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Isoangoletin

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavanol Glycoside

Canonical Smiles	Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C(=O)[C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15-,17+,18+,19+,20+,21-/m0/s1
InChIKey	VQUPQWGKORWZII-RPJYBVRZSA-N
Formula	C₂₁H₂₂O₁₀
HBA	10
HBD	6
MW	434.4
Rotatable Bonds	3
TPSA	166.14
LogP	0.33
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	434.12
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Uvaria puguensis	Annonaceae	Plantae	174969

Showing of synonyms

Makangara JJ, Jonker SA, et al. (2002). A novel phenanthrenolide and C-benzyl dihydrochalcones from Uvaria puguensis. Natural Product Letters,2002,16(4),267-272. [View] [PubMed]

Pubchem: 101937309

Cas: 30987-58-7

Zinc: ZINC000033830717

Nmrshiftdb2: 60027045

No compound-protein relationship available.

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)OC4CCCCO4

Level: 2

Mol. Weight: 434.4 g/mol

SMILES: c1cccc(c12)OCC(C2=O)OC3CCCCO3

Level: 1

Mol. Weight: 434.4 g/mol

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

Level: 1

Mol. Weight: 434.4 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 434.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.92
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.330
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.11

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: 78.69
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-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: 14.190
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.200
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.770
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.400
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: Safe
T. Pyriformis: -41.970
Rat (Acute): 2.270
Rat (Chronic Oral): 3.990
Fathead Minnow: 4.010
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 542.610
Hydration Free Energy: -7.110
Log(D) at pH=7.4: 1.000
Log(P): 1.05
Log S: -4.53
Log(Vapor Pressure): -10.95
Melting Point: 194.49
pKa Acid: 5.66
pKa Basic: 4.88

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9223
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9223
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8814
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8814
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8708
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8708
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8588
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8588
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8367
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8367
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8151
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8151
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8075
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8075
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8052
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8052
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7990
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7990
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7919
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7919
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7900
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7900
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7799
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7799
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7769
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7769
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7713
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7713
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7669
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7669
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7612
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7612
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7600
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7600
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7576
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7576
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.7575
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	3	0.7575
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7497
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7497
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7487
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7487
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7440
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7440
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7428
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7428
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7393
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7393
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7388
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7388
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7370
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7370
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7358
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7358
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7352
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7352
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7307
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7307
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7302
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7302
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7286
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7286
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7256
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7256
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7247
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7247
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7221
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7221
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7212
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7212
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7151
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	4	0.7151
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7138
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7138
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7113
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7113
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7061
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7061
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7036
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7036
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7034
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7034
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7030
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7030

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