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Diosfeboside A

Family: Plantae - Ebenaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Coumarin Glycoside

Canonical Smiles	OCC1(O)CO[C@@H]([C@@H]1O)OCC1O[C@H](Oc2cc(=O)oc3c2c(C)ccc3)[C@@H](C([C@H]1O)O)O
InChI	InChI=1S/C21H26O12/c1-9-3-2-4-10-14(9)11(5-13(23)31-10)32-19-17(26)16(25)15(24)12(33-19)6-29-20-18(27)21(28,7-22)8-30-20/h2-5,12,15-20,22,24-28H,6-8H2,1H3/t12?,15-,16?,17+,18-,19-,20-,21?/m0/s1
InChIKey	UQDQFRQJERKTJN-WIYJBSPASA-N
Formula	C₂₁H₂₆O₁₂
HBA	12
HBD	6
MW	470.43
Rotatable Bonds	6
TPSA	188.51
LogP	-2.25
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.57
Exact Mass	470.14
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Diospyros crassiflora	Ebenaceae	Plantae	570480

Showing of synonyms

Akak CM, Djama CM, et al. (2010). New coumarin glycosides from the leaves of Diospyros crassiflora (Hiern).. Fitoterapia,2010, 81(7), 873-877. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCC1OCC2CCCC(O2)Oc3cc(=O)oc(c34)cccc4

Level: 2

Mol. Weight: 470.43 g/mol

SMILES: c1cccc(c12)oc(=O)cc2OC3CCCCO3

Level: 1

Mol. Weight: 470.43 g/mol

SMILES: O1CCCCC1COC2CCCO2

Level: 1

Mol. Weight: 470.43 g/mol

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 470.43 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 470.43 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 470.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.17
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.18
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.95
Plasma Protein Binding: 62.96
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: 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: 3.68
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.82
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.92
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.13
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: -130.49
Rat (Acute): 2.43
Rat (Chronic Oral): 3.62
Fathead Minnow: 3.84
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 556.25
Hydration Free Energy: -3.44
Log(D) at pH=7.4: -0.2
Log(P): -1.17
Log S: -1.9
Log(Vapor Pressure): -15.07
Melting Point: 186.78
pKa Acid: 4.05
pKa Basic: 5.71

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.9763
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8961
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8485
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8276
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8266
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7670
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7436
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7418
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	2	0.7412
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7358
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7332
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7313
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7275
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7239
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.7213
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7206
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7205
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7191
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7147
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7127
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7097
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7096
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7091
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7051
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7049
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7044
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7035
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7017

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