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Acuminavone

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene-Fused Flavone

Canonical Smiles	C=C1CCCC2C1CC1C(C2)(C)C(C2(C1(O)c1c(=O)cc(oc1C(C2=O)(C)C)c1ccccc1)C)(C)C
InChI	InChI=1S/C33H40O4/c1-19-12-11-15-21-18-31(6)25(16-22(19)21)33(36)26-23(34)17-24(20-13-9-8-10-14-20)37-27(26)29(2,3)28(35)32(33,7)30(31,4)5/h8-10,13-14,17,21-22,25,36H,1,11-12,15-16,18H2,2-7H3
InChIKey	MAUDJFZRMGWDAY-UHFFFAOYSA-N
Formula	C₃₃H₄₀O₄
HBA	4
HBD	1
MW	500.68
Rotatable Bonds	1
TPSA	67.51
LogP	6.79
Number Rings	6
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.58
Exact Mass	500.29
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Uvaria acuminata	Annonaceae	Plantae	672960

Showing of synonyms

Said SA. (2011). Two new special flavones from Uvaria accuminata. Natural Product Research,2011,25(10),987-994. [View] [PubMed]

No compound-protein relationship available.

SMILES: C1CCC(=C)C(C2)C1CC(C2C34)CC3C(=O)Cc5c4c(=O)cc(o5)-c6ccccc6

Level: 1

Mol. Weight: 500.68 g/mol

SMILES: C1CCC(=C)C(C2)C1CC(C2C34)CC3C(=O)Cc5c4c(=O)cco5

Level: 0

Mol. Weight: 500.68 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 500.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.69
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.63
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.88
Plasma Protein Binding: 55.91
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: Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-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: 6.5
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.57
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.75
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.74
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Toxic
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: -898.65
Rat (Acute): 4.1
Rat (Chronic Oral): 1.57
Fathead Minnow: 7.62
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 494.65
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 5.19
Log(P): 7.76
Log S: -5.63
Log(Vapor Pressure): -8.99
Melting Point: 193.04
pKa Acid: 8.11
pKa Basic: 4.83

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9214
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9214
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9113
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9113
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8503
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8503
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8413
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8413
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8222
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8222
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8170
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8170
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7942
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7942
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7809
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7809
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7733
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7733
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7515
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7515
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7290
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7290
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	2	0.7229
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	2	0.7229
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7203
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7203
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7165
NAD(P) transhydrogenase subunit alpha part 1	Q2RSB2	PNTAA_RHORT	Rhodospirillum rubrum	3	0.7165
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7061
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7061
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7038
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7038

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