NPASS Compound

Natural Product: NPC282239

Natural Product ID	NPC282239
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YBVNNKHLQUZXTL-DDEUFHSZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL187679
PubChem CID	14240926
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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 2D 86 90 0 0 0 0 0 0 0 0999 V2000 7.1443 -0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6443 -0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2309 -1.5274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8943 1.2135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 3.8116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3557 2.5126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5048 1.5484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3943 -1.2135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 -1.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 -2.6836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6443 -0.0855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 0.8787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2029 0.3656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2814 -1.1323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3520 1.3298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7615 0.8168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9106 1.7810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6501 3.2582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2406 3.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0915 2.8070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3442 -2.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 -0.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0323 0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3907 1.0037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8173 0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1291 -0.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9320 1.5439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5048 3.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6338 5.2888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7829 6.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2445 5.9156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5224 7.7302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7934 3.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2029 2.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1265 1.7818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3520 3.9279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7615 3.4149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9106 4.3790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6501 5.8563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2406 6.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0915 5.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6331 -0.2684 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1443 -1.5855 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5073 1.3699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9320 2.6139 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9320 -0.1868 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1116 2.2009 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3038 4.3246 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0152 4.3246 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6548 5.2888 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7628 0.7315 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6018 2.5714 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 0.2002 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6004 -0.7041 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0283 -2.5730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5259 -1.2991 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2001 -0.6177 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3201 1.2679 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9081 4.0751 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9801 5.2484 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 3.9219 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6560 -3.6844 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8384 -2.0865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0741 -2.7056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0159 -0.4364 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8615 -2.0548 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5503 0.9066 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7707 2.7875 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3416 1.0310 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3946 2.9443 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9663 3.1394 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2619 9.2074 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9996 7.9907 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0452 7.4697 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0220 1.9377 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3721 4.0417 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7992 6.8204 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9801 7.8465 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7550 6.0861 0.0000 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 6 5 1 6 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 14 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 13 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 10 35 1 1 8 36 1 0 36 37 1 0 37 38 2 0 37 39 1 0 7 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 17 6 1 0 26 21 1 0 48 43 1 0 12 6 1 0 12 30 1 1 1 49 1 0 1 50 1 0 1 51 1 0 5 52 1 0 5 53 1 0 7 54 1 1 8 55 1 1 9 56 1 0 9 57 1 0 11 58 1 0 11 59 1 0 11 60 1 0 13 61 1 1 14 62 1 6 17 63 1 1 22 64 1 0 23 65 1 0 24 66 1 0 25 67 1 0 26 68 1 0 28 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 29 74 1 0 34 75 1 0 34 76 1 0 34 77 1 0 35 78 1 0 39 79 1 0 39 80 1 0 39 81 1 0 44 82 1 0 45 83 1 0 46 84 1 0 47 85 1 0 48 86 1 0 M END

Standard InCHIKey	YBVNNKHLQUZXTL-DDEUFHSZSA-N
Standard InCHI	InChI=1S/C35H38O13/c1-19(36)43-18-34-27(46-30(40)22-13-9-7-10-14-22)24(44-20(2)37)17-33(6,42)35(34)28(45-21(3)38)25(32(4,5)48-35)26(39)29(34)47-31(41)23-15-11-8-12-16-23/h7-16,24-25,27-29,42H,17-18H2,1-6H3/t24-,25+,27-,28+,29+,33-,34-,35-/m0/s1
SMILES	CC(=O)OC[C@]12[C@H]([C@H](C[C@@](C)([C@]32[C@@H]([C@@H](C(=O)[C@H]1OC(=O)c1ccccc1)C(C)(C)O3)OC(=O)C)O)OC(=O)C)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	666.23	Volume:	653.769 ? Van der Waals volume.
Dense:	1.019	LogP:	2.911 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.971 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.709 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	32.0
TPSA:	178.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.322	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.909	Fsp³:	0.486
MCE-18:	175.385 ? 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:	0.138	Fluc inhibitor:	0.018 ? 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:	0.352 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.086	Promiscuous compounds:	0.122

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.478	MDCK Permeability:	-4.794
Pgp-inhibitor:	0.864	Pgp-substrate:	0.042
PAMPA:	0.274 ? 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%):	0.003	30% Bioavailability (F30%):	0.018
50% Bioavailability (F50%):	0.652

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.524	MRP1:	0.999
Plasma Protein Binding (PPB):	81.856%	Volume Distribution (VD):	-0.241
Fu:	19.398% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.962	BCRP inhibitor:	0.0
BSEP inhibitor:	0.896

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.351
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.912	CYP3A4-substrate:	0.079
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

1.401

Half-life (T1/2):

1.324

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.242
Human Hepatotoxicity (H-HT):	0.05	Drug-induced Liver Injury (DILI):	0.98
AMES Toxicity:	0.886	Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.416	Skin Sensitization:	1.0
Carcinogencity:	0.898	Eye Corrosion:	0.0
Eye Irritation:	0.555	Respiratory Toxicity:	0.019
Drug-induced Neurotoxicity:	0.773	Ototoxicity:	0.109
Hematotoxicity:	0.058	Drug-induced Nephrotoxicity:	0.793
Genotoxicity:	0.861	RPMI-8226 Immunitoxicity:	0.173
A549 Cytotoxicity:	0.528	Hek293 Cytotoxicity:	0.727
BCF:	0.679 ? 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:	3.526 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.907 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.496 ? 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
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Ki	1
Activity	5

Activity Type	# Activity
Cell line	2
Others	4

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
NPT886	Cell line	NIH3T3	Mus musculus	Ki	=	3009.0	nM	PMID[24033131]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[18183025]
NPT2	Others	Unspecified	n.a.	Activity	=	10.0	%	PMID[23013292]
NPT2	Others	Unspecified	n.a.	Activity	=	49.2	%	PMID[19738013]
NPT2	Others	Unspecified	n.a.	Activity	=	80.0	%	PMID[17711348]
NPT2	Others	Unspecified	n.a.	Activity	=	98.4	%	PubChem BioAssay data set

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 NPC282239 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	12673
0.1-0.2	34739
0.2-0.3	1793
0.3-0.4	504
0.4-0.5	105
0.5-0.6	24
0.6-0.7	14
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC471102
0.7162	Intermediate Similarity	NPC106895
0.7027	Intermediate Similarity	NPC11685
0.7027	Intermediate Similarity	NPC16912
0.6986	Remote Similarity	NPC254558
0.6842	Remote Similarity	NPC51602
0.68	Remote Similarity	NPC472570
0.6711	Remote Similarity	NPC97667
0.6579	Remote Similarity	NPC472569
0.6538	Remote Similarity	NPC481489
0.6533	Remote Similarity	NPC471107
0.6533	Remote Similarity	NPC471100
0.6533	Remote Similarity	NPC605884
0.6494	Remote Similarity	NPC95265
0.641	Remote Similarity	NPC472568
0.6329	Remote Similarity	NPC479042
0.6282	Remote Similarity	NPC70716
0.625	Remote Similarity	NPC481488
0.5974	Remote Similarity	NPC483842
0.5952	Remote Similarity	NPC610134
0.5949	Remote Similarity	NPC57628
0.5921	Remote Similarity	NPC281717
0.5795	Remote Similarity	NPC479045
0.5696	Remote Similarity	NPC471104
0.5696	Remote Similarity	NPC171207
0.5625	Remote Similarity	NPC471103
0.5618	Remote Similarity	NPC294512
0.561	Remote Similarity	NPC481490
0.557	Remote Similarity	NPC471101
0.5556	Remote Similarity	NPC483868
0.5513	Remote Similarity	NPC483886
0.5476	Remote Similarity	NPC481486
0.5316	Remote Similarity	NPC473060
0.5294	Remote Similarity	NPC481487
0.5275	Remote Similarity	NPC176413
0.5275	Remote Similarity	NPC483885
0.5233	Remote Similarity	NPC488917
0.5185	Remote Similarity	NPC148062
0.5181	Remote Similarity	NPC479043
0.5125	Remote Similarity	NPC51314
0.5119	Remote Similarity	NPC96903
0.5062	Remote Similarity	NPC147880

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3569
0.1-0.2	5394
0.2-0.3	185
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