Methyl 5,10-dihydroxy-7-methoxy-3-methyl-3-(4-methyl-3-pentenyl)-3H-benzo[f]chromene-9-carboxylate - Compound Card

Methyl 5,10-dihydroxy-7-methoxy-3-methyl-3-(4-methyl-3-pentenyl)-3H-benzo[f]chromene-9-carboxylate

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Methyl 5,10-dihydroxy-7-methoxy-3-methyl-3-(4-methyl-3-pentenyl)-3H-benzo[f]chromene-9-carboxylate

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Quinone
    • Subclass: Naphthohydroquinone
Canonical Smiles COC(=O)c1cc(OC)c2c(c1O)c1C=CC(Oc1c(c2)O)(C)CCC=C(C)C
InChI InChI=1S/C23H26O6/c1-13(2)7-6-9-23(3)10-8-14-19-15(11-17(24)21(14)29-23)18(27-4)12-16(20(19)25)22(26)28-5/h7-8,10-12,24-25H,6,9H2,1-5H3
InChIKey KOZKSXRTQNRWGJ-UHFFFAOYSA-N
Formula C23H26O6
HBA 6
HBD 2
MW 398.46
Rotatable Bonds 5
TPSA 85.22
LogP 4.96
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 398.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pentas bussei Rubiaceae Plantae 387051
2 Pentas bussei Rubiaceae Plantae 387051
3 Pentas bussei Rubiaceae Plantae 387051
4 Pentas bussei Rubiaceae Plantae 387051
5 Pentas parvifolia Rubiaceae Plantae 296969

Showing of synonyms

  • Bukuru JF, Van TN, et al. (2002). A benzochromene from the roots of Pentas bussei. Journal of Natural Products,2002,65(5),783-785. [View] [PubMed]
  • Endale M, Ekberg A, et al. (2012). Busseihydroquinones A-D from the roots of Pentas bussei. Journal of Natural Products,2012,75(7),1299-1304. [View] [PubMed]
  • Bukuru J, De Kimpe N, et al. (2003). Isolation and structural elucidation of natural products from Pentas bussei K. Krause, Pentas lanceolata (Forsk.) Deflers and Pentas parvifolia Hiern (Rubiaceae). Ph.D. Thesis, University of Ghent, Faculty of Bioscience Engineering, Belgium,2003. [View] [PubMed]
  • Abdissa N, Pan F, et al. (2016). Naphthalene derivatives from the roots of Pentas parvifolia and Pentas bussei. Journal of Natural Products,2016,79(9),2181-2187. [View] [PubMed]
Pubchem: 11112105
Nmrshiftdb2: 2579

No compound-protein relationship available.

Structure

SMILES: C1=CCOc(c1c23)ccc2cccc3

Level: 0

Mol. Weight: 398.46 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-4.43
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.350
Plasma Protein Binding
49.46
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.360
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.350
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.790
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.720
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
-8.200
Rat (Acute)
2.280
Rat (Chronic Oral)
2.790
Fathead Minnow
5.010
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
440.950
Hydration Free Energy
-7.280
Log(D) at pH=7.4
4.990
Log(P)
6.7
Log S
-6.8
Log(Vapor Pressure)
-7.7
Melting Point
160.7
pKa Acid
8.25
pKa Basic
5.74
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8887
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8887
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8880
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.8880
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8706
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8706
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8662
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8662
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8655
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8655
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8361
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8361
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8358
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8358
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8324
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8324
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8287
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8287
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7916
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7916
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 5 0.7863
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 5 0.7863
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7774
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7774
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7707
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7707
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7672
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7672
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7582
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7582
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7565
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.7565
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7529
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7529
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7516
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7516
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7497
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.7497
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7494
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7494
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7493
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7493
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7492
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7492
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7464
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7464
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7463
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7463
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7418
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7418
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7417
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7417
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7407
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7407
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7405
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.7405
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7367
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7367
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7356
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7356
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7319
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7319
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7244
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7244
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7237
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7237
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7228
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7227
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7227
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7216
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 3 0.7216
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7214
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7214
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7196
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7196
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7191
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7191
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7165
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7165
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7152
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7152
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7118
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7118
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7114
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7114
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7085
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7085
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7072
Vanillate porin OpdK Q9HUR5 Q9HUR5_PSEAE Pseudomonas aeruginosa 3 0.7072
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7058
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7058
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7042
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7042
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7017
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7017
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7004
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7004

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