NPASS Compound

Natural Product: NPC488520

Natural Product ID	NPC488520
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TZTSALAWVKNRKH-YTGDWNJJSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	11800316
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 90 94 0 0 0 0 0 0 0 0999 V2000 8.6011 1.9807 -0.9259 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1200 1.8938 -0.8115 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4334 2.9481 -0.7749 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4383 0.6834 -0.7413 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0326 0.6045 -0.6328 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4599 -0.0866 -1.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9773 -0.0957 -1.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4331 -0.7307 -0.4871 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6444 -2.1865 -0.6345 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1058 -0.0966 0.6841 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5389 -0.6923 1.9418 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1046 -0.1742 2.0404 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2935 -0.5214 0.8402 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0102 -2.0047 0.9404 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9825 -0.2898 -0.4666 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2032 -0.7373 -1.6415 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1916 -0.2594 -1.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7160 0.1929 -0.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1280 0.6599 -0.3986 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7076 1.0077 -1.7113 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1028 1.5288 -1.5209 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1002 2.9874 -1.0587 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7835 1.5264 -2.8815 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9430 0.7457 -0.5803 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2592 0.3112 0.6705 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8995 -0.3203 0.4283 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2251 -0.6159 1.7281 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8968 -0.0570 1.9944 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9925 0.3026 0.8669 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6339 1.7690 1.0038 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1029 -0.2031 2.7715 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1679 -1.5675 -0.3272 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8021 -1.7911 -1.4940 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8903 -2.5857 0.3103 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1861 -3.8059 -0.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5876 -0.0567 0.6475 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2796 -1.3531 0.8718 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0372 0.8901 1.7741 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0744 1.0362 -0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9584 2.7779 -0.2480 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8851 2.2819 -1.9567 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5929 1.6426 -0.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7413 0.5425 -2.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9310 -1.0704 -2.0202 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5661 0.8951 -1.9561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6109 -0.7737 -2.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5465 -2.7960 0.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0484 -2.5400 -1.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7158 -2.3276 -0.9733 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7640 0.9848 0.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0894 -0.2258 2.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6140 -1.7695 2.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1646 0.8627 2.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6722 -0.7268 2.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1786 -2.5567 -0.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0265 -2.2315 1.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 -2.5187 1.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0669 0.8348 -0.5936 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6463 -0.2147 -2.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1940 -1.7876 -1.8826 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7470 -0.3175 -2.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1976 1.6242 0.2122 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6877 0.2786 -2.5070 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1122 1.8904 -2.0961 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1614 3.3191 -1.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8066 3.0067 0.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4312 3.6045 -1.6845 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5750 2.4589 -3.4419 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8742 1.3266 -2.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3597 0.6988 -3.4833 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8099 1.3781 -0.2839 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4041 -0.1179 -1.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8935 -0.4366 1.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1315 1.1649 1.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2812 -1.7440 1.8635 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0193 0.8185 2.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3475 -0.8008 2.6528 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0493 2.1640 1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4087 2.0245 0.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1843 2.4143 0.2529 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8535 -0.8121 2.8847 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9441 -4.6556 0.3160 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2603 -3.7716 -0.6258 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6170 -3.8103 -1.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1170 -1.2688 1.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6477 -2.1720 1.2334 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8256 -1.6144 -0.0828 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0681 0.2933 2.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0817 1.1744 1.5296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3606 1.7616 1.8372 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 6 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 27 31 1 0 26 32 1 6 32 33 2 0 32 34 1 0 34 35 1 0 10 36 1 0 36 37 1 0 36 38 1 0 36 5 1 0 15 8 1 0 29 18 1 0 29 13 1 0 26 19 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 1 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 9 47 1 0 9 48 1 0 9 49 1 0 10 50 1 1 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 14 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 16 59 1 0 16 60 1 0 17 61 1 0 19 62 1 1 20 63 1 0 20 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 25 73 1 0 25 74 1 0 27 75 1 1 28 76 1 0 28 77 1 0 30 78 1 0 30 79 1 0 30 80 1 0 31 81 1 0 35 82 1 0 35 83 1 0 35 84 1 0 37 85 1 0 37 86 1 0 37 87 1 0 38 88 1 0 38 89 1 0 38 90 1 0 M END

Standard InCHIKey	TZTSALAWVKNRKH-YTGDWNJJSA-N
Standard InCHI	InChI=1S/C33H52O5/c1-20(34)38-26-13-14-30(6)23(29(26,4)5)12-15-31(7)24(30)11-10-21-22-18-28(2,3)16-17-33(22,27(36)37-9)25(35)19-32(21,31)8/h10,22-26,35H,11-19H2,1-9H3/t22-,23+,24-,25-,26+,30+,31-,32-,33-/m1/s1
SMILES	CC(=O)O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)CC[C@@]4([C@@H](C[C@@]32C)O)C(=O)OC)C1(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.38	Volume:	572.583 ? Van der Waals volume.
Dense:	0.923	LogP:	4.939 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.188 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.115 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.313	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.835	Fsp³:	0.879
MCE-18:	108.452 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.923	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.336	Promiscuous compounds:	0.296

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.285	MDCK Permeability:	-4.953
Pgp-inhibitor:	0.982	Pgp-substrate:	0.001
PAMPA:	0.927 ? 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%):	0.529	30% Bioavailability (F30%):	0.707
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.325	MRP1:	0.902
Plasma Protein Binding (PPB):	96.728%	Volume Distribution (VD):	-0.14
Fu:	3.08% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.988	BCRP inhibitor:	0.305
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.479	CYP2C19-substrate:	0.55
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.031	CYP3A4-substrate:	0.017
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.986
HLM stability:	0.974 ? 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):

8.207

Half-life (T1/2):

0.44

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.165
Human Hepatotoxicity (H-HT):	0.578	Drug-induced Liver Injury (DILI):	0.506
AMES Toxicity:	0.332	Rat Oral Acute Toxicity:	0.394
Maximum Recommended Daily Dose:	0.68	Skin Sensitization:	0.826
Carcinogencity:	0.878	Eye Corrosion:	0.042
Eye Irritation:	0.254	Respiratory Toxicity:	0.732
Drug-induced Neurotoxicity:	0.104	Ototoxicity:	0.389
Hematotoxicity:	0.352	Drug-induced Nephrotoxicity:	0.799
Genotoxicity:	0.665	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.308	Hek293 Cytotoxicity:	0.319
BCF:	1.84 ? 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:	4.417 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.851 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.33 ? 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
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[7494144]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7631	Gleditsia japonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27443	Gymnocladus chinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7631	Gleditsia japonica	Species	Fabaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Cell line	1
Organism	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
NPT759	Cell line	H9	Homo sapiens	IC50	=	7600.0	nM	PMID[7494144]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5100.0	nM	PMID[7494144]

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 NPC488520 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	18188
0.1-0.2	25280
0.2-0.3	5138
0.3-0.4	981
0.4-0.5	219
0.5-0.6	36
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC488522
0.8806	High Similarity	NPC488524
0.7463	Intermediate Similarity	NPC488519
0.7164	Intermediate Similarity	NPC162107
0.7164	Intermediate Similarity	NPC46912
0.6818	Remote Similarity	NPC195334
0.6812	Remote Similarity	NPC191965
0.6757	Remote Similarity	NPC86368
0.6716	Remote Similarity	NPC224145
0.6479	Remote Similarity	NPC286786
0.6471	Remote Similarity	NPC1046
0.6301	Remote Similarity	NPC488523
0.6196	Remote Similarity	NPC488526
0.6133	Remote Similarity	NPC488525
0.5972	Remote Similarity	NPC127855
0.589	Remote Similarity	NPC10005
0.589	Remote Similarity	NPC91525
0.5867	Remote Similarity	NPC164349
0.5851	Remote Similarity	NPC164389
0.5753	Remote Similarity	NPC137306
0.567	Remote Similarity	NPC64715
0.5634	Remote Similarity	NPC290495
0.5616	Remote Similarity	NPC246708
0.5484	Remote Similarity	NPC480420
0.5446	Remote Similarity	NPC104137
0.5446	Remote Similarity	NPC26626
0.5392	Remote Similarity	NPC11242
0.5375	Remote Similarity	NPC488518
0.5342	Remote Similarity	NPC470588
0.5326	Remote Similarity	NPC475208
0.5316	Remote Similarity	NPC294360
0.5278	Remote Similarity	NPC34177
0.5275	Remote Similarity	NPC214484
0.5263	Remote Similarity	NPC136313
0.5256	Remote Similarity	NPC120840
0.5238	Remote Similarity	NPC123522
0.5205	Remote Similarity	NPC235341
0.5205	Remote Similarity	NPC253807
0.5205	Remote Similarity	NPC158662
0.5195	Remote Similarity	NPC481361
0.5125	Remote Similarity	NPC477875
0.5122	Remote Similarity	NPC477876
0.5093	Remote Similarity	NPC283417
0.5093	Remote Similarity	NPC200049
0.507	Remote Similarity	NPC290598
0.507	Remote Similarity	NPC30590
0.5067	Remote Similarity	NPC267517
0.5067	Remote Similarity	NPC480944
0.5062	Remote Similarity	NPC488521
0.5051	Remote Similarity	NPC2370

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC488520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6854
0.1-0.2	2213
0.2-0.3	77
0.3-0.4	5
0.4-0.5	1
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