NPASS Compound

Natural Product: NPC310482

Natural Product ID	NPC310482
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OESLKRXCBRUCJZ-CGRFPGENSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102090518
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 82 86 0 0 0 0 0 0 0 0999 V2000 5.4386 -2.0736 1.8086 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4540 -1.8823 0.9404 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4537 -3.0021 0.8780 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4144 -0.7203 0.0986 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6206 0.2331 0.2851 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2155 1.4815 -0.4996 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8622 1.1385 -1.0110 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0259 0.3670 -2.2728 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9656 2.3069 -1.2599 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6410 1.6593 -1.7011 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0254 1.0670 -0.4560 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9857 2.2212 0.5408 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9418 -0.0652 0.0394 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3258 -0.4630 1.3640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0853 -1.2533 0.9655 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8811 -0.2241 0.4689 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3051 -0.6866 0.3565 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5289 -1.9015 -0.4521 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7678 -1.0136 1.7908 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2119 -1.4379 1.8231 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0460 -0.9480 0.7013 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6057 0.3348 0.0947 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2481 0.4409 -1.2915 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2656 1.4624 0.9053 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1309 0.5286 -0.0002 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6951 1.2167 -1.2615 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2684 1.6937 -1.0383 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3593 0.4970 -0.7148 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3053 -0.2943 -1.9812 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3526 -0.7483 1.2144 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7431 -1.0247 3.0559 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3388 0.2896 0.1679 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5099 -2.9589 2.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2012 -1.3312 1.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8511 -2.8490 -0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9919 -3.9750 0.7010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7985 -3.0541 1.7409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5867 -1.0837 -0.9699 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5389 -0.2201 -0.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6971 0.4893 1.3764 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1312 2.3284 0.2052 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9425 1.6821 -1.3159 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8137 1.0853 -3.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3704 -0.4845 -2.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1050 0.0908 -2.4786 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3426 2.8227 -2.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8621 3.0239 -0.4604 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9131 0.9242 -2.4566 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0473 2.4919 -2.1133 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9071 3.2087 -0.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1253 2.2251 1.2034 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8850 2.2852 1.1584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8061 -0.8836 -0.6623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9553 0.5006 1.8415 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9613 -0.9167 2.0902 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2130 -1.8082 1.8477 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3905 -1.9203 0.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9372 0.5315 1.3127 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5138 -2.3485 -0.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0281 -2.7390 0.1266 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1509 -1.7942 -1.3505 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1943 -1.8183 2.2456 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6323 -0.1040 2.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2952 -2.5637 1.8415 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1979 -1.7042 -0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3066 1.5381 -1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7265 -0.1334 -2.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3048 0.1285 -1.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9888 1.2440 1.9747 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3523 1.3846 0.8430 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8385 2.4355 0.6594 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8638 1.2699 0.8207 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3206 2.1443 -1.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8579 0.6720 -2.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3126 2.4220 -0.2160 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9594 2.1680 -1.9945 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0179 0.4356 -2.7978 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3101 -1.1876 -1.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3176 -0.6321 -2.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7341 -1.6574 1.3386 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6287 -1.4731 3.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5701 0.9089 1.0976 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 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 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 20 31 1 0 13 32 1 0 32 4 1 0 32 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 6 5 39 1 0 5 40 1 0 6 41 1 0 6 42 1 0 8 43 1 0 8 44 1 0 8 45 1 0 9 46 1 0 9 47 1 0 10 48 1 0 10 49 1 0 12 50 1 0 12 51 1 0 12 52 1 0 13 53 1 6 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 1 18 59 1 0 18 60 1 0 18 61 1 0 19 62 1 0 19 63 1 0 20 64 1 1 21 65 1 6 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 1 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 0 32 82 1 1 M END

Standard InCHIKey	OESLKRXCBRUCJZ-CGRFPGENSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-18(2)19-11-13-27(5)15-16-29(7)20(24(19)27)9-10-23-28(6)17-21(31)25(32)26(3,4)22(28)12-14-30(23,29)8/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21+,22-,23+,24+,25+,27+,28-,29+,30+/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@]2(C)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)C[C@H]([C@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	5.856 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.752 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.363 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.429	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.853	Fsp³:	0.933
MCE-18:	103.517 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.97	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.554	Promiscuous compounds:	0.236

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.093	MDCK Permeability:	-4.88
Pgp-inhibitor:	0.325	Pgp-substrate:	0.056
PAMPA:	0.083 ? 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%):	0.038	30% Bioavailability (F30%):	0.159
50% Bioavailability (F50%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.421	MRP1:	0.949
Plasma Protein Binding (PPB):	94.725%	Volume Distribution (VD):	0.464
Fu:	5.316% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.41
BSEP inhibitor:	0.993

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.508	CYP2C19-substrate:	0.018
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.016	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.508	CYP3A4-substrate:	0.704
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.788
HLM stability:	0.522 ? 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):

11.798

Half-life (T1/2):

0.655

ADMET: Toxicity

hERG Blockers:	0.109	hERG Blockers (10um):	0.413
Human Hepatotoxicity (H-HT):	0.429	Drug-induced Liver Injury (DILI):	0.143
AMES Toxicity:	0.157	Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.496	Skin Sensitization:	0.758
Carcinogencity:	0.776	Eye Corrosion:	0.213
Eye Irritation:	0.825	Respiratory Toxicity:	0.719
Drug-induced Neurotoxicity:	0.041	Ototoxicity:	0.707
Hematotoxicity:	0.452	Drug-induced Nephrotoxicity:	0.664
Genotoxicity:	0.071	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.081	Hek293 Cytotoxicity:	0.261
BCF:	2.811 ? 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:	4.65 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.346 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.336 ? 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
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6321	Agathosma thymifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12800	Glycine falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22758	Picradeniopsis pringlei	Species	Asteraceae	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

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

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 NPC310482 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	30878
0.1-0.2	16929
0.2-0.3	1702
0.3-0.4	250
0.4-0.5	58
0.5-0.6	30
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC102708
0.7059	Intermediate Similarity	NPC192638
0.7059	Intermediate Similarity	NPC25511
0.7059	Intermediate Similarity	NPC600137
0.6226	Remote Similarity	NPC35652
0.6111	Remote Similarity	NPC80297
0.6111	Remote Similarity	NPC475727
0.6111	Remote Similarity	NPC116119
0.6071	Remote Similarity	NPC248830
0.6071	Remote Similarity	NPC212241
0.5902	Remote Similarity	NPC488506
0.5902	Remote Similarity	NPC220498
0.5893	Remote Similarity	NPC202540
0.5893	Remote Similarity	NPC14112
0.5862	Remote Similarity	NPC57469
0.5862	Remote Similarity	NPC269396
0.5833	Remote Similarity	NPC471900
0.5714	Remote Similarity	NPC43300
0.5614	Remote Similarity	NPC104387
0.5517	Remote Similarity	NPC231256
0.5517	Remote Similarity	NPC178383
0.5424	Remote Similarity	NPC93662
0.5345	Remote Similarity	NPC240235
0.5333	Remote Similarity	NPC305835
0.5333	Remote Similarity	NPC246956
0.5333	Remote Similarity	NPC74595
0.5333	Remote Similarity	NPC264665
0.5246	Remote Similarity	NPC103754
0.5179	Remote Similarity	NPC142712
0.5161	Remote Similarity	NPC12774
0.5161	Remote Similarity	NPC474233
0.5156	Remote Similarity	NPC607755
0.5152	Remote Similarity	NPC488213
0.5147	Remote Similarity	NPC475416
0.5088	Remote Similarity	NPC480925
0.5088	Remote Similarity	NPC48079
0.5085	Remote Similarity	NPC78067
0.5085	Remote Similarity	NPC144075
0.5085	Remote Similarity	NPC278091
0.5085	Remote Similarity	NPC301226

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC310482 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8076
0.1-0.2	1051
0.2-0.3	21
0.3-0.4	1
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