NPASS Compound

Natural Product: NPC489791

Natural Product ID	NPC489791
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PXBRGMAJKPPNOG-JHFAAVTGSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101602259
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 6.6929 3.0522 0.2262 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2577 1.6893 0.2375 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5902 0.6696 -0.2070 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2346 0.8343 -0.7433 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2119 0.0156 0.0372 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8622 0.2590 -0.6033 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9683 -0.2426 -2.0343 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7405 -0.4205 0.0648 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6125 -0.0154 1.5496 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2905 -0.6755 1.9134 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4332 -0.9593 0.6235 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4280 -2.3847 0.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8246 -0.4630 0.6164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5051 -0.5312 1.7443 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9009 -0.0317 1.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4887 -0.2834 0.3894 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9616 -0.0890 0.4292 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5362 -1.2168 1.3007 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4250 1.1946 1.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6225 -0.2418 -0.9223 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8657 0.4579 -2.0110 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3975 0.0873 -2.0205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7722 0.4662 -0.7054 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8015 1.9591 -0.5033 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3399 0.0515 -0.6471 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5636 0.1447 -1.7160 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1171 -0.2716 -1.6908 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3519 -0.0385 -0.3232 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0871 1.3837 0.0539 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8824 0.3650 -0.8203 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5604 -1.8968 2.5264 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5467 -1.3468 0.0673 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9040 -2.0732 1.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9516 -1.5097 2.2682 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2246 -3.5204 0.9935 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6206 1.5066 0.7741 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2901 2.4753 1.2111 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2236 0.2573 0.8200 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3962 3.2862 -0.8212 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4010 3.8034 0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7919 3.1158 0.8881 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0221 -0.3268 -0.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1590 0.7624 -1.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9248 1.9056 -0.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2849 0.3802 1.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 1.3438 -0.6945 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9746 -0.7459 -2.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2678 -1.1016 -2.2287 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8117 0.5162 -2.7940 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8415 -1.5234 0.0841 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 1.0666 1.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4486 -0.4093 2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2816 -0.0458 2.6268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4595 -2.7372 -0.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2917 -2.6574 -0.5790 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1193 -2.9928 1.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0598 -0.9489 2.6595 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8564 1.0337 2.0271 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4660 -0.6452 2.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3092 -1.3778 0.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5789 -1.4432 1.0079 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5123 -0.8679 2.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8942 -2.1306 1.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6628 1.8105 1.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2288 1.0447 1.8064 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9310 1.8494 0.2569 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7892 -1.3042 -1.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0262 1.5548 -2.0089 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2797 0.0993 -2.9869 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9679 0.6193 -2.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3198 -0.9935 -2.1568 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7759 2.4172 -0.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2983 2.1918 0.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1333 2.3868 -1.3079 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9702 0.5252 -2.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4632 0.3543 -2.4064 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0569 -1.3171 -2.0708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4388 1.4393 1.0405 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6716 1.8363 -0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9463 2.0359 -0.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9992 1.0979 -1.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5318 -2.1399 2.4553 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2281 -3.6271 0.5217 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4878 -3.9211 0.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1316 -4.0756 1.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2221 0.1986 0.6007 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 1 20 30 1 0 10 31 1 0 5 32 1 0 32 33 1 0 33 34 2 0 33 35 1 0 2 36 1 0 36 37 2 0 36 38 1 0 28 8 1 0 28 11 1 0 25 13 1 0 23 16 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 1 6 46 1 6 7 47 1 0 7 48 1 0 7 49 1 0 8 50 1 1 9 51 1 0 9 52 1 0 10 53 1 1 12 54 1 0 12 55 1 0 12 56 1 0 14 57 1 0 15 58 1 0 15 59 1 0 16 60 1 6 18 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 19 66 1 0 20 67 1 6 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 24 72 1 0 24 73 1 0 24 74 1 0 26 75 1 0 27 76 1 0 27 77 1 0 29 78 1 0 29 79 1 0 29 80 1 0 30 81 1 0 31 82 1 0 35 83 1 0 35 84 1 0 35 85 1 0 38 86 1 0 M END

Standard InCHIKey	PXBRGMAJKPPNOG-JHFAAVTGSA-N
Standard InCHI	InChI=1S/C32H48O6/c1-18(28(36)37)9-11-24(38-20(3)33)19(2)23-17-27(35)32(8)22-10-12-25-29(4,5)26(34)14-15-30(25,6)21(22)13-16-31(23,32)7/h9-10,13,19,23-27,34-35H,11-12,14-17H2,1-8H3,(H,36,37)/b18-9+/t19-,23+,24-,25-,26-,27-,30+,31+,32+/m0/s1
SMILES	C/C(=CC[C@@H]([C@@H](C)[C@H]1C[C@@H]([C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)O)O)OC(=O)C)/C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	528.35	Volume:	567.361 ? Van der Waals volume.
Dense:	0.931	LogP:	3.071 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.971 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.42 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.296	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.317	Fsp³:	0.75
MCE-18:	86.25 ? 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:	0.757	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.062 ? 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:	0.36	Promiscuous compounds:	0.294

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.397	MDCK Permeability:	-5.057
Pgp-inhibitor:	0.05	Pgp-substrate:	0.371
PAMPA:	0.996 ? 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):	0.027
20% Bioavailability (F20%):	0.808	30% Bioavailability (F30%):	0.663
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.925
Plasma Protein Binding (PPB):	80.482%	Volume Distribution (VD):	-0.454
Fu:	14.029% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.053
BSEP inhibitor:	0.634

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.051	CYP2C19-substrate:	0.108
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.976	CYP3A4-substrate:	0.909
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.937 ? 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):

6.955

Half-life (T1/2):

1.183

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.043
Human Hepatotoxicity (H-HT):	0.73	Drug-induced Liver Injury (DILI):	0.416
AMES Toxicity:	0.115	Rat Oral Acute Toxicity:	0.256
Maximum Recommended Daily Dose:	0.559	Skin Sensitization:	0.89
Carcinogencity:	0.363	Eye Corrosion:	0.0
Eye Irritation:	0.077	Respiratory Toxicity:	0.533
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.899
Hematotoxicity:	0.319	Drug-induced Nephrotoxicity:	0.662
Genotoxicity:	0.694	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.143	Hek293 Cytotoxicity:	0.092
BCF:	0.495 ? 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:	3.326 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.015 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.175 ? 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	=	95000.0	nM	PMID[28504879]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	6.25	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 NPC489791 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	17741
0.1-0.2	26444
0.2-0.3	5245
0.3-0.4	326
0.4-0.5	61
0.5-0.6	33
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8143	Intermediate Similarity	NPC166120
0.7794	Intermediate Similarity	NPC141401
0.7571	Intermediate Similarity	NPC58410
0.7101	Intermediate Similarity	NPC138536
0.6364	Remote Similarity	NPC94393
0.6053	Remote Similarity	NPC85742
0.6053	Remote Similarity	NPC22421
0.5974	Remote Similarity	NPC39082
0.5974	Remote Similarity	NPC610107
0.5921	Remote Similarity	NPC276127
0.5921	Remote Similarity	NPC478307
0.5875	Remote Similarity	NPC489797
0.5844	Remote Similarity	NPC478312
0.5823	Remote Similarity	NPC92022
0.5802	Remote Similarity	NPC76162
0.5769	Remote Similarity	NPC489808
0.5769	Remote Similarity	NPC478301
0.5769	Remote Similarity	NPC489800
0.575	Remote Similarity	NPC482571
0.5732	Remote Similarity	NPC489794
0.5714	Remote Similarity	NPC147568
0.5663	Remote Similarity	NPC489809
0.5658	Remote Similarity	NPC214697
0.5641	Remote Similarity	NPC285702
0.5641	Remote Similarity	NPC166745
0.5641	Remote Similarity	NPC235464
0.56	Remote Similarity	NPC212948
0.5556	Remote Similarity	NPC201852
0.5526	Remote Similarity	NPC203035
0.5294	Remote Similarity	NPC146822
0.5119	Remote Similarity	NPC478304
0.5119	Remote Similarity	NPC231673
0.5116	Remote Similarity	NPC482569
0.5065	Remote Similarity	NPC222845
0.5065	Remote Similarity	NPC296577
0.5063	Remote Similarity	NPC484975
0.5063	Remote Similarity	NPC48647
0.5063	Remote Similarity	NPC321301
0.5063	Remote Similarity	NPC477812
0.506	Remote Similarity	NPC482568

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489791 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5949
0.1-0.2	3112
0.2-0.3	87
0.3-0.4	2
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