NPASS Compound

Natural Product: NPC252292

Natural Product ID	NPC252292
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Jionoside D
IUPAC Name	[(2R,3R,4R,5R,6R)-5-hydroxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms	Jionoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL555710
PubChem CID	9895632
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

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 83 86 0 0 0 0 0 0 0 0999 V2000 3.8208 -4.3617 0.6407 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7466 -3.4740 -0.5813 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5270 -4.3211 -1.8058 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1281 -4.1527 -2.3596 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1502 -3.9725 -1.2229 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5384 -2.6976 -0.5098 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8726 -2.4318 -0.4574 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8204 -1.6011 -1.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0362 -1.0392 -0.1122 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4838 -1.1125 -0.5750 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2676 -0.1916 0.3702 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4943 0.9883 -0.3112 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8544 1.2006 -0.4163 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5433 1.3777 0.9111 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0031 1.5908 0.6011 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4786 2.8512 0.4126 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8290 3.0567 0.1269 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6804 1.9704 0.0358 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1938 0.6876 0.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8547 0.5102 0.5103 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0183 -0.4151 0.1417 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9997 2.1285 -0.2417 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7488 3.2628 -0.4663 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6021 0.0708 1.5372 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4825 0.8347 1.3727 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7374 2.3143 1.4816 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4478 3.0187 1.2717 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2376 0.4238 0.1151 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6247 0.6980 0.2391 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3182 1.5532 -0.5970 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6293 2.0987 -1.5049 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7372 1.8515 -0.5010 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5463 1.3365 0.4079 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9621 1.6268 0.5120 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7081 1.0320 1.4950 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0809 1.2956 1.6187 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7019 2.1606 0.7489 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9501 2.7679 -0.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5887 2.4838 -0.3455 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6060 3.6342 -1.1096 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0482 2.4214 0.8646 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0031 -2.3932 -0.4463 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1051 -5.0089 -0.3288 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7477 -5.1680 -3.2084 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5007 -4.0802 -2.7631 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1131 -4.0675 1.4369 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7203 -5.4465 0.3514 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8347 -4.3255 1.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 -3.0154 -0.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6282 -5.3823 -1.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1439 -3.2015 -2.9330 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1083 -3.8305 -1.6017 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1832 -2.7952 0.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0311 -1.5460 0.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5510 -0.7038 -1.5777 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2302 -0.7012 0.6537 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2687 0.2843 -0.9241 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0203 2.0985 -1.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1707 2.3242 1.4026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4295 0.5345 1.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8258 3.7058 0.4814 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1951 4.0425 -0.0218 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4108 -0.4701 0.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4114 -0.7906 0.9851 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9007 3.4831 -1.5435 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7736 3.1626 0.0083 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3363 4.2036 -0.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2708 0.6235 2.2064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9935 2.4963 2.5733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5800 2.6950 0.9185 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1721 2.6983 1.8674 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2110 0.9810 -0.7372 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1600 2.5318 -1.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0563 0.6478 1.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3069 0.3404 2.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6665 0.8213 2.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0878 2.9994 -1.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3535 4.2500 -0.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4112 3.3794 0.9199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8363 -2.4188 0.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3290 -4.8786 0.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9371 -5.6446 -2.9403 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0260 -3.9111 -3.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 18 22 1 0 22 23 1 0 11 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 38 40 1 0 37 41 1 0 10 42 1 0 5 43 1 0 4 44 1 0 3 45 1 0 7 2 1 0 28 9 1 0 39 34 1 0 20 15 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 6 3 50 1 1 4 51 1 6 5 52 1 6 6 53 1 1 9 54 1 1 10 55 1 6 11 56 1 1 13 57 1 0 13 58 1 0 14 59 1 0 14 60 1 0 16 61 1 0 17 62 1 0 20 63 1 0 21 64 1 0 23 65 1 0 23 66 1 0 23 67 1 0 25 68 1 1 26 69 1 0 26 70 1 0 27 71 1 0 28 72 1 6 32 73 1 0 33 74 1 0 35 75 1 0 36 76 1 0 39 77 1 0 40 78 1 0 41 79 1 0 42 80 1 0 43 81 1 0 44 82 1 0 45 83 1 0 M END

Standard InCHIKey	WKQLGHCWJNLUKK-CPPDSBOHSA-N
Standard InCHI	InChI=1S/C30H38O15/c1-14-23(36)24(37)25(38)30(42-14)45-28-26(39)29(41-10-9-16-4-7-20(40-2)19(34)12-16)43-21(13-31)27(28)44-22(35)8-5-15-3-6-17(32)18(33)11-15/h3-8,11-12,14,21,23-34,36-39H,9-10,13H2,1-2H3/b8-5+/t14-,21+,23-,24+,25+,26+,27+,28+,29+,30-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H](OCCc2ccc(c(c2)O)OC)O[C@H](CO)[C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.22	Volume:	603.972 ? Van der Waals volume.
Dense:	1.057	LogP:	-0.121 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.748 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.38 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	26.0
TPSA:	234.29 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.707	Fsp³:	0.5
MCE-18:	99.889 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.729	Fluc inhibitor:	0.665 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.154 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.554 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.143	Promiscuous compounds:	0.326

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.325	MDCK Permeability:	-5.37
Pgp-inhibitor:	0.001	Pgp-substrate:	0.575
PAMPA:	0.999 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.757
20% Bioavailability (F20%):	0.978	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.022
Plasma Protein Binding (PPB):	73.024%	Volume Distribution (VD):	-0.269
Fu:	24.398% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.072	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.109	CYP3A4-substrate:	0.985
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.77 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.629

Half-life (T1/2):

3.545

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.339
Human Hepatotoxicity (H-HT):	0.362	Drug-induced Liver Injury (DILI):	0.664
AMES Toxicity:	0.954	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.026	Skin Sensitization:	1.0
Carcinogencity:	0.032	Eye Corrosion:	0.0
Eye Irritation:	0.037	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.993
Hematotoxicity:	0.139	Drug-induced Nephrotoxicity:	0.471
Genotoxicity:	0.158	RPMI-8226 Immunitoxicity:	0.088
A549 Cytotoxicity:	0.949	Hek293 Cytotoxicity:	0.638
BCF:	0.576 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.284 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.946 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.225 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361168]
NPO33389	strobilanthes cusia	Species	Acanthaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25427242]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28152	Jacaranda caucana	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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
EC50	1

Activity Type	# Activity
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	1100.0	nM	PMID[19361168]

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 NPC252292 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	13035
0.1-0.2	30998
0.2-0.3	5112
0.3-0.4	583
0.4-0.5	64
0.5-0.6	23
0.6-0.7	22
0.7-0.8	0
0.8-0.85	2
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.881	High Similarity	NPC34927
0.8625	High Similarity	NPC472350
0.8625	High Similarity	NPC197316
0.8625	High Similarity	NPC89105
0.8372	Intermediate Similarity	NPC100998
0.8023	Intermediate Similarity	NPC269141
0.7816	Intermediate Similarity	NPC34587
0.764	Intermediate Similarity	NPC112
0.75	Intermediate Similarity	NPC46137
0.7396	Intermediate Similarity	NPC306890
0.7391	Intermediate Similarity	NPC259347
0.7368	Intermediate Similarity	NPC470933
0.7159	Intermediate Similarity	NPC76406
0.7143	Intermediate Similarity	NPC298257
0.7143	Intermediate Similarity	NPC175214
0.7126	Intermediate Similarity	NPC483705
0.7079	Intermediate Similarity	NPC611289
0.7045	Intermediate Similarity	NPC134405
0.7011	Intermediate Similarity	NPC483706
0.7	Intermediate Similarity	NPC263829
0.697	Remote Similarity	NPC473427
0.6774	Remote Similarity	NPC205864
0.6774	Remote Similarity	NPC247032
0.6737	Remote Similarity	NPC96795
0.6737	Remote Similarity	NPC264632
0.6667	Remote Similarity	NPC300894
0.6667	Remote Similarity	NPC23845
0.6634	Remote Similarity	NPC94871
0.6531	Remote Similarity	NPC106818
0.6526	Remote Similarity	NPC296954
0.6436	Remote Similarity	NPC87403
0.6304	Remote Similarity	NPC68092
0.6279	Remote Similarity	NPC473285
0.6186	Remote Similarity	NPC600370
0.6176	Remote Similarity	NPC471062
0.6163	Remote Similarity	NPC35731
0.6117	Remote Similarity	NPC470934
0.61	Remote Similarity	NPC476382
0.6061	Remote Similarity	NPC610636
0.6055	Remote Similarity	NPC470927
0.6044	Remote Similarity	NPC81515
0.604	Remote Similarity	NPC476384
0.5981	Remote Similarity	NPC476386
0.5938	Remote Similarity	NPC106677
0.593	Remote Similarity	NPC886
0.5914	Remote Similarity	NPC64141
0.581	Remote Similarity	NPC64195
0.5769	Remote Similarity	NPC476381
0.5766	Remote Similarity	NPC257970
0.57	Remote Similarity	NPC119537
0.5619	Remote Similarity	NPC476380
0.5556	Remote Similarity	NPC476385
0.5524	Remote Similarity	NPC196063
0.5524	Remote Similarity	NPC604195
0.5464	Remote Similarity	NPC222433
0.5437	Remote Similarity	NPC232992
0.5417	Remote Similarity	NPC205195
0.5364	Remote Similarity	NPC229505
0.5354	Remote Similarity	NPC476377
0.5283	Remote Similarity	NPC476375
0.5222	Remote Similarity	NPC287597
0.5189	Remote Similarity	NPC141455
0.5179	Remote Similarity	NPC188393
0.5052	Remote Similarity	NPC260425
0.5052	Remote Similarity	NPC235294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4352
0.1-0.2	4645
0.2-0.3	149
0.3-0.4	3
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8625	High Similarity	NPD7266	Phase 2

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