NPASS Compound

Natural Product: NPC57628

Natural Product ID	NPC57628
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MKTPOWHSEPOJAK-MBERIJSPSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL508131
PubChem CID	10556235
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 3D 87 91 0 0 0 0 0 0 0 0999 V2000 0.9490 3.8066 1.8309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9308 2.3768 2.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0342 1.9737 3.3787 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7960 1.3925 1.2031 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7834 0.0122 1.6020 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6245 -0.8520 0.3799 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7354 -0.6901 -0.6240 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8458 -1.6869 -0.5346 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1009 -2.2552 0.8108 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8555 -2.7645 1.4928 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6324 -2.3273 0.7639 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6089 -3.0357 -0.4558 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6856 -3.3605 -0.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5732 -2.7671 0.2941 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8622 -1.3196 0.1341 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6613 -0.4810 -0.2698 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1020 0.8540 -0.0018 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4692 1.7350 -0.9982 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3870 1.2903 -2.1790 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9316 3.0921 -0.8108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0998 3.7069 0.3998 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5490 5.0185 0.5398 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8466 5.7561 -0.5889 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6869 5.1630 -1.8229 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2431 3.8713 -1.9280 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9391 -0.9974 -0.6965 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0775 -0.3301 -0.2600 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0938 -0.0174 0.9677 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2315 0.0322 -1.0846 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6007 -2.7601 1.5006 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4797 -4.0503 2.0341 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7254 -4.3971 3.3247 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0973 -3.5274 4.1525 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5781 -5.7985 3.8504 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8541 -4.8774 -0.6507 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0355 -2.9939 -2.1624 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 -2.4723 2.9649 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8750 -4.1805 1.3841 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1783 0.6405 -0.6710 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1023 1.4724 -1.7392 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 1.0380 -2.7741 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6008 2.8274 -1.6880 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4809 3.6917 -2.7743 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9806 4.9868 -2.7213 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6110 5.4564 -1.5911 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7415 4.6183 -0.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2365 3.3362 -0.5802 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7494 3.9210 0.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1409 4.3597 2.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9571 4.2397 2.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7694 -0.1132 2.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0818 -0.1296 2.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2770 -0.8629 -1.6323 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8179 -1.2085 -0.8656 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7122 -2.5254 -1.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5869 -1.5566 1.5233 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8300 -3.0880 0.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4777 -3.3228 0.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1382 -0.9295 1.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6379 -0.5528 -1.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8698 3.1398 1.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6766 5.4892 1.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2009 6.7842 -0.5364 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9082 5.7011 -2.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1292 3.4394 -2.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9996 0.2596 -2.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6657 0.9905 -0.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.7050 -0.9903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8967 -2.0001 2.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3856 -5.9678 4.3233 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3798 -5.9773 4.5964 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7844 -6.5355 3.0239 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5892 -5.3292 -1.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -5.3493 0.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9399 -5.0466 -0.4510 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9172 -2.3710 -2.2814 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2174 -3.8965 -2.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1262 -2.5257 -2.6455 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9922 -1.9638 3.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8400 -1.9318 3.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9733 -3.4047 3.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0869 -4.4134 0.4477 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9931 3.3290 -3.6496 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8826 5.6565 -3.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9805 6.4716 -1.6033 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2383 5.0045 0.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3708 2.7142 0.3197 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 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 15 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 14 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 13 35 1 0 13 36 1 0 10 37 1 0 10 38 1 1 7 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 16 6 1 0 25 20 1 0 47 42 1 0 11 6 1 0 30 11 1 0 1 48 1 0 1 49 1 0 1 50 1 0 5 51 1 0 5 52 1 0 7 53 1 6 8 54 1 0 8 55 1 0 9 56 1 0 9 57 1 0 14 58 1 1 15 59 1 1 16 60 1 6 21 61 1 0 22 62 1 0 23 63 1 0 24 64 1 0 25 65 1 0 29 66 1 0 29 67 1 0 29 68 1 0 30 69 1 1 34 70 1 0 34 71 1 0 34 72 1 0 35 73 1 0 35 74 1 0 35 75 1 0 36 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 37 80 1 0 37 81 1 0 38 82 1 0 43 83 1 0 44 84 1 0 45 85 1 0 46 86 1 0 47 87 1 0 M END

Standard InCHIKey	MKTPOWHSEPOJAK-MBERIJSPSA-N
Standard InCHI	InChI=1S/C35H40O12/c1-20(36)42-19-34-25(45-30(39)23-13-9-7-10-14-23)17-18-33(6,41)35(34)28(44-22(3)38)26(32(4,5)47-35)27(43-21(2)37)29(34)46-31(40)24-15-11-8-12-16-24/h7-16,25-29,41H,17-19H2,1-6H3/t25-,26+,27-,28+,29+,33-,34-,35-/m0/s1
SMILES	CC(=O)OC[C@]12[C@H](CC[C@]([C@@]32OC([C@H]([C@@H]([C@H]1OC(=O)c1ccccc1)OC(=O)C)[C@H]3OC(=O)C)(C)C)(C)O)OC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.25	Volume:	647.615 ? Van der Waals volume.
Dense:	1.007	LogP:	2.892 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.807 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.462 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	31.0
TPSA:	160.96 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.327	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.8	Fsp³:	0.514
MCE-18:	172.189 ? 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:	0.337	Fluc inhibitor:	0.008 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.181 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.083	Promiscuous compounds:	0.085

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.522	MDCK Permeability:	-4.818
Pgp-inhibitor:	1.0	Pgp-substrate:	0.559
PAMPA:	0.699 ? 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%):	0.015	30% Bioavailability (F30%):	0.468
50% Bioavailability (F50%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028	MRP1:	1.0
Plasma Protein Binding (PPB):	76.801%	Volume Distribution (VD):	-0.439
Fu:	21.759% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.019
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.565
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.322
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.005
CYP3A4-inhibitor:	0.558	CYP3A4-substrate:	0.192
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.953 ? 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):

3.617

Half-life (T1/2):

0.734

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.535
Human Hepatotoxicity (H-HT):	0.078	Drug-induced Liver Injury (DILI):	0.657
AMES Toxicity:	0.546	Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.212	Skin Sensitization:	0.98
Carcinogencity:	0.876	Eye Corrosion:	0.0
Eye Irritation:	0.319	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.26	Ototoxicity:	0.157
Hematotoxicity:	0.017	Drug-induced Nephrotoxicity:	0.48
Genotoxicity:	0.472	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.051	Hek293 Cytotoxicity:	0.352
BCF:	0.692 ? 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:	3.635 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.423 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.833 ? 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
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[10579879]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461656]
NPO18386	Maytenus macrocarpa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18386	Maytenus macrocarpa	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
IC50	4

Activity Type	# Activity
Cell line	3
Non-molecular	1

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
NPT168	Cell line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[17253840]
NPT81	Cell line	A549	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[17253840]
NPT139	Cell line	HT-29	Homo sapiens	IC50	>	25.0	ug.mL-1	DailyMed
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[10579879]

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 NPC57628 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	12594
0.1-0.2	34652
0.2-0.3	1892
0.3-0.4	504
0.4-0.5	117
0.5-0.6	57
0.6-0.7	29
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	Natural Product ID
0.7465	Intermediate Similarity	NPC472569
0.7465	Intermediate Similarity	NPC16912
0.7397	Intermediate Similarity	NPC294803
0.7183	Intermediate Similarity	NPC171207
0.7143	Intermediate Similarity	NPC163719
0.7143	Intermediate Similarity	NPC95810
0.7067	Intermediate Similarity	NPC481486
0.6986	Remote Similarity	NPC11685
0.6986	Remote Similarity	NPC472570
0.6933	Remote Similarity	NPC481062
0.6933	Remote Similarity	NPC481058
0.6933	Remote Similarity	NPC481489
0.6933	Remote Similarity	NPC481060
0.6842	Remote Similarity	NPC481488
0.6625	Remote Similarity	NPC10904
0.6494	Remote Similarity	NPC481064
0.6447	Remote Similarity	NPC70716
0.6447	Remote Similarity	NPC97667
0.6438	Remote Similarity	NPC90257
0.6438	Remote Similarity	NPC69357
0.6437	Remote Similarity	NPC6981
0.6375	Remote Similarity	NPC125106
0.6375	Remote Similarity	NPC472573
0.6301	Remote Similarity	NPC483886
0.6282	Remote Similarity	NPC479042
0.6234	Remote Similarity	NPC95265
0.6234	Remote Similarity	NPC96903
0.622	Remote Similarity	NPC180668
0.622	Remote Similarity	NPC148896
0.6173	Remote Similarity	NPC610927
0.6098	Remote Similarity	NPC301368
0.6098	Remote Similarity	NPC84815
0.6081	Remote Similarity	NPC473060
0.6	Remote Similarity	NPC483845
0.6	Remote Similarity	NPC200471
0.6	Remote Similarity	NPC472575
0.5974	Remote Similarity	NPC483844
0.5949	Remote Similarity	NPC282239
0.5949	Remote Similarity	NPC471102
0.593	Remote Similarity	NPC479045
0.5909	Remote Similarity	NPC471013
0.5882	Remote Similarity	NPC253738
0.5867	Remote Similarity	NPC281717
0.575	Remote Similarity	NPC483848
0.5714	Remote Similarity	NPC472572
0.5696	Remote Similarity	NPC479043
0.5696	Remote Similarity	NPC252314
0.5676	Remote Similarity	NPC476094
0.5658	Remote Similarity	NPC51314
0.5641	Remote Similarity	NPC471104
0.5584	Remote Similarity	NPC291599
0.5584	Remote Similarity	NPC147880
0.5568	Remote Similarity	NPC176413
0.5568	Remote Similarity	NPC483885
0.5568	Remote Similarity	NPC294512
0.5556	Remote Similarity	NPC472568
0.5529	Remote Similarity	NPC610134
0.5513	Remote Similarity	NPC483846
0.5513	Remote Similarity	NPC137718
0.5513	Remote Similarity	NPC148062
0.5488	Remote Similarity	NPC483849
0.5467	Remote Similarity	NPC66761
0.5467	Remote Similarity	NPC483843
0.5455	Remote Similarity	NPC87448
0.5443	Remote Similarity	NPC473088
0.5441	Remote Similarity	NPC470154
0.5375	Remote Similarity	NPC41481
0.5366	Remote Similarity	NPC51602
0.5357	Remote Similarity	NPC488917
0.5325	Remote Similarity	NPC90614
0.5263	Remote Similarity	NPC475429
0.5256	Remote Similarity	NPC17877
0.5244	Remote Similarity	NPC106895
0.519	Remote Similarity	NPC4341
0.519	Remote Similarity	NPC479047
0.519	Remote Similarity	NPC291638
0.5181	Remote Similarity	NPC147340
0.5181	Remote Similarity	NPC481490
0.5181	Remote Similarity	NPC476970
0.5169	Remote Similarity	NPC476974
0.5165	Remote Similarity	NPC483868
0.5128	Remote Similarity	NPC241951
0.5128	Remote Similarity	NPC483862
0.5125	Remote Similarity	NPC147217
0.5125	Remote Similarity	NPC483842
0.5125	Remote Similarity	NPC158663
0.5116	Remote Similarity	NPC479040
0.5065	Remote Similarity	NPC481047
0.5065	Remote Similarity	NPC211137
0.5065	Remote Similarity	NPC481045
0.5063	Remote Similarity	NPC472577
0.5062	Remote Similarity	NPC473758
0.506	Remote Similarity	NPC481063

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC57628 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3723
0.1-0.2	5253
0.2-0.3	174
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