NPASS Compound

Natural Product: NPC472575

Natural Product ID	NPC472575
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LMIPYGWHPWHYTN-SANLPJBXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3577219
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 82 86 0 0 0 0 0 0 0 0999 V2000 -1.3182 4.3763 -1.8414 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2490 3.5806 -0.5671 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7471 4.0092 0.4986 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6308 2.3616 -0.5623 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5063 1.5252 0.5804 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9218 1.3769 0.9331 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6086 0.2284 0.1768 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9689 0.2726 0.4292 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9177 0.5420 -0.5660 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4472 0.7430 -1.7155 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3410 0.5835 -0.2794 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8400 0.3626 0.9794 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1930 0.3988 1.2663 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0878 0.6693 0.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6176 0.8951 -1.0295 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2484 0.8505 -1.2812 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8342 -0.8915 0.7367 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4791 -0.9199 -0.0690 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2922 0.2466 0.4253 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3504 0.6085 -0.4861 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6778 0.6119 -0.1617 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9769 0.2759 1.0189 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7499 0.9732 -1.0787 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0565 0.9423 -0.6470 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1229 1.2709 -1.4570 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8819 1.6493 -2.7613 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5777 1.6853 -3.2094 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5098 1.3482 -2.3718 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2667 -0.6682 -1.5345 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1454 -2.2360 0.0747 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3657 -2.2443 -0.6323 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5463 -2.7236 -0.0850 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5276 -3.1625 1.0729 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8065 -2.7158 -0.8578 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2873 -3.2936 -0.6296 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1578 -3.1647 -0.3560 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4595 -2.2159 0.8116 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9514 -2.2912 0.9454 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9389 -2.8995 1.9357 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5097 -3.3275 -2.0022 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4987 -0.5103 2.0591 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9380 0.7368 2.3248 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2694 0.8884 2.9853 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0299 1.5338 3.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1731 5.4285 -1.5810 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4989 4.0722 -2.5050 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2802 4.1716 -2.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 2.0893 1.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4598 2.3050 0.8747 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4601 0.4333 -0.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1548 0.1508 1.7863 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5873 0.2272 2.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1418 0.6994 0.4573 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3370 1.1028 -1.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9119 1.0322 -2.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7875 -0.0649 1.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2738 0.6478 0.3758 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1547 1.2514 -1.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7026 1.9152 -3.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3702 1.9760 -4.2171 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4936 1.3791 -2.7301 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1542 -1.1087 -2.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3394 0.4121 -1.8137 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6223 -1.0765 -1.9835 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2580 -2.6070 1.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5806 -2.0568 -0.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2603 -3.7295 -0.8737 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6542 -2.4025 -1.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7082 -4.2797 -0.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8188 -2.9869 -1.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5151 -4.1704 0.0324 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4127 -2.2637 -0.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4133 -1.6441 1.6761 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1705 -3.3471 1.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0912 -3.8710 1.8645 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2795 -4.2013 -2.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2259 1.4854 3.9516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9025 1.5648 2.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7694 -0.0338 3.2721 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0427 1.1586 3.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 1.4257 4.2878 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0773 2.6332 3.0303 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 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 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 18 29 1 6 18 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 30 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 37 39 1 1 35 40 1 0 17 41 1 1 41 42 1 0 42 43 1 0 42 44 1 0 19 5 1 0 28 23 1 0 42 6 1 0 16 11 1 0 37 17 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 1 6 49 1 1 7 50 1 6 12 51 1 0 13 52 1 0 14 53 1 0 15 54 1 0 16 55 1 0 19 56 1 1 24 57 1 0 25 58 1 0 26 59 1 0 27 60 1 0 28 61 1 0 29 62 1 0 29 63 1 0 29 64 1 0 30 65 1 1 34 66 1 0 34 67 1 0 34 68 1 0 35 69 1 1 36 70 1 0 36 71 1 0 38 72 1 0 38 73 1 0 38 74 1 0 39 75 1 0 40 76 1 0 43 77 1 0 43 78 1 0 43 79 1 0 44 80 1 0 44 81 1 0 44 82 1 0 M END

Standard InCHIKey	LMIPYGWHPWHYTN-SANLPJBXSA-N
Standard InCHI	InChI=1S/C33H38O11/c1-18(34)40-24-23-26(42-28(37)20-13-9-7-10-14-20)33(44-30(23,3)4)31(5,39)17-22(36)25(41-19(2)35)32(33,6)27(24)43-29(38)21-15-11-8-12-16-21/h7-16,22-27,36,39H,17H2,1-6H3/t22-,23+,24+,25-,26+,27+,31-,32-,33-/m0/s1
SMILES	CC(=O)O[C@@H]1[C@@H]2[C@@H](OC(=O)c3ccccc3)[C@]3([C@@]([C@@H]1OC(=O)c1ccccc1)(C)[C@@H](OC(=O)C)[C@H](C[C@]3(C)O)O)OC2(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.24	Volume:	606.87 ? Van der Waals volume.
Dense:	1.006	LogP:	2.601 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.765 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.057 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.366	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.801	Fsp³:	0.515
MCE-18:	173.16 ? 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:	0.377	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.026 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.112	Promiscuous compounds:	0.269

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.428	MDCK Permeability:	-4.913
Pgp-inhibitor:	0.941	Pgp-substrate:	0.566
PAMPA:	0.968 ? 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%):	0.424	30% Bioavailability (F30%):	0.939
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082	MRP1:	0.999
Plasma Protein Binding (PPB):	80.692%	Volume Distribution (VD):	-0.246
Fu:	18.96% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.019
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.014	CYP3A4-substrate:	0.045
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.969 ? 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):

4.207

Half-life (T1/2):

1.109

ADMET: Toxicity

hERG Blockers:	0.033	hERG Blockers (10um):	0.4
Human Hepatotoxicity (H-HT):	0.093	Drug-induced Liver Injury (DILI):	0.408
AMES Toxicity:	0.464	Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.37	Skin Sensitization:	0.964
Carcinogencity:	0.427	Eye Corrosion:	0.001
Eye Irritation:	0.619	Respiratory Toxicity:	0.161
Drug-induced Neurotoxicity:	0.351	Ototoxicity:	0.389
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.347
Genotoxicity:	0.139	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.239	Hek293 Cytotoxicity:	0.295
BCF:	0.541 ? 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:	3.381 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.963 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.246 ? 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
Activity	1

Activity Type	# Activity
Individual protein	1

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	Activity	=	73.2	%	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 NPC472575 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	11271
0.1-0.2	35826
0.2-0.3	2064
0.3-0.4	540
0.4-0.5	103
0.5-0.6	33
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC200471
0.7576	Intermediate Similarity	NPC163719
0.7576	Intermediate Similarity	NPC95810
0.6986	Remote Similarity	NPC481486
0.6912	Remote Similarity	NPC483886
0.6714	Remote Similarity	NPC472572
0.6429	Remote Similarity	NPC281717
0.641	Remote Similarity	NPC301368
0.641	Remote Similarity	NPC84815
0.6216	Remote Similarity	NPC472570
0.6173	Remote Similarity	NPC253738
0.6076	Remote Similarity	NPC610927
0.6026	Remote Similarity	NPC603877
0.6	Remote Similarity	NPC57628
0.5921	Remote Similarity	NPC96903
0.5904	Remote Similarity	NPC30171
0.5875	Remote Similarity	NPC125106
0.5875	Remote Similarity	NPC472573
0.5833	Remote Similarity	NPC483862
0.5823	Remote Similarity	NPC470159
0.5811	Remote Similarity	NPC471101
0.5789	Remote Similarity	NPC472569
0.5789	Remote Similarity	NPC16912
0.5775	Remote Similarity	NPC66761
0.5775	Remote Similarity	NPC483843
0.5775	Remote Similarity	NPC476094
0.5753	Remote Similarity	NPC87448
0.5616	Remote Similarity	NPC90614
0.557	Remote Similarity	NPC481489
0.5556	Remote Similarity	NPC481047
0.5556	Remote Similarity	NPC481045
0.5526	Remote Similarity	NPC471104
0.55	Remote Similarity	NPC481488
0.5467	Remote Similarity	NPC291599
0.5385	Remote Similarity	NPC11685
0.5342	Remote Similarity	NPC475429
0.5342	Remote Similarity	NPC211137
0.527	Remote Similarity	NPC118080
0.52	Remote Similarity	NPC241951
0.5195	Remote Similarity	NPC270590
0.5119	Remote Similarity	NPC611111
0.5067	Remote Similarity	NPC607964
0.5065	Remote Similarity	NPC472576
0.5065	Remote Similarity	NPC90257
0.5065	Remote Similarity	NPC69357
0.506	Remote Similarity	NPC212768
0.506	Remote Similarity	NPC4421

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3623
0.1-0.2	5350
0.2-0.3	175
0.3-0.4	2
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