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Knipholone mannich base

Family: Plantae - Asphodelaceae
Kingdom: Plantae
Class: Quinone
- Subclass: Anthraquinone

Canonical Smiles	CCN(Cc1c(O)c(c(c(c1OC)C(=O)C)O)c1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O)CC
InChI	InChI=1S/C29H29NO8/c1-6-30(7-2)12-16-26(35)24(27(36)20(14(4)31)29(16)38-5)19-13(3)11-18(33)22-23(19)25(34)15-9-8-10-17(32)21(15)28(22)37/h8-11,32-33,35-36H,6-7,12H2,1-5H3
InChIKey	NAQPIPBICQLKDS-UHFFFAOYSA-N
Formula	C₂₉H₂₉NO₈
HBA	9
HBD	4
MW	519.55
Rotatable Bonds	7
TPSA	144.6
LogP	4.31
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	38
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	519.19
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bulbine frutescens	Asphodelaceae	Plantae	210954

Showing of synonyms

Abdissa N, Heydenreich M, et al. (2014). A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters,2014,9,67-73. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(C2=O)c1C(=O)c(c23)cccc3-c4ccccc4

Level: 1

Mol. Weight: 519.55 g/mol

SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3

Level: 0

Mol. Weight: 519.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 519.55 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -5.96
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.96
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.47

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 81.18
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: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.04
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.11
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.79
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.29
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: -1036.76
Rat (Acute): 2.56
Rat (Chronic Oral): 3.54
Fathead Minnow: 7.01
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: 552.46
Hydration Free Energy: -3.1
Log(D) at pH=7.4: 2.83
Log(P): 5.42
Log S: -6.6
Log(Vapor Pressure): -9.11
Melting Point: 192.35
pKa Acid: 7.61
pKa Basic: 8.18

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8945
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8945
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8877
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8877
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8478
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8478
L-malyl-CoA/beta-methylmalyl-CoA lyase	Q3J5L6	MCAL_RHOS4	Cereibacter sphaeroides	4	0.8216
L-malyl-CoA/beta-methylmalyl-CoA lyase	Q3J5L6	MCAL_RHOS4	Cereibacter sphaeroides	4	0.8216
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8208
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8208
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8109
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8109
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.8094
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.8094
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8011
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8011
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8001
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8001
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7931
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7931
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7876
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7876
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7706
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7706
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7701
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7701
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7660
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7660
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7642
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7642
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7621
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7621
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7571
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7571
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7533
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7533
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7482
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7482
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7479
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7479
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7472
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7472
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7471
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7471
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7457
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7457
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7447
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7447
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7412
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7412
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7334
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7334
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7260
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7260
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7231
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7231
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7223
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7223
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7218
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7218
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7209
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7209
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7166
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7166
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7165
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7165
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7161
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7161
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7145
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7145
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7144
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7144
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7109
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.7109
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7056
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7056
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7056
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7056
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7020
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	4	0.7020
Epothilone C/D epoxidase	Q9KIZ4	C167_SORCE	Sorangium cellulosum	3	0.7001
Epothilone C/D epoxidase	Q9KIZ4	C167_SORCE	Sorangium cellulosum	3	0.7001

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