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Cis-martynoside

Family: Plantae - Plantaginaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenylpropanoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)OC)[C@@H]([C@H]([C@@H]1OC(=O)/C=C\c1ccc(c(c1)OC)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C31H40O15/c1-15-24(36)25(37)26(38)31(43-15)46-29-27(39)30(42-11-10-17-5-8-20(40-2)19(34)12-17)44-22(14-32)28(29)45-23(35)9-6-16-4-7-18(33)21(13-16)41-3/h4-9,12-13,15,22,24-34,36-39H,10-11,14H2,1-3H3/b9-6-/t15-,22+,24-,25+,26+,27+,28+,29+,30+,31-/m0/s1
InChIKey	WLWAYPFRKDSFCL-LDMHTXDHSA-N
Formula	C₃₁H₄₀O₁₅
HBA	15
HBD	7
MW	652.65
Rotatable Bonds	12
TPSA	223.29
LogP	-0.41
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	46
Formal Charge	0
Fraction CSP3	0.52
Exact Mass	652.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Verbascum atlanticum	Plantaginaceae	Plantae	39257

Showing of synonyms

Khentoul H, Bensouici C, et al. (2020). Chemical constituents and HRESI-MS analysis of an Algerian endemic plant - Verbascum atlanticum batt. - extracts and their antioxidant activity. Natural product research, 2020, 34(20), 3008-3012. [View] [PubMed]

Pubchem: 10349304

Cas: 155899-92-6

Zinc: ZINC000095912152

Nmrshiftdb2: 60029224

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4

Level: 3

Mol. Weight: 652.65 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OCCc3ccccc3

Level: 2

Mol. Weight: 652.65 g/mol

SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 652.65 g/mol

SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 652.65 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 652.65 g/mol

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 652.65 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 652.65 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 652.65 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 652.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.47
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.960
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 29.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.840
Plasma Protein Binding: 71.13
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: 9.550
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.970
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.660
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.370
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: -55539.360
Rat (Acute): 2.300
Rat (Chronic Oral): 4.260
Fathead Minnow: 86.300
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 1089.920
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.100
Log(P): 0.42
Log S: -4.48
Log(Vapor Pressure): -55.96
Melting Point: 170.6
pKa Acid: 5.18
pKa Basic: 1.03

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	0.9508
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9483
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.9460
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9368
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9341
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9152
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8938
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8896
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8870
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8845
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8837
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8757
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8725
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8701
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8691
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8686
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8686
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8621
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8543
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8510
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8472
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8461
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8325
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8316
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8176
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8168
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8159
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8086
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8079
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8059
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7969
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7938
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7835
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7797
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7767
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7753
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7740
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7695
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7690
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7674
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7671
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7670
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7612
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7526
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7521
Purine nucleoside phosphorylase 2	P45563	XAPA_ECOLI	Escherichia coli	3	0.7494
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7471
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7445
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7403
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7395
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7363
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7351
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7351
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7345
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7327
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7320
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7308
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7305
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7298
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7292
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7285
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7276
Purine nucleoside phosphorylase	Q9BMI9	Q9BMI9_SCHMA	Schistosoma mansoni	3	0.7271
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7261
SKP1-like protein 1A	Q39255	SKP1A_ARATH	Arabidopsis thaliana	3	0.7258
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7253
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7251
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7246
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7242
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7238
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7227
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	2	0.7227
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7204
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7187
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7171
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7160
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7154
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7132
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7129
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7119
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7118
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7117
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7111
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7106
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7098
Type II methyltransferase M.HhaI	P05102	MTH1_HAEPH	Haemophilus parahaemolyticus	3	0.7089
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	3	0.7089
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	3	0.7084
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7082
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7077
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7071
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	2	0.7071
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7069
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7069
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7067
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7059
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7053
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7040
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7028
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	3	0.7025
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7025
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7017
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7009
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7008
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7000

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