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Dorsmanin J

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Prenylated Flavanone

Canonical Smiles	CC(=CCc1c2O[C@@H](CC(=O)c2c(c2c1OC(C)(C)CC2)O)c1ccc(c(c1)O)O)C
InChI	InChI=1S/C25H28O6/c1-13(2)5-7-16-23-15(9-10-25(3,4)31-23)22(29)21-19(28)12-20(30-24(16)21)14-6-8-17(26)18(27)11-14/h5-6,8,11,20,26-27,29H,7,9-10,12H2,1-4H3/t20-/m0/s1
InChIKey	LXBLJHYLZRJNSA-FQEVSTJZSA-N
Formula	C₂₅H₂₈O₆
HBA	6
HBD	3
MW	424.49
Rotatable Bonds	3
TPSA	96.22
LogP	5.12
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.4
Exact Mass	424.19
Number of Lipinski Rule Violations	1

#	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: 42608002

Cas: 329703-76-6

Zinc: ZINC000059777206

Nmrshiftdb2: 70009547

No compound-protein relationship available.

SMILES: O1CCCc(c2)c1cc(c23)OC(CC3=O)c4ccccc4

Level: 1

Mol. Weight: 424.49 g/mol

SMILES: O=C1CCOc(c12)cc3c(c2)CCCO3

Level: 0

Mol. Weight: 424.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 424.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.18
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.82
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.49

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.11
Plasma Protein Binding: 85.55
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: 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: 9.4
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.34
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.45
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.09
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -32.35
Rat (Acute): 2.26
Rat (Chronic Oral): 2.28
Fathead Minnow: 4.9
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 501.43
Hydration Free Energy: -4.97
Log(D) at pH=7.4: 3.61
Log(P): 5.96
Log S: -5.58
Log(Vapor Pressure): -9.87
Melting Point: 197.44
pKa Acid: 7.9
pKa Basic: 5.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9286
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.9024
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8942
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8938
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8926
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8762
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8718
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8647
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8590
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8566
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8361
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8324
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8303
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8167
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.8136
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8047
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8042
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8040
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8032
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.8009
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7938
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7900
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7897
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7881
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7768
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7702
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7701
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7687
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7682
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7664
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7661
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7659
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7637
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7624
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7569
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7563
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7531
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7503
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7473
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7465
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7460
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A	Q13946	PDE7A_HUMAN	Homo sapiens	4	0.7437
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7436
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7432
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7428
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7426
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7426
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7420
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7336
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7329
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7314
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7313
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7304
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7302
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7289
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7274
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7272
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7272
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7270
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7248
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7248
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7241
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7240
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7201
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	3	0.7196
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7169
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7155
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7152
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7124
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7124
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7104
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7097
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7092
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7072
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7069
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7069
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7064
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7061
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7051
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7044
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7043
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7042
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7031
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7026
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7023
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	5	0.7020
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7012
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7010
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7001

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