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6-O-(2''-O-acetyl-3'',4''-O-di-trans-cinnamoyl)-alpha-L-rhamnopyranosylcatalpol

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Monoterpene Glycoside

Canonical Smiles	OCC1O[C@@H](O[C@@H]2OC=CC3C2[C@@]2(CO)O[C@H]2[C@H]3O[C@@H]2O[C@@H](C)[C@@H](C(C2OC(=O)C)OC(=O)/C=C/c2ccccc2)OC(=O)/C=C/c2ccccc2)[C@@H](C([C@@H]1O)O)O
InChI	InChI=1S/C41H46O17/c1-21-33(54-27(45)15-13-23-9-5-3-6-10-23)35(55-28(46)16-14-24-11-7-4-8-12-24)36(52-22(2)44)40(51-21)56-34-25-17-18-50-38(29(25)41(20-43)37(34)58-41)57-39-32(49)31(48)30(47)26(19-42)53-39/h3-18,21,25-26,29-40,42-43,47-49H,19-20H2,1-2H3/b15-13+,16-14+/t21-,25?,26?,29?,30+,31?,32+,33-,34-,35?,36?,37-,38-,39-,40-,41+/m0/s1
InChIKey	PCHWYSGBVKSPAM-YQXICLTPSA-N
Formula	C₄₁H₄₆O₁₇
HBA	17
HBD	5
MW	810.8
Rotatable Bonds	13
TPSA	238.73
LogP	0.36
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	58
Formal Charge	0
Fraction CSP3	0.49
Exact Mass	810.27
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Gmelina arborea	Lamiaceae	Plantae	201509

Showing of synonyms

Hosny M, Rosazza J.P. (1998). Gmelinosides A-L, twelve acylated iridoid glycosides from Gmelina arborea. Journal of natural products, 1998, 61(6), 734-42. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)COC(C2)OC(C(O4)C45)C6C5C(OC=C6)OC7CCCCO7

Level: 4

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)COC(C2)OC(C(O4)C45)C6C5COC=C6

Level: 3

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(COCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 810.8 g/mol

SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5

Level: 2

Mol. Weight: 810.8 g/mol

SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 810.8 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 810.8 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 810.8 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 810.8 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.48
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 229.84
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 30739.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.71
Plasma Protein Binding: 51.27
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: 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: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 6.5
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -714.5
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.61
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.92
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: -55794485.95
Rat (Acute): 3.28
Rat (Chronic Oral): 4.4
Fathead Minnow: 70436.17
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 6270265.93
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.52
Log(P): 2.2
Log S: -3.49
Log(Vapor Pressure): -206411.7
Melting Point: 134.11
pKa Acid: -1442.67
pKa Basic: -3.37

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.9297
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8790
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8597
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	2	0.8487
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8199
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8148
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8076
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7921
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7906
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7888
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	2	0.7886
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	2	0.7842
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7834
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7823
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7763
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7760
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	2	0.7759
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7738
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7709
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	2	0.7701
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	2	0.7698
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7691
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7686
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7685
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7670
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7656
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7627
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7627
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7627
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7618
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7616
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7608
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7540
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7537
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7532
Thymidylate synthase	P45352	TYSY_RAT	Rattus norvegicus	2	0.7506
Prostatic acid phosphatase	P15309	PPAP_HUMAN	Homo sapiens	2	0.7505
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7487
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7482
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7453
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	2	0.7449
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7439
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7438
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7434
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7433
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7431
Copper-transporting ATPase	Q97UU7	Q97UU7_SACS2	Saccharolobus solfataricus	3	0.7392
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7381
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7377
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7365
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7362
Tyrosine-protein kinase HCK	P08631	HCK_HUMAN	Homo sapiens	2	0.7357
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	2	0.7356
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7347
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7346
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7345
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7337
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7334
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7321
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7316
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7291
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7270
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	2	0.7246
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	2	0.7245
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7231
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	2	0.7223
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7221
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7217
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7178
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7175
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7175
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7163
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7150
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7129
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7127
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7113
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7111
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7097
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	2	0.7090
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	2	0.7081
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	2	0.7066
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7050
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7049
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7048
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	2	0.7035
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7031
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7025
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7015
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7012
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7011
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	2	0.7002

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