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Bignanoside B

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Iridoid Glucoside

Canonical Smiles	COC(=O)C1=CO[C@H]([C@H]2[C@]1(O)C[C@@H](C2=C)O)OC1OC(COC(=O)/C=C/c2ccc(c(c2)O)O)C(C(C1O)O)O
InChI	InChI=1S/C26H30O14/c1-11-16(29)8-26(35)13(23(34)36-2)9-38-24(19(11)26)40-25-22(33)21(32)20(31)17(39-25)10-37-18(30)6-4-12-3-5-14(27)15(28)7-12/h3-7,9,16-17,19-22,24-25,27-29,31-33,35H,1,8,10H2,2H3/b6-4+/t16-,17?,19-,20?,21?,22?,24-,25?,26-/m0/s1
InChIKey	VWHQCGCMPMSYQY-SFZLPYSUSA-N
Formula	C₂₆H₃₀O₁₄
HBA	14
HBD	7
MW	566.51
Rotatable Bonds	7
TPSA	221.9
LogP	-1.44
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.46
Exact Mass	566.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Bignonia binata	Bignoniaceae	Plantae	680235

Showing of synonyms

Mahmoud B, Samy M, et al. (2020). Bignanoside A "A new neolignan glucoside" and bignanoside B "A new iridoid glucoside" from Bignonia binata leaves. Phytochemistry Letters, 2020, 35, 200-205. [View]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3OC=CC(C34)CCC4=C

Level: 2

Mol. Weight: 566.51 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 566.51 g/mol

SMILES: C=C1CCC(C12)C=COC2OC3CCCCO3

Level: 1

Mol. Weight: 566.51 g/mol

SMILES: C=C1CCC(C12)C=COC2

Level: 0

Mol. Weight: 566.51 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 566.51 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 566.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.65
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.060
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.11

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.720
Plasma Protein Binding: 38.38
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: Non-Inhibitor

Excretion

Clearance: 8.730
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.790
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.490
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.310
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2875.610
Rat (Acute): 2.610
Rat (Chronic Oral): 4.330
Fathead Minnow: 9.310
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 523.540
Hydration Free Energy: -2.930
Log(D) at pH=7.4: 0.450
Log(P): 0.17
Log S: -2.73
Log(Vapor Pressure): -10.63
Melting Point: 173.88
pKa Acid: 5.09
pKa Basic: 2.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9249
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9190
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9138
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9117
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.9045
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8857
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8710
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8557
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8488
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8423
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8422
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8369
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8340
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8318
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8225
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8211
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8142
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7994
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7960
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7939
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.7883
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7882
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7878
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7856
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7823
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7789
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7772
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7769
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7760
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7712
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7646
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7602
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7593
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7593
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7564
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7557
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7538
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7535
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7496
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7445
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	3	0.7413
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7412
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7399
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7361
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7359
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7356
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7334
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7332
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7322
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7310
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7295
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7276
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7276
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7269
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7266
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7241
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7237
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7219
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7217
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7208
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7206
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7188
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7183
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7181
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7168
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7155
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7149
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7148
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7146
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7138
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7134
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7127
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7090
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7087
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7077
Glucanase	B7X9Z2	B7X9Z2_COPCI	Coprinopsis cinerea	4	0.7052
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7043
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7030
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7030
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7028
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7026
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7024
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7007

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