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Ceibapentain A

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-/m1/s1
InChIKey	UEKKPVDOFDIGFG-WNHYQHMGSA-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: -0.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.89
Plasma Protein Binding: 86.24
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: 12.86
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.02
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: 5.98
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: -144.76
Rat (Acute): 2.38
Rat (Chronic Oral): 3.23
Fathead Minnow: 4.47
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: 602.81
Hydration Free Energy: -3.52
Log(D) at pH=7.4: 1.46
Log(P): 1.05
Log S: -3.88
Log(Vapor Pressure): -11.06
Melting Point: 302.43
pKa Acid: 7.62
pKa Basic: 5.78

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	0.9338
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9038
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8964
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8876
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.8868
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8703
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8633
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8417
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8411
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8360
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8337
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8311
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8310
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8307
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8279
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8015
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7940
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7927
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7697
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7669
Uncharacterized protein MJ0489	Q57913	Y489_METJA	Methanocaldococcus jannaschii	4	0.7639
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7629
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7618
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7598
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7591
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7554
TamL	D3Y1I2	D3Y1I2_9ACTN	Streptomyces sp. 307-9	3	0.7537
RNA polymerase sigma factor SigA	Q5SKW1	Q5SKW1_THET8	Thermus thermophilus	3	0.7510
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7437
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7432
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7411
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7393
High affinity nerve growth factor receptor	P04629	NTRK1_HUMAN	Homo sapiens	3	0.7392
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7367
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7353
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7352
Bifunctional adenosylcobalamin biosynthesis protein CobU	Q05599	COBU_SALTY	Salmonella typhimurium	4	0.7345
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7345
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7339
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7322
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7320
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7308
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7303
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7300
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7295
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7262
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7253
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7203
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7196
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7183
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7182
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7177
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7140
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7127
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7122
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7122
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7093
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7091
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7078
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7052
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7043
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7039
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7026
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7021
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7017
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7017
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7015

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