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Dorsmanin D

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	COc1cc(ccc1O)c1oc2c(CC=C(C)C)c(O)c(c(c2c(=O)c1O)O)CC=C(C)C
InChI	InChI=1S/C26H28O7/c1-13(2)6-9-16-21(28)17(10-7-14(3)4)26-20(22(16)29)23(30)24(31)25(33-26)15-8-11-18(27)19(12-15)32-5/h6-8,11-12,27-29,31H,9-10H2,1-5H3
InChIKey	YRKLNCSPCWVPPC-UHFFFAOYSA-N
Formula	C₂₆H₂₈O₇
HBA	7
HBD	4
MW	452.5
Rotatable Bonds	6
TPSA	120.36
LogP	5.31
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	452.18
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dorstenia mannii	Moraceae	Plantae	194258

Showing of synonyms

Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]

Pubchem: 10599726

Cas: 211255-16-2

Nmrshiftdb2: 70009390

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 452.5 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 452.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 452.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.030
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.13

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.180
Plasma Protein Binding: 86.82
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: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.940
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.100
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.240
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.890
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: -73.120
Rat (Acute): 2.360
Rat (Chronic Oral): 3.120
Fathead Minnow: 5.610
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 544.370
Hydration Free Energy: -3.860
Log(D) at pH=7.4: 3.130
Log(P): 5.29
Log S: -6.62
Log(Vapor Pressure): -9.13
Melting Point: 195.18
pKa Acid: 6.3
pKa Basic: 6.85

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9301
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9134
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9069
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.9007
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8997
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8979
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8946
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	5	0.8678
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.8674
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8668
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8668
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8628
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8587
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8567
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8457
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8427
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8383
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8370
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8341
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8329
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.8228
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	5	0.8175
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8174
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8173
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.8142
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.8123
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8089
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8073
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7983
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7905
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7897
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7839
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7739
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7710
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7703
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7693
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7685
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7639
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7602
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7602
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7584
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7575
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7566
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7564
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7541
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7520
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7513
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7474
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7474
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7466
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	5	0.7458
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7453
Phosphodiesterase	Q53I60	Q53I60_TRYCR	Trypanosoma cruzi	4	0.7425
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7405
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7403
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.7387
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7374
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7371
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7369
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7352
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7347
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7336
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7322
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7320
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7313
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7303
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7292
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7290
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7284
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7282
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7281
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7266
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7251
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7245
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7244
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7191
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7189
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7186
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7170
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7163
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7152
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7138
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7134
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7132
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7123
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7113
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7113
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7079
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7077
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7070
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7057
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7056
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7021
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7008
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7006
Tryptophan synthase alpha chain	P00929	TRPA_SALTY	Salmonella typhimurium	2	0.7005

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