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Hexamethylchamaejasmin

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

Canonical Smiles	COc1ccc(cc1)[C@H]1Oc2cc(OC)cc(c2C(=O)[C@@H]1[C@@H]1[C@H](Oc2c(C1=O)c(OC)cc(c2)OC)c1ccc(cc1)OC)OC
InChI	InChI=1S/C36H34O10/c1-39-21-11-7-19(8-12-21)35-31(33(37)29-25(43-5)15-23(41-3)17-27(29)45-35)32-34(38)30-26(44-6)16-24(42-4)18-28(30)46-36(32)20-9-13-22(40-2)14-10-20/h7-18,31-32,35-36H,1-6H3/t31-,32-,35+,36+/m0/s1
InChIKey	QYGAWYLOEOELQE-BSTNIHDZSA-N
Formula	C₃₆H₃₄O₁₀
HBA	10
HBD	0
MW	626.66
Rotatable Bonds	9
TPSA	107.98
LogP	6.3
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	626.22
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ormocarpum kirkii	Leguminosae/Fabaceae	Plantae	77284

Showing of synonyms

Nyandat E, Hassanali A, et al. (1990). The 7,7''-β-diglucoside of (2S,3R)-chamaejasmin from Ormocarpum kirkii.. Phytochemistry,1990,29(7),2361-2364. [View] [PubMed]

Pubchem: 11250612

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 626.66 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 626.66 g/mol

SMILES: c1cccc(c12)OCC(C2=O)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 626.66 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 626.66 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 626.66 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 626.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.93
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.220
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 77.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.630
Plasma Protein Binding: 78.46
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.140
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.940
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.110
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 8.990
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: Toxic
T. Pyriformis: -143224.210
Rat (Acute): 4.130
Rat (Chronic Oral): 2.900
Fathead Minnow: 196.420
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 11045.020
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 4.830
Log(P): 5.97
Log S: -8.38
Log(Vapor Pressure): -382.15
Melting Point: 221.37
pKa Acid: 8.95
pKa Basic: -2.94

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9663
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9663
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9201
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9201
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9198
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9198
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8839
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8839
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8836
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8836
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8752
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8752
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8483
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8483
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8401
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8401
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8369
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8369
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8251
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8251
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8228
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8228
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8180
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8180
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8148
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8148
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	4	0.8138
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	4	0.8138
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8081
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8081
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7992
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7992
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7967
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7967
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7898
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7898
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7894
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7894
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7882
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7882
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7875
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7875
Genome polyprotein	Q99AU2	Q99AU2_9HEPC	Hepatitis C virus subtype 1b	3	0.7870
Genome polyprotein	Q99AU2	Q99AU2_9HEPC	Hepatitis C virus subtype 1b	3	0.7870
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7817
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7817
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7777
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7777
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7758
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7758
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7724
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7724
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7710
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7710
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7708
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7708
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7582
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7582
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7553
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7553
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7542
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7542
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7482
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7482
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7455
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7455
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7417
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7417
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7389
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7389
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7387
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7387
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7383
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7383
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7365
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7365
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7346
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7346
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7337
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7337
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7300
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7300
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7294
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7294
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7277
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7277
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7267
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7267
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7238
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7238
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7210
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7210
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7190
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7190
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7179
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	2	0.7179
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7155
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7155
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7154
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7154
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7136
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7136
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7126
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7126
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7126
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7126
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7121
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7121
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7116
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	4	0.7116
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7112
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7112
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7110
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7110
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7074
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7074
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7050
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7050
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7049
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7049
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7049
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7049
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7037
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7037
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7031
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7031
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7022
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7022
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7009
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7009
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7001
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7001

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