NPASS Compound

Natural Product: NPC293330

Natural Product ID	NPC293330
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-Glucopyranosyl-(1->3)-Alpha-L-Rhamnopyranosyl-(1->2)-Alpha-L-Abinopyranosyl]16Alpha, 23Dihydroxyolean-28-O-[Alpha-L-Rhamnopyranosyl(1->4)-[Beta-D-Quinovopyranosyl-(1->)2-Beta-D-Glucopyranosyl-(1->6)-Beta-D-Glucopyranosyl]Ester
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-4-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-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	CHEMBL508736
PubChem CID	44575200
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 2D 222233 0 0 0 0 0 0 0 0999 V2000 9.0481 14.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5481 14.3324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1386 14.8454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9895 13.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 12.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6595 11.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 12.8552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 10.5920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6595 9.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 8.7799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 8.7799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9895 7.3027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1386 6.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5481 6.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 8.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5586 9.6278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0481 6.8515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7981 5.5525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9472 6.5167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3567 6.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6172 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1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 13 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 1 0 35 36 1 0 35 37 1 0 37 38 1 0 38 39 2 0 40 38 1 1 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 43 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 1 52 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 1 57 59 1 0 59 60 1 0 57 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 1 64 66 1 0 66 67 1 6 66 68 1 0 68 69 1 0 56 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 74 77 1 0 73 78 1 0 72 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 84 86 1 0 83 87 1 0 82 88 1 0 88 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 93 94 1 0 94 95 1 0 93 96 1 0 92 97 1 0 91 98 1 0 90 99 1 0 81100 1 0 34101 1 0 33102 1 0 32103 1 0 5104 1 0 4105 1 0 3106 1 0 7 2 1 0 15 9 1 0 25 18 1 0 36 31 1 0 69 40 1 0 76 71 1 0 86 80 1 0 96 89 1 0 47 40 1 0 66 48 1 0 64 51 1 0 61 52 1 0 1107 1 0 1108 1 0 1109 1 0 2110 1 1 3111 1 6 4112 1 1 5113 1 1 6114 1 6 9115 1 6 10116 1 1 11117 1 0 11118 1 0 11119 1 0 13120 1 1 14121 1 6 15122 1 1 16123 1 0 18124 1 6 19125 1 1 20126 1 6 21127 1 1 22128 1 6 23129 1 0 23130 1 0 24131 1 0 26132 1 0 27133 1 0 28134 1 0 30135 1 0 30136 1 0 31137 1 1 32138 1 6 33139 1 1 34140 1 6 35141 1 1 41142 1 0 41143 1 0 42144 1 0 42145 1 0 44146 1 0 44147 1 0 44148 1 0 45149 1 0 45150 1 0 45151 1 0 46152 1 0 46153 1 0 47154 1 1 49155 1 0 50156 1 0 50157 1 0 51158 1 6 53159 1 0 53160 1 0 53161 1 0 54162 1 0 54163 1 0 55164 1 0 55165 1 0 56166 1 6 58167 1 0 58168 1 0 58169 1 0 59170 1 0 59171 1 0 60172 1 0 61173 1 6 62174 1 0 62175 1 0 63176 1 0 63177 1 0 65178 1 0 65179 1 0 65180 1 0 67181 1 0 67182 1 0 67183 1 0 68184 1 0 68185 1 0 69186 1 0 69187 1 0 71188 1 6 72189 1 1 73190 1 6 74191 1 6 75192 1 0 75193 1 0 77194 1 0 78195 1 0 80196 1 6 81197 1 1 82198 1 1 83199 1 6 84200 1 1 85201 1 0 85202 1 0 85203 1 0 87204 1 0 89205 1 6 90206 1 1 91207 1 6 92208 1 1 93209 1 6 94210 1 0 94211 1 0 95212 1 0 97213 1 0 98214 1 0 99215 1 0 100216 1 0 101217 1 0 102218 1 0 103219 1 0 104220 1 0 105221 1 0 106222 1 0 M END

Standard InCHIKey	DTZUYTUOLCJVSI-UPVUTMMPSA-N
Standard InCHI	InChI=1S/C71H116O35/c1-26-38(76)44(82)48(86)58(95-26)102-54-28(3)97-63(57(52(54)90)105-60-50(88)46(84)42(80)33(22-73)99-60)94-24-34-43(81)47(85)51(89)61(100-34)106-65(92)71-18-16-66(4,5)20-30(71)29-10-11-36-67(6)14-13-37(68(7,25-74)35(67)12-15-70(36,9)69(29,8)17-19-71)101-64-56(40(78)31(75)23-93-64)104-62-53(91)55(39(77)27(2)96-62)103-59-49(87)45(83)41(79)32(21-72)98-59/h10,26-28,30-64,72-91H,11-25H2,1-9H3/t26-,27-,28+,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-,59-,60-,61-,62-,63+,64-,67-,68-,69+,70+,71-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)[C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)CC[C@@H]([C@@](C)(CO)[C@@H]4CC[C@@]3(C)[C@]2(C)CC1)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1528.73	Volume:	1436.279 ? Van der Waals volume.
Dense:	1.064	LogP:	-0.033 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.841 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.191 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	69.0
TPSA:	550.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	35.0
H-Bond Donor:	20.0	Rings:	12.0
Heavy Atoms:	35.0

MedChem Properties

QED Drug-Likeness Score:	0.035	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.287	Fsp³:	0.958
MCE-18:	262.388 ? 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:	0.687	Fluc inhibitor:	0.324 ? 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:	0.446	Promiscuous compounds:	0.064

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.456	MDCK Permeability:	-4.757
Pgp-inhibitor:	0.0	Pgp-substrate:	0.925
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%):	0.969	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019	MRP1:	0.0
Plasma Protein Binding (PPB):	53.447%	Volume Distribution (VD):	-0.26
Fu:	22.115% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.086
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):

-2.035

Half-life (T1/2):

5.921

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.681	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.799	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.126	RPMI-8226 Immunitoxicity:	0.643
A549 Cytotoxicity:	0.979	Hek293 Cytotoxicity:	0.306
BCF:	1.139 ? 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:	3.482 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.04 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.001 ? 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
NPO33015	trevesia palmata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757708]

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
NPT1886	Cell line	J774	Mus musculus	IC50	=	100.0	nM	PMID[9513595]
NPT71	Cell line	HEK293	Homo sapiens	IC50	=	320.0	nM	PMID[17081761]
NPT3470	Cell line	WEHI-164	Mus musculus	IC50	=	260.0	nM	PubChem BioAssay data set

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 NPC293330 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	25522
0.1-0.2	20634
0.2-0.3	2454
0.3-0.4	698
0.4-0.5	318
0.5-0.6	112
0.6-0.7	58
0.7-0.8	0
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8632	High Similarity	NPC298034
0.8632	High Similarity	NPC71065
0.8305	Intermediate Similarity	NPC65105
0.8235	Intermediate Similarity	NPC202828
0.8235	Intermediate Similarity	NPC119592
0.8158	Intermediate Similarity	NPC79643
0.8083	Intermediate Similarity	NPC305981
0.8017	Intermediate Similarity	NPC261506
0.8017	Intermediate Similarity	NPC4328
0.8	Intermediate Similarity	NPC475504
0.7917	Intermediate Similarity	NPC41061
0.7917	Intermediate Similarity	NPC227551
0.7863	Intermediate Similarity	NPC123199
0.7759	Intermediate Similarity	NPC76972
0.7759	Intermediate Similarity	NPC469782
0.7759	Intermediate Similarity	NPC204414
0.7705	Intermediate Similarity	NPC43550
0.768	Intermediate Similarity	NPC250247
0.7642	Intermediate Similarity	NPC236638
0.7642	Intermediate Similarity	NPC294453
0.75	Intermediate Similarity	NPC481078
0.7417	Intermediate Similarity	NPC135904
0.7321	Intermediate Similarity	NPC112352
0.7281	Intermediate Similarity	NPC63159
0.7222	Intermediate Similarity	NPC481081
0.7167	Intermediate Similarity	NPC60557
0.7167	Intermediate Similarity	NPC475287
0.7167	Intermediate Similarity	NPC67857
0.7073	Intermediate Similarity	NPC100639
0.696	Remote Similarity	NPC481080
0.6923	Remote Similarity	NPC220160
0.6855	Remote Similarity	NPC155410
0.6842	Remote Similarity	NPC295371
0.6833	Remote Similarity	NPC241909
0.681	Remote Similarity	NPC309714
0.6772	Remote Similarity	NPC57484
0.6759	Remote Similarity	NPC469775
0.6735	Remote Similarity	NPC469774
0.6733	Remote Similarity	NPC469777
0.6719	Remote Similarity	NPC110633
0.6711	Remote Similarity	NPC469772
0.6692	Remote Similarity	NPC136768
0.6667	Remote Similarity	NPC471550
0.6641	Remote Similarity	NPC476068
0.66	Remote Similarity	NPC100925
0.6591	Remote Similarity	NPC70809
0.656	Remote Similarity	NPC192600
0.6541	Remote Similarity	NPC224381
0.6535	Remote Similarity	NPC475160
0.6535	Remote Similarity	NPC473714
0.6516	Remote Similarity	NPC469773
0.6471	Remote Similarity	NPC46665
0.6466	Remote Similarity	NPC150400
0.6393	Remote Similarity	NPC276093
0.6358	Remote Similarity	NPC469778
0.6357	Remote Similarity	NPC488560
0.6348	Remote Similarity	NPC48499
0.6341	Remote Similarity	NPC481079
0.6309	Remote Similarity	NPC469776
0.6291	Remote Similarity	NPC32723
0.629	Remote Similarity	NPC295823
0.629	Remote Similarity	NPC174720
0.629	Remote Similarity	NPC475467
0.6288	Remote Similarity	NPC258617
0.6282	Remote Similarity	NPC295941
0.625	Remote Similarity	NPC481323
0.625	Remote Similarity	NPC323341
0.625	Remote Similarity	NPC133818
0.625	Remote Similarity	NPC165204
0.6232	Remote Similarity	NPC480422
0.6198	Remote Similarity	NPC473459
0.6187	Remote Similarity	NPC33012
0.6169	Remote Similarity	NPC135334
0.6154	Remote Similarity	NPC191827
0.6129	Remote Similarity	NPC481324
0.6119	Remote Similarity	NPC471385
0.6116	Remote Similarity	NPC160415
0.6115	Remote Similarity	NPC8524
0.6083	Remote Similarity	NPC469946
0.6077	Remote Similarity	NPC219180
0.6066	Remote Similarity	NPC102439
0.6066	Remote Similarity	NPC480475
0.605	Remote Similarity	NPC473373
0.6033	Remote Similarity	NPC223301
0.6033	Remote Similarity	NPC171544
0.6031	Remote Similarity	NPC470218
0.6	Remote Similarity	NPC161717
0.5984	Remote Similarity	NPC104071
0.5983	Remote Similarity	NPC29069
0.597	Remote Similarity	NPC473452
0.5966	Remote Similarity	NPC475516
0.5952	Remote Similarity	NPC324875
0.5952	Remote Similarity	NPC292677
0.5938	Remote Similarity	NPC75287
0.5887	Remote Similarity	NPC139044
0.5873	Remote Similarity	NPC104372
0.5873	Remote Similarity	NPC114484
0.584	Remote Similarity	NPC297263
0.5833	Remote Similarity	NPC166422
0.5833	Remote Similarity	NPC251263
0.5806	Remote Similarity	NPC10607
0.5781	Remote Similarity	NPC187618
0.576	Remote Similarity	NPC475591
0.576	Remote Similarity	NPC236870
0.5746	Remote Similarity	NPC54636
0.5736	Remote Similarity	NPC187290
0.5724	Remote Similarity	NPC475368
0.5714	Remote Similarity	NPC222580
0.5703	Remote Similarity	NPC301449
0.5703	Remote Similarity	NPC601290
0.5693	Remote Similarity	NPC475514
0.568	Remote Similarity	NPC251768
0.568	Remote Similarity	NPC164389
0.5669	Remote Similarity	NPC486563
0.5662	Remote Similarity	NPC21691
0.5659	Remote Similarity	NPC80986
0.5659	Remote Similarity	NPC480474
0.5645	Remote Similarity	NPC192791
0.5639	Remote Similarity	NPC475899
0.5638	Remote Similarity	NPC472268
0.5634	Remote Similarity	NPC102505
0.5634	Remote Similarity	NPC488514
0.5625	Remote Similarity	NPC477464
0.562	Remote Similarity	NPC480418
0.5615	Remote Similarity	NPC31838
0.5613	Remote Similarity	NPC23020
0.561	Remote Similarity	NPC473884
0.56	Remote Similarity	NPC30735
0.5597	Remote Similarity	NPC480419
0.5594	Remote Similarity	NPC153673
0.5591	Remote Similarity	NPC609763
0.5586	Remote Similarity	NPC275225
0.5574	Remote Similarity	NPC174679
0.5574	Remote Similarity	NPC235405
0.5574	Remote Similarity	NPC279554
0.5574	Remote Similarity	NPC59804
0.5571	Remote Similarity	NPC302543
0.557	Remote Similarity	NPC297950
0.5565	Remote Similarity	NPC473343
0.5565	Remote Similarity	NPC161674
0.5556	Remote Similarity	NPC159309
0.5556	Remote Similarity	NPC86222
0.5538	Remote Similarity	NPC96641
0.5538	Remote Similarity	NPC480473
0.5538	Remote Similarity	NPC163183
0.5538	Remote Similarity	NPC69811
0.5528	Remote Similarity	NPC249848
0.5528	Remote Similarity	NPC107966
0.5524	Remote Similarity	NPC480417
0.5522	Remote Similarity	NPC471384
0.5512	Remote Similarity	NPC148417
0.5508	Remote Similarity	NPC256798
0.5507	Remote Similarity	NPC286457
0.55	Remote Similarity	NPC214484
0.55	Remote Similarity	NPC135849
0.5496	Remote Similarity	NPC475486
0.5489	Remote Similarity	NPC313110
0.5478	Remote Similarity	NPC237503
0.5474	Remote Similarity	NPC85154
0.5469	Remote Similarity	NPC257468
0.5468	Remote Similarity	NPC470876
0.5462	Remote Similarity	NPC486564
0.5462	Remote Similarity	NPC323359
0.5439	Remote Similarity	NPC167383
0.5435	Remote Similarity	NPC237191
0.5417	Remote Similarity	NPC68767
0.5396	Remote Similarity	NPC13998
0.5391	Remote Similarity	NPC68175
0.5391	Remote Similarity	NPC235438
0.5391	Remote Similarity	NPC471383
0.538	Remote Similarity	NPC472269
0.5379	Remote Similarity	NPC110385
0.5379	Remote Similarity	NPC104137
0.5379	Remote Similarity	NPC26626
0.5372	Remote Similarity	NPC90856
0.536	Remote Similarity	NPC39211
0.5352	Remote Similarity	NPC309223
0.5352	Remote Similarity	NPC144644
0.5352	Remote Similarity	NPC170407
0.5344	Remote Similarity	NPC218954
0.5324	Remote Similarity	NPC484545
0.5323	Remote Similarity	NPC139894
0.5317	Remote Similarity	NPC263756
0.5317	Remote Similarity	NPC213674
0.5312	Remote Similarity	NPC305267
0.5303	Remote Similarity	NPC488564
0.5287	Remote Similarity	NPC485563
0.5285	Remote Similarity	NPC475208
0.5271	Remote Similarity	NPC162574
0.5267	Remote Similarity	NPC281148
0.5263	Remote Similarity	NPC36831
0.526	Remote Similarity	NPC45606
0.5252	Remote Similarity	NPC4749
0.5246	Remote Similarity	NPC189884
0.5246	Remote Similarity	NPC138334
0.5234	Remote Similarity	NPC109588
0.5231	Remote Similarity	NPC481082
0.5231	Remote Similarity	NPC164419
0.5224	Remote Similarity	NPC815

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC293330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7839
0.1-0.2	1263
0.2-0.3	44
0.3-0.4	4
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