NPASS Compound

Natural Product: NPC472728

Natural Product ID	NPC472728
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IDXNDMRSSYBBIJ-WGCTUJHDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3581912
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

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 87 0 0 0 0 0 0 0 0999 V2000 -2.2313 -1.4367 4.7767 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1266 -0.4515 4.6217 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1558 0.2073 3.2082 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5119 0.8921 3.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9094 -0.8378 2.2414 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9340 -2.0062 2.7373 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6337 -0.8099 0.7885 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5206 0.0694 -0.0175 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4378 -0.1281 -1.3461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9914 1.1030 -1.9654 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0937 1.4441 -0.9676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4351 1.0600 0.2262 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4312 2.9111 -0.9829 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2206 3.7822 -0.9183 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1955 3.2867 -2.2393 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2682 3.2171 0.0876 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8867 -1.3808 -1.9031 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5874 -1.3722 -3.1165 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7050 -2.5956 -1.0270 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1302 -2.1843 0.3126 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -2.8391 1.0049 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8024 -2.8338 -0.8167 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3817 -1.4767 -0.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7848 -0.6092 0.4345 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6390 -0.9479 1.6726 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1545 0.8025 -0.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9412 1.8969 0.8930 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2888 3.2574 0.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6834 3.7022 -0.7200 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9376 3.0234 -1.9953 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9384 5.2140 -0.7903 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8772 -1.7106 -0.3830 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3880 -2.4289 -1.6087 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9448 -3.6316 -1.5330 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4486 -4.3407 -2.7421 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0777 -4.2998 -0.2102 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4027 -3.7947 -1.5580 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8038 -1.2536 5.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9024 -1.5391 3.9268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7575 -2.4504 4.9288 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1235 -0.9160 4.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1859 0.3287 5.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3653 0.9667 3.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2375 0.2378 2.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9312 1.0381 4.1741 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4563 1.9306 2.7480 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2560 1.9305 -1.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4164 0.9076 -2.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9559 0.8022 -1.2255 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5788 4.8080 -0.6073 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7026 3.9169 -1.8907 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5561 3.4481 -0.1045 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2560 2.9261 -2.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7727 2.8458 -3.1468 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2621 4.3993 -2.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7931 2.3927 0.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2088 -3.2756 -1.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9316 -3.4064 0.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3301 -0.9744 -1.6368 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6754 -0.6316 1.5580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5265 -2.0717 1.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2505 -0.5579 2.5985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7263 0.9938 -1.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2840 0.7602 -0.2315 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4315 1.7777 1.8905 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1544 1.9903 1.1784 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1837 4.0549 1.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5805 2.1552 -1.9910 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9686 2.7670 -2.5196 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4472 3.7296 -2.7384 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9664 5.6639 0.1996 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1770 5.6095 -1.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9775 5.2849 -1.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0542 -2.3812 0.4619 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4669 -0.8087 -0.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2829 -1.9229 -2.5619 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5725 -4.7918 -3.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9146 -3.6296 -3.4472 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2161 -5.0835 -2.4430 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0604 -4.5002 0.1731 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6720 -5.2418 -0.3062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6278 -3.6726 0.5188 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8113 -4.7387 -1.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4386 -3.8864 -1.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4862 -3.6855 -2.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 0 13 15 1 0 13 16 1 0 9 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 2 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 2 3 29 30 1 0 29 31 1 0 23 32 1 0 32 33 1 0 33 34 2 3 34 35 1 0 34 36 1 0 19 37 1 0 20 7 1 0 24 7 1 0 12 8 1 0 1 38 1 0 1 39 1 0 1 40 1 0 2 41 1 0 2 42 1 0 3 43 1 0 4 44 1 0 4 45 1 0 4 46 1 0 10 47 1 0 10 48 1 0 11 49 1 0 14 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 22 57 1 0 22 58 1 0 23 59 1 0 25 60 1 0 25 61 1 0 25 62 1 0 26 63 1 0 26 64 1 0 27 65 1 0 27 66 1 0 28 67 1 0 30 68 1 0 30 69 1 0 30 70 1 0 31 71 1 0 31 72 1 0 31 73 1 0 32 74 1 0 32 75 1 0 33 76 1 0 35 77 1 0 35 78 1 0 35 79 1 0 36 80 1 0 36 81 1 0 36 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 M END

Standard InCHIKey	IDXNDMRSSYBBIJ-WGCTUJHDSA-N
Standard InCHI	InChI=1S/C32H48O5/c1-11-21(6)25(33)32-27-23(17-24(37-27)29(7,8)36)26(34)30(9,28(32)35)18-22(15-14-20(4)5)31(32,10)16-12-13-19(2)3/h13-14,21-22,24,36H,11-12,15-18H2,1-10H3/t21-,22-,24-,30+,31+,32-/m0/s1
SMILES	CCC(C)C(=O)C12C3=C(CC(O3)C(C)(C)O)C(=O)C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	512.35	Volume:	564.491 ? Van der Waals volume.
Dense:	0.908	LogP:	5.861 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.558 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.911 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	19.0
TPSA:	80.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.275	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.037	Fsp³:	0.719
MCE-18:	69.891 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.515	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.047 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.485 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.479	Promiscuous compounds:	0.036

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.76	MDCK Permeability:	-4.687
Pgp-inhibitor:	0.173	Pgp-substrate:	0.0
PAMPA:	0.573 ? 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%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187	MRP1:	0.968
Plasma Protein Binding (PPB):	86.769%	Volume Distribution (VD):	0.004
Fu:	9.537% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.72
OATP1B3 inhibitor:	0.983	BCRP inhibitor:	0.0
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.983
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	0.478
CYP2B6-substrate:	0.151	CYP2C8-inhibitor:	0.935
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):

6.593

Half-life (T1/2):

0.663

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.213
Human Hepatotoxicity (H-HT):	0.667	Drug-induced Liver Injury (DILI):	0.081
AMES Toxicity:	0.236	Rat Oral Acute Toxicity:	0.189
Maximum Recommended Daily Dose:	0.146	Skin Sensitization:	0.901
Carcinogencity:	0.708	Eye Corrosion:	0.001
Eye Irritation:	0.036	Respiratory Toxicity:	0.368
Drug-induced Neurotoxicity:	0.129	Ototoxicity:	0.669
Hematotoxicity:	0.548	Drug-induced Nephrotoxicity:	0.829
Genotoxicity:	0.745	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.031	Hek293 Cytotoxicity:	0.096
BCF:	2.021 ? 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:	4.841 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.471 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.993 ? 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
NPO32997	Hypericum monogynum	Species	Hypericaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[25924023]
NPO32997	Hypericum monogynum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27525351]

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
Inhibition	1

Activity Type	# Activity
Cell line	2

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	23700.0	nM	PMID[18558669]
NPT65	Cell line	HepG2	Homo sapiens	Inhibition	=	15.03	%	PMID[28958618]

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 NPC472728 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	16254
0.1-0.2	31986
0.2-0.3	1500
0.3-0.4	41
0.4-0.5	36
0.5-0.6	25
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472727
0.8947	High Similarity	NPC472729
0.8947	High Similarity	NPC472730
0.7869	Intermediate Similarity	NPC483068
0.746	Intermediate Similarity	NPC483080
0.7188	Intermediate Similarity	NPC472732
0.7188	Intermediate Similarity	NPC472731
0.6984	Remote Similarity	NPC483067
0.6615	Remote Similarity	NPC472733
0.6615	Remote Similarity	NPC472734
0.6389	Remote Similarity	NPC482995
0.6232	Remote Similarity	NPC472675
0.6143	Remote Similarity	NPC471330
0.6143	Remote Similarity	NPC472687
0.5946	Remote Similarity	NPC482993
0.5789	Remote Similarity	NPC47466
0.5789	Remote Similarity	NPC116274
0.5753	Remote Similarity	NPC483052
0.5753	Remote Similarity	NPC483051
0.5676	Remote Similarity	NPC483055
0.5676	Remote Similarity	NPC483056
0.5634	Remote Similarity	NPC483076
0.5634	Remote Similarity	NPC471331
0.5634	Remote Similarity	NPC99657
0.5634	Remote Similarity	NPC483078
0.5634	Remote Similarity	NPC203388
0.5571	Remote Similarity	NPC483058
0.5493	Remote Similarity	NPC21681
0.5479	Remote Similarity	NPC483060
0.5316	Remote Similarity	NPC471333
0.5316	Remote Similarity	NPC471332
0.5263	Remote Similarity	NPC483061
0.5263	Remote Similarity	NPC483062
0.5143	Remote Similarity	NPC177680
0.5143	Remote Similarity	NPC153776
0.5135	Remote Similarity	NPC483054
0.5135	Remote Similarity	NPC483053
0.5125	Remote Similarity	NPC146239
0.5125	Remote Similarity	NPC483095

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC472728 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6482
0.1-0.2	2641
0.2-0.3	27
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