NPASS Compound

Natural Product: NPC56953

Natural Product ID	NPC56953
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YFRPRSJNPDRRQZ-QXIWUYFJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1829522
PubChem CID	56589608
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 3.8105 3.0091 -0.7914 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5814 2.3716 -1.3374 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0226 2.8120 -2.3470 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0733 1.2810 -0.7066 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9062 0.5496 -1.1199 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4098 -0.8145 -1.5137 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6105 -1.0429 -0.7846 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8639 -1.0542 -1.3627 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9391 -0.8509 -2.6005 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0786 -1.2960 -0.5611 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3024 -1.2969 -1.1869 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4433 -1.5196 -0.4590 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3998 -1.7451 0.8962 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1611 -1.7395 1.5018 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9947 -1.5183 0.7960 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5156 -1.9643 -1.4634 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7022 -1.8509 -0.5923 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1527 -0.4440 -0.4568 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0665 0.5320 -0.0158 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6794 0.0109 1.2156 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7107 1.7892 0.3919 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1062 2.9165 0.1721 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5086 3.7549 1.2142 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1042 3.4102 2.3719 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3236 4.9453 1.0455 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8423 5.5654 -0.0460 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5185 6.6228 0.3474 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4869 6.7524 1.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7475 5.7237 2.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0597 2.0995 -0.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9691 0.9382 -0.3945 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3338 -0.2240 0.3881 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2183 -1.3172 0.4741 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7068 -1.7694 1.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3374 -1.1691 2.7147 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6297 -2.9062 1.7840 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0885 -3.3156 3.0162 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9627 -4.3863 3.1743 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3981 -5.0776 2.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9451 -4.6764 0.8226 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0711 -3.6036 0.6819 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7364 0.4419 -1.8113 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4647 -0.0415 -1.7707 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7805 -0.4873 -2.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7168 1.6328 -2.7870 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5984 -2.6235 0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7548 -2.4859 -1.3139 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6700 2.3609 -1.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7470 3.1385 0.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9311 3.9818 -1.2848 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5068 1.1038 -2.0088 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7728 -0.6650 -2.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3272 -1.1192 -2.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3813 -1.5092 -1.0043 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3226 -1.9162 1.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1306 -1.9174 2.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0218 -1.5123 1.2623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2516 -2.3066 -2.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0954 -2.8482 -1.0510 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4932 0.7850 1.3690 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2020 -0.9217 1.0637 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0689 0.0971 2.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9066 1.7686 1.5098 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6949 5.2075 -1.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9676 7.5443 2.2041 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5285 5.5414 3.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5856 2.8268 0.4739 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8638 2.6926 -1.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0125 1.0912 -0.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1024 0.1877 1.3873 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7233 -2.7451 3.8788 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2828 -4.6513 4.1885 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0793 -5.9086 2.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2973 -5.2302 -0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7278 -3.3057 -0.3036 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1774 -1.2260 -1.6361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3113 -1.0682 -3.1682 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5891 0.1080 -2.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1242 1.3074 -3.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6794 1.9538 -3.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3832 2.4390 -2.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8324 -2.0440 1.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4009 -3.1506 0.7713 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3174 -3.4974 0.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5440 -2.5305 -2.2727 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 1 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 1 0 28 29 2 0 21 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 31 42 1 0 42 43 1 0 42 44 1 0 42 45 1 0 17 46 1 0 17 47 1 6 19 5 1 0 29 25 1 0 41 36 1 0 15 10 1 0 18 43 1 6 32 18 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 6 6 52 1 6 11 53 1 0 12 54 1 0 13 55 1 0 14 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 1 26 64 1 0 28 65 1 0 29 66 1 0 30 67 1 0 30 68 1 0 31 69 1 1 32 70 1 1 37 71 1 0 38 72 1 0 39 73 1 0 40 74 1 0 41 75 1 0 44 76 1 0 44 77 1 0 44 78 1 0 45 79 1 0 45 80 1 0 45 81 1 0 46 82 1 0 46 83 1 0 46 84 1 0 47 85 1 0 M END

Standard InCHIKey	YFRPRSJNPDRRQZ-QXIWUYFJSA-N
Standard InCHI	InChI=1S/C36H38O11/c1-21(37)43-29-26(44-30(38)22-12-8-6-9-13-22)19-34(4,41)36-28(46-31(39)23-14-10-7-11-15-23)25(33(2,3)47-36)18-27(35(29,36)5)45-32(40)24-16-17-42-20-24/h6-17,20,25-29,41H,18-19H2,1-5H3/t25-,26+,27+,28-,29+,34+,35-,36+/m1/s1
SMILES	CC(=O)O[C@H]1[C@@H](OC(=O)c2ccccc2)C[C@]([C@@]23[C@]1(C)[C@@H](OC(=O)c1cocc1)C[C@H]([C@H]3OC(=O)c1ccccc1)C(O2)(C)C)(C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	646.24	Volume:	644.928 ? Van der Waals volume.
Dense:	1.002	LogP:	4.413 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.736 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.695 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	35.0
TPSA:	147.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.276	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.837	Fsp³:	0.444
MCE-18:	185.769 ? 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:	0.543	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.087 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.108	Promiscuous compounds:	0.043

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.504	MDCK Permeability:	-4.903
Pgp-inhibitor:	0.788	Pgp-substrate:	0.298
PAMPA:	0.829 ? 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%):	0.166	30% Bioavailability (F30%):	0.271
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.581	MRP1:	1.0
Plasma Protein Binding (PPB):	93.721%	Volume Distribution (VD):	-0.317
Fu:	7.766% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.837	BCRP inhibitor:	0.019
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

3.807

Half-life (T1/2):

0.863

ADMET: Toxicity

hERG Blockers:	0.084	hERG Blockers (10um):	0.674
Human Hepatotoxicity (H-HT):	0.035	Drug-induced Liver Injury (DILI):	0.956
AMES Toxicity:	0.301	Rat Oral Acute Toxicity:	0.212
Maximum Recommended Daily Dose:	0.467	Skin Sensitization:	0.951
Carcinogencity:	0.859	Eye Corrosion:	0.0
Eye Irritation:	0.25	Respiratory Toxicity:	0.042
Drug-induced Neurotoxicity:	0.511	Ototoxicity:	0.204
Hematotoxicity:	0.008	Drug-induced Nephrotoxicity:	0.483
Genotoxicity:	0.521	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.347	Hek293 Cytotoxicity:	0.615
BCF:	0.827 ? 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:	3.806 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.139 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.825 ? 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
Inhibition	1
Ki	1
Imax	1
Ratio IC50	6
Activity	2

Activity Type	# Activity
Cell line	2
Individual protein	9

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	Inhibition	=	70.0	%	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ki	=	380.0	nM	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Imax	>	90.0	%	PMID[21856049]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	4.36	n.a.	PMID[25442304]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	10.35	n.a.	DailyMed
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	33.97	n.a.	PMID[10091690]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	11.14	n.a.	PMID[11495593]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	30.32	n.a.	PMID[17189664]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio IC50	=	125.31	n.a.	PMID[18161942]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	108.24	%	PMID[26443549]
NPT886	Cell line	NIH3T3	Mus musculus	Activity	=	98.02	%	PMID[18955526]

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 NPC56953 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	12715
0.1-0.2	34630
0.2-0.3	1977
0.3-0.4	376
0.4-0.5	100
0.5-0.6	42
0.6-0.7	11
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC176413
0.7683	Intermediate Similarity	NPC294512
0.7625	Intermediate Similarity	NPC483870
0.747	Intermediate Similarity	NPC479045
0.7262	Intermediate Similarity	NPC483885
0.6835	Remote Similarity	NPC127720
0.6707	Remote Similarity	NPC6815
0.6506	Remote Similarity	NPC479049
0.6437	Remote Similarity	NPC483869
0.6395	Remote Similarity	NPC127026
0.6395	Remote Similarity	NPC483890
0.6353	Remote Similarity	NPC610927
0.6279	Remote Similarity	NPC479041
0.622	Remote Similarity	NPC70716
0.622	Remote Similarity	NPC95265
0.6125	Remote Similarity	NPC270590
0.5977	Remote Similarity	NPC479048
0.5909	Remote Similarity	NPC301368
0.5909	Remote Similarity	NPC84815
0.5882	Remote Similarity	NPC609309
0.587	Remote Similarity	NPC483868
0.5833	Remote Similarity	NPC97667
0.5795	Remote Similarity	NPC611111
0.5769	Remote Similarity	NPC270498
0.5765	Remote Similarity	NPC36021
0.5732	Remote Similarity	NPC158663
0.5679	Remote Similarity	NPC483886
0.5667	Remote Similarity	NPC75600
0.5667	Remote Similarity	NPC483884
0.5652	Remote Similarity	NPC30171
0.557	Remote Similarity	NPC473081
0.557	Remote Similarity	NPC200592
0.557	Remote Similarity	NPC610542
0.5556	Remote Similarity	NPC610134
0.5542	Remote Similarity	NPC471101
0.5521	Remote Similarity	NPC471980
0.5517	Remote Similarity	NPC479042
0.5465	Remote Similarity	NPC481071
0.5393	Remote Similarity	NPC88593
0.5393	Remote Similarity	NPC14499
0.5385	Remote Similarity	NPC483874
0.5375	Remote Similarity	NPC195647
0.5366	Remote Similarity	NPC483879
0.5354	Remote Similarity	NPC483880
0.5354	Remote Similarity	NPC156941
0.5333	Remote Similarity	NPC481069
0.5301	Remote Similarity	NPC281717
0.5294	Remote Similarity	NPC473673
0.5238	Remote Similarity	NPC163719
0.5238	Remote Similarity	NPC95810
0.5222	Remote Similarity	NPC276735
0.5169	Remote Similarity	NPC481068
0.5158	Remote Similarity	NPC86800
0.5116	Remote Similarity	NPC66985
0.5116	Remote Similarity	NPC171207
0.5114	Remote Similarity	NPC96903
0.5057	Remote Similarity	NPC472574
0.5055	Remote Similarity	NPC608007

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC56953 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3126
0.1-0.2	5867
0.2-0.3	155
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