23-galloylarjunic acid - Compound Card

23-galloylarjunic acid

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23-galloylarjunic acid

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=C(c1cc(O)c(c(c1)O)O)OC[C@]1(C)[C@@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
InChI InChI=1S/C37H52O9/c1-32(2)11-13-37(31(44)45)14-12-35(5)21(22(37)17-32)7-8-27-33(3)18-25(40)29(42)34(4,26(33)9-10-36(27,35)6)19-46-30(43)20-15-23(38)28(41)24(39)16-20/h7,15-16,22,25-27,29,38-42H,8-14,17-19H2,1-6H3,(H,44,45)/t22-,25+,26+,27+,29-,33-,34-,35+,36+,37-/m0/s1
InChIKey LXTNFTYLTNCGNG-RWZVSUPFSA-N
Formula C37H52O9
HBA 8
HBD 6
MW 640.81
Rotatable Bonds 4
TPSA 164.75
LogP 6.16
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 640.36
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia brownii Combretaceae Plantae 1548809

Showing of synonyms

  • Machumi F, Midiwo JO, et al. (2013). Phytochemical, antimicrobial and antiplasmodial investigations of Terminalia brownii. Natural Product Communications,2013,8(6),761-764. [View] [PubMed]
Pubchem: 15385514
Nmrshiftdb2: 60043822

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC(CCC2)C(CC3)C2C(CC4)C3C(C=45)CCC6C5CCCC6

Level: 1

Mol. Weight: 640.81 g/mol

Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 640.81 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 640.81 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-5.86
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.16
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
20.06

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.1
Plasma Protein Binding
103.88
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
5.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.93
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.41
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.88
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Toxic
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
-38557.49
Rat (Acute)
2.43
Rat (Chronic Oral)
3.65
Fathead Minnow
67.15
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
791.58
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.99
Log(P)
5.91
Log S
-5.28
Log(Vapor Pressure)
-30.89
Melting Point
277.1
pKa Acid
6.42
pKa Basic
5.69
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9216
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9216
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8724
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8724
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8636
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8636
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8535
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8535
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8507
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8507
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8439
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8439
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8437
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8437
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8392
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8392
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8344
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8344
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8249
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8144
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8144
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8012
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8012
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7997
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7997
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7985
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7985
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7969
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7969
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7951
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7951
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7906
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7906
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7836
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7836
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7818
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7818
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7691
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7691
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7659
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7659
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7647
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7647
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7629
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7629
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7596
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7596
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7564
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7564
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7548
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7548
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7407
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7407
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7403
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7403
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7362
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7362
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7280
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7280
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7258
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7258
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7185
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7185
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7181
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7181
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7164
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7164
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7158
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7158
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7134
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7134
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7122
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7122
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7092
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7092
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7077
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7077
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7055
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7055
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7044
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7044

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