3alpha-(3'',4''-dihydroxy-trans-cinnamoyloxy)-D-friedoolean-14-en-28-oic acid - Compound Card

3alpha-(3'',4''-dihydroxy-trans-cinnamoyloxy)-D-friedoolean-14-en-28-oic acid

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3alpha-(3'',4''-dihydroxy-trans-cinnamoyloxy)-D-friedoolean-14-en-28-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=C(O[C@@H]1CC[C@]2(C(C1(C)C)CC[C@@]1([C@]2(C)CC[C@@]2(C1=CC[C@@]1(C2CC(C)(C)CC1)C(=O)O)C)C)C)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C40H56O6/c1-34(2)19-22-40(33(44)45)18-14-29-36(5,30(40)24-34)20-21-39(8)37(6)17-15-31(35(3,4)28(37)13-16-38(29,39)7)46-32(43)12-10-25-9-11-26(41)27(42)23-25/h9-12,14,23,28,30-31,41-42H,13,15-22,24H2,1-8H3,(H,44,45)/b12-10+/t28?,30?,31-,36-,37+,38+,39-,40-/m1/s1
InChIKey ZCPLWGYJCVMNNC-PDPQOQCNSA-N
Formula C40H56O6
HBA 5
HBD 3
MW 632.88
Rotatable Bonds 4
TPSA 104.06
LogP 9.3
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 46
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 632.41
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Tamarix nilotica Tamaricaceae Plantae 189799
2 Tamarix nilotica Tamaricaceae Plantae 189799

Showing of synonyms

  • Abouzid SF, Ali SA, et al. (2009). A new ferulic acid ester and other constituents from Tamarix nilotica leaves. Chemical and Pharmaceutical Bulletin,2009,57(7),740-742. [View] [PubMed]
  • AbouZid S (2013). Chemical and biological studies on Tamarix nilotica growing in Egypt. Planta Medica,2013,79-PI3. [View]
Pubchem: 162817063
Nmrshiftdb2: 70051506

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC(CC2)CC(CC3)C2C(C3C=45)CCC5C6C(CC4)CCCC6

Level: 1

Mol. Weight: 632.88 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(C2C=34)CCC4C5C(CC3)CCCC5

Level: 0

Mol. Weight: 632.88 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 632.88 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.51
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.93
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
19.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.85
Plasma Protein Binding
101.96
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
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
4.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.62
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.19
Micronucleos
Safe
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
-38298.98
Rat (Acute)
2.08
Rat (Chronic Oral)
2.67
Fathead Minnow
68.46
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
896.78
Hydration Free Energy
-2.92
Log(D) at pH=7.4
5.34
Log(P)
9.17
Log S
-7.41
Log(Vapor Pressure)
-46.64
Melting Point
287.59
pKa Acid
7.59
pKa Basic
7.31
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 0.9354
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9354
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9194
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9194
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9114
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9114
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9113
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9113
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8877
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8877
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8789
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8789
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8681
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8681
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8607
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8607
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8361
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8361
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8309
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8309
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8266
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8266
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8251
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8251
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8168
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8168
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8142
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8142
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8120
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8120
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8106
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8106
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8035
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8000
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8000
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7982
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7982
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7943
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7943
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7934
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7934
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7900
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7900
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7879
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7879
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7848
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7848
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7844
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7844
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7830
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7830
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7805
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7805
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7769
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7769
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7754
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7754
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7675
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7675
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7637
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7637
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7635
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7635
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7634
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7634
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7522
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7522
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7521
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7521
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7502
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7502
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7495
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7487
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7487
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7472
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7472
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7397
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7397
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7358
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7358
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7326
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7326
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7311
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7311
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7283
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7283
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7274
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7274
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7247
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7247
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7247
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7247
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7191
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7191
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7189
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7189
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7184
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7184
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7182
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7182
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7177
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7177
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7157
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7157
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7154
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7154
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7153
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7153
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7148
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7148
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7140
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7140
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7111
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7111
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7108
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7108
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7105
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7105
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7103
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7103
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7094
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7094
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7090
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7090
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7084
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7084
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7074
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7074
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7056
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7056
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7052
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7052
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7045
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7045
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7035
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7035
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7033
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7033
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7027
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7027
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7024
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7024
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7022
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7022
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7016
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7016
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7008
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7008
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7004
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7004

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