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Drimiopsin B

Family: Hyacinthaceae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	COc1c(OC)c(OC)c(c2c1oc1cc(O)cc(c1c2=O)C)O
InChI	InChI=1S/C17H16O7/c1-7-5-8(18)6-9-10(7)12(19)11-13(20)15(21-2)17(23-4)16(22-3)14(11)24-9/h5-6,18,20H,1-4H3
InChIKey	WCLGXYKABCIDCB-UHFFFAOYSA-N
Formula	C₁₇H₁₆O₇
HBA	7
HBD	2
MW	332.31
Rotatable Bonds	3
TPSA	98.36
LogP	2.69
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	332.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Drimiopsis maculata	Hyacinthaceae	Plantae	81747

Showing of synonyms

Mulholland DA, Koorbanally C, et al. (2004). Xanthones from Drimiopsis maculata. Journal of natural products, 2004, 67(10), 1726–1728. [View]

Pubchem: 11186597

Zinc: ZINC000014647659

Nmrshiftdb2: 70105803

No compound-protein relationship available.

SMILES: c1cccc(c12)oc3c(c2=O)cccc3

Level: 0

Mol. Weight: 196.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.840
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.65

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.280
Plasma Protein Binding: 67.04
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.570
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.220
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.800
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.920
Micronucleos: Toxic
NR-AhR: Toxic
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: 3.420
Rat (Acute): 2.150
Rat (Chronic Oral): 2.680
Fathead Minnow: 5.020
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 443.960
Hydration Free Energy: -8.780
Log(D) at pH=7.4: 2.600
Log(P): 3.39
Log S: -4.8
Log(Vapor Pressure): -7.16
Melting Point: 212.22
pKa Acid: 7.61
pKa Basic: 1.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9283
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9262
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9228
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9069
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	4	0.8963
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8955
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.8944
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8901
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8790
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8659
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.8592
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8587
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8586
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8565
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8545
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.8532
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8512
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8424
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8383
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8334
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8309
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8296
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8266
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8250
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8249
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8242
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8235
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8170
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8143
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8115
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8035
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.8026
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7896
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7889
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7847
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7840
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7809
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7804
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7777
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7771
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7736
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7723
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7642
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7620
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	2	0.7612
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.7590
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.7580
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7573
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7564
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7528
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7527
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7479
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7479
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7478
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7451
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7451
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7445
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7441
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7434
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7422
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7408
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7406
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7391
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7378
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7375
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7369
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7355
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7345
Glutamate receptor 2	P42262	GRIA2_HUMAN	Homo sapiens	5	0.7341
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7290
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7276
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7271
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7234
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7206
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7201
Actin-related protein 3	P61157	ARP3_BOVIN	Bos taurus	4	0.7191
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7190
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7186
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7184
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7179
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7166
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7164
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7149
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7145
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7120
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7119
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7118
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7087
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7087
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7074
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7057
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7039
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7036
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7032
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	3	0.7031
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7021
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7020
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7005

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