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6-transcaffeoyl ajugol

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Iridoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@](C)(O)C[C@H]3OC(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C24H30O11/c1-24(31)10-15(33-17(27)7-4-12-2-5-13(26)6-3-12)14-8-9-32-22(18(14)24)35-23-21(30)20(29)19(28)16(11-25)34-23/h2-9,14-16,18-23,25-26,28-31H,10-11H2,1H3/b7-4+/t14-,15+,16+,18+,19+,20-,21+,22-,23-,24-/m0/s1
InChIKey	VNLQWWMRJUXEDD-HXBOHEENSA-N
Formula	C₂₄H₃₀O₁₁
HBA	11
HBD	6
MW	494.49
Rotatable Bonds	6
TPSA	175.37
LogP	-0.61
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	494.18
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Kigelia pinnata	Bignoniaceae	Plantae	70070

Showing of synonyms

Gouda YG, Abdel-baky AM, et al. (2003). Iridoids from Kigelia pinnata DC. Fruits. Phytochemistry,2003,63(8),887-892. [View] [PubMed]

Pubchem: 14396655

Zinc: ZINC000255273338

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2CCC(C23)C(OC=C3)OC4CCCCO4

Level: 2

Mol. Weight: 494.49 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(C23)COC=C3

Level: 1

Mol. Weight: 494.49 g/mol

SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3

Level: 1

Mol. Weight: 494.49 g/mol

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 494.49 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 494.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 494.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.0
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.960
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.21

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 59.85
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.920
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.680
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.810
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.470
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: -327.600
Rat (Acute): 2.610
Rat (Chronic Oral): 3.650
Fathead Minnow: 4.190
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: 526.210
Hydration Free Energy: -3.240
Log(D) at pH=7.4: 0.360
Log(P): 0.36
Log S: -1.9
Log(Vapor Pressure): -12.03
Melting Point: 159.56
pKa Acid: 4.68
pKa Basic: 3.69

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8796
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8796
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8176
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8176
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8169
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8169
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7800
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7800
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7799
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7799
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7512
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7512
Raucaffricine-O-beta-D-glucosidase	Q9SPP9	RG1_RAUSE	Rauvolfia serpentina	4	0.7453
Raucaffricine-O-beta-D-glucosidase	Q9SPP9	RG1_RAUSE	Rauvolfia serpentina	4	0.7453
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7445
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7445
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7422
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7422
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7403
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7403
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7378
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7378
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7333
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7333
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7290
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7290
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7280
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7280
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7262
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7262
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7260
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7260
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7239
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7239
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7239
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7239
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7236
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7236
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7212
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7212
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7208
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7208
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7207
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7207
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7204
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7204
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7190
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7190
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7158
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7158
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7157
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7157
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7152
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7152
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7151
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7151
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7135
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7135
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7135
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7135
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7097
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7097
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7096
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7096
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7095
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7095
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7081
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7081
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7072
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7072
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7064
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7064
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7062
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7062
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7062
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7062
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7057
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7057
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7055
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7055
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7052
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7052
RIO-type serine/threonine-protein kinase Rio1	O28471	RIO1_ARCFU	Archaeoglobus fulgidus	2	0.7052
RIO-type serine/threonine-protein kinase Rio1	O28471	RIO1_ARCFU	Archaeoglobus fulgidus	2	0.7052
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7047
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7047
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7044
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7044
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7030
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7030
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7020
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7020
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7017
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7017
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7016
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7016
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7011
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7011
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7009
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7009
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7008
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7008
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7005
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7005

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