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Drimiopsin D

Family: Plantae - Hyacinthaceae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	COc1c(O)cc2c(c1O)c(=O)c1c(o2)c(OC)c(cc1C)O
InChI	InChI=1S/C16H14O7/c1-6-4-7(17)15(22-3)16-10(6)12(19)11-9(23-16)5-8(18)14(21-2)13(11)20/h4-5,17-18,20H,1-3H3
InChIKey	PWBCXOKCVLBBMI-UHFFFAOYSA-N
Formula	C₁₆H₁₄O₇
HBA	7
HBD	3
MW	318.28
Rotatable Bonds	2
TPSA	109.36
LogP	2.39
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	318.07
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: 91885216

Cas: 773850-91-2

Zinc: ZINC000096023815

No compound-protein relationship available.

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

Level: 0

Mol. Weight: 318.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.15
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.060
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.190
Plasma Protein Binding: 71.55
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 6.330
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.140
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.100
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.540
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: 4.050
Rat (Acute): 2.230
Rat (Chronic Oral): 3.060
Fathead Minnow: 4.510
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: 447.980
Hydration Free Energy: -9.010
Log(D) at pH=7.4: 2.480
Log(P): 2.91
Log S: -4.79
Log(Vapor Pressure): -6.93
Melting Point: 242.51
pKa Acid: 6.62
pKa Basic: 3.77

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9237
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9214
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.9032
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9017
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.9006
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8841
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8804
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.8799
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.8749
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8699
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8679
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8624
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8620
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.8577
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.8487
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8481
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.8442
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8442
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8415
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	4	0.8409
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8372
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8299
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8286
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.8264
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8244
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.8243
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8175
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	4	0.8164
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8153
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8134
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	4	0.8132
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.8131
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8118
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8117
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8103
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8093
Lactoperoxidase	A0A452E9Y6	PERL_CAPHI	Capra hircus	3	0.7997
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7990
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7986
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7986
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	4	0.7983
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7952
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7950
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7946
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7908
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q02127	PYRD_HUMAN	Homo sapiens	4	0.7892
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7861
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7844
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7839
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7836
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7831
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7824
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7817
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7806
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7786
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	4	0.7782
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7782
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	4	0.7746
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7731
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.7725
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7718
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7705
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7695
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7644
EbrA repressor	Q79SH7	Q79SH7_STRLI	Streptomyces lividans	3	0.7630
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7626
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	3	0.7613
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7523
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7523
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	4	0.7518
Riboflavin kinase	Q969G6	RIFK_HUMAN	Homo sapiens	4	0.7506
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7486
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7467
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7465
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7444
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7438
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7438
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7428
Oxygen-insensitive NAD(P)H nitroreductase	P38489	NFSB_ECOLI	Escherichia coli	3	0.7407
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7402
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7402
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7401
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7400
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7399
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7389
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	4	0.7383
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7327
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7319
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7315
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7314
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7312
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	4	0.7307
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7298
Dodecin	Q5SIE3	DODEC_THET8	Thermus thermophilus	4	0.7291
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7288
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.7284
mitogen-activated protein kinase kinase	Q7YTF7	Q7YTF7_PLAF7	Plasmodium falciparum	4	0.7283
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	4	0.7268
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7264
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7247
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7232
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7229
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7224
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7222
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7192
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7190
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	4	0.7186
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7180
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7161
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7158
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7153
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7152
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7146
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7139
Hepatocyte growth factor receptor	P08581	MET_HUMAN	Homo sapiens	4	0.7135
Glutamate receptor 2	P42262	GRIA2_HUMAN	Homo sapiens	5	0.7123
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7068
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7065
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7064
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7052
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7050
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7049
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7044
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7039
Methyltransferase	D0VX01	D0VX01_WSLV	Wesselsbron virus	4	0.7018
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7018
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7012
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	5	0.7010
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7002

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