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Anhydrophlegmacin

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Quinone

Canonical Smiles	COc1cc(O)c2c(c1)c(c1c(OC)cc3c(c1O)C(=O)c1c(C3)cc(cc1O)C)c1c(c2O)C(=O)CC(C1)(C)O
InChI	InChI=1S/C32H28O9/c1-13-5-14-7-15-8-22(41-4)28(30(37)24(15)29(36)23(14)19(33)6-13)25-17-9-16(40-3)10-20(34)26(17)31(38)27-18(25)11-32(2,39)12-21(27)35/h5-6,8-10,33-34,37-39H,7,11-12H2,1-4H3
InChIKey	PBRWKDURCHPDEL-UHFFFAOYSA-N
Formula	C₃₂H₂₈O₉
HBA	9
HBD	5
MW	556.57
Rotatable Bonds	3
TPSA	153.75
LogP	4.67
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	556.17
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Senna multiglandulosa	Leguminosae/Fabaceae	Plantae	1574110

Showing of synonyms

Alemayehu G, Abegaz BM. (1996). Bianthraquinones from the seeds of Senna multiglandulosa. Phytochemistry,1996,41(3),919-921. [View] [PubMed]

Pubchem: 623126

Cas: 40451-45-4

Nmrshiftdb2: 70014449

No compound-protein relationship available.

SMILES: c1cccc(c12)cc3c(CCCC3=O)c2-c(c4)ccc(c45)Cc6c(C5=O)cccc6

Level: 1

Mol. Weight: 556.57 g/mol

SMILES: O=C1CCCc(c12)cc3c(c2)cccc3

Level: 0

Mol. Weight: 556.57 g/mol

SMILES: c1cccc(c12)Cc3c(C2=O)cccc3

Level: 0

Mol. Weight: 556.57 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.86
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.940
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.170
Plasma Protein Binding: 73.68
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-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: 8.580
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.770
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.810
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.780
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: Toxic
T. Pyriformis: -5808.150
Rat (Acute): 2.530
Rat (Chronic Oral): 4.020
Fathead Minnow: 19.480
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 528.520
Hydration Free Energy: -3.070
Log(D) at pH=7.4: 4.340
Log(P): 5.59
Log S: -7.18
Log(Vapor Pressure): -7.92
Melting Point: 257.15
pKa Acid: 8.12
pKa Basic: 4.73

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	0.8968
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8968
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8890
E3 ubiquitin-protein ligase Mdm2	P56273	MDM2_XENLA	Xenopus laevis	3	0.8890
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8858
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8858
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8616
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8616
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8565
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8565
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8418
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8418
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8310
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8310
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8181
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8181
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7960
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7960
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7888
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7888
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7815
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7815
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7753
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7753
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7741
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7741
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7712
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7712
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7683
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7683
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7486
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7486
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7430
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.7430
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7387
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7387
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7373
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7373
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.7362
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	4	0.7362
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7349
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7349
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7345
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7345
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7321
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7321
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7261
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7261
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7260
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.7260
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7227
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7227
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7168
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7168
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7164
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7164
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7138
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7138
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7060
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7060
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7045
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7045
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7028
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7028
Bcl-2-like protein 1	Q07817	B2CL1_HUMAN	Homo sapiens	3	0.7003
Bcl-2-like protein 1	Q07817	B2CL1_HUMAN	Homo sapiens	3	0.7003

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