NPASS Compound

Natural Product: NPC200154

Natural Product ID	NPC200154
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MATMMZLIQOKUNK-QUOFPCSNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL445186
PubChem CID	24879539
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic 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 87 90 0 0 0 0 0 0 0 0999 V2000 -0.1432 -1.6022 0.7992 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0351 -1.0236 -0.5411 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5324 0.0757 -1.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3543 1.1453 -0.4197 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5842 0.7624 0.3022 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4224 1.1366 1.7694 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6417 -0.0048 2.7086 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0564 1.7717 1.9185 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4849 1.9432 0.5691 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2352 3.3803 0.1863 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3270 3.3970 -0.1126 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9379 3.6489 1.2047 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3457 1.9777 -0.6155 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4392 1.3624 -1.2908 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3718 0.4364 -0.6362 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1710 1.1593 0.4871 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4568 0.0759 -1.6663 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9222 -0.8177 -0.0230 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2747 -1.9019 -0.7490 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9847 -1.7652 -1.4399 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3954 -3.0320 -1.6432 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0459 -3.4736 -2.9095 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2459 -2.7521 -3.9193 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5741 -4.8040 -3.1331 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1776 -1.3989 0.4469 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4913 -1.5954 1.7529 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6445 -1.2560 2.6362 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7662 -2.1849 2.2340 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2680 2.3978 -1.8387 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7874 1.3545 0.5043 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5155 4.2928 1.2012 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3852 5.3480 0.9663 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9222 5.4831 -0.1622 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6708 6.3107 2.0629 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0224 -0.5479 0.1093 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2866 -0.8231 -0.3954 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0318 0.1822 -0.6753 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8174 -2.1241 -0.6252 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0817 -2.2962 -1.1270 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6092 -3.5690 -1.3554 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8596 -4.6865 -1.0773 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5921 -4.5287 -0.5745 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0863 -3.2534 -0.3546 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1463 -0.9177 1.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0695 -2.2372 0.9277 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6685 -2.3380 1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3525 0.2325 -2.1331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6188 1.9349 -1.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4475 1.4323 -0.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1562 1.9385 2.0847 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7411 -0.9844 2.1986 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7559 -0.1351 3.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5175 0.1479 3.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1277 2.7990 2.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4303 1.1994 2.6343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7581 3.5985 -0.7492 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4437 4.1713 -0.8565 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4329 4.5509 1.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0121 3.8869 1.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6798 2.8138 1.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4851 2.0536 -1.3861 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1319 0.8401 -2.2637 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0630 0.5263 0.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 1.1997 1.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5070 2.1285 0.1047 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0267 0.0074 -2.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2570 0.8431 -1.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9482 -0.8877 -1.3731 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4113 -0.6215 0.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0250 -2.2359 -1.5494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2457 -2.8247 -0.0948 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0785 -1.2894 -2.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2621 -5.0558 -2.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1920 -4.7664 -4.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1869 -5.6079 -3.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6898 -3.2721 2.4364 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0518 -1.6521 3.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6022 -1.9644 1.5083 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8343 2.0315 -2.5356 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7753 6.3860 2.1417 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2068 7.2803 1.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2607 5.9849 3.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7055 -1.4227 -1.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6027 -3.7087 -1.7496 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2595 -5.7011 -1.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0161 -5.4170 -0.3616 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0907 -3.1483 0.0397 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 9 8 1 1 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 18 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 14 29 1 0 13 30 1 0 10 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 5 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 20 2 1 0 43 38 1 0 9 4 1 0 30 9 1 0 1 44 1 0 1 45 1 0 1 46 1 0 3 47 1 0 4 48 1 6 5 49 1 6 6 50 1 1 7 51 1 0 7 52 1 0 7 53 1 0 8 54 1 0 8 55 1 0 10 56 1 6 11 57 1 6 12 58 1 0 12 59 1 0 12 60 1 0 13 61 1 6 14 62 1 6 16 63 1 0 16 64 1 0 16 65 1 0 17 66 1 0 17 67 1 0 17 68 1 0 18 69 1 1 19 70 1 0 19 71 1 0 20 72 1 6 24 73 1 0 24 74 1 0 24 75 1 0 28 76 1 0 28 77 1 0 28 78 1 0 29 79 1 0 34 80 1 0 34 81 1 0 34 82 1 0 39 83 1 0 40 84 1 0 41 85 1 0 42 86 1 0 43 87 1 0 M END

Standard InCHIKey	MATMMZLIQOKUNK-QUOFPCSNSA-N
Standard InCHI	InChI=1S/C33H44O10/c1-17-14-24-27(42-31(38)23-12-10-9-11-13-23)18(2)16-33(24)30(41-22(6)36)19(3)28(43-33)29(37)32(7,8)26(40-21(5)35)15-25(17)39-20(4)34/h9-14,18-19,24-30,37H,15-16H2,1-8H3/b17-14+/t18-,19-,24-,25+,26+,27-,28-,29+,30-,33+/m0/s1
SMILES	C/C/1=C[C@H]2[C@H]([C@@H](C)C[C@@]32[C@H]([C@@H](C)[C@@H]([C@H](C(C)(C)[C@@H](C[C@H]1OC(=O)C)OC(=O)C)O)O3)OC(=O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	600.29	Volume:	611.909 ? Van der Waals volume.
Dense:	0.981	LogP:	2.73 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.941 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.957 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	28.0
TPSA:	134.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.298	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.594	Fsp³:	0.636
MCE-18:	147.889 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.853	Fluc inhibitor:	0.067 ? 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:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.109	Promiscuous compounds:	0.356

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.194	MDCK Permeability:	-4.867
Pgp-inhibitor:	1.0	Pgp-substrate:	0.895
PAMPA:	0.615 ? 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):	0.0
20% Bioavailability (F20%):	0.362	30% Bioavailability (F30%):	0.884
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.999
Plasma Protein Binding (PPB):	79.564%	Volume Distribution (VD):	-0.429
Fu:	11.77% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.019
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.024	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.978 ? 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):

6.429

Half-life (T1/2):

0.52

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.276
Human Hepatotoxicity (H-HT):	0.125	Drug-induced Liver Injury (DILI):	0.845
AMES Toxicity:	0.774	Rat Oral Acute Toxicity:	0.375
Maximum Recommended Daily Dose:	0.151	Skin Sensitization:	0.996
Carcinogencity:	0.294	Eye Corrosion:	0.002
Eye Irritation:	0.063	Respiratory Toxicity:	0.045
Drug-induced Neurotoxicity:	0.169	Ototoxicity:	0.35
Hematotoxicity:	0.59	Drug-induced Nephrotoxicity:	0.454
Genotoxicity:	0.791	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.801	Hek293 Cytotoxicity:	0.209
BCF:	0.551 ? 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:	3.518 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.534 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.806 ? 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
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18321057]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19099222]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724086]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550154]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	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
Inhibition	4
IC50	2
Activity	2

Activity Type	# Activity
Individual protein	4
Cell line	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2854	Individual protein	Voltage-gated potassium channel subunit Kv1.3	Homo sapiens	Inhibition	=	96.16	%	PMID[35245067]
NPT2854	Individual protein	Voltage-gated potassium channel subunit Kv1.3	Homo sapiens	Inhibition	=	20.98	%	PMID[35245067]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[12828470]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[8410974]
NPT71	Cell line	HEK293	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35245067]

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 NPC200154 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	10358
0.1-0.2	36136
0.2-0.3	2765
0.3-0.4	554
0.4-0.5	26
0.5-0.6	14
0.6-0.7	4
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
0.7273	Intermediate Similarity	NPC475508
0.6875	Remote Similarity	NPC605737
0.6795	Remote Similarity	NPC604501
0.6265	Remote Similarity	NPC601593
0.6145	Remote Similarity	NPC604735
0.5854	Remote Similarity	NPC153617
0.5542	Remote Similarity	NPC482320
0.5465	Remote Similarity	NPC472248
0.5349	Remote Similarity	NPC209778
0.5349	Remote Similarity	NPC168369
0.5287	Remote Similarity	NPC600781
0.5287	Remote Similarity	NPC601581
0.5287	Remote Similarity	NPC604953
0.5287	Remote Similarity	NPC605971
0.5287	Remote Similarity	NPC611288
0.5269	Remote Similarity	NPC608808
0.5227	Remote Similarity	NPC242355
0.5172	Remote Similarity	NPC482360
0.5056	Remote Similarity	NPC473301

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC200154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4005
0.1-0.2	5025
0.2-0.3	119
0.3-0.4	1
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