NPASS Compound

Natural Product: NPC473085

Natural Product ID	NPC473085
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MDCKQLXQBJQOMX-LCEQPYDFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3609592
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 84 88 0 0 0 0 0 0 0 0999 V2000 1.8315 -6.9357 1.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0134 -5.6915 1.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1440 -5.5458 1.9448 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1567 -4.7057 0.1064 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3630 -3.5186 0.0860 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2965 -3.5280 -1.3082 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1499 -2.2995 -1.5279 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1332 -1.4201 -0.3264 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2564 -1.1009 0.1794 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1695 -2.2889 -0.0770 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5268 -2.2267 -1.4361 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9816 -3.2585 -2.1196 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8313 -4.4832 -2.2524 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6290 -2.7751 -3.5138 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4398 -2.2165 0.6784 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3429 -2.7675 2.0848 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0305 -0.8515 0.6221 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3983 0.1481 -0.2654 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9368 0.0051 -0.5746 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2609 1.2402 -0.5660 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2678 1.8184 -1.7124 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1203 1.1770 -2.7897 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9779 3.1094 -1.7651 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6213 1.4343 0.3380 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3865 2.3934 -0.2472 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9097 2.1328 -1.3555 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5997 3.6794 0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3762 4.6124 -0.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5681 5.8302 0.3660 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9973 6.1183 1.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2210 5.1512 2.1969 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0211 3.9330 1.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0557 -0.8109 1.6422 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8059 -0.1919 -0.4712 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9339 0.1265 0.2751 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2958 -0.7756 1.0913 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6764 1.3738 0.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7415 1.6339 0.9003 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5237 2.8614 0.8387 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2394 3.8997 0.0014 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0617 5.0159 0.0359 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1393 5.1072 0.8760 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4205 4.0503 1.7214 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6139 2.9594 1.6854 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2664 -7.0442 2.1029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1287 -7.8100 0.9692 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5735 -6.9540 0.2831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3575 -3.4911 0.8986 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7672 -4.4728 -1.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9007 -1.7347 -2.4239 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2005 -2.6698 -1.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6670 -2.0381 0.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1666 -5.3800 -2.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2144 -4.5906 -3.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7139 -4.5145 -1.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3763 -3.1157 -3.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7633 -1.6806 -3.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3424 -3.2318 -4.2532 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1406 -2.9314 0.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8173 -2.0203 2.7677 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9224 -3.7032 2.2366 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3003 -3.0104 2.3732 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1163 -0.9368 0.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2087 -0.4464 1.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9801 0.2127 -1.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8968 -0.3426 -1.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2474 3.8600 -2.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3140 3.3539 -0.7332 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8415 2.9924 -2.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8315 4.3873 -1.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1870 6.5716 -0.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1334 7.0679 2.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7534 5.3481 3.1712 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3959 3.1877 2.1063 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5702 0.1100 1.6909 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6278 -1.6243 2.0257 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9192 -0.6495 2.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3610 2.1233 -0.5272 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0262 0.8433 1.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3881 3.8441 -0.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8493 5.8491 -0.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8038 5.9645 0.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2759 4.1201 2.3902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8689 2.1374 2.3731 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 1 0 9 10 1 0 10 11 1 6 11 12 1 0 12 13 1 0 12 14 1 0 10 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 18 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 9 33 1 1 8 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 10 5 1 0 32 27 1 0 44 39 1 0 12 6 1 0 19 9 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 1 6 49 1 6 7 50 1 0 7 51 1 0 8 52 1 1 13 53 1 0 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 14 58 1 0 15 59 1 6 16 60 1 0 16 61 1 0 16 62 1 0 17 63 1 0 17 64 1 0 18 65 1 6 19 66 1 6 23 67 1 0 23 68 1 0 23 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 31 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 37 78 1 0 38 79 1 0 40 80 1 0 41 81 1 0 42 82 1 0 43 83 1 0 44 84 1 0 M END

Standard InCHIKey	MDCKQLXQBJQOMX-LCEQPYDFSA-N
Standard InCHI	InChI=1S/C35H40O9/c1-21-19-27(42-32(39)25-15-11-8-12-16-25)31(41-23(3)37)34(6)28(43-29(38)18-17-24-13-9-7-10-14-24)20-26-30(40-22(2)36)35(21,34)44-33(26,4)5/h7-18,21,26-28,30-31H,19-20H2,1-6H3/b18-17+/t21-,26-,27+,28+,30-,31+,34-,35-/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]2C[C@@H]([C@]3([C@@]1(OC2(C)C)[C@H](C)C[C@@H]([C@@H]3OC(=O)C)OC(=O)c1ccccc1)C)OC(=O)/C=C/c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	604.27	Volume:	621.245 ? Van der Waals volume.
Dense:	0.973	LogP:	4.262 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.62 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.718 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	31.0
TPSA:	114.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.236	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.749	Fsp³:	0.486
MCE-18:	159.231 ? 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:	0.924	Fluc inhibitor:	0.739 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.027 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.376 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.259	Promiscuous compounds:	0.092

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.084	MDCK Permeability:	-4.725
Pgp-inhibitor:	1.0	Pgp-substrate:	0.105
PAMPA:	0.137 ? 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%):	0.418	30% Bioavailability (F30%):	0.896
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194	MRP1:	0.988
Plasma Protein Binding (PPB):	95.79%	Volume Distribution (VD):	-0.263
Fu:	3.943% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.934	BCRP inhibitor:	0.017
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.625
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.544
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.868 ? 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):

6.857

Half-life (T1/2):

0.552

ADMET: Toxicity

hERG Blockers:	0.127	hERG Blockers (10um):	0.656
Human Hepatotoxicity (H-HT):	0.362	Drug-induced Liver Injury (DILI):	0.837
AMES Toxicity:	0.408	Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.543	Skin Sensitization:	0.996
Carcinogencity:	0.213	Eye Corrosion:	0.002
Eye Irritation:	0.212	Respiratory Toxicity:	0.076
Drug-induced Neurotoxicity:	0.571	Ototoxicity:	0.328
Hematotoxicity:	0.087	Drug-induced Nephrotoxicity:	0.77
Genotoxicity:	0.305	RPMI-8226 Immunitoxicity:	0.066
A549 Cytotoxicity:	0.13	Hek293 Cytotoxicity:	0.25
BCF:	1.005 ? 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:	4.141 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.709 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.386 ? 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
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	seeds	Jilin, China	n.a.	PMID[26295746]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11250	Celastrus flagellaris	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11250	Celastrus flagellaris	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	2

Activity Type	# Activity
Cell line	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
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	79.6	%	DOI[10.6019/CHEMBL1201861]
NPT519	Cell line	SH-SY5Y	Homo sapiens	Activity	=	86.2	%	DrugMatrix in vivo data: Biochemistry

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 NPC473085 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	15256
0.1-0.2	31895
0.2-0.3	2118
0.3-0.4	420
0.4-0.5	101
0.5-0.6	37
0.6-0.7	14
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8824	High Similarity	NPC473112
0.8551	High Similarity	NPC607428
0.8333	Intermediate Similarity	NPC70973
0.8333	Intermediate Similarity	NPC473111
0.8028	Intermediate Similarity	NPC473613
0.7727	Intermediate Similarity	NPC473081
0.7273	Intermediate Similarity	NPC483865
0.7206	Intermediate Similarity	NPC195647
0.7206	Intermediate Similarity	NPC270498
0.6974	Remote Similarity	NPC481050
0.6933	Remote Similarity	NPC210591
0.6933	Remote Similarity	NPC214550
0.6753	Remote Similarity	NPC609221
0.6714	Remote Similarity	NPC200592
0.6714	Remote Similarity	NPC610542
0.6667	Remote Similarity	NPC311175
0.65	Remote Similarity	NPC605086
0.6447	Remote Similarity	NPC472574
0.64	Remote Similarity	NPC139067
0.6341	Remote Similarity	NPC188865
0.6341	Remote Similarity	NPC184817
0.6267	Remote Similarity	NPC4341
0.6076	Remote Similarity	NPC184747
0.5974	Remote Similarity	NPC67777
0.5974	Remote Similarity	NPC43241
0.5904	Remote Similarity	NPC473109
0.5844	Remote Similarity	NPC479047
0.5844	Remote Similarity	NPC191082
0.5844	Remote Similarity	NPC291638
0.5783	Remote Similarity	NPC88593
0.5783	Remote Similarity	NPC483878
0.5765	Remote Similarity	NPC488916
0.5696	Remote Similarity	NPC473673
0.5676	Remote Similarity	NPC474608
0.5625	Remote Similarity	NPC479044
0.561	Remote Similarity	NPC475652
0.5595	Remote Similarity	NPC14499
0.5584	Remote Similarity	NPC37641
0.5584	Remote Similarity	NPC114927
0.557	Remote Similarity	NPC177340
0.5532	Remote Similarity	NPC483880
0.5532	Remote Similarity	NPC156941
0.5526	Remote Similarity	NPC481047
0.5526	Remote Similarity	NPC481045
0.5467	Remote Similarity	NPC183122
0.5443	Remote Similarity	NPC483883
0.5443	Remote Similarity	NPC151585
0.5412	Remote Similarity	NPC603877
0.5349	Remote Similarity	NPC25768
0.5349	Remote Similarity	NPC483866
0.5287	Remote Similarity	NPC125106
0.5287	Remote Similarity	NPC472573
0.5287	Remote Similarity	NPC174982
0.5263	Remote Similarity	NPC283375
0.5233	Remote Similarity	NPC472571
0.5227	Remote Similarity	NPC171525
0.5181	Remote Similarity	NPC609924
0.5119	Remote Similarity	NPC473082
0.5114	Remote Similarity	NPC469349
0.5062	Remote Similarity	NPC48017

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4694
0.1-0.2	4364
0.2-0.3	91
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