NPASS Compound

Natural Product: NPC480919

Natural Product ID	NPC480919
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PLWKNPLWZASRGR-KYHAFUHBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 -3.9646 5.0891 1.1160 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3073 3.7820 1.1394 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7796 3.3705 2.1935 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1751 2.8900 0.1220 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5724 1.6560 0.0866 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2516 1.6071 -0.6264 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5125 0.3286 -0.3725 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3169 -0.3497 -1.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2484 -0.6081 0.4993 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5552 -1.4329 1.2745 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9202 -1.5278 1.3733 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5689 -0.7716 0.2393 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0431 -0.8307 0.2751 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5982 -1.0947 1.6743 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5001 -2.0671 -0.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9607 -2.2159 -0.6108 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7925 -1.0192 -0.7404 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1986 0.3025 -0.4150 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5731 1.2954 -1.5420 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8030 0.9268 0.8263 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7129 0.2932 -0.4259 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0868 1.5827 0.0050 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6823 1.5391 -0.6279 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8948 0.5642 0.1796 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7352 1.1734 1.5542 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9273 -1.1705 0.0990 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7350 -0.7021 0.6106 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3247 -2.0337 0.4708 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0615 -2.3687 -0.7748 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5529 -2.5758 -0.5604 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5505 -3.6803 -1.3518 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8153 -1.3227 -1.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0130 0.0969 -1.3214 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4544 0.4503 -0.0326 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6566 0.8760 0.8682 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2208 2.0319 0.3372 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6723 0.8967 -2.4065 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3018 1.9157 -1.9801 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2921 5.4475 2.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7878 5.1411 0.3688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2005 5.8322 0.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2324 1.5827 1.1751 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6907 2.4891 -0.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0734 0.0592 -2.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5725 -1.4433 -1.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6428 -0.1688 -2.1923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1113 -2.1374 1.9389 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1884 -1.1067 2.3684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2323 -2.5860 1.2675 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2280 -1.3369 -0.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6523 -1.4915 1.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0433 -1.8919 2.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6531 -0.2227 2.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0596 -2.9795 -0.0641 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0735 -1.9479 -1.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2917 -2.8717 0.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1496 -2.9104 -1.4893 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2591 -0.9910 -1.7731 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5899 2.3327 -1.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8424 1.2727 -2.3532 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6138 1.0762 -1.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5945 1.6866 0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3463 0.1852 1.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0474 1.5063 1.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4353 0.1741 -1.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6209 2.4429 -0.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0480 1.7479 1.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3403 2.5756 -0.5743 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8639 1.2926 -1.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1856 0.8017 2.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5534 0.9020 2.2514 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6515 2.2938 1.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1435 -2.1404 0.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8849 -0.4529 1.7358 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5578 -2.7997 0.7414 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0747 -2.2037 1.3109 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8132 -3.6639 -0.5203 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1659 -2.0335 -1.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7876 -2.1977 0.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0255 -4.5305 -0.8286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7935 -3.7308 -2.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4357 -3.7175 -1.1820 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5969 -1.4961 -2.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8612 -1.4897 -2.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1525 0.1951 -1.3175 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4326 0.1220 0.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2894 1.0303 1.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2330 2.0961 -0.6243 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3581 0.9802 -3.0882 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5113 2.3796 -2.3082 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 6 7 9 1 0 9 10 2 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 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 17 26 1 0 9 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 29 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 35 36 1 0 33 37 1 0 6 38 1 0 34 5 1 0 24 7 1 0 34 27 1 0 24 12 1 0 21 13 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 1 6 43 1 1 8 44 1 0 8 45 1 0 8 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 12 50 1 6 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 6 19 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 6 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 27 74 1 1 28 75 1 0 28 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 31 82 1 0 32 83 1 0 32 84 1 0 33 85 1 1 35 86 1 0 35 87 1 0 36 88 1 0 37 89 1 0 38 90 1 0 M END

Standard InCHIKey	PLWKNPLWZASRGR-KYHAFUHBSA-N
Standard InCHI	InChI=1S/C32H52O6/c1-18(34)38-26-25(37)31(8)19(20-15-27(2,3)16-24(36)32(20,26)17-33)9-10-22-29(6)13-12-23(35)28(4,5)21(29)11-14-30(22,31)7/h9,20-26,33,35-37H,10-17H2,1-8H3/t20-,21-,22+,23-,24-,25-,26+,29-,30+,31-,32+/m0/s1
SMILES	CC(=O)O[C@@H]1[C@@H]([C@]2(C)C(=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]23C)O)[C@@H]2CC(C)(C)C[C@@H]([C@]12CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.38	Volume:	566.714 ? Van der Waals volume.
Dense:	0.939	LogP:	3.404 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.322 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.318 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.305	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.183	Fsp³:	0.906
MCE-18:	111.541 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.539	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.073 ? 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:	0.275	Promiscuous compounds:	0.345

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.508	MDCK Permeability:	-5.088
Pgp-inhibitor:	0.004	Pgp-substrate:	0.626
PAMPA:	0.998 ? 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%):	0.939	30% Bioavailability (F30%):	0.658
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983	MRP1:	0.783
Plasma Protein Binding (PPB):	88.391%	Volume Distribution (VD):	-0.142
Fu:	8.112% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.399	BCRP inhibitor:	0.249
BSEP inhibitor:	0.294

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.788	CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.789	CYP3A4-substrate:	0.924
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.978
HLM stability:	0.757 ? 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):

8.521

Half-life (T1/2):

1.041

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.098
Human Hepatotoxicity (H-HT):	0.481	Drug-induced Liver Injury (DILI):	0.379
AMES Toxicity:	0.921	Rat Oral Acute Toxicity:	0.771
Maximum Recommended Daily Dose:	0.722	Skin Sensitization:	0.998
Carcinogencity:	0.964	Eye Corrosion:	0.002
Eye Irritation:	0.477	Respiratory Toxicity:	0.936
Drug-induced Neurotoxicity:	0.27	Ototoxicity:	0.494
Hematotoxicity:	0.888	Drug-induced Nephrotoxicity:	0.954
Genotoxicity:	0.959	RPMI-8226 Immunitoxicity:	0.168
A549 Cytotoxicity:	0.984	Hek293 Cytotoxicity:	0.842
BCF:	0.924 ? 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:	3.487 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.232 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.464 ? 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
NPO40059	Camellia crapnelliana	Species	Theaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29064696]

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	1
Activity	1

Activity Type	# Activity
Individual protein	1
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	47350.0	nM	PMID[29064696]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21742	Cell line	L02	Homo sapiens	Activity	>	90.0	%	PMID[29064696]

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 NPC480919 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	17173
0.1-0.2	25701
0.2-0.3	5848
0.3-0.4	998
0.4-0.5	97
0.5-0.6	27
0.6-0.7	10
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
0.7794	Intermediate Similarity	NPC480923
0.75	Intermediate Similarity	NPC294360
0.7222	Intermediate Similarity	NPC480920
0.6944	Remote Similarity	NPC273668
0.6712	Remote Similarity	NPC88349
0.6667	Remote Similarity	NPC238992
0.6533	Remote Similarity	NPC480921
0.6494	Remote Similarity	NPC474190
0.6133	Remote Similarity	NPC475263
0.6133	Remote Similarity	NPC175006
0.6119	Remote Similarity	NPC311078
0.6104	Remote Similarity	NPC476132
0.6029	Remote Similarity	NPC480924
0.5974	Remote Similarity	NPC473160
0.597	Remote Similarity	NPC474989
0.5875	Remote Similarity	NPC476195
0.5714	Remote Similarity	NPC470588
0.5714	Remote Similarity	NPC480922
0.5652	Remote Similarity	NPC237344
0.5641	Remote Similarity	NPC283343
0.5571	Remote Similarity	NPC253807
0.5571	Remote Similarity	NPC158662
0.5493	Remote Similarity	NPC53744
0.5476	Remote Similarity	NPC473586
0.5429	Remote Similarity	NPC101475
0.5395	Remote Similarity	NPC164349
0.5352	Remote Similarity	NPC235341
0.5342	Remote Similarity	NPC246708
0.5333	Remote Similarity	NPC488519
0.5243	Remote Similarity	NPC610461
0.5217	Remote Similarity	NPC290598
0.5217	Remote Similarity	NPC30590
0.5211	Remote Similarity	NPC34177
0.52	Remote Similarity	NPC99254
0.5195	Remote Similarity	NPC49776
0.5195	Remote Similarity	NPC63118
0.5195	Remote Similarity	NPC474436
0.5068	Remote Similarity	NPC230295
0.5068	Remote Similarity	NPC159168
0.5068	Remote Similarity	NPC98386

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC480919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6713
0.1-0.2	2355
0.2-0.3	78
0.3-0.4	3
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