NPASS Compound

Natural Product: NPC188865

Natural Product ID	NPC188865
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OJPNPGSTVDRSGU-RSMIBNGDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1076618
PubChem CID	46880539
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 91 95 0 0 0 0 0 0 0 0999 V2000 -3.8308 1.4385 3.3123 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4747 1.2601 1.8866 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8168 2.1418 1.0770 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7894 0.1748 1.4125 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4396 -0.0026 0.0205 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9635 0.1496 -0.1740 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4575 -0.8285 -1.1990 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1399 -0.5767 -2.5457 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9979 -0.6896 -1.4238 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7747 -1.9823 -1.6321 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2609 -3.1173 -0.8555 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1834 -3.3338 -1.4164 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8472 -2.2184 -0.7002 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3240 -2.4364 -0.6052 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8911 -3.3355 -1.6689 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1176 -1.1655 -0.5089 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3008 -1.3673 0.2947 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5627 -1.2536 -0.2029 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7063 -0.9538 -1.4284 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8008 -1.4589 0.6071 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5502 -3.1036 0.6174 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3147 -2.2452 0.6177 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9065 -2.8996 0.5720 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9651 -2.1974 1.3849 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7769 -4.3096 1.1810 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5626 -4.5926 -0.8919 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7397 -5.7454 -1.5933 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -5.7484 -2.8311 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1359 -6.9894 -0.9139 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7373 0.0711 -0.4854 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6004 1.1110 -0.8397 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7150 1.3690 -2.0565 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3348 1.8598 0.1938 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1637 2.8435 -0.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8970 3.5939 0.9221 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7954 3.3694 2.2613 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5224 4.1087 3.1949 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3720 5.0985 2.7673 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4981 5.3514 1.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7648 4.6015 0.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6472 1.4996 -0.4230 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0338 2.4124 0.3703 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3094 1.9889 1.5091 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2347 3.7951 -0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8852 4.6156 0.8704 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1615 5.9509 0.5339 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7768 6.4362 -0.6937 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1246 5.6189 -1.5889 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1373 4.3092 -1.2386 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0302 1.0408 3.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8953 2.5316 3.5550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7669 0.9104 3.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8893 0.9204 -0.4667 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -0.0868 0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3382 -0.3108 -3.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6860 -1.3959 -2.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7602 0.3453 -2.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1888 -0.1504 -2.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8460 -1.7360 -1.5072 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.2821 -2.7198 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8763 -4.0034 -1.0543 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0682 -3.2801 -2.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2491 -3.5728 -2.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8825 -2.8934 -2.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2289 -4.3358 -1.2649 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5268 -0.9429 -1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3235 -0.5001 0.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4917 -2.0728 -0.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5283 -2.0118 1.5097 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2070 -2.5290 1.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3073 -2.8184 2.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5416 -1.2933 1.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9037 -2.0225 0.8254 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2169 -5.0822 0.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2590 -4.5533 1.4153 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3298 -4.3829 2.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6706 -6.8423 0.0339 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1832 -7.5274 -0.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7868 -7.6302 -1.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1887 1.5905 1.2205 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2859 3.0859 -1.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1606 2.6194 2.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4254 3.9065 4.2626 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9550 5.6926 3.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1749 6.1380 1.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8474 4.7815 -0.5409 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2244 4.3144 1.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6723 6.5889 1.2420 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0062 7.4774 -0.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1547 6.0446 -2.5422 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6480 3.6503 -1.9217 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 7 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 14 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 14 21 1 1 13 22 1 1 22 23 1 0 23 24 1 0 23 25 1 0 12 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 9 30 1 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 6 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 16 5 1 0 40 35 1 0 49 44 1 0 13 7 1 0 23 11 1 0 1 50 1 0 1 51 1 0 1 52 1 0 5 53 1 6 6 54 1 1 8 55 1 0 8 56 1 0 8 57 1 0 9 58 1 6 10 59 1 0 10 60 1 0 11 61 1 1 12 62 1 6 15 63 1 0 15 64 1 0 15 65 1 0 16 66 1 6 20 67 1 0 20 68 1 0 20 69 1 0 21 70 1 0 24 71 1 0 24 72 1 0 24 73 1 0 25 74 1 0 25 75 1 0 25 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 33 80 1 0 34 81 1 0 36 82 1 0 37 83 1 0 38 84 1 0 39 85 1 0 40 86 1 0 45 87 1 0 46 88 1 0 47 89 1 0 48 90 1 0 49 91 1 0 M END

Standard InCHIKey	OJPNPGSTVDRSGU-RSMIBNGDSA-N
Standard InCHI	InChI=1S/C37H42O12/c1-21(38)44-29-31(48-33(42)25-16-12-9-13-17-25)35(6)27(47-28(41)19-18-24-14-10-8-11-15-24)20-26-30(45-22(2)39)37(35,49-34(26,4)5)36(7,43)32(29)46-23(3)40/h8-19,26-27,29-32,43H,20H2,1-7H3/b19-18+/t26-,27+,29+,30-,31+,32+,35-,36+,37-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H]([C@@]2(C)[C@H](C[C@@H]3[C@H]([C@@]2([C@](C)([C@H]1OC(=O)C)O)OC3(C)C)OC(=O)C)OC(=O)/C=C/c1ccccc1)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	678.27	Volume:	679.571 ? Van der Waals volume.
Dense:	0.998	LogP:	3.45 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.138 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.082 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	32.0
TPSA:	160.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.243	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.999	Fsp³:	0.486
MCE-18:	176.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.864	Fluc inhibitor:	0.792 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.45 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.156	Promiscuous compounds:	0.209

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.293	MDCK Permeability:	-4.796
Pgp-inhibitor:	1.0	Pgp-substrate:	0.06
PAMPA:	0.392 ? 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):	0.001
20% Bioavailability (F20%):	0.568	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.974
Plasma Protein Binding (PPB):	88.177%	Volume Distribution (VD):	-0.409
Fu:	13.161% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.014
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.393
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.32 ? 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):

6.494

Half-life (T1/2):

0.623

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.19
Human Hepatotoxicity (H-HT):	0.289	Drug-induced Liver Injury (DILI):	0.662
AMES Toxicity:	0.464	Rat Oral Acute Toxicity:	0.433
Maximum Recommended Daily Dose:	0.713	Skin Sensitization:	0.998
Carcinogencity:	0.321	Eye Corrosion:	0.006
Eye Irritation:	0.349	Respiratory Toxicity:	0.158
Drug-induced Neurotoxicity:	0.152	Ototoxicity:	0.24
Hematotoxicity:	0.084	Drug-induced Nephrotoxicity:	0.762
Genotoxicity:	0.899	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.058	Hek293 Cytotoxicity:	0.159
BCF:	0.686 ? 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:	3.78 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.405 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.983 ? 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
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20146433]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	fruits	n.a.	n.a.	PMID[21856049]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27541714]
NPO26437	Maytenus jelskii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26437	Maytenus jelskii	Species	Celastraceae	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	5

Activity Type	# Activity
Cell line	1
Others	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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[8411013]
NPT2	Others	Unspecified	n.a.	Activity	=	8.9	%	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	Activity	=	39.6	%	PMID[23964644]
NPT2	Others	Unspecified	n.a.	Activity	=	87.4	%	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	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 NPC188865 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	11624
0.1-0.2	34849
0.2-0.3	2672
0.3-0.4	544
0.4-0.5	121
0.5-0.6	30
0.6-0.7	9
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC483880
0.8095	Intermediate Similarity	NPC156941
0.75	Intermediate Similarity	NPC184817
0.7284	Intermediate Similarity	NPC483859
0.725	Intermediate Similarity	NPC25768
0.7073	Intermediate Similarity	NPC171525
0.6548	Remote Similarity	NPC483865
0.6506	Remote Similarity	NPC483867
0.6395	Remote Similarity	NPC127026
0.6395	Remote Similarity	NPC483890
0.6353	Remote Similarity	NPC483861
0.6341	Remote Similarity	NPC473085
0.6163	Remote Similarity	NPC125106
0.6163	Remote Similarity	NPC472573
0.6163	Remote Similarity	NPC483860
0.5952	Remote Similarity	NPC473112
0.593	Remote Similarity	NPC483878
0.5795	Remote Similarity	NPC469349
0.5765	Remote Similarity	NPC607428
0.5732	Remote Similarity	NPC158663
0.5647	Remote Similarity	NPC210591
0.5618	Remote Similarity	NPC174982
0.5581	Remote Similarity	NPC476970
0.5556	Remote Similarity	NPC152440
0.5556	Remote Similarity	NPC483882
0.5556	Remote Similarity	NPC483888
0.5506	Remote Similarity	NPC483866
0.5488	Remote Similarity	NPC70973
0.5488	Remote Similarity	NPC473111
0.5366	Remote Similarity	NPC311175
0.5361	Remote Similarity	NPC471980
0.5361	Remote Similarity	NPC483891
0.5357	Remote Similarity	NPC270590
0.5333	Remote Similarity	NPC70403
0.5333	Remote Similarity	NPC177940
0.5287	Remote Similarity	NPC214550
0.5222	Remote Similarity	NPC472571
0.5213	Remote Similarity	NPC476974
0.5169	Remote Similarity	NPC481050
0.5111	Remote Similarity	NPC29704
0.5111	Remote Similarity	NPC470157
0.5056	Remote Similarity	NPC473613
0.5056	Remote Similarity	NPC51602
0.5055	Remote Similarity	NPC470159
0.5055	Remote Similarity	NPC603877

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC188865 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4316
0.1-0.2	4730
0.2-0.3	104
0.3-0.4	0
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