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6a,12a-dehydromillettone

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

Canonical Smiles	O=c1c2c(COc3c2cc2OCOc2c3)oc2c1ccc1c2C=CC(O1)(C)C
InChI	InChI=1S/C22H16O6/c1-22(2)6-5-11-14(28-22)4-3-12-20(23)19-13-7-16-17(26-10-25-16)8-15(13)24-9-18(19)27-21(11)12/h3-8H,9-10H2,1-2H3
InChIKey	JOEPOINDECTPQI-UHFFFAOYSA-N
Formula	C₂₂H₁₆O₆
HBA	6
HBD	0
MW	376.36
Rotatable Bonds	0
TPSA	67.13
LogP	4.27
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	376.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Millettia usaramensis usaramensis	Leguminosae/Fabaceae	Plantae	53625

Showing of synonyms

Yenesew A, Derese S, et al. (2003). Anti-plasmodial activities and X-ray crystal structures of rotenoids from Millettia usaramensis subspecies usaramensis.. Phytochemistry,2003,64(3),773-779. [View] [PubMed]

Pubchem: 7040274

Cas: 43016-04-2

Zinc: ZINC000003203078

Nmrshiftdb2: 70021709

No compound-protein relationship available.

SMILES: O1COc(c12)cc3c(c2)c4c(CO3)oc5c(c4=O)ccc6c5C=CCO6

Level: 0

Mol. Weight: 376.36 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp): -4.92
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.460
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.500
Plasma Protein Binding: 82.21
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.060
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.770
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.810
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.800
Micronucleos: Toxic
NR-AhR: Toxic
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: Safe
T. Pyriformis: -22.560
Rat (Acute): 3.430
Rat (Chronic Oral): 1.220
Fathead Minnow: 5.500
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 507.940
Hydration Free Energy: -5.720
Log(D) at pH=7.4: 3.360
Log(P): 4.81
Log S: -6.06
Log(Vapor Pressure): -10.11
Melting Point: 251.84
pKa Acid: 8.83
pKa Basic: 2.27

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9206
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9206
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9132
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9132
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9127
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.9127
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8902
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8902
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8900
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8900
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8636
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8636
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8405
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8405
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8292
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8292
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8183
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8183
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8111
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8111
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7960
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7960
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7906
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7906
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7780
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7780
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7773
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7773
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7680
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7680
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7660
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7660
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7657
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7657
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7641
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7641
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7625
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7625
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7597
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7597
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7543
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7543
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7466
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7466
Poly [ADP-ribose] polymerase tankyrase-1	O95271	TNKS1_HUMAN	Homo sapiens	4	0.7432
Poly [ADP-ribose] polymerase tankyrase-1	O95271	TNKS1_HUMAN	Homo sapiens	4	0.7432
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7425
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7425
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7415
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7415
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7364
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7364
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7343
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7343
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7329
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7329
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7311
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7311
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7301
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7301
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7263
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7263
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7260
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7260
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7243
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7243
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7226
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7226
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7174
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7174
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7174
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7174
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7173
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7173
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7136
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	3	0.7136
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7134
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7134
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7133
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7133
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7119
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7119
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7116
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7116
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7078
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7078
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7071
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7071
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7048
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7048
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7045
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7045
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7015
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7015
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7009
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7009
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7005
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7005
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7003
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7003

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