NPASS Compound

Natural Product: NPC288416

Natural Product ID	NPC288416
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Eutigoside A
IUPAC Name	[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL478931
PubChem CID	10026568
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 58 60 0 0 0 0 0 0 0 0999 V2000 1.2230 -0.1489 1.9040 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2629 -0.4681 1.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4303 -1.7121 0.7710 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5247 -2.7703 0.8264 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2372 -2.5140 0.1382 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5243 -1.4732 0.5868 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7855 -1.5373 0.0126 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5974 -0.5631 0.5887 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7179 -1.1370 1.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6238 -0.1332 1.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1511 0.8615 0.8659 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4302 2.0202 0.6687 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9244 2.9600 -0.2285 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0946 2.7293 -0.8910 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8224 1.5721 -0.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3321 0.6476 0.1861 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6053 3.6703 -1.8003 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6895 -1.3048 -1.4858 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7218 -2.3059 -2.0824 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5816 -2.1902 -1.3255 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5419 -3.0537 -1.8085 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5891 -2.1313 -3.4375 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9336 -1.5829 -2.0702 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3169 0.5594 1.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4296 0.2613 0.5072 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5255 1.1962 0.3108 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6633 0.7827 -0.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7240 1.6282 -0.5936 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7213 2.9272 -0.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6082 3.3592 0.5550 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5311 2.4940 0.7670 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7925 3.7895 -0.3432 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0199 -3.6194 0.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4057 -3.1865 1.8536 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3979 -3.4469 0.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2560 -2.5150 0.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3477 -1.8128 1.9793 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2846 -1.6632 0.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1038 0.3404 2.6825 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4840 -0.6847 2.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5061 2.2263 1.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3603 3.8640 -0.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7563 1.4191 -1.2467 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8640 -0.2778 0.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0111 4.5338 -1.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4369 -0.2672 -1.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1413 -3.3204 -1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9205 -1.1353 -1.3276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1242 -3.9521 -1.8648 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0377 -2.8999 -3.9032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 -2.5395 -2.3302 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1961 1.5445 1.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5071 -0.7421 0.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6625 -0.2535 -0.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6042 1.2991 -1.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5912 4.3767 0.9229 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6878 2.8702 1.3055 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7120 3.4094 -0.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 14 17 1 0 7 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 18 23 1 0 2 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 20 5 1 0 31 26 1 0 16 11 1 0 4 33 1 0 4 34 1 0 5 35 1 6 7 36 1 6 9 37 1 0 9 38 1 0 10 39 1 0 10 40 1 0 12 41 1 0 13 42 1 0 15 43 1 0 16 44 1 0 17 45 1 0 18 46 1 1 19 47 1 6 20 48 1 1 21 49 1 0 22 50 1 0 23 51 1 0 24 52 1 0 25 53 1 0 27 54 1 0 28 55 1 0 30 56 1 0 31 57 1 0 32 58 1 0 M END

Standard InCHIKey	CACGKEKIUJWMQD-XLWWBJCMSA-N
Standard InCHI	InChI=1S/C23H26O9/c24-16-6-1-14(2-7-16)5-10-19(26)31-13-18-20(27)21(28)22(29)23(32-18)30-12-11-15-3-8-17(25)9-4-15/h1-10,18,20-25,27-29H,11-13H2/b10-5+/t18-,20-,21+,22-,23-/m1/s1
SMILES	O=C(OC[C@H]1O[C@@H](OCCc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(cc1)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33318	eurya tigang	Species	Pentaphylacaceae	Eukaryota	leaves	n.a.	n.a.	PMID[1431944]
NPO33318	eurya tigang	Species	Pentaphylacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT550	Cell line	T-24	Homo sapiens	IC50	=	28.7	ug.mL-1	DrugMatrix in vitro pharmacology data

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC288416 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	12220
0.1-0.2	31982
0.2-0.3	4629
0.3-0.4	718
0.4-0.5	228
0.5-0.6	60
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC34293
0.8125	Intermediate Similarity	NPC287597
0.7606	Intermediate Similarity	NPC235294
0.7273	Intermediate Similarity	NPC479473
0.7273	Intermediate Similarity	NPC275721
0.7273	Intermediate Similarity	NPC479468
0.7273	Intermediate Similarity	NPC479474
0.6667	Remote Similarity	NPC252114
0.6622	Remote Similarity	NPC281798
0.6377	Remote Similarity	NPC470572
0.6375	Remote Similarity	NPC476383
0.6286	Remote Similarity	NPC140151
0.6282	Remote Similarity	NPC64141
0.6282	Remote Similarity	NPC205195
0.6197	Remote Similarity	NPC229784
0.6176	Remote Similarity	NPC84789
0.6076	Remote Similarity	NPC611142
0.6029	Remote Similarity	NPC52097
0.6027	Remote Similarity	NPC291153
0.5968	Remote Similarity	NPC157338
0.5949	Remote Similarity	NPC46137
0.5909	Remote Similarity	NPC476872
0.5857	Remote Similarity	NPC184633
0.5823	Remote Similarity	NPC220942
0.5789	Remote Similarity	NPC219677
0.575	Remote Similarity	NPC476869
0.575	Remote Similarity	NPC476866
0.5732	Remote Similarity	NPC600647
0.5732	Remote Similarity	NPC610492
0.5692	Remote Similarity	NPC11724
0.5641	Remote Similarity	NPC225307
0.5632	Remote Similarity	NPC476397
0.557	Remote Similarity	NPC10205
0.5542	Remote Similarity	NPC600302
0.5542	Remote Similarity	NPC603754
0.5529	Remote Similarity	NPC263829
0.5529	Remote Similarity	NPC300262
0.55	Remote Similarity	NPC28637
0.5488	Remote Similarity	NPC471881
0.5455	Remote Similarity	NPC600370
0.5432	Remote Similarity	NPC260425
0.5432	Remote Similarity	NPC81515
0.5432	Remote Similarity	NPC204937
0.5432	Remote Similarity	NPC138777
0.5402	Remote Similarity	NPC125823
0.5402	Remote Similarity	NPC7145
0.5402	Remote Similarity	NPC143480
0.5395	Remote Similarity	NPC474641
0.5376	Remote Similarity	NPC476380
0.5376	Remote Similarity	NPC476381
0.5366	Remote Similarity	NPC226005
0.5341	Remote Similarity	NPC65262
0.5341	Remote Similarity	NPC84429
0.5341	Remote Similarity	NPC101686
0.5309	Remote Similarity	NPC476867
0.5301	Remote Similarity	NPC321638
0.5287	Remote Similarity	NPC609173
0.5287	Remote Similarity	NPC611338
0.5281	Remote Similarity	NPC119537
0.527	Remote Similarity	NPC90318
0.5263	Remote Similarity	NPC886
0.5244	Remote Similarity	NPC246869
0.5244	Remote Similarity	NPC225384
0.5222	Remote Similarity	NPC201148
0.5213	Remote Similarity	NPC476378
0.5211	Remote Similarity	NPC470825
0.5132	Remote Similarity	NPC477293
0.5128	Remote Similarity	NPC157898
0.5116	Remote Similarity	NPC76406
0.5116	Remote Similarity	NPC472876
0.5111	Remote Similarity	NPC112
0.5104	Remote Similarity	NPC476398
0.5075	Remote Similarity	NPC266045
0.5075	Remote Similarity	NPC313193
0.5072	Remote Similarity	NPC213552
0.5065	Remote Similarity	NPC473924
0.506	Remote Similarity	NPC476864
0.5057	Remote Similarity	NPC611289
0.5054	Remote Similarity	NPC141455

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC288416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4512
0.1-0.2	4501
0.2-0.3	133
0.3-0.4	2
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data