4′,6,6′-trihydroxy-2′-(4-hydroxyphenyl)-7′-((E)-3-(4-hydroxyphenyl)acryloyl)-2′H,3H-2,3′-spirobi[benzofuran]-3-one - Compound Card

4′,6,6′-trihydroxy-2′-(4-hydroxyphenyl)-7′-((E)-3-(4-hydroxyphenyl)acryloyl)-2′H,3H-2,3′-spirobi[benzofuran]-3-one

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4′,6,6′-trihydroxy-2′-(4-hydroxyphenyl)-7′-((E)-3-(4-hydroxyphenyl)acryloyl)-2′H,3H-2,3′-spirobi[benzofuran]-3-one

Structure
Zoomed Structure
  • Family: Plantae - Ochnaceae
  • Kingdom: Plantae
  • Class: Benzofuran
Canonical Smiles Oc1ccc(cc1)C1Oc2c([C@@]31OC(CC3=O)c1ccc(cc1)O)c(O)cc(c2C(=O)/C=C/c1ccc(cc1)O)O
InChI InChI=1S/C32H24O9/c33-20-8-1-17(2-9-20)3-14-23(36)28-24(37)15-25(38)29-30(28)40-31(19-6-12-22(35)13-7-19)32(29)27(39)16-26(41-32)18-4-10-21(34)11-5-18/h1-15,26,31,33-35,37-38H,16H2/b14-3+/t26?,31?,32-/m0/s1
InChIKey VXONQYZCTRYEFP-BGSVZQEVSA-N
Formula C32H24O9
HBA 9
HBD 5
MW 552.54
Rotatable Bonds 5
TPSA 153.75
LogP 5.17
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 41
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 552.14
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Ochna kirkii Ochnaceae Plantae 2699567

Showing of synonyms

  • Kalenga TM, Ndoile MM, et al. (2021). Antibacterial and cytotoxic biflavonoids from the root bark of Ochna kirkii. Fitoterapia,2021, 151(), 104857. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)c(ccc2)c(OC3c4ccccc4)c2C35C(=O)CC(O5)c6ccccc6

Level: 3

Mol. Weight: 552.54 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)c(ccc2)c(c2C34C(=O)CCO4)OC3c5ccccc5

Level: 2

Mol. Weight: 552.54 g/mol

Structure

SMILES: c1ccccc1C=CC(=O)c(ccc2)c(OC3)c2C34C(=O)CC(O4)c5ccccc5

Level: 2

Mol. Weight: 552.54 g/mol

Structure

SMILES: c1ccccc1C2Oc(cccc3)c3C24C(=O)CC(O4)c5ccccc5

Level: 2

Mol. Weight: 552.54 g/mol

Structure

SMILES: O1CCC(=O)C12c3c(OC2)c(ccc3)C(=O)C=Cc4ccccc4

Level: 1

Mol. Weight: 552.54 g/mol

Structure

SMILES: c1cccc(OC2)c1C23C(=O)CC(O3)c4ccccc4

Level: 1

Mol. Weight: 552.54 g/mol

Structure

SMILES: O1CCC(=O)C12c3c(cccc3)OC2c4ccccc4

Level: 1

Mol. Weight: 552.54 g/mol

Structure

SMILES: O1CCC(=O)C12c3c(OC2)cccc3

Level: 0

Mol. Weight: 552.54 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 552.54 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
5.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.190
Plasma Protein Binding
87.45
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
9.700
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.570
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.870
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.300
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-12332.410
Rat (Acute)
2.380
Rat (Chronic Oral)
3.140
Fathead Minnow
34.070
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
474.230
Hydration Free Energy
-3.060
Log(D) at pH=7.4
3.580
Log(P)
4.12
Log S
-6.04
Log(Vapor Pressure)
-14.87
Melting Point
288.16
pKa Acid
7.86
pKa Basic
4.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9433
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9431
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9229
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9058
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.8936
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8895
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8828
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.8711
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8637
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 4 0.8524
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8497
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8412
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.8322
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8322
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8310
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8307
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.8284
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8228
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8175
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8152
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8124
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8100
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8028
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 5 0.8006
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8004
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 3 0.7994
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7951
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7944
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7916
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7891
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7864
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7824
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7818
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 3 0.7803
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7771
Decaprenylphosphoryl-beta-D-ribose oxidase I6X8C4 I6X8C4_MYCTU Mycobacterium tuberculosis 3 0.7740
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7727
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.7700
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7695
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7692
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7683
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7682
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7668
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7658
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 5 0.7606
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7600
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7597
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7542
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 3 0.7519
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7514
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7509
Transthyretin P02767 TTHY_RAT Rattus norvegicus 3 0.7497
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7490
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7486
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7482
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7472
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7425
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7393
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7387
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7379
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.7379
Protease O38732 O38732_9HIV1 Human immunodeficiency virus 1 5 0.7376
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7345
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7309
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7284
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7258
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7253
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7247
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7239
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7231
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7206
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7206
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7202
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7201
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7187
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.7168
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7165
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7153
Nitrogenase iron protein 1 P00459 NIFH1_AZOVI Azotobacter vinelandii 3 0.7133
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7118
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7099
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7073
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7073
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7062
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7049
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7042
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 3 0.7042
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7037
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7022
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7015
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7012
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7009
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7003
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7002

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