NPASS Compound

Natural Product: NPC259294

Natural Product ID	NPC259294
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Murucoidin Vi
IUPAC Name	n.a.
Synonyms	Murucoidin VI
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL509611
PubChem CID	24898687
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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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0 0 0 0 0 0 0 0 0 0 0 8.5548 7.0767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4542 8.2772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3536 9.4776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2530 10.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1524 11.8785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0518 13.0789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0624 6.9254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7000 6.2977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6153 5.2617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1757 5.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8209 7.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9056 8.1765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5706 9.5211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2356 10.8656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3452 7.7552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9889 8.3887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 5.5867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9257 3.9296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -7.2079 0.0000 C 0 0 0 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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 42 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 53 56 1 0 52 57 1 0 51 58 1 0 50 59 1 0 28 60 1 0 17 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 66 68 1 0 65 69 1 0 69 70 1 0 70 71 2 0 70 72 1 0 72 73 1 0 72 74 1 0 74 75 1 0 64 76 1 0 63 77 1 0 16 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 83 85 1 0 82 86 1 0 81 87 1 0 80 88 1 0 21 15 1 0 29 23 1 0 56 49 1 0 68 62 1 0 85 79 1 0 59 27 1 0 1 89 1 0 1 90 1 0 1 91 1 0 2 92 1 0 2 93 1 0 3 94 1 0 3 95 1 0 4 96 1 0 4 97 1 0 5 98 1 0 5 99 1 0 6100 1 0 6101 1 0 7102 1 0 7103 1 0 8104 1 0 8105 1 0 9106 1 0 9107 1 0 10108 1 0 10109 1 0 11110 1 0 11111 1 0 15112 1 6 16113 1 6 17114 1 1 18115 1 6 19116 1 0 19117 1 0 19118 1 0 21119 1 1 23120 1 6 24121 1 1 25122 1 0 25123 1 0 25124 1 0 27125 1 6 28126 1 1 29127 1 1 33128 1 0 33129 1 0 34130 1 0 34131 1 0 35132 1 0 35133 1 0 36134 1 0 36135 1 0 37136 1 0 37137 1 0 38138 1 0 38139 1 0 39140 1 0 39141 1 0 40142 1 0 40143 1 0 41144 1 0 41145 1 0 42146 1 6 43147 1 0 43148 1 0 44149 1 0 44150 1 0 45151 1 0 45152 1 0 46153 1 0 46154 1 0 47155 1 0 47156 1 0 47157 1 0 49158 1 6 50159 1 1 51160 1 6 52161 1 1 53162 1 6 54163 1 0 54164 1 0 55165 1 0 57166 1 0 58167 1 0 60168 1 0 62169 1 1 63170 1 6 64171 1 6 65172 1 1 66173 1 6 67174 1 0 67175 1 0 67176 1 0 72177 1 6 73178 1 0 73179 1 0 73180 1 0 74181 1 0 74182 1 0 75183 1 0 75184 1 0 75185 1 0 76186 1 0 77187 1 0 79188 1 1 80189 1 6 81190 1 6 82191 1 1 83192 1 6 84193 1 0 84194 1 0 84195 1 0 86196 1 0 87197 1 0 88198 1 0 M END

Standard InCHIKey	NIWJOMXGCMYTST-LVWHWYSVSA-N
Standard InCHI	InChI=1S/C63H110O25/c1-9-12-14-15-16-17-20-23-28-32-42(66)83-57-56(88-59-48(72)45(69)43(67)35(5)76-59)53(85-60-49(73)47(71)51(36(6)77-60)84-58(75)34(4)11-3)38(8)79-63(57)86-52-37(7)78-61-50(74)54(52)82-41(65)31-27-24-21-18-19-22-26-30-39(29-25-13-10-2)80-62-55(87-61)46(70)44(68)40(33-64)81-62/h34-40,43-57,59-64,67-74H,9-33H2,1-8H3/t34-,35-,36-,37-,38-,39-,40+,43-,44+,45+,46-,47-,48+,49+,50+,51-,52-,53-,54-,55+,56+,57+,59-,60-,61-,62+,63-/m0/s1
SMILES	CCCCCCCCCCCC(=O)O[C@@H]1[C@@H]([C@H]([C@H](C)O[C@H]1O[C@H]1[C@H](C)O[C@@H]2[C@@H]([C@@H]1OC(=O)CCCCCCCCC[C@H](CCCCC)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O2)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)OC(=O)[C@@H](C)CC)O)O)O[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1266.73	Volume:	1258.711 ? Van der Waals volume.
Dense:	1.006	LogP:	4.496 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.187 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.121 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	27.0	Rigid Bonds:	49.0
TPSA:	353.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	9.0	Rings:	6.0
Heavy Atoms:	25.0

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:	5.28	Fsp³:	0.952
MCE-18:	123.317 ? 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:	0.998	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.54	Promiscuous compounds:	0.182

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.611	MDCK Permeability:	-5.038
Pgp-inhibitor:	0.0	Pgp-substrate:	0.992
PAMPA:	0.995 ? 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):	0.249
20% Bioavailability (F20%):	0.056	30% Bioavailability (F30%):	0.931
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.992
Plasma Protein Binding (PPB):	93.65%	Volume Distribution (VD):	-0.134
Fu:	5.658% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.837
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.06

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:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.205 ? 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):

0.688

Half-life (T1/2):

3.222

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.108
Human Hepatotoxicity (H-HT):	0.473	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.464	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.619	Drug-induced Nephrotoxicity:	0.969
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.648
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.252
BCF:	0.868 ? 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:	4.695 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.211 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.942 ? 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
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	Roots	Ixpantepec, in the state of Oaxaca, Mexico	1996-DEC	PMID[16124750]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16643033]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18500841]
NPO2520	Ipomoea murucoides	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
MIC	4
ED50	3

Activity Type	# Activity
Cell line	3
Organism	4

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
NPT91	Cell line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[11421741]
NPT1171	Cell line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[14510600]
NPT165	Cell line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[14510600]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	512.0	ug.mL-1	PubChem BioAssay data set
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[8254346]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	256.0	ug.mL-1	PMID[23822611]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	512.0	ug.mL-1	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 NPC259294 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	23376
0.1-0.2	22742
0.2-0.3	3271
0.3-0.4	328
0.4-0.5	26
0.5-0.6	39
0.6-0.7	37
0.7-0.8	0
0.8-0.85	10
0.85-0.9	5
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC183888
0.9125	High Similarity	NPC307400
0.9125	High Similarity	NPC27289
0.9024	High Similarity	NPC126685
0.8889	High Similarity	NPC143421
0.8765	High Similarity	NPC477319
0.869	High Similarity	NPC123204
0.8675	High Similarity	NPC290012
0.8659	High Similarity	NPC472204
0.8415	Intermediate Similarity	NPC267592
0.8395	Intermediate Similarity	NPC477326
0.825	Intermediate Similarity	NPC113745
0.825	Intermediate Similarity	NPC477320
0.825	Intermediate Similarity	NPC477323
0.825	Intermediate Similarity	NPC477325
0.825	Intermediate Similarity	NPC609436
0.8148	Intermediate Similarity	NPC604005
0.8148	Intermediate Similarity	NPC605014
0.814	Intermediate Similarity	NPC184915
0.7955	Intermediate Similarity	NPC44782
0.7952	Intermediate Similarity	NPC477344
0.7831	Intermediate Similarity	NPC478734
0.775	Intermediate Similarity	NPC146380
0.7701	Intermediate Similarity	NPC483170
0.7647	Intermediate Similarity	NPC478733
0.759	Intermediate Similarity	NPC22742
0.759	Intermediate Similarity	NPC477346
0.7528	Intermediate Similarity	NPC224953
0.7471	Intermediate Similarity	NPC297768
0.7471	Intermediate Similarity	NPC472205
0.7386	Intermediate Similarity	NPC119583
0.7326	Intermediate Similarity	NPC600446
0.7326	Intermediate Similarity	NPC605013
0.7222	Intermediate Similarity	NPC115013
0.7111	Intermediate Similarity	NPC238264
0.7111	Intermediate Similarity	NPC477345
0.7045	Intermediate Similarity	NPC109887
0.7	Intermediate Similarity	NPC10121
0.7	Intermediate Similarity	NPC198918
0.6988	Remote Similarity	NPC477350
0.6966	Remote Similarity	NPC146992
0.6966	Remote Similarity	NPC85759
0.6941	Remote Similarity	NPC281563
0.6939	Remote Similarity	NPC35338
0.6939	Remote Similarity	NPC204214
0.6939	Remote Similarity	NPC92283
0.6882	Remote Similarity	NPC472200
0.6848	Remote Similarity	NPC169345
0.6848	Remote Similarity	NPC477317
0.6848	Remote Similarity	NPC477318
0.6818	Remote Similarity	NPC89843
0.6813	Remote Similarity	NPC294748
0.6768	Remote Similarity	NPC63404
0.6667	Remote Similarity	NPC238056
0.6548	Remote Similarity	NPC606819
0.6518	Remote Similarity	NPC147032
0.65	Remote Similarity	NPC124878
0.65	Remote Similarity	NPC231888
0.6481	Remote Similarity	NPC471024
0.6449	Remote Similarity	NPC472352
0.6444	Remote Similarity	NPC477331
0.6404	Remote Similarity	NPC477349
0.6383	Remote Similarity	NPC476087
0.6383	Remote Similarity	NPC475667
0.6316	Remote Similarity	NPC478732
0.625	Remote Similarity	NPC475270
0.625	Remote Similarity	NPC475327
0.6211	Remote Similarity	NPC478726
0.62	Remote Similarity	NPC475241
0.619	Remote Similarity	NPC290276
0.619	Remote Similarity	NPC10883
0.617	Remote Similarity	NPC173328
0.6075	Remote Similarity	NPC471025
0.6022	Remote Similarity	NPC158302
0.6019	Remote Similarity	NPC600721
0.6019	Remote Similarity	NPC605872
0.5938	Remote Similarity	NPC186992
0.5905	Remote Similarity	NPC77651
0.59	Remote Similarity	NPC475164
0.5833	Remote Similarity	NPC478724
0.5824	Remote Similarity	NPC477329
0.5816	Remote Similarity	NPC478731
0.5795	Remote Similarity	NPC478729
0.5773	Remote Similarity	NPC478730
0.5766	Remote Similarity	NPC600940
0.5755	Remote Similarity	NPC28069
0.5745	Remote Similarity	NPC477332
0.5741	Remote Similarity	NPC611287
0.5729	Remote Similarity	NPC478722
0.5729	Remote Similarity	NPC478725
0.5714	Remote Similarity	NPC477330
0.5688	Remote Similarity	NPC600672
0.5686	Remote Similarity	NPC473605
0.5686	Remote Similarity	NPC475375
0.567	Remote Similarity	NPC478723
0.5644	Remote Similarity	NPC269318
0.5567	Remote Similarity	NPC479061
0.5543	Remote Similarity	NPC477328
0.551	Remote Similarity	NPC479060
0.5437	Remote Similarity	NPC478728
0.5435	Remote Similarity	NPC475425
0.5405	Remote Similarity	NPC610996
0.5392	Remote Similarity	NPC163409
0.5392	Remote Similarity	NPC475525
0.5392	Remote Similarity	NPC475540
0.5385	Remote Similarity	NPC478727
0.5361	Remote Similarity	NPC479059
0.5351	Remote Similarity	NPC610997
0.534	Remote Similarity	NPC476066
0.534	Remote Similarity	NPC477347
0.5204	Remote Similarity	NPC216883
0.52	Remote Similarity	NPC479058
0.5189	Remote Similarity	NPC477348
0.5172	Remote Similarity	NPC471026
0.51	Remote Similarity	NPC60849

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC259294 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7460
0.1-0.2	1609
0.2-0.3	79
0.3-0.4	2
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