NPASS Compound

Natural Product: NPC123199

Natural Product ID	NPC123199
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Xylopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-Beta-D-Xylopyranosyloleanolic Acid 28-O-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451064
PubChem CID	21577277
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 177186 0 0 0 0 0 0 0 0999 V2000 7.7228 -0.2913 -3.2860 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3828 0.2655 -2.0749 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8862 0.4700 -2.3079 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4816 0.6354 -0.9355 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8623 1.8285 -0.2738 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3975 1.9138 -0.4457 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8236 1.4262 -1.5788 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6798 1.5585 0.7050 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1945 2.6446 1.4031 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7603 2.7298 2.7996 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6577 3.0523 3.7680 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6316 4.0080 3.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4229 4.0131 1.9077 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7207 2.6546 1.4661 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1093 2.5076 0.2234 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8775 1.8601 0.3255 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8630 2.9506 0.0021 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4915 2.4332 0.1463 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2377 1.1823 -0.7115 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2448 1.6563 -2.1303 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2709 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0 0 0 4.1280 -0.6525 1.2484 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2133 2.1012 4.6220 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6286 3.2862 3.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0193 3.1594 -1.6889 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7454 -0.9952 0.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9392 -0.3772 -1.9786 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8825 -2.5421 -0.8130 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8404 -2.3246 1.6197 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1339 -0.3831 2.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4755 -1.0247 2.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8030 -3.2646 1.8056 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2868 0.2061 -0.1801 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5559 -2.5739 -2.3609 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1893 -0.2175 -3.6419 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 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 1 37 42 1 6 42 43 2 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 54 61 1 0 53 62 1 0 49 63 1 0 48 64 1 0 47 65 1 0 46 66 1 0 21 67 1 0 67 68 1 0 67 69 1 0 11 70 1 0 10 71 1 0 5 72 1 0 4 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 77 80 1 0 76 81 1 0 75 82 1 0 3 83 1 0 7 2 1 0 14 9 1 0 67 16 1 0 79 74 1 0 26 19 1 0 40 29 1 0 63 45 1 0 40 24 1 0 59 52 1 0 37 30 1 0 1 84 1 0 1 85 1 0 1 86 1 0 2 87 1 1 3 88 1 6 4 89 1 1 5 90 1 1 6 91 1 6 9 92 1 6 10 93 1 1 11 94 1 1 12 95 1 0 12 96 1 0 14 97 1 1 16 98 1 1 17 99 1 0 17100 1 0 18101 1 0 18102 1 0 20103 1 0 20104 1 0 20105 1 0 21106 1 1 22107 1 0 22108 1 0 23109 1 0 23110 1 0 25111 1 0 25112 1 0 25113 1 0 26114 1 1 27115 1 0 27116 1 0 28117 1 0 30118 1 1 31119 1 0 31120 1 0 33121 1 0 33122 1 0 33123 1 0 34124 1 0 34125 1 0 34126 1 0 35127 1 0 35128 1 0 36129 1 0 36130 1 0 38131 1 0 38132 1 0 39133 1 0 39134 1 0 41135 1 0 41136 1 0 41137 1 0 45138 1 6 46139 1 1 47140 1 6 48141 1 1 49142 1 6 50143 1 0 50144 1 0 52145 1 6 53146 1 1 54147 1 6 55148 1 1 56149 1 6 57150 1 0 57151 1 0 58152 1 0 60153 1 0 61154 1 0 62155 1 0 64156 1 0 65157 1 0 66158 1 0 68159 1 0 68160 1 0 68161 1 0 69162 1 0 69163 1 0 69164 1 0 70165 1 0 71166 1 0 72167 1 0 74168 1 1 75169 1 6 76170 1 6 77171 1 1 78172 1 0 78173 1 0 80174 1 0 81175 1 0 82176 1 0 83177 1 0 M END

Standard InCHIKey	BGKLFKHHSFCDKC-WMRAFNHZSA-N
Standard InCHI	InChI=1S/C58H94O25/c1-24-34(62)45(81-48-41(69)35(63)27(60)21-74-48)44(72)50(77-24)82-46-36(64)28(61)22-75-51(46)80-33-12-13-55(6)31(54(33,4)5)11-14-57(8)32(55)10-9-25-26-19-53(2,3)15-17-58(26,18-16-56(25,57)7)52(73)83-49-43(71)40(68)38(66)30(79-49)23-76-47-42(70)39(67)37(65)29(20-59)78-47/h9,24,26-51,59-72H,10-23H2,1-8H3/t24-,26-,27+,28+,29+,30+,31-,32+,33-,34-,35-,36-,37+,38+,39-,40-,41+,42+,43+,44+,45+,46+,47+,48-,49-,50-,51-,55-,56+,57+,58-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H](CO[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)O)O)O)C1(C)C)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1190.61	Volume:	1140.642 ? Van der Waals volume.
Dense:	1.044	LogP:	0.93 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.77 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.912 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	57.0
TPSA:	392.59 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	14.0	Rings:	10.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.058	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.139	Fsp³:	0.948
MCE-18:	215.327 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.82	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.263	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.505	MDCK Permeability:	-5.16
Pgp-inhibitor:	0.0	Pgp-substrate:	0.099
PAMPA:	1.0 ? 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):	0.796
20% Bioavailability (F20%):	0.135	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154	MRP1:	0.0
Plasma Protein Binding (PPB):	59.18%	Volume Distribution (VD):	-0.316
Fu:	24.759% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.936
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.066 ? 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):

-0.838

Half-life (T1/2):

5.108

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.589	Drug-induced Liver Injury (DILI):	0.893
AMES Toxicity:	0.925	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.237	Drug-induced Nephrotoxicity:	0.994
Genotoxicity:	0.021	RPMI-8226 Immunitoxicity:	0.365
A549 Cytotoxicity:	0.769	Hek293 Cytotoxicity:	0.5
BCF:	1.82 ? 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:	3.922 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.463 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.628 ? 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
NPO27055	Scabiosa tschiliensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104490]
NPO27055	Scabiosa tschiliensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27055	Scabiosa tschiliensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27055	Scabiosa tschiliensis	Species	Caprifoliaceae	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
IC50	3

Activity Type	# Activity
Cell line	3

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
NPT1083	Cell line	A-375	Homo sapiens	IC50	>	20000.0	nM	PMID[23639650]
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[23639650]
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[23639650]

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 NPC123199 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	24385
0.1-0.2	21380
0.2-0.3	2796
0.3-0.4	661
0.4-0.5	344
0.5-0.6	56
0.6-0.7	93
0.7-0.8	0
0.8-0.85	8
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9608	High Similarity	NPC79643
0.9406	High Similarity	NPC481078
0.8909	High Similarity	NPC41061
0.8909	High Similarity	NPC227551
0.875	High Similarity	NPC236638
0.875	High Similarity	NPC294453
0.875	High Similarity	NPC305981
0.8673	High Similarity	NPC261506
0.8673	High Similarity	NPC4328
0.8627	High Similarity	NPC63159
0.8584	High Similarity	NPC481081
0.8448	Intermediate Similarity	NPC250247
0.8304	Intermediate Similarity	NPC481080
0.8103	Intermediate Similarity	NPC202828
0.8103	Intermediate Similarity	NPC119592
0.8036	Intermediate Similarity	NPC135904
0.8034	Intermediate Similarity	NPC298034
0.8034	Intermediate Similarity	NPC71065
0.8017	Intermediate Similarity	NPC43550
0.7981	Intermediate Similarity	NPC112352
0.7863	Intermediate Similarity	NPC293330
0.7768	Intermediate Similarity	NPC60557
0.7768	Intermediate Similarity	NPC475287
0.7768	Intermediate Similarity	NPC67857
0.7714	Intermediate Similarity	NPC469946
0.7692	Intermediate Similarity	NPC110633
0.7685	Intermediate Similarity	NPC475504
0.7636	Intermediate Similarity	NPC481079
0.7603	Intermediate Similarity	NPC220160
0.7573	Intermediate Similarity	NPC48499
0.7453	Intermediate Similarity	NPC295371
0.7417	Intermediate Similarity	NPC65105
0.7364	Intermediate Similarity	NPC297263
0.7355	Intermediate Similarity	NPC136768
0.7288	Intermediate Similarity	NPC488560
0.7257	Intermediate Similarity	NPC295823
0.7257	Intermediate Similarity	NPC174720
0.7257	Intermediate Similarity	NPC475467
0.7236	Intermediate Similarity	NPC70809
0.7203	Intermediate Similarity	NPC475160
0.7203	Intermediate Similarity	NPC473714
0.7193	Intermediate Similarity	NPC31838
0.7168	Intermediate Similarity	NPC301449
0.7168	Intermediate Similarity	NPC601290
0.7167	Intermediate Similarity	NPC476068
0.7155	Intermediate Similarity	NPC76972
0.7155	Intermediate Similarity	NPC469782
0.7155	Intermediate Similarity	NPC204414
0.704	Intermediate Similarity	NPC224381
0.7025	Intermediate Similarity	NPC57484
0.6944	Remote Similarity	NPC475516
0.6917	Remote Similarity	NPC470218
0.6875	Remote Similarity	NPC480475
0.6847	Remote Similarity	NPC223301
0.6847	Remote Similarity	NPC171544
0.6833	Remote Similarity	NPC219180
0.6822	Remote Similarity	NPC480422
0.6783	Remote Similarity	NPC104372
0.6783	Remote Similarity	NPC469778
0.6777	Remote Similarity	NPC191827
0.6774	Remote Similarity	NPC258617
0.6752	Remote Similarity	NPC187290
0.675	Remote Similarity	NPC165204
0.6738	Remote Similarity	NPC469776
0.6729	Remote Similarity	NPC90856
0.6726	Remote Similarity	NPC473459
0.6726	Remote Similarity	NPC46665
0.6713	Remote Similarity	NPC32723
0.6667	Remote Similarity	NPC481323
0.6667	Remote Similarity	NPC241909
0.6637	Remote Similarity	NPC160415
0.6609	Remote Similarity	NPC222580
0.6579	Remote Similarity	NPC251768
0.6577	Remote Similarity	NPC295941
0.6575	Remote Similarity	NPC135334
0.6557	Remote Similarity	NPC166422
0.6532	Remote Similarity	NPC4749
0.6531	Remote Similarity	NPC481324
0.6514	Remote Similarity	NPC29069
0.6504	Remote Similarity	NPC100639
0.6441	Remote Similarity	NPC324875
0.6441	Remote Similarity	NPC292677
0.6404	Remote Similarity	NPC192791
0.6387	Remote Similarity	NPC480473
0.6387	Remote Similarity	NPC480474
0.6356	Remote Similarity	NPC114484
0.6341	Remote Similarity	NPC471384
0.6325	Remote Similarity	NPC481082
0.6325	Remote Similarity	NPC164419
0.6296	Remote Similarity	NPC128925
0.6293	Remote Similarity	NPC10607
0.6293	Remote Similarity	NPC159309
0.6293	Remote Similarity	NPC164389
0.6293	Remote Similarity	NPC488526
0.6293	Remote Similarity	NPC86222
0.629	Remote Similarity	NPC155410
0.6283	Remote Similarity	NPC150400
0.6276	Remote Similarity	NPC469775
0.6273	Remote Similarity	NPC214484
0.6269	Remote Similarity	NPC33012
0.6267	Remote Similarity	NPC469777
0.6259	Remote Similarity	NPC469774
0.625	Remote Similarity	NPC80986
0.624	Remote Similarity	NPC283417
0.624	Remote Similarity	NPC471550
0.624	Remote Similarity	NPC200049
0.6239	Remote Similarity	NPC475591
0.6239	Remote Similarity	NPC236870
0.6231	Remote Similarity	NPC302543
0.6228	Remote Similarity	NPC39211
0.622	Remote Similarity	NPC21691
0.6207	Remote Similarity	NPC309714
0.6202	Remote Similarity	NPC161717
0.6198	Remote Similarity	NPC475486
0.6194	Remote Similarity	NPC8524
0.6174	Remote Similarity	NPC263756
0.6174	Remote Similarity	NPC213674
0.6172	Remote Similarity	NPC480418
0.6172	Remote Similarity	NPC13998
0.6144	Remote Similarity	NPC469772
0.6143	Remote Similarity	NPC472268
0.6142	Remote Similarity	NPC85154
0.6133	Remote Similarity	NPC100925
0.6126	Remote Similarity	NPC204458
0.6124	Remote Similarity	NPC475514
0.608	Remote Similarity	NPC323341
0.6071	Remote Similarity	NPC297950
0.6071	Remote Similarity	NPC78046
0.6068	Remote Similarity	NPC30735
0.6066	Remote Similarity	NPC104137
0.6066	Remote Similarity	NPC26626
0.6065	Remote Similarity	NPC469773
0.6053	Remote Similarity	NPC235405
0.605	Remote Similarity	NPC609763
0.6045	Remote Similarity	NPC102505
0.6045	Remote Similarity	NPC488514
0.6032	Remote Similarity	NPC251263
0.6032	Remote Similarity	NPC480419
0.6016	Remote Similarity	NPC75287
0.6	Remote Similarity	NPC192600
0.6	Remote Similarity	NPC473373
0.6	Remote Similarity	NPC249848
0.6	Remote Similarity	NPC107966
0.5966	Remote Similarity	NPC148417
0.5966	Remote Similarity	NPC235438
0.595	Remote Similarity	NPC276093
0.5948	Remote Similarity	NPC157868
0.5932	Remote Similarity	NPC104071
0.5929	Remote Similarity	NPC1046
0.5923	Remote Similarity	NPC286457
0.5887	Remote Similarity	NPC11242
0.5882	Remote Similarity	NPC102439
0.5882	Remote Similarity	NPC173859
0.5882	Remote Similarity	NPC148603
0.5865	Remote Similarity	NPC309223
0.5862	Remote Similarity	NPC173583
0.5857	Remote Similarity	NPC489208
0.584	Remote Similarity	NPC185466
0.5839	Remote Similarity	NPC472269
0.5827	Remote Similarity	NPC470911
0.5812	Remote Similarity	NPC470512
0.5809	Remote Similarity	NPC480417
0.5806	Remote Similarity	NPC207738
0.5794	Remote Similarity	NPC167383
0.5794	Remote Similarity	NPC610204
0.5776	Remote Similarity	NPC139894
0.5763	Remote Similarity	NPC161674
0.575	Remote Similarity	NPC40775
0.575	Remote Similarity	NPC232237
0.5748	Remote Similarity	NPC123522
0.5726	Remote Similarity	NPC58448
0.5726	Remote Similarity	NPC69811
0.5714	Remote Similarity	NPC471385
0.5714	Remote Similarity	NPC256798
0.5703	Remote Similarity	NPC475899
0.5702	Remote Similarity	NPC470515
0.5692	Remote Similarity	NPC54636
0.5691	Remote Similarity	NPC281148
0.5688	Remote Similarity	NPC237503
0.5674	Remote Similarity	NPC475368
0.5667	Remote Similarity	NPC23020
0.5667	Remote Similarity	NPC117714
0.5667	Remote Similarity	NPC30289
0.5652	Remote Similarity	NPC489209
0.5639	Remote Similarity	NPC470876
0.563	Remote Similarity	NPC473343
0.562	Remote Similarity	NPC104400
0.562	Remote Similarity	NPC10320
0.5616	Remote Similarity	NPC45606
0.561	Remote Similarity	NPC64715
0.5593	Remote Similarity	NPC127056
0.5591	Remote Similarity	NPC288205
0.5591	Remote Similarity	NPC51465
0.5581	Remote Similarity	NPC133818
0.5574	Remote Similarity	NPC105800
0.5574	Remote Similarity	NPC68175
0.5571	Remote Similarity	NPC477464
0.5565	Remote Similarity	NPC189884
0.5565	Remote Similarity	NPC138334

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC123199 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7704
0.1-0.2	1397
0.2-0.3	43
0.3-0.4	6
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	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