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Indole-3-carboxylic acid-(6’-O-caffeoyl)-beta-D-glucoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid Glucoside

Canonical Smiles	O=C(/C=C/c1ccc(c(c1)O)O)OC[C@H]1O[C@@H](OC(=O)c2c[nH]c3c2cccc3)C(C(C1O)O)O
InChI	InChI=1S/C24H23NO10/c26-16-7-5-12(9-17(16)27)6-8-19(28)33-11-18-20(29)21(30)22(31)24(34-18)35-23(32)14-10-25-15-4-2-1-3-13(14)15/h1-10,18,20-22,24-27,29-31H,11H2/b8-6+/t18-,20?,21?,22?,24+/m1/s1
InChIKey	OREAATBTCDTFTG-OXERSFDGSA-N
Formula	C₂₄H₂₃NO₁₀
HBA	10
HBD	6
MW	485.45
Rotatable Bonds	6
TPSA	178.77
LogP	0.8
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	485.13
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Saccocalyx saturejoides	Lamiaceae	Plantae	751886

Showing of synonyms

Kherkhache H, Benabdelaziz I, et al. (2020). A new indole alkaloid, antioxidant and antibacterial activities of crude extracts from Saccocalyx satureioides. Natural product research, 2020, 34(11), 1528-1534. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(=O)c3c[nH]c(c34)cccc4

Level: 2

Mol. Weight: 485.45 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 485.45 g/mol

SMILES: O1CCCCC1OC(=O)c2c[nH]c(c23)cccc3

Level: 1

Mol. Weight: 485.45 g/mol

SMILES: c1c[nH]c(c12)cccc2

Level: 0

Mol. Weight: 485.45 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 485.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 485.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.66
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.03
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.98
Plasma Protein Binding: 56.28
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: 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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.59
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.57
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.59
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.72
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: -437.86
Rat (Acute): 2.26
Rat (Chronic Oral): 3.88
Fathead Minnow: 4.73
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 582.99
Hydration Free Energy: -3.19
Log(D) at pH=7.4: 1.68
Log(P): 1.87
Log S: -4.02
Log(Vapor Pressure): -12.27
Melting Point: 202.78
pKa Acid: 6.15
pKa Basic: 6.67

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	0.9352
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.9173
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9140
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9089
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.9042
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8984
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8957
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8810
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8805
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8763
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8682
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8543
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8522
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8518
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8457
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8370
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8348
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8346
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8313
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.8296
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	4	0.8265
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8257
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8204
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8140
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8133
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8114
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8100
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8079
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8027
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8023
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7987
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7959
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7951
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7898
Copper-transporting ATPase	Q97UU7	Q97UU7_SACS2	Saccharolobus solfataricus	4	0.7891
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7891
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7856
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7849
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7739
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7736
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7697
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7691
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7689
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7674
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7628
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7627
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7609
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7597
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7577
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7560
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7540
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7524
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7503
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7494
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7465
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7433
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7397
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7392
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7383
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7374
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7360
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7350
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7342
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7339
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7331
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7307
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7304
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7290
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7286
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7277
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7247
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7243
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7241
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7235
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7234
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7230
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7229
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7229
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7220
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7202
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7196
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7191
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7186
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7179
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7176
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7163
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7159
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7154
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7153
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7152
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7144
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	2	0.7144
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7132
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7130
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7127
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7111
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7105
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7102
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	4	0.7101
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7092
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7091
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7079
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7079
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7079
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7070
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7066
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7055
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7052
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7051
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7047
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7035
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	4	0.7030
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7026
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7024
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7023
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7020
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7019
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7016
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7015

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