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Globularidin

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

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OCC[C@@H]3[C@H]2[C@@]2(COC(=O)/C=C/c4ccccc4)O[C@H]2[C@H]3O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C24H30O11/c25-10-14-18(28)19(29)20(30)23(33-14)34-22-16-13(8-9-31-22)17(27)21-24(16,35-21)11-32-15(26)7-6-12-4-2-1-3-5-12/h1-7,13-14,16-23,25,27-30H,8-11H2/b7-6+/t13-,14-,16-,17+,18-,19+,20-,21+,22+,23+,24-/m1/s1
InChIKey	CPHCYIDKOAOKCL-LUVHZPKESA-N
Formula	C₂₄H₃₀O₁₁
HBA	11
HBD	5
MW	494.49
Rotatable Bonds	7
TPSA	167.67
LogP	-1.45
Number Rings	5
Number Aromatic Rings	1
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.62
Exact Mass	494.18
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Globularia alypum	Globulariaceae	Plantae	1533088

Showing of synonyms

Es-Safi NE, Khlifi S, et al. (2006). Iridoid glucosides from the aerial parts of Globularia alypum L. (Globulariaceae). Chemical and Pharmaceutical Bulletin,2006,54(1),85-88. [View] [PubMed]

Pubchem: 21603203

Zinc: ZINC000139721163

Nmrshiftdb2: 60072226

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC23C(O3)CC4C2C(OCC4)OC5CCCCO5

Level: 2

Mol. Weight: 494.49 g/mol

SMILES: c1ccccc1C=CC(=O)OCC23C(O3)CC4C2COCC4

Level: 1

Mol. Weight: 494.49 g/mol

SMILES: C12C(O2)CC3C1C(OCC3)OC4CCCCO4

Level: 1

Mol. Weight: 494.49 g/mol

SMILES: C12C(O2)CC3C1COCC3

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): -5.62
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.800
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.900
Plasma Protein Binding: 54.51
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.870
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.900
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.050
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.430
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: -756.230
Rat (Acute): 3.590
Rat (Chronic Oral): 3.330
Fathead Minnow: 3.190
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 536.710
Hydration Free Energy: -3.190
Log(D) at pH=7.4: 0.190
Log(P): -0.56
Log S: -2.1
Log(Vapor Pressure): -13.09
Melting Point: 145.03
pKa Acid: 4.93
pKa Basic: 3.59

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9099
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.9099
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8287
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8287
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7920
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7920
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7723
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7723
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7694
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7694
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7631
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7631
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7589
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7589
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7511
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7511
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7415
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7415
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7414
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7414
LD-carboxypeptidase	A0A6L8PVW7	A0A1Q4LWC0_BACAN	Bacillus anthracis	3	0.7359
LD-carboxypeptidase	A0A6L8PVW7	A0A1Q4LWC0_BACAN	Bacillus anthracis	3	0.7359
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7266
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7266
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7241
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7241
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7198
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7198
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7033
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7033
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7016
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7016
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7000
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7000

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