Salvianolic acid B - Compound Card

Salvianolic acid B

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Salvianolic acid B

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Acid
Canonical Smiles O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc(c2c1[C@H](C(=O)O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)[C@H](O2)c1ccc(c(c1)O)O)O
InChI InChI=1S/C36H30O16/c37-20-6-1-16(11-24(20)41)13-27(34(45)46)50-29(44)10-5-18-3-9-23(40)33-30(18)31(32(52-33)19-4-8-22(39)26(43)15-19)36(49)51-28(35(47)48)14-17-2-7-21(38)25(42)12-17/h1-12,15,27-28,31-32,37-43H,13-14H2,(H,45,46)(H,47,48)/b10-5+/t27-,28-,31+,32-/m1/s1
InChIKey SNKFFCBZYFGCQN-VWUOOIFGSA-N
Formula C36H30O16
HBA 14
HBD 9
MW 718.62
Rotatable Bonds 12
TPSA 278.04
LogP 3.33
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 52
Formal Charge 0
Fraction CSP3 0.17
Exact Mass 718.15
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Rosmarinuseriocalyx Lamiaceae Plantae

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
CPRiL: 54745
Structure

SMILES: c1ccccc1CCOC(=O)C=Cc2cccc(c23)OC(c4ccccc4)C3C(=O)OCCc5ccccc5

Level: 3

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)C=Cc2cccc(c23)OCC3C(=O)OCCc4ccccc4

Level: 2

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)C=Cc2cccc(c23)OC(C3)c4ccccc4

Level: 2

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)C2C(=O)OCCc4ccccc4

Level: 2

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1ccccc1CCOC(=O)C=Cc2cccc(c23)OCC3

Level: 1

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1cccc(c12)OCC2C(=O)OCCc3ccccc3

Level: 1

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 718.62 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 718.62 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 718.62 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.2
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-1.960
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
580.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.080
Plasma Protein Binding
84.7
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
7.110
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-15.240
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.090
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.720
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1061873.610
Rat (Acute)
2.100
Rat (Chronic Oral)
2.880
Fathead Minnow
1350.080
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
110778.630
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-0.590
Log(P)
2.54
Log S
-3.09
Log(Vapor Pressure)
-3732.48
Melting Point
353.77
pKa Acid
-3.92
pKa Basic
3.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.9212
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9046
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8931
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.8885
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8823
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8678
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 3 0.8662
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8648
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 4 0.8612
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8610
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8608
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8499
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8494
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8442
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8414
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.8413
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.8360
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8360
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8332
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8297
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8275
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8152
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 3 0.8127
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8080
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8077
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8076
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8042
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7899
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7864
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7864
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7858
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7824
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7792
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7773
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7765
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7762
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7738
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7730
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7721
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 3 0.7687
Tryptophan synthase beta chain 2 Q97TX6 TRPB2_SACS2 Saccharolobus solfataricus 3 0.7685
Protease O38896 O38896_9HIV1 Human immunodeficiency virus 1 3 0.7658
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7656
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.7621
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7613
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7597
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7589
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7588
Nickel-binding periplasmic protein P33590 NIKA_ECOLI Escherichia coli 3 0.7578
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.7570
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7562
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7537
Protein RecA Q59560 RECA_MYCS2 Mycolicibacterium smegmatis155) 4 0.7536
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7515
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.7509
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7501
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7490
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7481
Caffeic acid 3-O-methyltransferase P28002 COMT1_MEDSA Medicago sativa 3 0.7476
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7475
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 4 0.7465
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7442
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7440
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7439
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7414
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7390
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7370
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7350
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7347
Basic phospholipase A2 homolog piratoxin-1 P58399 PA2H1_BOTPI Bothrops pirajai 4 0.7326
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7315
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7315
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7311
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7302
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7285
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7284
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7269
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7263
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7259
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 3 0.7254
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 3 0.7242
VioE domain-containing protein Q7NSZ5 Q7NSZ5_CHRVO Chromobacterium violaceum 3 0.7241
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7236
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7236
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7232
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7226
Formylmethanofuran--tetrahydromethanopterin formyltransferase Q49610 FTR_METKA Methanopyrus kandleri 3 0.7215
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7205
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7200
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7199
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7195
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7195
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7193
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 3 0.7186
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7179
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7176
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7167
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7157
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7149
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7148
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7143
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7135
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7134
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7125
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7123
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7122
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7121
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7121
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7114
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 3 0.7112
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7111
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7110
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7110
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7097
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7084
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7073
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7072
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7072
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7070
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7070
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7061
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7056
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7051
Protease Q5RTL1 Q5RTL1_9HIV1 Human immunodeficiency virus 1 4 0.7050
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7049
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.7044
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7044
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7042
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7040
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 4 0.7039
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7032
Uncharacterized protein Q55S71 Q55S71_CRYNB Cryptococcus neoformans var. neoformans serotype D 4 0.7027
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7024
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7014
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7001
Salicylate synthase P9WFX1 MBTI_MYCTU Mycobacterium tuberculosis 3 0.7001

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