NPASS Compound

Natural Product: NPC158846

Natural Product ID	NPC158846
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sootepin E
IUPAC Name	n.a.
Synonyms	Sootepin E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL557656
PubChem CID	44179870
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 80 83 0 0 0 0 0 0 0 0999 V2000 7.8622 -0.3356 0.5080 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6862 0.2045 1.2610 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4702 0.0368 0.8187 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1565 -0.7025 -0.4661 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4397 0.1822 -1.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1084 0.7608 -1.0383 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8220 1.7038 -2.2482 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0456 -0.2695 -0.9899 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2829 -1.3323 0.0146 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9081 -1.6831 0.6323 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0069 -1.1680 -0.4332 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2090 -2.0974 -1.5967 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4455 -1.0722 -0.0273 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2582 -2.1086 -0.7596 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7305 -1.9595 -0.7094 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2949 -0.9224 0.1862 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5102 -1.3175 1.5894 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0635 -2.4667 2.0341 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2421 -0.4186 2.5145 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5190 0.3424 0.0211 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2732 1.4428 -0.7351 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5457 1.8321 -0.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2069 2.9037 -0.8302 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6950 3.3229 -1.8951 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4092 3.4701 -0.4271 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6811 0.8785 1.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0698 0.2615 -0.1478 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5002 1.1540 -1.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1204 0.8839 -1.6661 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6651 0.1977 -0.6397 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7359 0.9799 0.6184 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9733 0.9327 2.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7096 -1.4292 0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8051 -0.2327 1.0791 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9432 0.1697 -0.4701 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6589 0.4527 1.4044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2184 -0.8136 -0.9231 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8173 -1.7008 -0.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3680 -0.3711 -2.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1734 1.0057 -1.6743 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2395 1.4024 -0.1580 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2622 1.1423 -2.9952 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4420 2.6661 -1.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8186 1.9105 -2.6859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9639 -0.6496 -2.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7175 -2.2663 -0.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8689 -1.0025 0.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8750 -2.7894 0.6831 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7723 -1.3081 1.6265 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2488 -2.4601 -1.7253 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3102 -3.0652 -1.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1242 -1.6998 -2.5668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4675 -1.3817 1.0605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9832 -2.0809 -1.8594 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0220 -3.1330 -0.3456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2464 -2.9308 -0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1626 -1.7783 -1.7478 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3563 -0.7637 -0.2129 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2577 -2.7057 3.1011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5229 -3.2043 1.4465 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9065 0.6153 2.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3216 -0.8359 3.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3075 -0.4014 2.1365 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5621 1.0703 -1.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6598 2.3716 -0.8076 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2309 2.3598 0.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2237 1.0098 0.1978 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6651 4.4065 -0.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6050 0.2310 2.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5720 1.9454 1.2987 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1916 1.1182 -2.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6285 2.2124 -0.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1745 0.3293 -2.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2584 1.8943 -1.9970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4772 2.0510 0.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7708 0.9739 1.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1092 0.5971 1.4474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0337 1.2737 3.0173 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5985 0.2988 3.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5587 1.8597 2.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 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 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 16 20 1 0 20 21 1 6 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 20 26 1 0 27 26 1 1 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 2 32 1 0 30 8 1 0 30 11 1 0 27 13 1 0 27 20 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 5 39 1 0 5 40 1 0 6 41 1 1 7 42 1 0 7 43 1 0 7 44 1 0 8 45 1 6 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 1 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 6 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 25 68 1 0 26 69 1 0 26 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 32 79 1 0 32 80 1 0 M END

Standard InCHIKey	KNVUFXYCGYEIRS-DZWGBXGJSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-20(2)9-8-10-22(5)24-13-15-28(7)25-12-11-23(21(3)4)29(16-14-26(31)32)19-30(25,29)18-17-27(24,28)6/h9,22-25H,3,8,10-19H2,1-2,4-7H3,(H,31,32)/t22-,23+,24-,25+,27-,28+,29-,30+/m1/s1
SMILES	CC(=CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H](C(=C)C)[C@@]4(CCC(=O)O)C[C@@]34CC[C@]12C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	502.881 ? Van der Waals volume.
Dense:	0.876	LogP:	5.954 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.087 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.305 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	20.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.384	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.271	Fsp³:	0.833
MCE-18:	108.782 ? 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:	0.889	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:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.763	Promiscuous compounds:	0.334

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.086	MDCK Permeability:	-4.862
Pgp-inhibitor:	0.095	Pgp-substrate:	0.0
PAMPA:	0.038 ? 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%):	0.303	30% Bioavailability (F30%):	0.03
50% Bioavailability (F50%):	0.685

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.755	MRP1:	0.999
Plasma Protein Binding (PPB):	97.053%	Volume Distribution (VD):	0.028
Fu:	3.075% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.758	BCRP inhibitor:	0.014
BSEP inhibitor:	0.983

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.863	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.978
HLM stability:	0.001 ? 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):

2.595

Half-life (T1/2):

1.074

ADMET: Toxicity

hERG Blockers:	0.065	hERG Blockers (10um):	0.14
Human Hepatotoxicity (H-HT):	0.507	Drug-induced Liver Injury (DILI):	0.122
AMES Toxicity:	0.087	Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.163	Skin Sensitization:	0.859
Carcinogencity:	0.477	Eye Corrosion:	0.586
Eye Irritation:	0.909	Respiratory Toxicity:	0.896
Drug-induced Neurotoxicity:	0.191	Ototoxicity:	0.651
Hematotoxicity:	0.687	Drug-induced Nephrotoxicity:	0.604
Genotoxicity:	0.101	RPMI-8226 Immunitoxicity:	0.047
A549 Cytotoxicity:	0.034	Hek293 Cytotoxicity:	0.064
BCF:	2.096 ? 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:	4.713 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.805 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.361 ? 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
NPO11647	Gardenia sootepensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19456120]
NPO33315	gardenia spp.	Species	Rubiaceae	Eukaryota	n.a.	Thai	n.a.	PMID[22142538]
NPO11647	Gardenia sootepensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11647	Gardenia sootepensis	Species	Rubiaceae	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

Activity Type	# Activity
IC50	5
Inhibition	1

Activity Type	# Activity
Cell line	3
Non-molecular	2
Tissue	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
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	3.14	ug.mL-1	PMID[15633995]
NPT323	Cell line	SW-620	Homo sapiens	IC50	=	4.22	ug.mL-1	DOI[10.1016/0960-894X(96)00096-0]
NPT845	Cell line	BT-474	Homo sapiens	IC50	=	6.07	ug.mL-1	PMID[17261619]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1.91	ug.mL-1	PMID[19456120]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	5.2	ug.mL-1	PMID[19456120]
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	=	92.0	%	PMID[22088956]

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 NPC158846 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	29518
0.1-0.2	17883
0.2-0.3	2158
0.3-0.4	182
0.4-0.5	77
0.5-0.6	23
0.6-0.7	7
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC194937
0.8421	Intermediate Similarity	NPC476038
0.807	Intermediate Similarity	NPC186975
0.7458	Intermediate Similarity	NPC162481
0.7167	Intermediate Similarity	NPC488282
0.7097	Intermediate Similarity	NPC482629
0.7049	Intermediate Similarity	NPC128496
0.6557	Remote Similarity	NPC236618
0.6349	Remote Similarity	NPC488286
0.6324	Remote Similarity	NPC476303
0.6308	Remote Similarity	NPC475007
0.619	Remote Similarity	NPC321690
0.6154	Remote Similarity	NPC488278
0.6	Remote Similarity	NPC117122
0.597	Remote Similarity	NPC488280
0.597	Remote Similarity	NPC488281
0.5915	Remote Similarity	NPC488284
0.5909	Remote Similarity	NPC488976
0.5882	Remote Similarity	NPC482627
0.5797	Remote Similarity	NPC488283
0.5667	Remote Similarity	NPC214770
0.5667	Remote Similarity	NPC477856
0.5652	Remote Similarity	NPC327788
0.5634	Remote Similarity	NPC488285
0.5634	Remote Similarity	NPC488279
0.5616	Remote Similarity	NPC176883
0.5522	Remote Similarity	NPC283733
0.55	Remote Similarity	NPC85346
0.55	Remote Similarity	NPC65897
0.55	Remote Similarity	NPC80237
0.5397	Remote Similarity	NPC139206
0.5323	Remote Similarity	NPC302041
0.5286	Remote Similarity	NPC98868
0.5217	Remote Similarity	NPC66344
0.5152	Remote Similarity	NPC110923
0.5152	Remote Similarity	NPC74296
0.5075	Remote Similarity	NPC16287

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7117
0.1-0.2	1957
0.2-0.3	76
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