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Ceibapentain B

Family: Plantae - Bombacaceae
Kingdom: Plantae
Class: Lignan
- Subclass: Flavonolignan

Canonical Smiles	O=C1C[C@@H](c2ccc(c(c2)O)O)c2c(O1)c1C[C@@H](O)[C@H](Oc1cc2O)c1cc(O)cc(c1)O
InChI	InChI=1S/C24H20O9/c25-12-3-11(4-13(26)6-12)23-19(30)7-15-20(32-23)9-18(29)22-14(8-21(31)33-24(15)22)10-1-2-16(27)17(28)5-10/h1-6,9,14,19,23,25-30H,7-8H2/t14-,19+,23+/m0/s1
InChIKey	UEKKPVDOFDIGFG-LEDSTXDGSA-N
Formula	C₂₄H₂₀O₉
HBA	9
HBD	6
MW	452.42
Rotatable Bonds	2
TPSA	156.91
LogP	2.69
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	452.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ceiba pentandra	Bombacaceae	Plantae	193163

Showing of synonyms

Abouelela M.E, Orabi M.A.A, et al. (2020). Anti-Alzheimer's flavanolignans from Ceiba pentandra aerial parts. Fitoterapia, 2020, 143, 104541. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(CC(=O)O2)c(c2c34)ccc3OC(CC4)c5ccccc5

Level: 2

Mol. Weight: 452.42 g/mol

SMILES: O=C(O1)CCc(c1c23)ccc2OC(CC3)c4ccccc4

Level: 1

Mol. Weight: 452.42 g/mol

SMILES: C1CCOc2ccc(c3c12)C(CC(=O)O3)c4ccccc4

Level: 1

Mol. Weight: 452.42 g/mol

SMILES: O=C(O1)CCc(c1c23)ccc2OCCC3

Level: 0

Mol. Weight: 452.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 452.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.84
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.18
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 85.82
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.85
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.01
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.87
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.97
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: -145.06
Rat (Acute): 2.39
Rat (Chronic Oral): 3.23
Fathead Minnow: 4.46
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 603.02
Hydration Free Energy: -3.53
Log(D) at pH=7.4: 1.44
Log(P): 0.91
Log S: -3.87
Log(Vapor Pressure): -11.06
Melting Point: 297.19
pKa Acid: 7.62
pKa Basic: 5.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9087
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9038
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8912
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8883
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8873
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8770
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8578
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8531
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8455
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.8447
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8352
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8350
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8330
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.8269
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8246
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8220
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8194
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8158
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8137
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8114
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8105
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8099
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7898
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7891
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7858
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7831
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7729
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7725
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7713
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7675
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7640
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7610
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7595
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7541
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	3	0.7522
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7515
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7484
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7483
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7421
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7413
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7363
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7331
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7328
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7328
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7311
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7311
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7302
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7285
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7278
Uncharacterized protein MJ0489	Q57913	Y489_METJA	Methanocaldococcus jannaschii	4	0.7275
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7253
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7247
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.7246
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7186
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7180
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7158
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7156
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7144
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7129
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	4	0.7126
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7070
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7053
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	3	0.7051
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7045
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7036
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7033
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7004

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