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Manniflavanone

Family: Plantae - Thymelaeaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Biflavonoid

Canonical Smiles	Oc1cc(O)c2c(c1)O[C@@H]([C@H](C2=O)c1c(O)cc(c2c1O[C@H](c1ccc(c(c1)O)O)[C@H](C2=O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C30H22O13/c31-12-7-17(36)21-20(8-12)42-28(10-1-3-13(32)15(34)5-10)24(25(21)39)22-18(37)9-19(38)23-26(40)27(41)29(43-30(22)23)11-2-4-14(33)16(35)6-11/h1-9,24,27-29,31-38,41H/t24-,27-,28+,29+/m0/s1
InChIKey	UKRJEVDCOVVSAB-BENTYHEHSA-N
Formula	C₃₀H₂₂O₁₃
HBA	13
HBD	9
MW	590.49
Rotatable Bonds	3
TPSA	234.67
LogP	3.11
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	590.11
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Gnidia involucrata	Thymelaeaceae	Plantae	142743

Showing of synonyms

Ferrari J, Terreaux C, et al. (2000). Benzophenone glycosides from Gnidia involucrata. Phytochemistry,2000,54(8),883-889. [View] [PubMed]

Pubchem: 198549

Cas: 73428-17-8

Zinc: ZINC000004098328

Kegg Ligand: C09763

Nmrshiftdb2: 70049688

Comptox: DTXSID20223658

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 590.49 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 590.49 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)C(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 590.49 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 590.49 g/mol

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

Level: 1

Mol. Weight: 590.49 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 590.49 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 590.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.54
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.35
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 11.45

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.91
Plasma Protein Binding: 86.05
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: 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: 12.14
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.14
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.09
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.6
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: Toxic
T. Pyriformis: -17619.53
Rat (Acute): 2.5
Rat (Chronic Oral): 4.18
Fathead Minnow: 41.01
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: 510.74
Hydration Free Energy: -3.16
Log(D) at pH=7.4: 1.44
Log(P): 3.44
Log S: -5.07
Log(Vapor Pressure): -15.69
Melting Point: 308.22
pKa Acid: 6.99
pKa Basic: 5.97

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9304
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9304
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8953
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8953
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8855
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8855
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8841
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8841
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8507
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8507
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8418
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8418
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8372
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8372
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8331
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8331
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8257
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8257
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8249
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8249
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8185
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8185
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8141
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8141
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8135
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.8135
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8023
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.8023
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7983
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7983
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7924
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7924
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7849
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7849
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7826
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7826
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7815
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7815
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7742
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7742
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7695
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7695
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7691
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7691
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7679
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7679
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7611
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7611
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7562
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7562
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7553
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7553
Prostaglandin reductase 3	Q8N4Q0	PTGR3_HUMAN	Homo sapiens	5	0.7543
Prostaglandin reductase 3	Q8N4Q0	PTGR3_HUMAN	Homo sapiens	5	0.7543
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7542
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7542
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7521
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	3	0.7521
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7506
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7506
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7494
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7494
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7488
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7488
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7461
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7461
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7432
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7432
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7407
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7407
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7343
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7343
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7332
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7332
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7324
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7324
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7320
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7320
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7277
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7277
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7270
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	4	0.7270
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7265
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7265
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7265
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7265
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7225
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7225
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7208
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7208
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7202
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7202
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7199
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7199
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	5	0.7195
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	5	0.7195
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7175
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7175
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7169
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7169
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7160
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7160
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7138
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7138
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7111
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7111
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7097
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7097
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7085
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7085
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7077
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7077
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7040
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7040
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	5	0.7008
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	5	0.7008

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