NPASS Compound

Natural Product: NPC79643

Natural Product ID	NPC79643
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-Glucopyranosyl-(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-[[(2S,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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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	CHEMBL451529
PubChem CID	21577278
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 181190 0 0 0 0 0 0 0 0999 V2000 -7.7250 2.7623 -1.9331 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6515 2.7191 -0.7345 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.0855 2.6727 -1.1216 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6827 1.3461 -0.8127 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7499 0.1713 -1.0425 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3871 0.4427 -0.4454 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3435 1.7093 0.1379 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1923 -0.4729 0.5857 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0833 -1.3098 0.3293 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5319 -2.7180 0.3851 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9098 -3.5711 1.4419 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5442 -2.8438 2.6973 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7517 -1.4716 2.6161 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1025 -1.0170 1.4422 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9259 -1.6862 1.2220 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8153 -0.8479 1.1706 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9504 -1.1397 2.3620 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5964 -0.5110 2.2787 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8723 -1.0467 1.0326 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6970 -2.5096 1.2251 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6889 -0.6354 -0.1477 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9824 -1.1273 -1.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2381 -0.2314 -1.5620 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1037 -0.2747 -0.3571 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0818 -1.4356 -0.5259 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4152 -0.2692 0.9623 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4041 -0.6133 2.0263 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7150 0.0325 1.7664 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0031 0.7649 0.6923 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3917 1.3240 0.6339 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3947 2.4899 1.6027 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7482 3.0620 1.8545 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5648 4.5252 2.2336 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4541 2.4015 3.0256 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6258 2.9039 0.6302 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7409 2.9751 -0.5740 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8319 1.7510 -0.7146 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7386 2.1477 -1.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5765 1.2162 -1.7148 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9761 0.9897 -0.3548 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1515 2.2244 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0.9535 -1.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7677 0.4208 -0.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9601 -0.3688 -2.0801 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6628 -5.4201 1.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4322 -2.9289 -1.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3349 -0.5304 -2.8052 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5262 1.0582 0.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9709 2.2604 -1.8692 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.1186 2.1333 -0.3187 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.3031 -0.0383 0.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5299 -0.4922 1.4206 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.5367 -1.9623 -0.3237 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3175 -2.1705 1.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5816 -3.3453 1.1471 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7852 1.9101 1.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.1599 0.6293 -2.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7093 3.9090 -0.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9513 3.3120 0.5520 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 1 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 79 80 1 0 78 81 1 0 77 82 1 0 76 83 1 0 75 84 1 0 3 85 1 0 7 2 1 0 14 9 1 0 67 16 1 0 81 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 86 1 0 1 87 1 0 1 88 1 0 2 89 1 1 3 90 1 6 4 91 1 1 5 92 1 1 6 93 1 6 9 94 1 6 10 95 1 1 11 96 1 6 12 97 1 0 12 98 1 0 14 99 1 1 16100 1 1 17101 1 0 17102 1 0 18103 1 0 18104 1 0 20105 1 0 20106 1 0 20107 1 0 21108 1 6 22109 1 0 22110 1 0 23111 1 0 23112 1 0 25113 1 0 25114 1 0 25115 1 0 26116 1 1 27117 1 0 27118 1 0 28119 1 0 30120 1 1 31121 1 0 31122 1 0 33123 1 0 33124 1 0 33125 1 0 34126 1 0 34127 1 0 34128 1 0 35129 1 0 35130 1 0 36131 1 0 36132 1 0 38133 1 0 38134 1 0 39135 1 0 39136 1 0 41137 1 0 41138 1 0 41139 1 0 45140 1 6 46141 1 1 47142 1 6 48143 1 6 49144 1 6 50145 1 0 50146 1 0 52147 1 1 53148 1 6 54149 1 6 55150 1 1 56151 1 1 57152 1 0 57153 1 0 58154 1 0 60155 1 0 61156 1 0 62157 1 0 64158 1 0 65159 1 0 66160 1 0 68161 1 0 68162 1 0 68163 1 0 69164 1 0 69165 1 0 69166 1 0 70167 1 0 71168 1 0 72169 1 0 74170 1 1 75171 1 6 76172 1 1 77173 1 1 78174 1 1 79175 1 0 79176 1 0 80177 1 0 82178 1 0 83179 1 0 84180 1 0 85181 1 0 M END

Standard InCHIKey	UTALRKDQMPEZAD-OOQFFGIESA-N
Standard InCHI	InChI=1S/C59H96O26/c1-24-34(63)46(83-49-43(72)40(69)37(66)29(21-61)80-49)45(74)51(78-24)84-47-35(64)27(62)22-76-52(47)82-33-12-13-56(6)31(55(33,4)5)11-14-58(8)32(56)10-9-25-26-19-54(2,3)15-17-59(26,18-16-57(25,58)7)53(75)85-50-44(73)41(70)38(67)30(81-50)23-77-48-42(71)39(68)36(65)28(20-60)79-48/h9,24,26-52,60-74H,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-,52-,56-,57+,58+,59-/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]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1220.62	Volume:	1166.728 ? Van der Waals volume.
Dense:	1.046	LogP:	0.649 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.634 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.06 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	57.0
TPSA:	412.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	15.0	Rings:	10.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.051	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.193	Fsp³:	0.949
MCE-18:	217.043 ? 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:	0.803	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.293	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.715	MDCK Permeability:	-5.109
Pgp-inhibitor:	0.0	Pgp-substrate:	0.037
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):	0.934
20% Bioavailability (F20%):	0.097	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222	MRP1:	0.0
Plasma Protein Binding (PPB):	60.494%	Volume Distribution (VD):	-0.29
Fu:	23.214% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
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:	0.994	CYP3A4-substrate:	0.966
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.044 ? 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):

-1.024

Half-life (T1/2):

5.682

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.658	Drug-induced Liver Injury (DILI):	0.957
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.35	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.07	RPMI-8226 Immunitoxicity:	0.35
A549 Cytotoxicity:	0.892	Hek293 Cytotoxicity:	0.566
BCF:	1.705 ? 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:	3.813 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.355 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.483 ? 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 NPC79643 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	24166
0.1-0.2	21520
0.2-0.3	2845
0.3-0.4	667
0.4-0.5	370
0.5-0.6	56
0.6-0.7	86
0.7-0.8	0
0.8-0.85	13
0.85-0.9	3
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9608	High Similarity	NPC123199
0.9252	High Similarity	NPC41061
0.9252	High Similarity	NPC227551
0.9083	High Similarity	NPC305981
0.902	High Similarity	NPC481078
0.9	High Similarity	NPC261506
0.9	High Similarity	NPC4328
0.899	High Similarity	NPC63159
0.8571	High Similarity	NPC236638
0.8571	High Similarity	NPC294453
0.8407	Intermediate Similarity	NPC481081
0.8349	Intermediate Similarity	NPC135904
0.8333	Intermediate Similarity	NPC298034
0.8333	Intermediate Similarity	NPC71065
0.8319	Intermediate Similarity	NPC43550
0.8317	Intermediate Similarity	NPC112352
0.8276	Intermediate Similarity	NPC250247
0.8158	Intermediate Similarity	NPC293330
0.8125	Intermediate Similarity	NPC481080
0.8073	Intermediate Similarity	NPC60557
0.8073	Intermediate Similarity	NPC475287
0.8073	Intermediate Similarity	NPC67857
0.8	Intermediate Similarity	NPC475504
0.7931	Intermediate Similarity	NPC202828
0.7931	Intermediate Similarity	NPC119592
0.79	Intermediate Similarity	NPC48499
0.7731	Intermediate Similarity	NPC220160
0.7692	Intermediate Similarity	NPC65105
0.7521	Intermediate Similarity	NPC110633
0.7455	Intermediate Similarity	NPC481079
0.7434	Intermediate Similarity	NPC76972
0.7434	Intermediate Similarity	NPC469782
0.7434	Intermediate Similarity	NPC204414
0.7358	Intermediate Similarity	NPC469946
0.7328	Intermediate Similarity	NPC475160
0.7328	Intermediate Similarity	NPC473714
0.7288	Intermediate Similarity	NPC476068
0.719	Intermediate Similarity	NPC136768
0.7179	Intermediate Similarity	NPC470218
0.7156	Intermediate Similarity	NPC480475
0.713	Intermediate Similarity	NPC223301
0.713	Intermediate Similarity	NPC171544
0.7119	Intermediate Similarity	NPC488560
0.7103	Intermediate Similarity	NPC295371
0.7094	Intermediate Similarity	NPC219180
0.708	Intermediate Similarity	NPC295823
0.708	Intermediate Similarity	NPC174720
0.708	Intermediate Similarity	NPC475467
0.7075	Intermediate Similarity	NPC475516
0.7073	Intermediate Similarity	NPC70809
0.7054	Intermediate Similarity	NPC104372
0.7027	Intermediate Similarity	NPC297263
0.7025	Intermediate Similarity	NPC258617
0.7009	Intermediate Similarity	NPC165204
0.7	Intermediate Similarity	NPC473459
0.7	Intermediate Similarity	NPC46665
0.7	Intermediate Similarity	NPC469778
0.6957	Remote Similarity	NPC469776
0.6929	Remote Similarity	NPC32723
0.6909	Remote Similarity	NPC160415
0.688	Remote Similarity	NPC224381
0.6879	Remote Similarity	NPC481323
0.6875	Remote Similarity	NPC222580
0.687	Remote Similarity	NPC31838
0.686	Remote Similarity	NPC57484
0.6847	Remote Similarity	NPC251768
0.6842	Remote Similarity	NPC301449
0.6842	Remote Similarity	NPC601290
0.6783	Remote Similarity	NPC135334
0.6781	Remote Similarity	NPC295941
0.675	Remote Similarity	NPC100639
0.6736	Remote Similarity	NPC481324
0.6696	Remote Similarity	NPC324875
0.6696	Remote Similarity	NPC292677
0.6667	Remote Similarity	NPC192791
0.6667	Remote Similarity	NPC480422
0.6636	Remote Similarity	NPC29069
0.6612	Remote Similarity	NPC191827
0.6609	Remote Similarity	NPC114484
0.6581	Remote Similarity	NPC187290
0.6549	Remote Similarity	NPC10607
0.6549	Remote Similarity	NPC159309
0.6549	Remote Similarity	NPC86222
0.6545	Remote Similarity	NPC150400
0.6542	Remote Similarity	NPC214484
0.6529	Remote Similarity	NPC155410
0.6496	Remote Similarity	NPC480473
0.6496	Remote Similarity	NPC241909
0.6496	Remote Similarity	NPC80986
0.6496	Remote Similarity	NPC480474
0.6491	Remote Similarity	NPC475591
0.6491	Remote Similarity	NPC236870
0.6486	Remote Similarity	NPC39211
0.6479	Remote Similarity	NPC469775
0.6463	Remote Similarity	NPC469777
0.646	Remote Similarity	NPC309714
0.6458	Remote Similarity	NPC469774
0.6441	Remote Similarity	NPC475486
0.6429	Remote Similarity	NPC161717
0.6404	Remote Similarity	NPC164389
0.6393	Remote Similarity	NPC166422
0.6389	Remote Similarity	NPC90856
0.6341	Remote Similarity	NPC471550
0.6333	Remote Similarity	NPC469772
0.6327	Remote Similarity	NPC100925
0.632	Remote Similarity	NPC21691
0.6316	Remote Similarity	NPC30735
0.6306	Remote Similarity	NPC235405
0.6293	Remote Similarity	NPC609763
0.626	Remote Similarity	NPC251263
0.625	Remote Similarity	NPC469773
0.625	Remote Similarity	NPC473373
0.625	Remote Similarity	NPC249848
0.625	Remote Similarity	NPC75287
0.625	Remote Similarity	NPC107966
0.624	Remote Similarity	NPC4749
0.623	Remote Similarity	NPC192600
0.622	Remote Similarity	NPC475514
0.6207	Remote Similarity	NPC148417
0.6207	Remote Similarity	NPC235438
0.6186	Remote Similarity	NPC276093
0.6179	Remote Similarity	NPC471384
0.6174	Remote Similarity	NPC104071
0.6121	Remote Similarity	NPC488526
0.6121	Remote Similarity	NPC102439
0.6121	Remote Similarity	NPC173859
0.6121	Remote Similarity	NPC148603
0.6119	Remote Similarity	NPC33012
0.608	Remote Similarity	NPC283417
0.608	Remote Similarity	NPC200049
0.6077	Remote Similarity	NPC302543
0.6053	Remote Similarity	NPC470512
0.6053	Remote Similarity	NPC157868
0.6048	Remote Similarity	NPC470911
0.6045	Remote Similarity	NPC8524
0.6017	Remote Similarity	NPC481082
0.6017	Remote Similarity	NPC164419
0.6016	Remote Similarity	NPC480418
0.6016	Remote Similarity	NPC13998
0.6	Remote Similarity	NPC263756
0.6	Remote Similarity	NPC472268
0.6	Remote Similarity	NPC161674
0.6	Remote Similarity	NPC213674
0.5984	Remote Similarity	NPC85154
0.5983	Remote Similarity	NPC40775
0.5965	Remote Similarity	NPC173583
0.5963	Remote Similarity	NPC128925
0.5929	Remote Similarity	NPC297950
0.592	Remote Similarity	NPC323341
0.5917	Remote Similarity	NPC281148
0.5906	Remote Similarity	NPC54636
0.5905	Remote Similarity	NPC167383
0.5902	Remote Similarity	NPC104137
0.5902	Remote Similarity	NPC26626
0.5896	Remote Similarity	NPC102505
0.5896	Remote Similarity	NPC488514
0.5873	Remote Similarity	NPC480419
0.5862	Remote Similarity	NPC473343
0.5826	Remote Similarity	NPC58448
0.5826	Remote Similarity	NPC127056
0.582	Remote Similarity	NPC69811
0.5804	Remote Similarity	NPC204458
0.5798	Remote Similarity	NPC68175
0.5798	Remote Similarity	NPC470515
0.5794	Remote Similarity	NPC237503
0.5794	Remote Similarity	NPC133818
0.5769	Remote Similarity	NPC286457
0.5758	Remote Similarity	NPC135849
0.5752	Remote Similarity	NPC1046
0.5752	Remote Similarity	NPC78046
0.5726	Remote Similarity	NPC470915
0.5714	Remote Similarity	NPC309223
0.5714	Remote Similarity	NPC489208
0.5705	Remote Similarity	NPC472269
0.5702	Remote Similarity	NPC64715
0.568	Remote Similarity	NPC185466
0.5662	Remote Similarity	NPC480417
0.5645	Remote Similarity	NPC207738
0.5645	Remote Similarity	NPC36831
0.5635	Remote Similarity	NPC268184
0.5635	Remote Similarity	NPC610204
0.5625	Remote Similarity	NPC475209
0.5625	Remote Similarity	NPC209894
0.562	Remote Similarity	NPC470514
0.562	Remote Similarity	NPC257468
0.562	Remote Similarity	NPC470513
0.56	Remote Similarity	NPC11242
0.5593	Remote Similarity	NPC80843
0.5591	Remote Similarity	NPC123522
0.5583	Remote Similarity	NPC305267
0.5583	Remote Similarity	NPC232237
0.5565	Remote Similarity	NPC187618
0.5564	Remote Similarity	NPC471385
0.5547	Remote Similarity	NPC475899
0.5537	Remote Similarity	NPC258885
0.5533	Remote Similarity	NPC23020
0.5532	Remote Similarity	NPC475368
0.5508	Remote Similarity	NPC473884
0.5507	Remote Similarity	NPC489209

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79643 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7639
0.1-0.2	1453
0.2-0.3	52
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