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Dihydro-dehydro-diconiferyl alcohol 4-O-beta-D-glucoside

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Lignan

Canonical Smiles	OCCCc1cc(OC)c2c(c1)[C@@](C)(CO)[C@](O2)(C)c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C28H38O11/c1-27(14-31)17-10-15(6-5-9-29)11-20(36-4)25(17)39-28(27,2)16-7-8-18(19(12-16)35-3)37-26-24(34)23(33)22(32)21(13-30)38-26/h7-8,10-12,21-24,26,29-34H,5-6,9,13-14H2,1-4H3/t21-,22-,23+,24-,26-,27-,28+/m1/s1
InChIKey	ZDBFMBJCSIUDRT-ZBPXOPAKSA-N
Formula	C₂₈H₃₈O₁₁
HBA	11
HBD	6
MW	550.6
Rotatable Bonds	10
TPSA	167.53
LogP	0.37
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	39
Formal Charge	0
Fraction CSP3	0.57
Exact Mass	550.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Galium brunneum	Rubiaceae	Plantae	25168

Showing of synonyms

Smadi A, Bitam F, et al. (2020). Chemical constituents of the aerial parts of Algerian Galium brunneum:Isolation of new hydroperoxy sterol glucosyl derivatives. Phytochemistry Letters, 2020, 38, 39-45. [View]

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(C2)c3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 550.6 g/mol

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 550.6 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 550.6 g/mol

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 550.6 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 550.6 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 550.6 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.32
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.92
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.03
Plasma Protein Binding: 91.71
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: 5.62
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.77
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.51
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.02
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: -2260.44
Rat (Acute): 2.79
Rat (Chronic Oral): 3.77
Fathead Minnow: 8.91
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 513.2
Hydration Free Energy: -2.95
Log(D) at pH=7.4: 1.25
Log(P): -0.23
Log S: -3.56
Log(Vapor Pressure): -10.62
Melting Point: 176.79
pKa Acid: 7.38
pKa Basic: 2.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9179
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9028
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8109
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8093
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8055
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7889
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7887
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7882
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7848
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7846
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7824
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7815
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7628
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7575
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7530
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7493
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7463
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7434
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7344
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7317
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7237
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7231
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	3	0.7154
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7144
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7143
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7130
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7117
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7101
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7065
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7049
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7038
Thymidylate synthase	Q4JQW2	TYSY_VZVO	Varicella-zoster virus	3	0.7029
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7024

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