Hexacycloxylariolone - Compound Card

Hexacycloxylariolone

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Hexacycloxylariolone

Structure
Zoomed Structure
  • Family: Fungi - Xylariaceae
  • Kingdom: Fungi
  • Class: Chromane
Canonical Smiles CC(C1C=Cc2c(O1)cccc2O)O
InChI InChI=1S/C11H12O3/c1-7(12)10-6-5-8-9(13)3-2-4-11(8)14-10/h2-7,10,12-13H,1H3
InChIKey WFKYUZHQMVDDMO-UHFFFAOYSA-N
Formula C11H12O3
HBA 3
HBD 2
MW 192.21
Rotatable Bonds 1
TPSA 49.69
LogP 1.55
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 192.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Xylaria sp Xylariaceae Fungi 1715255

Showing of synonyms

  • Tegha HF, Jouda J-B, et al. (2021). A new chromene derivative and a new polyalcohol isolated from the fungus Xylaria sp. 111A associated with Garcinia polyantha leaves. Natural product communications, 2021, 16(1), 1-5. [View]
Pubchem: 170989939

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 192.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.12
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
3.56
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
6.89
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.51
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.13
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.94
Micronucleos
Toxic
NR-AhR
Safe
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
2.9
Rat (Acute)
2.52
Rat (Chronic Oral)
2.31
Fathead Minnow
3.91
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
305.18
Hydration Free Energy
-10.19
Log(D) at pH=7.4
1.48
Log(P)
1.95
Log S
-1.86
Log(Vapor Pressure)
-4.86
Melting Point
108.63
pKa Acid
9.41
pKa Basic
3.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.9148
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.9015
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8998
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8996
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8833
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8761
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8753
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.8677
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8667
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8662
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8618
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8548
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8466
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8368
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8353
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8310
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8274
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8210
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.8182
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8177
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8143
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8027
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7974
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7968
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7965
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7900
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7896
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7878
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7877
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7863
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7838
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7805
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7751
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7746
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7700
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7691
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7683
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7680
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7665
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7656
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7651
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7616
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7616
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7609
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7605
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7587
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7559
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7551
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7551
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7537
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7532
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7530
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7517
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7513
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7503
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7499
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7482
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7465
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7446
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7438
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7434
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7432
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7420
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7417
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7413
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7405
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7404
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7398
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7391
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7385
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7377
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7355
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7353
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7340
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7333
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7327
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7327
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7325
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7316
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7300
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7291
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7287
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7284
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7274
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7271
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7266
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7260
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7259
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7256
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7254
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7254
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7249
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7248
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7248
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7226
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7220
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7208
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7205
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7177
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7176
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7155
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7146
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7141
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7138
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7135
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7134
cysteine-S-conjugate beta-lyase Q8DST5 Q8DST5_STRMU Streptococcus mutans serotype c 3 0.7131
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7130
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7112
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7105
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7089
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7087
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7063
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7058
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7051
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7051
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 2 0.7049
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 2 0.7049
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7048
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7045
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7043
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7037
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7035
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7027
Aromatic/aminoadipate aminotransferase 1 P53090 ARO8_YEAST Saccharomyces cerevisiae 3 0.7018
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7017
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7004
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7003
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7002
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7002

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