NPASS Compound

Natural Product: NPC473714

Natural Product ID	NPC473714
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-[Beta-D-Glucopyranosyl-(1->4)-Beta-D-Glucopyranosyl-(1->3)-Alpha-L-Arabinopyranosyl] Olean-12-En-28-O-[Alpha-L-Rhamnopyranosyl-(1->4)-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl] Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S)-4-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-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	CHEMBL449916
PubChem CID	44585662
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

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7.8434 3.2740 2.0688 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0527 0.1726 2.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7093 -1.1340 1.7134 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0149 -1.1417 2.1475 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3442 -3.8832 1.7035 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2650 -5.2517 1.9643 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6305 -3.6380 2.3236 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4030 -6.2280 0.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9134 -5.1849 0.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8232 -5.4381 -1.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3472 -2.2755 -1.5586 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0535 -2.5003 -1.1206 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9588 -1.8092 2.9985 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7480 3.9812 -2.4367 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6993 2.2770 -2.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.1425 3.7051 -2.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.8026 0.8213 -3.8646 H 0 0 0 0 0 0 0 0 0 0 0 0 -19.2942 -0.7764 -1.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 -18.6533 2.8287 0.0188 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 13 16 1 0 12 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 42 52 1 0 42 53 1 0 41 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 57 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 67 69 1 0 69 70 1 0 66 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 0 76 78 1 0 78 79 1 0 75 80 1 0 74 81 1 0 73 82 1 0 65 83 1 0 64 84 1 0 56 85 1 0 38 86 1 0 31 87 1 0 31 88 1 0 22 89 1 0 21 90 1 0 20 91 1 0 10 92 1 0 92 93 1 0 5 94 1 0 4 95 1 0 3 96 1 0 7 2 1 0 68 63 1 0 77 72 1 0 14 9 1 0 24 19 1 0 33 28 1 0 49 28 1 0 47 34 1 0 46 37 1 0 43 38 1 0 60 55 1 0 1 97 1 0 1 98 1 0 1 99 1 0 2100 1 0 3101 1 0 4102 1 0 5103 1 0 6104 1 0 9105 1 0 10106 1 0 12107 1 0 13108 1 0 14109 1 0 15110 1 0 16111 1 0 18112 1 0 18113 1 0 19114 1 0 20115 1 0 21116 1 0 22117 1 0 23118 1 0 29119 1 0 29120 1 0 30121 1 0 30122 1 0 32123 1 0 32124 1 0 33125 1 0 35126 1 0 36127 1 0 36128 1 0 37129 1 0 39130 1 0 39131 1 0 40132 1 0 40133 1 0 41134 1 0 43135 1 0 44136 1 0 44137 1 0 45138 1 0 45139 1 0 48140 1 0 48141 1 0 49142 1 0 49143 1 0 50144 1 0 50145 1 0 50146 1 0 51147 1 0 51148 1 0 51149 1 0 52150 1 0 52151 1 0 52152 1 0 53153 1 0 53154 1 0 53155 1 0 55156 1 0 56157 1 0 57158 1 0 58159 1 0 59160 1 0 59161 1 0 61162 1 0 63163 1 0 64164 1 0 65165 1 0 66166 1 0 67167 1 0 69168 1 0 69169 1 0 70170 1 0 72171 1 0 73172 1 0 74173 1 0 75174 1 0 76175 1 0 78176 1 0 78177 1 0 79178 1 0 80179 1 0 81180 1 0 82181 1 0 83182 1 0 84183 1 0 85184 1 0 86185 1 0 86186 1 0 86187 1 0 87188 1 0 87189 1 0 87190 1 0 88191 1 0 88192 1 0 88193 1 0 89194 1 0 90195 1 0 91196 1 0 92197 1 0 92198 1 0 93199 1 0 94200 1 0 95201 1 0 96202 1 0 M END

Standard InCHIKey	ZIQABFLRIOOAGP-MQHLRMBESA-N
Standard InCHI	InChI=1S/C65H106O31/c1-25-36(70)39(73)44(78)55(87-25)94-51-30(21-67)89-53(47(81)42(51)76)86-24-32-38(72)41(75)46(80)58(91-32)96-59(84)65-17-15-60(2,3)19-27(65)26-9-10-34-62(6)13-12-35(61(4,5)33(62)11-14-64(34,8)63(26,7)16-18-65)92-54-49(83)50(28(69)23-85-54)93-57-48(82)43(77)52(31(22-68)90-57)95-56-45(79)40(74)37(71)29(20-66)88-56/h9,25,27-58,66-83H,10-24H2,1-8H3/t25-,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+,52+,53+,54+,55-,56-,57-,58-,62-,63+,64+,65-/m0/s1
SMILES	CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(CC4C6=CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)C)OC9C(C(C(CO9)O)OC1C(C(C(C(O1)CO)OC1C(C(C(C(O1)CO)O)O)O)O)O)O)C)(C)C)O)O)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1382.67	Volume:	1305.899 ? Van der Waals volume.
Dense:	1.059	LogP:	-1.225 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.015 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.999 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	63.0
TPSA:	491.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	31.0
H-Bond Donor:	18.0	Rings:	11.0
Heavy Atoms:	31.0

MedChem Properties

QED Drug-Likeness Score:	0.039	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.695	Fsp³:	0.954
MCE-18:	239.717 ? 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:	0.005	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.276 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.418	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.527	MDCK Permeability:	-4.943
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	1.0
20% Bioavailability (F20%):	0.821	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	22.358%	Volume Distribution (VD):	-0.359
Fu:	31.848% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.007	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.985	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.198	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

-1.164

Half-life (T1/2):

4.448

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.181
Human Hepatotoxicity (H-HT):	0.299	Drug-induced Liver Injury (DILI):	0.427
AMES Toxicity:	0.613	Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.066	Skin Sensitization:	0.007
Carcinogencity:	0.002	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.505	Ototoxicity:	1.0
Hematotoxicity:	0.001	Drug-induced Nephrotoxicity:	0.009
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.019	Hek293 Cytotoxicity:	0.925
BCF:	0.76 ? 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:	4.337 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.673 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.474 ? 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
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18442289]
NPO24757	Meryta denhamii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24757	Meryta denhamii	Species	Araliaceae	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	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
NPT1182	Cell line	J774.A1	Mus musculus	IC50	=	3000.0	nM	DrugMatrix in vivo data: Pathology

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 NPC473714 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	23739
0.1-0.2	22072
0.2-0.3	2703
0.3-0.4	793
0.4-0.5	321
0.5-0.6	89
0.6-0.7	62
0.7-0.8	0
0.8-0.85	13
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475160
0.9528	High Similarity	NPC476068
0.934	High Similarity	NPC488560
0.8559	High Similarity	NPC481080
0.8491	Intermediate Similarity	NPC295823
0.8491	Intermediate Similarity	NPC174720
0.8491	Intermediate Similarity	NPC475467
0.8261	Intermediate Similarity	NPC43550
0.819	Intermediate Similarity	NPC305981
0.8174	Intermediate Similarity	NPC475514
0.8125	Intermediate Similarity	NPC135904
0.812	Intermediate Similarity	NPC261506
0.812	Intermediate Similarity	NPC4328
0.8067	Intermediate Similarity	NPC250247
0.8039	Intermediate Similarity	NPC475516
0.8017	Intermediate Similarity	NPC41061
0.8017	Intermediate Similarity	NPC227551
0.7881	Intermediate Similarity	NPC236638
0.7881	Intermediate Similarity	NPC294453
0.7857	Intermediate Similarity	NPC60557
0.7857	Intermediate Similarity	NPC67857
0.7843	Intermediate Similarity	NPC48499
0.7818	Intermediate Similarity	NPC241909
0.7739	Intermediate Similarity	NPC100639
0.7712	Intermediate Similarity	NPC258617
0.7685	Intermediate Similarity	NPC148417
0.7647	Intermediate Similarity	NPC65105
0.7632	Intermediate Similarity	NPC192600
0.7583	Intermediate Similarity	NPC481081
0.7521	Intermediate Similarity	NPC298034
0.7521	Intermediate Similarity	NPC71065
0.75	Intermediate Similarity	NPC104071
0.7431	Intermediate Similarity	NPC102439
0.7398	Intermediate Similarity	NPC224381
0.735	Intermediate Similarity	NPC155410
0.7328	Intermediate Similarity	NPC79643
0.7317	Intermediate Similarity	NPC70809
0.7295	Intermediate Similarity	NPC202828
0.7295	Intermediate Similarity	NPC119592
0.7241	Intermediate Similarity	NPC76972
0.7241	Intermediate Similarity	NPC469782
0.7241	Intermediate Similarity	NPC204414
0.7203	Intermediate Similarity	NPC123199
0.712	Intermediate Similarity	NPC220160
0.7117	Intermediate Similarity	NPC46665
0.7105	Intermediate Similarity	NPC481079
0.7054	Intermediate Similarity	NPC63159
0.7016	Intermediate Similarity	NPC136768
0.6949	Remote Similarity	NPC475287
0.6911	Remote Similarity	NPC110633
0.6909	Remote Similarity	NPC295371
0.6899	Remote Similarity	NPC480422
0.6881	Remote Similarity	NPC235405
0.687	Remote Similarity	NPC114484
0.6833	Remote Similarity	NPC165204
0.6818	Remote Similarity	NPC173583
0.6818	Remote Similarity	NPC249848
0.6818	Remote Similarity	NPC107966
0.6786	Remote Similarity	NPC223301
0.6786	Remote Similarity	NPC171544
0.6786	Remote Similarity	NPC112352
0.6754	Remote Similarity	NPC235438
0.6726	Remote Similarity	NPC30735
0.6724	Remote Similarity	NPC104372
0.6695	Remote Similarity	NPC481078
0.6667	Remote Similarity	NPC58448
0.6606	Remote Similarity	NPC29069
0.6562	Remote Similarity	NPC309223
0.656	Remote Similarity	NPC57484
0.6535	Remote Similarity	NPC293330
0.6522	Remote Similarity	NPC159309
0.6522	Remote Similarity	NPC473459
0.6522	Remote Similarity	NPC86222
0.6514	Remote Similarity	NPC214484
0.646	Remote Similarity	NPC39211
0.6452	Remote Similarity	NPC470218
0.6404	Remote Similarity	NPC469946
0.6395	Remote Similarity	NPC469778
0.6372	Remote Similarity	NPC473373
0.6364	Remote Similarity	NPC102505
0.6364	Remote Similarity	NPC488514
0.6345	Remote Similarity	NPC469776
0.6331	Remote Similarity	NPC472268
0.6327	Remote Similarity	NPC32723
0.6303	Remote Similarity	NPC281148
0.6284	Remote Similarity	NPC481323
0.6261	Remote Similarity	NPC76497
0.6259	Remote Similarity	NPC297950
0.625	Remote Similarity	NPC13998
0.6239	Remote Similarity	NPC101744
0.622	Remote Similarity	NPC85154
0.6216	Remote Similarity	NPC90856
0.6209	Remote Similarity	NPC295941
0.6204	Remote Similarity	NPC475368
0.62	Remote Similarity	NPC135334
0.619	Remote Similarity	NPC471550
0.6159	Remote Similarity	NPC481324
0.6148	Remote Similarity	NPC187290
0.6134	Remote Similarity	NPC222580
0.6134	Remote Similarity	NPC297263
0.6121	Remote Similarity	NPC161674
0.6102	Remote Similarity	NPC40775
0.6102	Remote Similarity	NPC10607
0.6102	Remote Similarity	NPC251768
0.6066	Remote Similarity	NPC80986
0.605	Remote Similarity	NPC475591
0.605	Remote Similarity	NPC236870
0.6034	Remote Similarity	NPC157868
0.6016	Remote Similarity	NPC31838
0.6016	Remote Similarity	NPC473826
0.5985	Remote Similarity	NPC33012
0.5984	Remote Similarity	NPC301449
0.5984	Remote Similarity	NPC601290
0.595	Remote Similarity	NPC134835
0.5948	Remote Similarity	NPC150400
0.5946	Remote Similarity	NPC128925
0.5932	Remote Similarity	NPC192791
0.5917	Remote Similarity	NPC68175
0.5912	Remote Similarity	NPC8524
0.5909	Remote Similarity	NPC469777
0.5906	Remote Similarity	NPC472269
0.5906	Remote Similarity	NPC469775
0.5894	Remote Similarity	NPC469774
0.5878	Remote Similarity	NPC286457
0.5868	Remote Similarity	NPC609763
0.5833	Remote Similarity	NPC173859
0.5833	Remote Similarity	NPC148603
0.5827	Remote Similarity	NPC123522
0.582	Remote Similarity	NPC469821
0.5796	Remote Similarity	NPC469772
0.5789	Remote Similarity	NPC161717
0.578	Remote Similarity	NPC237503
0.5779	Remote Similarity	NPC100925
0.5772	Remote Similarity	NPC73318
0.5741	Remote Similarity	NPC167383
0.5738	Remote Similarity	NPC475504
0.5736	Remote Similarity	NPC475209
0.5723	Remote Similarity	NPC469773
0.5714	Remote Similarity	NPC263756
0.5714	Remote Similarity	NPC473343
0.5704	Remote Similarity	NPC302543
0.5702	Remote Similarity	NPC164389
0.5659	Remote Similarity	NPC470911
0.5656	Remote Similarity	NPC470515
0.5652	Remote Similarity	NPC204458
0.5652	Remote Similarity	NPC480417
0.5649	Remote Similarity	NPC54636
0.562	Remote Similarity	NPC160415
0.5603	Remote Similarity	NPC1046
0.5603	Remote Similarity	NPC78046
0.5597	Remote Similarity	NPC470876
0.5574	Remote Similarity	NPC480475
0.5573	Remote Similarity	NPC191827
0.5565	Remote Similarity	NPC601659
0.5564	Remote Similarity	NPC21691
0.5526	Remote Similarity	NPC23020
0.5512	Remote Similarity	NPC104137
0.5512	Remote Similarity	NPC26626
0.5512	Remote Similarity	NPC36831
0.55	Remote Similarity	NPC473884
0.55	Remote Similarity	NPC470512
0.5492	Remote Similarity	NPC109588
0.5492	Remote Similarity	NPC309714
0.5478	Remote Similarity	NPC209894
0.5473	Remote Similarity	NPC45606
0.5469	Remote Similarity	NPC11242
0.5455	Remote Similarity	NPC213674
0.5433	Remote Similarity	NPC96641
0.5433	Remote Similarity	NPC163183
0.541	Remote Similarity	NPC242840
0.5407	Remote Similarity	NPC473452
0.5391	Remote Similarity	NPC256798
0.5385	Remote Similarity	NPC268184
0.5379	Remote Similarity	NPC251263
0.5349	Remote Similarity	NPC75287
0.5333	Remote Similarity	NPC473386
0.5303	Remote Similarity	NPC475899
0.5299	Remote Similarity	NPC47995
0.5294	Remote Similarity	NPC480418
0.5278	Remote Similarity	NPC480421
0.5263	Remote Similarity	NPC219180
0.5263	Remote Similarity	NPC480419
0.5259	Remote Similarity	NPC4749
0.5242	Remote Similarity	NPC117714
0.5231	Remote Similarity	NPC470915
0.5223	Remote Similarity	NPC472270
0.5223	Remote Similarity	NPC112492
0.5217	Remote Similarity	NPC471385
0.52	Remote Similarity	NPC473401
0.52	Remote Similarity	NPC488526
0.5197	Remote Similarity	NPC64715
0.5194	Remote Similarity	NPC480473
0.5194	Remote Similarity	NPC470516
0.5194	Remote Similarity	NPC480474
0.5191	Remote Similarity	NPC114287
0.5185	Remote Similarity	NPC471577
0.5167	Remote Similarity	NPC475208
0.5145	Remote Similarity	NPC484942
0.5132	Remote Similarity	NPC220838

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473714 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7697
0.1-0.2	1393
0.2-0.3	52
0.3-0.4	8
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