NPASS Compound

Natural Product: NPC185466

Natural Product ID	NPC185466
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mirabilin Lactone
IUPAC Name	n.a.
Synonyms	Mirabilin Lactone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505904
PubChem CID	44566611
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 177187 0 0 0 0 0 0 0 0999 V2000 0.7093 -5.0345 -1.3055 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1601 -4.9730 -2.5855 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9194 -3.9173 -2.6802 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3700 -2.6799 -2.3711 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3729 -1.7340 -2.2314 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9207 -0.5714 -1.6299 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5413 -0.3536 -0.4394 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6456 -0.0451 0.7350 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3938 -0.3238 1.8740 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7391 -0.3646 1.7282 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.6825 0.8037 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4952 0.8622 -0.4674 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2438 0.8684 -1.6203 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 0.5192 0.5489 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5423 1.3961 1.0276 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5981 0.9019 1.7166 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6237 0.3230 1.0433 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9897 -1.0041 1.7131 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0247 -1.5567 0.9816 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4642 -2.7883 1.4969 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1521 -3.8121 0.6439 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0724 -4.1295 -0.3137 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2068 -3.1500 -1.4362 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1822 -3.6306 -2.3192 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4152 -4.4717 0.3116 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.9084 -3.2794 1.0791 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.8648 -2.7506 2.0004 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9762 -3.4241 3.2312 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4537 -2.3044 0.2435 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.1910 -5.5066 1.2171 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2988 0.1080 -0.3886 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9526 1.4367 -1.0317 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0505 2.2525 -0.1608 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7120 3.3782 0.3264 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0455 4.5387 -0.0660 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6512 5.1686 1.1170 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7299 5.3030 1.9924 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7699 6.1646 1.3356 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2735 6.6270 -0.0025 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9189 5.4339 -0.9026 C 0 0 1 0 0 0 0 0 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0 0 0 0 0 0 0 0 0 0 0 0 6.8289 0.5884 2.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3177 -1.0538 2.5737 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7894 -1.2224 2.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2245 2.1750 1.8800 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7255 3.1247 0.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0079 2.9116 0.6723 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3198 2.5852 -1.5619 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5767 0.9681 -2.2062 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6779 1.6928 -2.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0905 -0.7921 -0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4765 -1.9394 1.5753 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7722 -1.6550 0.4393 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1866 -1.0534 3.6813 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5310 -0.7217 4.2768 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8949 -2.1737 3.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3489 1.1171 2.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0425 1.5705 3.0428 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5576 2.0759 0.8843 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9538 2.7772 1.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9889 -0.4710 -1.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5639 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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 39 42 1 0 38 43 1 0 32 44 1 0 31 45 1 0 8 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 52 54 1 0 51 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 2 0 61 62 1 0 62 63 1 1 62 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 1 69 71 1 0 71 72 1 0 69 73 1 0 73 74 2 0 73 75 1 0 75 76 1 0 65 77 1 0 57 78 1 6 50 79 1 6 5 80 1 0 80 81 1 0 81 82 1 0 82 83 1 0 81 84 1 0 80 85 1 0 82 3 1 0 12 7 1 0 33 15 1 0 40 35 1 0 52 47 1 0 62 57 1 0 66 76 1 6 27 20 1 0 58 50 1 0 67 61 1 0 72 66 1 0 1 86 1 0 2 87 1 0 2 88 1 0 3 89 1 1 5 90 1 1 7 91 1 1 8 92 1 1 10 93 1 0 10 94 1 0 11 95 1 1 12 96 1 1 13 97 1 0 15 98 1 1 17 99 1 6 18100 1 0 18101 1 0 20102 1 1 22103 1 6 23104 1 0 23105 1 0 24106 1 0 25107 1 6 26108 1 1 27109 1 1 28110 1 0 29111 1 0 30112 1 0 31113 1 1 32114 1 6 33115 1 6 35116 1 6 37117 1 0 37118 1 0 38119 1 1 39120 1 1 40121 1 6 41122 1 0 42123 1 0 43124 1 0 44125 1 0 45126 1 0 47127 1 1 48128 1 0 48129 1 0 49130 1 0 49131 1 0 51132 1 1 53133 1 0 53134 1 0 53135 1 0 54136 1 0 54137 1 0 54138 1 0 55139 1 0 55140 1 0 56141 1 0 56142 1 0 58143 1 1 59144 1 0 59145 1 0 60146 1 0 63147 1 0 63148 1 0 63149 1 0 64150 1 0 64151 1 0 65152 1 6 67153 1 6 68154 1 0 68155 1 0 70156 1 0 70157 1 0 70158 1 0 71159 1 0 71160 1 0 72161 1 0 72162 1 0 76163 1 0 76164 1 0 77165 1 0 78166 1 0 78167 1 0 78168 1 0 79169 1 0 79170 1 0 79171 1 0 80172 1 6 81173 1 6 82174 1 6 83175 1 0 84176 1 0 85177 1 0 M END

Standard InCHIKey	MMQDKDDIGRODID-SAMSJERTSA-N
Standard InCHI	InChI=1S/C58H92O27/c1-53(2)30-9-12-56(5)31(8-7-23-24-15-54(3)13-14-58(24,22-78-52(54)74)32(62)16-57(23,56)6)55(30,4)11-10-33(53)83-50-45(85-49-44(73)40(69)36(65)27(18-60)80-49)38(67)29(21-77-50)82-51-46(84-48-42(71)34(63)25(61)19-75-48)41(70)37(66)28(81-51)20-76-47-43(72)39(68)35(64)26(17-59)79-47/h7,24-51,59-73H,8-22H2,1-6H3/t24-,25-,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-,54-,55-,56+,57+,58+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](OC[C@@H]([C@@H]2O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)[C@H]([C@@H]([C@H]2O[C@@H]2OC[C@@H]([C@@H]([C@H]2O)O)O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]24[C@H]3C[C@](C)(CC4)C(=O)OC2)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1220.58	Volume:	1149.666 ? Van der Waals volume.
Dense:	1.062	LogP:	-0.717 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.255 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.184 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	61.0
TPSA:	422.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	27.0
H-Bond Donor:	15.0	Rings:	12.0
Heavy Atoms:	27.0

MedChem Properties

QED Drug-Likeness Score:	0.048	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.269	Fsp³:	0.948
MCE-18:	308.947 ? 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:	0.726	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:	0.355	Promiscuous compounds:	0.045

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.019	MDCK Permeability:	-5.045
Pgp-inhibitor:	0.0	Pgp-substrate:	0.613
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):	0.751
20% Bioavailability (F20%):	0.927	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.635	MRP1:	0.011
Plasma Protein Binding (PPB):	57.005%	Volume Distribution (VD):	-0.359
Fu:	29.295% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
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:	0.953	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.912
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):

-0.657

Half-life (T1/2):

3.977

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.892	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.215	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.937	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.98	RPMI-8226 Immunitoxicity:	0.725
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.962
BCF:	1.169 ? 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:	3.505 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.027 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.042 ? 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
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090874]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15237	Cyclamen mirabile	Species	Primulaceae	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
Activity	2
MIC	4

Activity Type	# Activity
Organism	4
Non-molecular	2

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	0.6	10'-6M	PMID[9090874]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	5.7	10'-6M	PMID[9090874]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	400.0	ug.mL-1	PMID[10560729]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	400.0	ug.mL-1	PubChem BioAssay data set
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	400.0	ug.mL-1	PMID[18990572]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	400.0	ug.mL-1	PMID[17190457]

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 NPC185466 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	23103
0.1-0.2	22301
0.2-0.3	3152
0.3-0.4	673
0.4-0.5	405
0.5-0.6	160
0.6-0.7	34
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	Natural Product ID
0.7304	Intermediate Similarity	NPC475140
0.7297	Intermediate Similarity	NPC207738
0.7217	Intermediate Similarity	NPC603137
0.7091	Intermediate Similarity	NPC471435
0.7091	Intermediate Similarity	NPC471434
0.6957	Remote Similarity	NPC610204
0.6696	Remote Similarity	NPC123796
0.6667	Remote Similarity	NPC606145
0.6667	Remote Similarity	NPC607904
0.6525	Remote Similarity	NPC473824
0.6525	Remote Similarity	NPC610461
0.6455	Remote Similarity	NPC470512
0.641	Remote Similarity	NPC609281
0.6404	Remote Similarity	NPC470514
0.6379	Remote Similarity	NPC481079
0.6379	Remote Similarity	NPC291903
0.6364	Remote Similarity	NPC609305
0.6356	Remote Similarity	NPC606553
0.6316	Remote Similarity	NPC105800
0.6303	Remote Similarity	NPC475119
0.6261	Remote Similarity	NPC470513
0.6228	Remote Similarity	NPC173859
0.6218	Remote Similarity	NPC473688
0.6218	Remote Similarity	NPC470915
0.6198	Remote Similarity	NPC151543
0.6167	Remote Similarity	NPC288205
0.6167	Remote Similarity	NPC51465
0.6106	Remote Similarity	NPC469946
0.6087	Remote Similarity	NPC488526
0.6087	Remote Similarity	NPC232237
0.6063	Remote Similarity	NPC470876
0.6034	Remote Similarity	NPC63159
0.6033	Remote Similarity	NPC172365
0.6016	Remote Similarity	NPC470911
0.6	Remote Similarity	NPC104137
0.6	Remote Similarity	NPC31838
0.6	Remote Similarity	NPC26626
0.6	Remote Similarity	NPC1046
0.6	Remote Similarity	NPC309714
0.5983	Remote Similarity	NPC297263
0.5948	Remote Similarity	NPC148603
0.5909	Remote Similarity	NPC250247
0.5882	Remote Similarity	NPC77717
0.5868	Remote Similarity	NPC138219
0.5868	Remote Similarity	NPC475234
0.5862	Remote Similarity	NPC30289
0.5852	Remote Similarity	NPC33012
0.584	Remote Similarity	NPC123199
0.582	Remote Similarity	NPC210729
0.582	Remote Similarity	NPC82931
0.5812	Remote Similarity	NPC164389
0.5794	Remote Similarity	NPC283417
0.5794	Remote Similarity	NPC470517
0.5794	Remote Similarity	NPC200049
0.5778	Remote Similarity	NPC8524
0.576	Remote Similarity	NPC471384
0.5745	Remote Similarity	NPC329893
0.5726	Remote Similarity	NPC117714
0.5725	Remote Similarity	NPC136768
0.5714	Remote Similarity	NPC166422
0.5714	Remote Similarity	NPC220160
0.5714	Remote Similarity	NPC482010
0.5683	Remote Similarity	NPC475177
0.568	Remote Similarity	NPC123522
0.568	Remote Similarity	NPC79643
0.5678	Remote Similarity	NPC480475
0.5667	Remote Similarity	NPC484832
0.562	Remote Similarity	NPC37134
0.562	Remote Similarity	NPC78034
0.561	Remote Similarity	NPC481078
0.5586	Remote Similarity	NPC300655
0.5586	Remote Similarity	NPC13989
0.5586	Remote Similarity	NPC196874
0.5583	Remote Similarity	NPC222580
0.5581	Remote Similarity	NPC85154
0.5578	Remote Similarity	NPC478559
0.5578	Remote Similarity	NPC478560
0.5564	Remote Similarity	NPC309223
0.5538	Remote Similarity	NPC57484
0.5537	Remote Similarity	NPC64715
0.553	Remote Similarity	NPC43550
0.5526	Remote Similarity	NPC48499
0.552	Remote Similarity	NPC51579
0.5515	Remote Similarity	NPC102505
0.5515	Remote Similarity	NPC488514
0.5508	Remote Similarity	NPC112352
0.5503	Remote Similarity	NPC488619
0.55	Remote Similarity	NPC470515
0.5496	Remote Similarity	NPC265841
0.5496	Remote Similarity	NPC488308
0.5496	Remote Similarity	NPC286457
0.5492	Remote Similarity	NPC470914
0.5487	Remote Similarity	NPC90856
0.5469	Remote Similarity	NPC135904
0.5462	Remote Similarity	NPC4749
0.5461	Remote Similarity	NPC489208
0.5455	Remote Similarity	NPC271610
0.5455	Remote Similarity	NPC312650
0.5455	Remote Similarity	NPC484831
0.5455	Remote Similarity	NPC257468
0.5447	Remote Similarity	NPC301449
0.5447	Remote Similarity	NPC601290
0.544	Remote Similarity	NPC471375
0.5436	Remote Similarity	NPC222951
0.5424	Remote Similarity	NPC213674
0.5417	Remote Similarity	NPC305267
0.5403	Remote Similarity	NPC488564
0.54	Remote Similarity	NPC23020
0.5391	Remote Similarity	NPC243680
0.5379	Remote Similarity	NPC13998
0.5362	Remote Similarity	NPC489209
0.536	Remote Similarity	NPC475630
0.536	Remote Similarity	NPC273189
0.5357	Remote Similarity	NPC128925
0.5349	Remote Similarity	NPC262567
0.5347	Remote Similarity	NPC484830
0.5339	Remote Similarity	NPC295371
0.5339	Remote Similarity	NPC488561
0.5338	Remote Similarity	NPC41061
0.5338	Remote Similarity	NPC227551
0.5328	Remote Similarity	NPC488517
0.5308	Remote Similarity	NPC470218
0.5294	Remote Similarity	NPC263756
0.5294	Remote Similarity	NPC70809
0.5294	Remote Similarity	NPC76497
0.5294	Remote Similarity	NPC80843
0.5285	Remote Similarity	NPC253611
0.5285	Remote Similarity	NPC488782
0.5285	Remote Similarity	NPC302887
0.5285	Remote Similarity	NPC488515
0.528	Remote Similarity	NPC160452
0.528	Remote Similarity	NPC470516
0.528	Remote Similarity	NPC69811
0.5271	Remote Similarity	NPC284449
0.5271	Remote Similarity	NPC205129
0.5271	Remote Similarity	NPC323341
0.5263	Remote Similarity	NPC106701
0.5259	Remote Similarity	NPC236638
0.5259	Remote Similarity	NPC294453
0.5259	Remote Similarity	NPC305981
0.5259	Remote Similarity	NPC481081
0.5255	Remote Similarity	NPC488309
0.5254	Remote Similarity	NPC473373
0.5254	Remote Similarity	NPC480420
0.5254	Remote Similarity	NPC18724
0.5234	Remote Similarity	NPC60557
0.5234	Remote Similarity	NPC67857
0.5232	Remote Similarity	NPC488618
0.5229	Remote Similarity	NPC113620
0.5227	Remote Similarity	NPC481080
0.5221	Remote Similarity	NPC261506
0.5221	Remote Similarity	NPC302543
0.5221	Remote Similarity	NPC4328
0.5203	Remote Similarity	NPC233223
0.5203	Remote Similarity	NPC183816
0.5203	Remote Similarity	NPC43589
0.5203	Remote Similarity	NPC220838
0.52	Remote Similarity	NPC471373
0.52	Remote Similarity	NPC40716
0.5197	Remote Similarity	NPC11242
0.5197	Remote Similarity	NPC475444
0.5197	Remote Similarity	NPC473679
0.5191	Remote Similarity	NPC471425
0.5191	Remote Similarity	NPC191827
0.5191	Remote Similarity	NPC602995
0.5188	Remote Similarity	NPC231566
0.5188	Remote Similarity	NPC21691
0.5172	Remote Similarity	NPC78046
0.5169	Remote Similarity	NPC139894
0.5167	Remote Similarity	NPC158051
0.5164	Remote Similarity	NPC2370
0.5161	Remote Similarity	NPC100612
0.5159	Remote Similarity	NPC295823
0.5159	Remote Similarity	NPC174720
0.5159	Remote Similarity	NPC475467
0.5159	Remote Similarity	NPC319719
0.5156	Remote Similarity	NPC209798
0.5152	Remote Similarity	NPC189575
0.5149	Remote Similarity	NPC22709
0.5149	Remote Similarity	NPC110633
0.5145	Remote Similarity	NPC224381
0.5135	Remote Similarity	NPC329878
0.5135	Remote Similarity	NPC484829
0.5128	Remote Similarity	NPC322904
0.5128	Remote Similarity	NPC488620
0.5126	Remote Similarity	NPC127056
0.512	Remote Similarity	NPC267238
0.512	Remote Similarity	NPC207693
0.5118	Remote Similarity	NPC187290
0.5116	Remote Similarity	NPC475287
0.5116	Remote Similarity	NPC200788
0.5115	Remote Similarity	NPC219180
0.5113	Remote Similarity	NPC471429
0.5111	Remote Similarity	NPC471427
0.5086	Remote Similarity	NPC204458
0.5083	Remote Similarity	NPC224003
0.5083	Remote Similarity	NPC488516
0.5082	Remote Similarity	NPC160415
0.5082	Remote Similarity	NPC323231

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC185466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7423
0.1-0.2	1670
0.2-0.3	51
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