012

No compound-protein relationship available.

Structure

SMILES: c1cc(=O)oc(c12)cc(cc2)OCC3C=CCC(C34)CCCC4

Level: 1

Mol. Weight: 310.39 g/mol

Structure

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 146.15 g/mol

Structure

SMILES: C1C=CCC(C12)CCCC2

Level: 0

Mol. Weight: 136.24 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.76
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.05

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.39
Plasma Protein Binding
95.2
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.32
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.65
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.41
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.62
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
-250.8
Rat (Acute)
2.65
Rat (Chronic Oral)
1.89
Fathead Minnow
4.8
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
499.3
Hydration Free Energy
-2.92
Log(D) at pH=7.4
4.12
Log(P)
4.41
Log S
-6.05
Log(Vapor Pressure)
-8.75
Melting Point
153.48
pKa Acid
8.56
pKa Basic
6.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9540
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.9540
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9476
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.9476
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9436
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.9436
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9418
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.9418
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9276
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.9276
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8993
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8993
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8960
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8960
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8950
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8950
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8740
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8740
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8424
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8424
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8421
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8421
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8341
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8341
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8141
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8141
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8124
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8124
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8122
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.8122
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8079
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8079
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7979
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7979
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7922
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7922
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7901
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7901
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7856
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7856
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7846
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7846
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7770
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7770
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7750
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7750
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7729
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7729
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7725
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7725
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7715
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7715
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7713
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7713
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7590
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7590
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7549
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 2 0.7549
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7512
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7512
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7493
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7493
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7487
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7487
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7457
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7457
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7439
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7439
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7432
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7432
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7428
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7412
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7412
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7328
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7328
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7315
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7315
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7297
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7297
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7281
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7281
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7278
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7278
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7256
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7256
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7243
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 2 0.7243
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7223
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7223
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7210
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7210
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7198
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7198
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7196
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7196
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7166
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7166
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7158
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7158
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7147
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7147
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7144
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7144
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7115
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7115
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7094
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7094
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7084
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7084
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7083
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7083
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7082
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7082
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7082
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7082
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7076
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7076
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7072
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7072
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7068
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7068
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7054
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7054
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7046
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7046
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7040
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7040
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7031
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7031
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7031
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7031
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7010
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7010
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7003
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7003

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