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Methyl neochebulanin

Family: Plantae - Combretaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Chebulic Ellagitannin

Canonical Smiles	OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(c(c2)O)O)[C@@H]([C@H](C1OC(=O)[C@H]([C@@H]1[C@H](OC(=O)c2c1c(O)c(c(c2)O)O)C(=O)OC)CC(=O)O)O)O
InChI	InChI=1S/C28H28O20/c1-44-27(43)23-16(15-8(25(41)47-23)4-12(32)18(36)19(15)37)9(5-14(33)34)26(42)46-22-13(6-29)45-28(21(39)20(22)38)48-24(40)7-2-10(30)17(35)11(31)3-7/h2-4,9,13,16,20-23,28-32,35-39H,5-6H2,1H3,(H,33,34)/t9-,13+,16-,20+,21+,22?,23-,28-/m0/s1
InChIKey	RDHOOOLYXCLSDL-NSVKKBJESA-N
Formula	C₂₈H₂₈O₂₀
HBA	19
HBD	10
MW	684.51
Rotatable Bonds	9
TPSA	333.8
LogP	-1.99
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	48
Formal Charge	0
Fraction CSP3	0.39
Exact Mass	684.12
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Terminalia species	Combretaceae	Plantae	39992

Showing of synonyms

Pfundstein B, El Desouky SK, et al. (2010). Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry,2010,71(10),1132-1148. [View] [PubMed]

Pubchem: 162941932

Nmrshiftdb2: 80004707

No compound-protein relationship available.

SMILES: c1cccc(c12)C(COC2=O)CC(=O)OC3CCC(OC3)OC(=O)c4ccccc4

Level: 2

Mol. Weight: 684.51 g/mol

SMILES: C1OCCCC1OC(=O)CC(COC2=O)c(c23)cccc3

Level: 1

Mol. Weight: 684.51 g/mol

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 684.51 g/mol

SMILES: c1cccc(c12)CCOC2=O

Level: 0

Mol. Weight: 684.51 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 684.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 684.51 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.36
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.69
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 44.35

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 51.93
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: 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: Inhibitor

Excretion

Clearance: 6.88
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -3.77
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.63
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.38
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: -86707.01
Rat (Acute): 2.24
Rat (Chronic Oral): 3.52
Fathead Minnow: 128.67
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 1371.65
Hydration Free Energy: -2.92
Log(D) at pH=7.4: -2.27
Log(P): -1.53
Log S: -3.36
Log(Vapor Pressure): -136.85
Melting Point: 196.66
pKa Acid: 4.53
pKa Basic: 3.88

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8621
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8621
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8292
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8292
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8207
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8207
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8167
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8167
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8136
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8136
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8012
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8012
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7997
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7997
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7987
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7987
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7938
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7938
Glucose-1-phosphate thymidylyltransferase 1	P37744	RMLA1_ECOLI	Escherichia coli	5	0.7801
Glucose-1-phosphate thymidylyltransferase 1	P37744	RMLA1_ECOLI	Escherichia coli	5	0.7801
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7709
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	4	0.7709
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7704
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7704
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7575
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7575
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7469
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7469
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7423
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7423
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7359
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7359
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7265
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7265
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7213
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7213
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7149
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7149
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.7136
D-alanyl-D-alanine carboxypeptidase	P15555	DAC_STRSR	Streptomyces sp	3	0.7136
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7130
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7130
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7057
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7057
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7031
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7031
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7004
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7004

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