6',7'-dihydroxybergamottin octanalacetal - Compound Card

6',7'-dihydroxybergamottin octanalacetal

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6',7'-dihydroxybergamottin octanalacetal

Structure
Zoomed Structure
  • Family: Plantae - Arecaceae
  • Kingdom: Plantae
  • Class: Coumarin
    • Subclass: Furanocoumarin
Canonical Smiles CCCCCCC1O[C@H](CC/C=C/CC)C(OC1Oc1c2ccoc2cc2c1ccc(=O)o2)(C)C
InChI InChI=1S/C29H38O6/c1-5-7-9-11-13-22-28(35-29(3,4)25(32-22)14-12-10-8-6-2)34-27-20-15-16-26(30)33-24(20)19-23-21(27)17-18-31-23/h8,10,15-19,22,25,28H,5-7,9,11-14H2,1-4H3/b10-8+/t22?,25-,28?/m1/s1
InChIKey ZRAKUHAWRMGDOD-GLAURCAPSA-N
Formula C29H38O6
HBA 6
HBD 0
MW 482.62
Rotatable Bonds 11
TPSA 71.04
LogP 7.52
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 482.27
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Syagrus romanzoffiana Arecaceae Plantae 290277

Showing of synonyms

  • El-Hawary S.S, Fathy F.I, et al. (2021). Anticholinesterase activity and metabolite profiling of Syagrus romanzoffiana (Cham.) Glassman leaves and fruits via UPLC–QTOF–PDA–MS. Natural product research, 2021, 35(10), 1671-1675. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1coc(c12)cc3c(ccc(=O)o3)c2OC4COCCO4

Level: 1

Mol. Weight: 482.62 g/mol

Structure

SMILES: c1coc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 482.62 g/mol

Structure

SMILES: C1COCCO1

Level: 0

Mol. Weight: 482.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
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
-1.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.44
Plasma Protein Binding
94.41
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
5.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.55
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.46
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
-470.38
Rat (Acute)
2.17
Rat (Chronic Oral)
1.96
Fathead Minnow
6.49
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
511.05
Hydration Free Energy
-3.0
Log(D) at pH=7.4
5.91
Log(P)
7.64
Log S
-6.94
Log(Vapor Pressure)
-8.55
Melting Point
48.81
pKa Acid
7.66
pKa Basic
7.59
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.9790
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9492
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9270
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9255
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.9143
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.9125
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8809
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8800
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8517
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8447
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8335
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8307
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8303
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8283
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8252
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8245
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8133
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.8101
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8088
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.8085
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8085
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.8073
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8069
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.8043
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7974
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7943
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7931
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 4 0.7873
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7860
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7848
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7846
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7841
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7836
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7826
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7803
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7786
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7776
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7773
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7772
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7769
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7762
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7759
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7758
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7757
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7749
Biphenyl dioxygenase subunit alpha P37333 BPHA_PARXL Paraburkholderia xenovorans 3 0.7736
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7732
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7724
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7724
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7722
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7711
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7681
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7634
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7631
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7615
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7605
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7605
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7600
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7594
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7582
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7581
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7578
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7574
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7564
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7564
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7552
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 2 0.7545
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7536
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7535
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7530
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7525
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7523
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 2 0.7521
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7514
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7473
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7472
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7470
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7465
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7464
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7464
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7457
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7451
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 3 0.7450
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7444
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7437
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7417
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7413
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 2 0.7401
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7383
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7375
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7374
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7369
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7364
Interleukin-2 P60568 IL2_HUMAN Homo sapiens 2 0.7363
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7356
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7344
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7342
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7340
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7334
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7330
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7317
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7302
Phosphodiesterase Q53I60 Q53I60_TRYCR Trypanosoma cruzi 4 0.7297
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 2 0.7297
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7296
Phospholipase A2, membrane associated P14555 PA2GA_HUMAN Homo sapiens 2 0.7291
Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Q9UDY8 MALT1_HUMAN Homo sapiens 3 0.7282
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7272
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7271
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7269
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7267
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7267
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7263
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7254
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7251
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 2 0.7249
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7247
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7241
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7234
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7234
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7231
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7229
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7228
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7227
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7226
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 2 0.7225
Acetyl-CoA carboxylase Q00955 ACAC_YEAST Saccharomyces cerevisiae 3 0.7213
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7204
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7197
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7187
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7181
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7177
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7170
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7162
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7159
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7126
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7125
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7124
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7121
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7115
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7110
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7109
Cell division cycle 7-related protein kinase O00311 CDC7_HUMAN Homo sapiens 3 0.7108
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.7107
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7098
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.7095
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7091
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7089
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7085
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7078
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7072
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7063
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7062
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7058
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7043
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7040
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 2 0.7038
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 2 0.7035
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7031
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7012
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7005
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7002
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7002

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