NPASS Compound

Natural Product: NPC489799

Natural Product ID	NPC489799
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	KXSRWTNYHOCSFB-TVURBSCFSA-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 86 89 0 0 0 0 0 0 0 0999 V2000 -4.0074 0.9564 0.8016 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8894 -0.1614 -0.1712 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1913 -0.9268 -0.2210 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3929 -0.1637 -0.6759 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8233 0.9761 0.1359 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9205 2.2232 -0.3388 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5675 2.4262 -1.7613 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3587 3.3237 0.5282 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4580 4.4917 0.1135 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6677 3.0400 1.8443 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8064 -1.1617 0.1176 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8143 -2.1805 -1.0171 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4192 -1.9691 -1.6554 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6059 -1.7287 -0.4563 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5179 -3.0176 0.3349 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7312 -1.1911 -0.6259 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2799 -0.6336 0.4590 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5818 -0.5556 1.7660 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8832 -0.7625 1.7050 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4353 -0.6675 0.2939 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1288 0.6731 -0.2820 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6591 -0.0577 0.4208 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5490 1.3889 0.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2836 -0.3330 1.7752 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6890 0.1182 1.8797 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4511 0.1801 0.5939 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9212 -0.6964 -0.4920 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3973 -0.0874 -1.8195 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6427 -2.0523 -0.4206 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4588 -0.8670 -0.5609 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8706 -0.6846 -1.9400 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4839 -1.2195 -1.8794 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9451 -1.6972 -2.8906 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6140 1.5255 0.1823 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8427 2.1550 0.1283 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9034 1.5222 0.4586 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8871 3.5682 -0.3192 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1307 -3.1656 -2.2870 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2090 1.9347 0.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8139 0.8322 1.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0820 1.0874 1.4272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7712 0.2801 -1.1878 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4543 -1.2570 0.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1139 -1.9193 -0.7280 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2727 -0.8598 -0.8407 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1924 0.1844 -1.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0961 0.8369 1.1580 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7404 3.5051 -1.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2350 1.8452 -2.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4952 2.2319 -1.9720 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1029 3.6807 2.4863 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1375 -1.6852 1.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9471 -3.1938 -0.6448 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5422 -1.9423 -1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5358 -1.1276 -2.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4760 -3.3289 0.7766 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1267 -3.7761 -0.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2379 -2.9657 1.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0320 -1.2065 2.5372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7805 0.4950 2.1372 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1426 -1.8013 2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3633 -0.0956 2.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7936 1.4061 0.5108 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9529 1.0993 -0.8760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2666 0.6143 -0.9868 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0196 1.9398 0.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5205 1.7993 0.0757 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 1.7357 -0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2630 -1.4552 1.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7109 0.0721 2.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1999 -0.5362 2.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7077 1.1361 2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4913 -0.1757 0.8329 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4445 0.3117 -1.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7864 0.7539 -2.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4613 -0.8398 -2.6156 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6717 -2.4319 0.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6668 -1.9626 -0.8653 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0840 -2.7397 -1.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2340 -1.9470 -0.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7900 0.3604 -2.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4694 -1.2716 -2.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8467 3.5391 -1.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9781 4.0805 0.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8128 4.0751 0.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5755 -3.9063 -1.8103 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 4 5 1 0 5 6 2 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 2 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 17 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 26 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 13 38 1 0 20 11 1 0 30 22 1 0 20 14 1 0 32 16 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 6 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 0 7 48 1 0 7 49 1 0 7 50 1 0 10 51 1 0 11 52 1 1 12 53 1 0 12 54 1 0 13 55 1 6 15 56 1 0 15 57 1 0 15 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 26 73 1 1 28 74 1 0 28 75 1 0 28 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 1 31 81 1 0 31 82 1 0 37 83 1 0 37 84 1 0 37 85 1 0 38 86 1 0 M END

Standard InCHIKey	KXSRWTNYHOCSFB-TVURBSCFSA-N
Standard InCHI	InChI=1S/C32H48O6/c1-18(10-9-11-19(2)28(36)37)22-16-25(35)32(8)27-21(12-15-31(22,32)7)30(6)14-13-26(38-20(3)33)29(4,5)24(30)17-23(27)34/h11,18,22,24-26,35H,9-10,12-17H2,1-8H3,(H,36,37)/b19-11+/t18-,22-,24+,25+,26+,30-,31-,32+/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1C[C@@H]([C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3=O)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.35	Volume:	567.361 ? Van der Waals volume.
Dense:	0.931	LogP:	3.397 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.945 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.239 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	24.0
TPSA:	100.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.311	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.991	Fsp³:	0.781
MCE-18:	87.193 ? 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:	0.809	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.313	Promiscuous compounds:	0.315

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.13	MDCK Permeability:	-4.835
Pgp-inhibitor:	0.999	Pgp-substrate:	0.0
PAMPA:	0.585 ? 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):	0.129
20% Bioavailability (F20%):	0.985	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.935
Plasma Protein Binding (PPB):	85.818%	Volume Distribution (VD):	-0.613
Fu:	11.022% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.027
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.26
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.028	CYP3A4-substrate:	0.012
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.665 ? 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):

5.229

Half-life (T1/2):

0.99

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.744	Drug-induced Liver Injury (DILI):	0.578
AMES Toxicity:	0.123	Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.271	Skin Sensitization:	0.954
Carcinogencity:	0.592	Eye Corrosion:	0.009
Eye Irritation:	0.487	Respiratory Toxicity:	0.254
Drug-induced Neurotoxicity:	0.018	Ototoxicity:	0.662
Hematotoxicity:	0.527	Drug-induced Nephrotoxicity:	0.837
Genotoxicity:	0.825	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.036	Hek293 Cytotoxicity:	0.115
BCF:	0.531 ? 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:	3.505 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.375 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.394 ? 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
NPO40519	Ganoderma orbiforme BCC 22325	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40520	Ganoderma sp. BCC 60695	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]
NPO40518	Ganoderma australe BCC 22314	Strain	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28504879]

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
MIC	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
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	92000.0	nM	PMID[28504879]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[28504879]

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 NPC489799 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	16036
0.1-0.2	26456
0.2-0.3	6825
0.3-0.4	427
0.4-0.5	80
0.5-0.6	20
0.6-0.7	8
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
0.7703	Intermediate Similarity	NPC489796
0.75	Intermediate Similarity	NPC489793
0.7403	Intermediate Similarity	NPC478306
0.7403	Intermediate Similarity	NPC137291
0.6795	Remote Similarity	NPC94393
0.6456	Remote Similarity	NPC478302
0.6375	Remote Similarity	NPC478303
0.6145	Remote Similarity	NPC489806
0.6104	Remote Similarity	NPC601194
0.6026	Remote Similarity	NPC478308
0.6	Remote Similarity	NPC489807
0.6	Remote Similarity	NPC478298
0.5904	Remote Similarity	NPC489797
0.5765	Remote Similarity	NPC489794
0.575	Remote Similarity	NPC489801
0.5732	Remote Similarity	NPC489803
0.5732	Remote Similarity	NPC489804
0.5698	Remote Similarity	NPC489809
0.5422	Remote Similarity	NPC604630
0.5402	Remote Similarity	NPC198442
0.5366	Remote Similarity	NPC478313
0.5366	Remote Similarity	NPC489790
0.5301	Remote Similarity	NPC136044
0.5238	Remote Similarity	NPC489808
0.5238	Remote Similarity	NPC489800
0.5233	Remote Similarity	NPC489795
0.5185	Remote Similarity	NPC479657
0.5185	Remote Similarity	NPC138536
0.5062	Remote Similarity	NPC8571
0.5059	Remote Similarity	NPC489802
0.5059	Remote Similarity	NPC39082
0.5059	Remote Similarity	NPC610107

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489799 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5609
0.1-0.2	3381
0.2-0.3	156
0.3-0.4	4
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