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Agrandol

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

Canonical Smiles	COc1c(O)c(CC=C(C)C)c2c(c1O)C(=O)C[C@H](O2)c1ccccc1
InChI	InChI=1S/C21H22O5/c1-12(2)9-10-14-18(23)21(25-3)19(24)17-15(22)11-16(26-20(14)17)13-7-5-4-6-8-13/h4-9,16,23-24H,10-11H2,1-3H3/t16-/m0/s1
InChIKey	DPWCTCFTFSFYCZ-INIZCTEOSA-N
Formula	C₂₁H₂₂O₅
HBA	5
HBD	2
MW	354.4
Rotatable Bonds	4
TPSA	75.99
LogP	4.32
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	354.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Cedrelopsis microfoliolata	Ptaeroxylaceae	Plantae	1304322

Showing of synonyms

Koorbanally NA, Randrianarivelojosia M, et al. (2002). Bioactive Constituents of Cedrelopsis microfoliata. Journal of natural products, 2002, 65(9), 1349–1352. [View]

Pubchem: 15895373

Cas: 253786-74-2

Zinc: ZINC000014819373

Nmrshiftdb2: 70090008

Chembl: CHEMBL491588

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 354.4 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 354.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.650
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.170
Plasma Protein Binding: 87.29
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: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.390
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.020
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: Toxic
Daphnia Maga: 7.030
Micronucleos: Toxic
NR-AhR: Toxic
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: Safe
T. Pyriformis: -0.600
Rat (Acute): 2.160
Rat (Chronic Oral): 2.790
Fathead Minnow: 4.850
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: 407.670
Hydration Free Energy: -9.020
Log(D) at pH=7.4: 3.310
Log(P): 4.75
Log S: -5.48
Log(Vapor Pressure): -8.03
Melting Point: 140.63
pKa Acid: 6.85
pKa Basic: 5.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9557
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9485
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9431
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9202
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9145
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9081
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9081
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8906
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8840
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.8816
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8738
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8719
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8704
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8682
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8671
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8631
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8617
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8611
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8567
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8562
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	4	0.8484
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8463
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.8443
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8438
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8406
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8394
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.8362
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8359
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8342
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8338
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.8319
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.8184
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8160
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8150
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.8134
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8109
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8088
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.8070
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8061
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8051
DNA topoisomerase 4 subunit B	H7C794	PARE_ENTFA	Enterococcus faecalis	3	0.8046
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8012
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7980
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7970
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7969
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7947
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7934
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	5	0.7911
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.7877
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7850
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7843
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7832
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7817
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7810
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7807
Aminoglycoside 3'-phosphotransferase AphA1-IAB	B0VD92	B0VD92_ACIBY	Acinetobacter baumannii	3	0.7788
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7788
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7768
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7764
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7760
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7758
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7755
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7711
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7689
Dihydrofolate reductase	O30463	O30463_MYCAV	Mycobacterium avium	4	0.7683
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7662
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7657
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7632
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7623
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7605
Dihydrofolate reductase	P00381	DYR_LACCA	Lacticaseibacillus casei	4	0.7597
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7597
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7564
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7561
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7545
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7537
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7528
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7524
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7524
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7507
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7507
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7497
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7496
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	4	0.7483
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7479
Estrogen receptor	P03372	ESR1_HUMAN	Homo sapiens	3	0.7477
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7475
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7441
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7439
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7436
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7431
Dihydrofolate reductase	P16184	DYR_PNECA	Pneumocystis carinii	4	0.7418
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7418
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7415
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7404
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7385
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7380
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7366
Dihydrofolate reductase	Q83AB2	Q83AB2_COXBU	Coxiella burnetii	4	0.7363
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7360
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7358
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	4	0.7353
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7348
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7323
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7322
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7313
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7297
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7282
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7282
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7279
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7271
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7271
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7259
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7257
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7254
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7234
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7233
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7233
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7225
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7215
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7204
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7204
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7197
Metallo-beta-lactamase type 2	P52699	BLAB_SERMA	Serratia marcescens	3	0.7180
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7170
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7160
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7155
Glutathione S-transferase	Q8ILQ7	GST_PLAFA	Plasmodium falciparum	3	0.7137
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7134
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7129
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	3	0.7121
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7119
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7107
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7104
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	2	0.7087
Diamine acetyltransferase 1	P21673	SAT1_HUMAN	Homo sapiens	2	0.7082
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7078
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7073
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7072
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7069
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7056
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7056
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7043
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7040
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7039
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7034
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7021
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7020
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7020
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7009
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7007
Phosphatidylinositol 3-kinase catalytic subunit type 3	Q8NEB9	PK3C3_HUMAN	Homo sapiens	3	0.7005
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7005
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7005

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