NPASS Compound

Natural Product: NPC489790

Natural Product ID	NPC489790
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FUERKWNAVROYFF-GCVMWHCASA-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 84 87 0 0 0 0 0 0 0 0999 V2000 5.1805 0.0505 -0.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0096 0.0619 -0.0377 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2479 -0.5874 1.2688 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3612 0.0720 2.0328 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6765 0.0661 1.4229 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2912 1.1974 1.1434 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6298 2.5138 1.4566 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6087 1.1745 0.5325 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1976 2.2709 0.2649 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1993 -0.0421 0.2527 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8020 -0.3589 -0.7711 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8177 -1.7288 -1.3874 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3284 -2.0424 -1.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6367 -0.7498 -1.3127 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8273 0.1837 -2.4892 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7570 -0.8381 -0.8858 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6368 -1.6042 -1.5580 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0542 -1.7001 -1.1366 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4543 -0.4069 -0.4130 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8945 -0.2492 -0.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6725 -1.4590 0.1618 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4974 0.2629 -1.5271 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1855 0.8369 0.8030 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4555 0.5380 2.0730 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9831 0.7305 1.7788 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5684 -0.3023 0.7709 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5099 -1.6320 1.5423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1840 -0.0827 0.2757 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3800 0.7793 0.9114 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0192 0.9900 0.4277 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4899 -0.3256 -0.1019 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2733 -1.4454 0.9190 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5517 1.0847 0.9749 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1726 2.2809 0.6633 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4911 3.2051 0.2007 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6409 2.3779 0.9090 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5990 1.0699 -1.1588 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7861 -0.2228 -2.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9279 -0.7255 -0.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8431 1.1646 0.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3334 -0.3814 1.9011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3995 -1.6865 1.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0402 1.1225 2.2594 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4231 -0.4357 3.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1851 -0.8566 1.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6372 2.5750 0.9469 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4588 2.6204 2.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2969 3.3256 1.1467 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0707 -0.0798 -0.2545 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7232 0.3478 -1.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3015 -2.4947 -0.7826 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3083 -1.7101 -2.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9974 -2.8625 -1.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1562 -2.2970 -2.7012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5611 -0.2403 -3.2063 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9849 1.2252 -2.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1540 0.1601 -3.0529 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3092 -2.1558 -2.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2646 -2.6019 -0.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6617 -1.7120 -2.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1182 0.4044 -1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7796 -1.6200 1.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7129 -1.3283 -0.2075 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3038 -2.3917 -0.3579 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1919 -0.3527 -2.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6183 0.3291 -1.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1515 1.3205 -1.6077 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7389 1.7773 0.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6937 1.2679 2.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6290 -0.4602 2.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8542 1.7600 1.4578 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4200 0.4942 2.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9405 -1.4852 2.4984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 -2.0075 1.8237 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9956 -2.4205 0.9964 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6936 1.3342 1.7618 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1340 1.7746 -0.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 1.2278 1.3182 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0748 -2.1811 0.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0414 -0.9778 1.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3313 -2.0219 0.6986 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9820 1.6225 1.6226 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2011 2.2411 -0.0337 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8767 3.4225 1.2588 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 6 14 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 26 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 1 23 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 31 11 1 0 31 14 1 0 28 16 1 0 26 19 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 1 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 5 45 1 0 7 46 1 0 7 47 1 0 7 48 1 0 10 49 1 0 11 50 1 6 12 51 1 0 12 52 1 0 13 53 1 0 13 54 1 0 15 55 1 0 15 56 1 0 15 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 6 21 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 22 67 1 0 23 68 1 6 24 69 1 0 24 70 1 0 25 71 1 0 25 72 1 0 27 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 30 77 1 0 30 78 1 0 32 79 1 0 32 80 1 0 32 81 1 0 36 82 1 0 36 83 1 0 36 84 1 0 M END

Standard InCHIKey	FUERKWNAVROYFF-GCVMWHCASA-N
Standard InCHI	InChI=1S/C32H48O4/c1-20(10-9-11-21(2)28(34)35)23-14-18-32(8)25-12-13-26-29(4,5)27(36-22(3)33)16-17-30(26,6)24(25)15-19-31(23,32)7/h11-12,15,20,23,26-27H,9-10,13-14,16-19H2,1-8H3,(H,34,35)/b21-11+/t20-,23-,26+,27+,30-,31-,32+/m1/s1
SMILES	C[C@H](CC/C=C(C)/C(=O)O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	496.36	Volume:	549.781 ? Van der Waals volume.
Dense:	0.903	LogP:	5.912 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.502 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.492 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.3	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.816	Fsp³:	0.75
MCE-18:	81.321 ? 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:	0.892	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.025 ? 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:	0.628	Promiscuous compounds:	0.225

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.092	MDCK Permeability:	-4.84
Pgp-inhibitor:	1.0	Pgp-substrate:	0.0
PAMPA:	0.071 ? 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):	0.039
20% Bioavailability (F20%):	0.984	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.902
Plasma Protein Binding (PPB):	89.274%	Volume Distribution (VD):	-0.407
Fu:	8.532% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.072
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.344
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.67
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.002 ? 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):

4.268

Half-life (T1/2):

0.602

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.049
Human Hepatotoxicity (H-HT):	0.713	Drug-induced Liver Injury (DILI):	0.687
AMES Toxicity:	0.098	Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.303	Skin Sensitization:	0.963
Carcinogencity:	0.352	Eye Corrosion:	0.035
Eye Irritation:	0.522	Respiratory Toxicity:	0.5
Drug-induced Neurotoxicity:	0.021	Ototoxicity:	0.578
Hematotoxicity:	0.517	Drug-induced Nephrotoxicity:	0.675
Genotoxicity:	0.821	RPMI-8226 Immunitoxicity:	0.03
A549 Cytotoxicity:	0.095	Hek293 Cytotoxicity:	0.21
BCF:	1.296 ? 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:	4.412 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.045 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.417 ? 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	>	101000.0	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 NPC489790 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	21721
0.1-0.2	23966
0.2-0.3	3756
0.3-0.4	290
0.4-0.5	84
0.5-0.6	25
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478313
0.791	Intermediate Similarity	NPC276127
0.791	Intermediate Similarity	NPC478307
0.7794	Intermediate Similarity	NPC136044
0.7361	Intermediate Similarity	NPC94393
0.7059	Intermediate Similarity	NPC212948
0.6812	Remote Similarity	NPC87552
0.662	Remote Similarity	NPC608955
0.6316	Remote Similarity	NPC478302
0.6267	Remote Similarity	NPC39082
0.6267	Remote Similarity	NPC610107
0.6133	Remote Similarity	NPC85742
0.6133	Remote Similarity	NPC22421
0.6104	Remote Similarity	NPC137552
0.6104	Remote Similarity	NPC99411
0.6	Remote Similarity	NPC141401
0.5921	Remote Similarity	NPC478312
0.5867	Remote Similarity	NPC478308
0.5641	Remote Similarity	NPC484969
0.557	Remote Similarity	NPC489803
0.557	Remote Similarity	NPC489804
0.5526	Remote Similarity	NPC214697
0.5443	Remote Similarity	NPC288464
0.5443	Remote Similarity	NPC477813
0.5443	Remote Similarity	NPC607198
0.5432	Remote Similarity	NPC478303
0.5432	Remote Similarity	NPC489796
0.5395	Remote Similarity	NPC138536
0.5366	Remote Similarity	NPC489799
0.5301	Remote Similarity	NPC489793
0.527	Remote Similarity	NPC475772
0.5256	Remote Similarity	NPC38232
0.525	Remote Similarity	NPC489807
0.525	Remote Similarity	NPC478298
0.5238	Remote Similarity	NPC478306
0.5238	Remote Similarity	NPC137291
0.5211	Remote Similarity	NPC205455
0.5205	Remote Similarity	NPC202389
0.5122	Remote Similarity	NPC489788
0.5122	Remote Similarity	NPC299325
0.506	Remote Similarity	NPC489795

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC489790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6391
0.1-0.2	2689
0.2-0.3	65
0.3-0.4	5
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