ANPDB

Select a section from the left sidebar

Dorsmanin A

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Chalconoid

Canonical Smiles	Oc1ccc(cc1)/C=C/C(=O)c1ccc2c(c1O)CCC(O2)(C)C
InChI	InChI=1S/C20H20O4/c1-20(2)12-11-16-18(24-20)10-8-15(19(16)23)17(22)9-5-13-3-6-14(21)7-4-13/h3-10,21,23H,11-12H2,1-2H3/b9-5+
InChIKey	UDSAJERKQRQHJR-WEVVVXLNSA-N
Formula	C₂₀H₂₀O₄
HBA	4
HBD	2
MW	324.38
Rotatable Bonds	3
TPSA	66.76
LogP	4.1
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	324.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dorstenia mannii	Moraceae	Plantae	194258
2	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]
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: 5472480

Cas: 162229-27-8

Zinc: ZINC000005963645

Nmrshiftdb2: 70005440

Chembl: CHEMBL492189

No compound-protein relationship available.

SMILES: C1CCOc(c12)ccc(c2)C(=O)C=Cc3ccccc3

Level: 1

Mol. Weight: 324.38 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 324.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 324.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.73
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.660
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.980
Plasma Protein Binding: 66.34
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: 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: 3.460
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.450
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.190
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.140
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Toxic
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 4.260
Rat (Acute): 2.030
Rat (Chronic Oral): 2.390
Fathead Minnow: 4.720
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 433.950
Hydration Free Energy: -10.220
Log(D) at pH=7.4: 4.220
Log(P): 5.29
Log S: -5.41
Log(Vapor Pressure): -7.86
Melting Point: 173.19
pKa Acid: 8.31
pKa Basic: 5.6

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9442
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.9318
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9248
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9181
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.9067
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8686
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8665
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8583
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8540
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8403
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.8333
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8306
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.8279
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8255
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8231
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.8179
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8175
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8173
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8173
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8157
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.8143
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8102
Beta-elicitin cinnamomin	P15569	ELIB_PHYCI	Phytophthora cinnamomi	3	0.8084
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8054
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7927
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7893
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7864
Isoliquiritigenin 2'-O-methyltransferase	P93324	CHOMT_MEDSA	Medicago sativa	3	0.7839
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7831
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7809
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7807
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7803
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7800
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7794
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7749
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7725
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7719
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7708
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7697
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7688
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7681
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7681
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7668
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7664
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7659
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7643
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7638
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7624
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7612
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7602
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7599
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7542
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7531
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7529
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7526
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7525
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7512
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7500
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7488
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7475
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7454
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7446
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7419
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7418
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7416
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7408
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7405
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7402
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7399
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7388
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7375
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7371
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.7366
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7352
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7348
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7343
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7338
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7332
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7325
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7324
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7313
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7301
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7294
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7272
Adenosine monophosphate-protein transferase	Q8ZVF7	Q8ZVF7_PYRAE	Pyrobaculum aerophilum	3	0.7268
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7260
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7260
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7258
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7252
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7242
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7238
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7236
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7232
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7226
Formate--tetrahydrofolate ligase	Q2RM91	FTHS_MOOTA	Moorella thermoacetica	2	0.7225
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7212
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	3	0.7187
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7181
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7180
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7166
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7161
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7151
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7143
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7141
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7131
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7130
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7115
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7115
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7110
Fatty acid-binding protein, intestinal	P12104	FABPI_HUMAN	Homo sapiens	3	0.7108
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7103
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7098
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7098
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7092
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7085
Subunit alpha of sarocosine oxidase	Q50LF0	Q50LF0_9CORY	Corynebacterium sp. U-96	4	0.7079
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7075
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7069
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7059
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7054
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7047
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7044
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7041
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7037
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7037
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7031
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7030
UDP-3-O-acyl-N-acetylglucosamine deacetylase	O67648	LPXC_AQUAE	Aquifex aeolicus	3	0.7026
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7021
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7018
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	3	0.7013
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7009
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7005
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7002

Download SDF