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Nympholide A

Family: Plantae - Nymphaeaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	O=C1OCC2O[C@@H](Oc3cc(c4oc5c([C@@H](C1)c1ccc(cc1)O)c(O)cc(c5c(=O)c4O)O)cc(c3O)O)C(C([C@@H]2O)O)O
InChI	InChI=1S/C30H26O15/c31-12-3-1-10(2-4-12)13-7-19(35)42-9-18-23(37)25(39)27(41)30(44-18)43-17-6-11(5-16(34)22(17)36)28-26(40)24(38)21-15(33)8-14(32)20(13)29(21)45-28/h1-6,8,13,18,23,25,27,30-34,36-37,39-41H,7,9H2/t13-,18?,23+,25?,27?,30+/m0/s1
InChIKey	GZTPVMNTZSEVRQ-JQTVVHERSA-N
Formula	C₃₀H₂₆O₁₅
HBA	15
HBD	9
MW	626.52
Rotatable Bonds	1
TPSA	257.04
LogP	0.96
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	626.13
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Nymphaea lotus	Nymphaeaceae	Plantae	264924

Showing of synonyms

Elegami AA, Bates C, et al. (2003). Two very unusual macrocyclic flavonoids from the water lily Nymphaea lotus. Phytochemistry,2003,63(6),727-731. [View] [PubMed]

Pubchem: 44259437

CPRiL: 410707

SMILES: c1ccccc1C(c(c2c34)ccc4)CC(=O)OCC5CCCC(O5)Oc6cc(c(o2)cc3=O)ccc6

Level: 1

Mol. Weight: 626.52 g/mol

SMILES: c1ccc(c2c13)CCC(=O)OCC4CCCC(O4)Oc5cc(c(o2)cc3=O)ccc5

Level: 0

Mol. Weight: 626.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 626.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.41
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 27.39

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.85
Plasma Protein Binding: 59.73
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: 10.24
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.43
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.8
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.68
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: -46810.93
Rat (Acute): 2.55
Rat (Chronic Oral): 3.9
Fathead Minnow: 79.54
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 393.19
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -0.84
Log(P): 0.08
Log S: -4.25
Log(Vapor Pressure): -33.34
Melting Point: 273.2
pKa Acid: 5.4
pKa Basic: 7.39

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8627
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8627
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8475
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8475
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8317
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8317
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8192
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8192
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8164
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8164
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7983
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7983
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7973
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7973
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7955
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7955
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7954
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7954
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7774
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7774
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7557
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7557
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7507
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7507
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7312
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7312
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7291
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7291
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7257
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7257
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7117
NADPH--cytochrome P450 reductase	P00388	NCPR_RAT	Rattus norvegicus	4	0.7117
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7106
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7106
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7049
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7049

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