NPASS Compound

Natural Product: NPC472574

Natural Product ID	NPC472574
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CEBQOGCIDLLPPG-LPWRDBNFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3577218
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 85 90 0 0 0 0 0 0 0 0999 V2000 0.5674 -4.2857 0.0196 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6039 -2.9471 0.6435 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5965 -2.7489 1.8981 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6493 -1.8257 -0.1719 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6769 -0.5072 0.3825 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0184 0.1287 0.1253 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0005 -0.8680 -0.1962 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0999 -1.1523 0.5963 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2019 -0.4720 1.6497 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0783 -2.1744 0.2352 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1312 -2.3681 1.1038 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1204 -3.3034 0.8745 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0572 -4.0847 -0.2776 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9966 -3.8731 -1.1296 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0114 -2.9310 -0.8866 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1006 1.1924 -0.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9621 2.1432 -0.9549 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1061 1.7113 -0.0071 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4916 0.2579 -0.1155 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7095 -0.1898 -1.5648 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8040 0.0130 0.5502 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9889 -1.3425 0.7987 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9795 -2.1088 0.1945 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7036 -1.4714 -0.6209 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 -3.5063 0.4066 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5933 -4.3245 1.2877 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9396 -5.6650 1.3839 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9249 -6.2225 0.6213 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5948 -5.4228 -0.2722 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2510 -4.1010 -0.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0842 0.9190 1.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7409 2.3407 1.4590 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3362 2.5501 -0.0217 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1029 3.8733 -0.2591 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8794 4.5217 -1.1074 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0074 4.2102 -1.8843 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7656 3.2279 -1.7035 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2207 5.1914 -2.9760 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1172 6.1953 -2.7889 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6226 5.9172 -1.4294 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0703 6.7609 -0.6835 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3552 2.5738 2.0755 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4615 1.8524 1.2788 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2902 2.0155 3.4856 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0392 4.0443 2.1627 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4942 2.4342 -2.3506 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1082 -4.1956 -0.8745 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2412 -5.0854 0.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5842 -4.4691 -0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5689 -0.6489 1.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3807 0.5438 1.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2307 -1.7798 2.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9559 -3.4772 1.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8261 -4.8121 -0.4564 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9482 -4.4793 -2.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1922 -2.7889 -1.5744 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3154 0.8381 -1.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0648 1.7540 -0.6682 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3176 3.1400 -0.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1394 -0.0639 -2.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8686 -1.3078 -1.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6844 0.1800 -1.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6281 0.2862 -0.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8254 -3.8903 1.8946 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3929 -6.2748 2.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1763 -7.2645 0.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3677 -5.8874 -0.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8151 -3.5170 -1.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5639 0.5189 2.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1815 0.8804 1.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4701 3.0767 1.7818 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1534 2.1159 -0.6160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1292 4.7162 -3.9751 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1804 5.7362 -2.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4728 7.2414 -2.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3254 6.0592 -3.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2631 2.0196 3.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3864 2.6589 4.1188 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2054 1.0087 3.4954 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7197 4.3729 1.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9804 4.6514 2.0792 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3875 4.3281 3.1657 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5543 2.2070 -2.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1941 1.9090 -3.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6169 3.5210 -2.6405 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 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 6 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 21 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 32 42 1 0 42 43 1 0 42 44 1 0 42 45 1 0 17 46 1 0 19 5 1 0 30 25 1 0 40 35 1 0 15 10 1 0 18 43 1 1 33 18 1 0 1 47 1 0 1 48 1 0 1 49 1 0 5 50 1 1 6 51 1 1 11 52 1 0 12 53 1 0 13 54 1 0 14 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 1 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 6 26 64 1 0 27 65 1 0 28 66 1 0 29 67 1 0 30 68 1 0 31 69 1 0 31 70 1 0 32 71 1 1 33 72 1 6 38 73 1 0 38 74 1 0 39 75 1 0 39 76 1 0 44 77 1 0 44 78 1 0 44 79 1 0 45 80 1 0 45 81 1 0 45 82 1 0 46 83 1 0 46 84 1 0 46 85 1 0 M END

Standard InCHIKey	CEBQOGCIDLLPPG-LPWRDBNFSA-N
Standard InCHI	InChI=1S/C35H39NO10/c1-20-18-25(43-31(40)22-12-8-6-9-13-22)30(42-21(2)37)34(5)26(44-32(41)23-14-10-7-11-15-23)19-24-29(35(20,34)46-33(24,3)4)45-36-27(38)16-17-28(36)39/h6-15,20,24-26,29-30H,16-19H2,1-5H3/t20-,24-,25+,26+,29-,30+,34-,35-/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H](OC(=O)c2ccccc2)C[C@H]([C@@]23[C@]1(C)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3ON1C(=O)CCC1=O)C(O2)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	633.26	Volume:	632.475 ? Van der Waals volume.
Dense:	1.001	LogP:	3.236 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.128 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.173 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	36.0
TPSA:	134.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	0.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.245	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.915	Fsp³:	0.514
MCE-18:	184.113 ? 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:	0.762	Fluc inhibitor:	0.025 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.341 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.014	Promiscuous compounds:	0.033

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.096	MDCK Permeability:	-4.695
Pgp-inhibitor:	0.952	Pgp-substrate:	0.001
PAMPA:	0.572 ? 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%):	0.001	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.125

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.664	MRP1:	0.999
Plasma Protein Binding (PPB):	92.653%	Volume Distribution (VD):	0.023
Fu:	7.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.972
OATP1B3 inhibitor:	0.976	BCRP inhibitor:	0.0
BSEP inhibitor:	0.979

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.222	CYP3A4-substrate:	0.041
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.982 ? 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):

5.724

Half-life (T1/2):

0.478

ADMET: Toxicity

hERG Blockers:	0.059	hERG Blockers (10um):	0.697
Human Hepatotoxicity (H-HT):	0.084	Drug-induced Liver Injury (DILI):	0.944
AMES Toxicity:	0.625	Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.157	Skin Sensitization:	0.988
Carcinogencity:	0.813	Eye Corrosion:	0.0
Eye Irritation:	0.08	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.812	Ototoxicity:	0.186
Hematotoxicity:	0.068	Drug-induced Nephrotoxicity:	0.466
Genotoxicity:	0.933	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.064	Hek293 Cytotoxicity:	0.642
BCF:	0.52 ? 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:	3.386 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.111 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.363 ? 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
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	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
Ratio IC50	6
Ki	1
Activity	1

Activity Type	# Activity
Individual protein	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	54.9	n.a.	PMID[17567069]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	33.6	n.a.	PMID[12502327]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	21.7	n.a.	PMID[22194678]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	17.3	n.a.	DOI[10.1007/s00044-013-0790-2]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	13.1	n.a.	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	6.9	n.a.	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	290.0	nM	PMID[20346682]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Activity	=	80.1	%	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC472574 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	19422
0.1-0.2	28861
0.2-0.3	1169
0.3-0.4	283
0.4-0.5	77
0.5-0.6	23
0.6-0.7	13
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	NPC473081
0.8095	Intermediate Similarity	NPC270498
0.7538	Intermediate Similarity	NPC195647
0.7538	Intermediate Similarity	NPC200592
0.7538	Intermediate Similarity	NPC610542
0.6447	Remote Similarity	NPC473613
0.6447	Remote Similarity	NPC473085
0.6447	Remote Similarity	NPC473112
0.6447	Remote Similarity	NPC607428
0.6438	Remote Similarity	NPC67777
0.6438	Remote Similarity	NPC139067
0.641	Remote Similarity	NPC88593
0.6301	Remote Similarity	NPC4341
0.6301	Remote Similarity	NPC191082
0.6203	Remote Similarity	NPC14499
0.6133	Remote Similarity	NPC473673
0.6	Remote Similarity	NPC43241
0.6	Remote Similarity	NPC177340
0.5915	Remote Similarity	NPC283375
0.5915	Remote Similarity	NPC474608
0.5897	Remote Similarity	NPC184747
0.5867	Remote Similarity	NPC479047
0.5867	Remote Similarity	NPC291638
0.5694	Remote Similarity	NPC183122
0.5658	Remote Similarity	NPC483883
0.5658	Remote Similarity	NPC151585
0.5541	Remote Similarity	NPC481047
0.5541	Remote Similarity	NPC481045
0.5526	Remote Similarity	NPC163087
0.5443	Remote Similarity	NPC479044
0.5349	Remote Similarity	NPC75600
0.5349	Remote Similarity	NPC483884
0.5128	Remote Similarity	NPC70973
0.5128	Remote Similarity	NPC473111
0.5122	Remote Similarity	NPC210591
0.5067	Remote Similarity	NPC481066
0.5063	Remote Similarity	NPC246480
0.5063	Remote Similarity	NPC48017
0.5062	Remote Similarity	NPC92293
0.506	Remote Similarity	NPC475652
0.5057	Remote Similarity	NPC56953

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4266
0.1-0.2	4763
0.2-0.3	121
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