NPASS Compound

Natural Product: NPC125399

Natural Product ID	NPC125399
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dihydroniloticin
IUPAC Name	(3S,5R,9R,10R,13S,14S,17S)-17-[(2S,4R)-4-[(2S)-3,3-dimethyloxiran-2-yl]-4-hydroxybutan-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2386303
PubChem CID	73351981
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 83 87 0 0 0 0 0 0 0 0999 V2000 4.1751 2.4035 -0.4097 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2480 1.1738 -0.5169 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0179 1.4353 0.1540 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9082 1.7583 1.5999 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3746 1.8583 1.7932 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2392 1.5305 0.4803 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8246 0.5520 -0.0656 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7927 -0.6257 0.8717 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4595 0.2608 -1.4686 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0128 0.0660 -1.7395 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8134 -0.1768 -0.5137 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5617 0.8948 0.4964 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4755 1.2799 1.3613 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8453 0.7148 1.4710 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0122 -0.3970 0.5182 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2913 -0.3099 -0.7950 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8031 0.7509 -1.7265 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 -1.6408 -1.4993 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9218 -2.0029 -1.6926 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7295 -1.9881 -0.4261 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4604 -0.7758 0.4326 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8345 -1.2156 1.8641 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4059 0.3119 0.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0836 -1.9316 -0.7994 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2864 2.8205 -0.3209 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0651 -0.0203 -0.5125 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9861 -0.3075 0.6263 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7498 -1.6311 0.3680 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6912 -1.9786 1.2977 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1371 -1.6346 -0.0062 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6451 -2.7479 -0.8868 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0124 -0.4015 0.0017 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3657 -0.5061 1.8412 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5877 2.4850 0.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5191 3.2966 -0.5489 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9202 2.4060 -1.2060 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9607 1.2925 -1.6692 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6624 2.4508 -0.3068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3001 2.7945 1.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3460 1.0927 2.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0551 1.2176 2.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0727 2.8900 2.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7794 -1.6103 0.3698 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7106 -0.6692 1.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0221 -0.5601 1.6488 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0309 -0.6661 -1.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8667 1.0561 -2.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 -0.8065 -2.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3643 0.9674 -2.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5033 -1.1427 -0.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2417 2.0894 2.0832 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5270 1.5777 1.3082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0347 0.3237 2.4974 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5298 -1.2991 1.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6747 1.7728 -1.3738 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8747 0.5023 -1.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 0.5581 -2.7194 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9945 -2.4677 -0.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0060 -1.6046 -2.4930 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4255 -1.3957 -2.4900 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9463 -3.0497 -2.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6028 -2.9384 0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0556 -1.8403 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8104 -1.7475 1.8496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9789 -0.3208 2.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9988 1.3137 -0.0477 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2556 0.4220 0.8057 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9549 0.0454 -0.8889 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6757 -1.8742 -0.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1702 3.6793 0.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3855 3.1077 -0.3420 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0193 2.7274 -1.3685 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7687 0.0345 -1.4171 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5160 -0.9751 -0.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7580 0.4713 0.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0706 -2.3921 -0.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0207 -2.7195 -1.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6906 -2.5603 -1.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5276 -3.7416 -0.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7263 0.2739 -0.8317 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9442 0.1646 0.9383 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0635 -0.7178 -0.1469 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0418 -1.4333 1.8771 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 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 6 25 1 6 2 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 27 33 1 0 7 3 1 0 16 11 1 0 30 28 1 0 12 6 1 0 21 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 6 3 38 1 6 4 39 1 0 4 40 1 0 5 41 1 0 5 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 11 50 1 1 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 1 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 1 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 1 28 76 1 6 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 M END

Standard InCHIKey	UMTABACRBSGXGK-ZAVAKTSASA-N
Standard InCHI	InChI=1S/C30H50O3/c1-18(17-22(31)25-27(4,5)33-25)19-11-15-30(8)21-9-10-23-26(2,3)24(32)13-14-28(23,6)20(21)12-16-29(19,30)7/h9,18-20,22-25,31-32H,10-17H2,1-8H3/t18-,19-,20-,22+,23-,24-,25-,28+,29-,30+/m0/s1
SMILES	C[C@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C[C@H]([C@@H]1OC1(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	458.38	Volume:	508.388 ? Van der Waals volume.
Dense:	0.902	LogP:	5.091 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.224 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.415 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	23.0
TPSA:	52.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.372	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.975	Fsp³:	0.933
MCE-18:	98.276 ? 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:	0.846	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.307	Promiscuous compounds:	0.1

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.97	MDCK Permeability:	-4.824
Pgp-inhibitor:	0.621	Pgp-substrate:	0.244
PAMPA:	0.922 ? 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%):	0.122	30% Bioavailability (F30%):	0.075
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.708	MRP1:	0.688
Plasma Protein Binding (PPB):	89.697%	Volume Distribution (VD):	-0.116
Fu:	12.297% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.968
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.946	CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.629
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.981 ? 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):

15.936

Half-life (T1/2):

1.165

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.356
Human Hepatotoxicity (H-HT):	0.559	Drug-induced Liver Injury (DILI):	0.103
AMES Toxicity:	0.23	Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.656	Skin Sensitization:	0.826
Carcinogencity:	0.777	Eye Corrosion:	0.009
Eye Irritation:	0.344	Respiratory Toxicity:	0.661
Drug-induced Neurotoxicity:	0.076	Ototoxicity:	0.74
Hematotoxicity:	0.261	Drug-induced Nephrotoxicity:	0.486
Genotoxicity:	0.18	RPMI-8226 Immunitoxicity:	0.065
A549 Cytotoxicity:	0.119	Hek293 Cytotoxicity:	0.407
BCF:	2.354 ? 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:	4.327 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.415 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.061 ? 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
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	twig	Dongfang, Hainan Province, China	2010-Mar	PMID[23734701]
NPO10033	Turraea pubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10033	Turraea pubescens	Species	Meliaceae	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	2

Activity Type	# Activity
Cell line	2

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	20000.0	nM	PMID[25437914]
NPT116	Cell line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[20619938]

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 NPC125399 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	20833
0.1-0.2	23335
0.2-0.3	4858
0.3-0.4	662
0.4-0.5	130
0.5-0.6	15
0.6-0.7	17
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	NPC486522
0.7458	Intermediate Similarity	NPC30166
0.7302	Intermediate Similarity	NPC486521
0.7302	Intermediate Similarity	NPC262870
0.7097	Intermediate Similarity	NPC470077
0.7097	Intermediate Similarity	NPC470049
0.6567	Remote Similarity	NPC324598
0.6515	Remote Similarity	NPC210268
0.6515	Remote Similarity	NPC190604
0.6462	Remote Similarity	NPC486523
0.6418	Remote Similarity	NPC472240
0.6418	Remote Similarity	NPC262858
0.6406	Remote Similarity	NPC470224
0.6176	Remote Similarity	NPC484789
0.6176	Remote Similarity	NPC484801
0.6176	Remote Similarity	NPC484786
0.6176	Remote Similarity	NPC484787
0.6176	Remote Similarity	NPC484788
0.6087	Remote Similarity	NPC471293
0.6	Remote Similarity	NPC484791
0.6	Remote Similarity	NPC5358
0.6	Remote Similarity	NPC484790
0.6	Remote Similarity	NPC216260
0.5758	Remote Similarity	NPC328052
0.5652	Remote Similarity	NPC318390
0.5455	Remote Similarity	NPC1319
0.5441	Remote Similarity	NPC73969
0.5362	Remote Similarity	NPC90652
0.5362	Remote Similarity	NPC155255
0.5352	Remote Similarity	NPC142361
0.5352	Remote Similarity	NPC474684
0.519	Remote Similarity	NPC609156
0.5143	Remote Similarity	NPC196485
0.5143	Remote Similarity	NPC245972
0.5143	Remote Similarity	NPC260992
0.5139	Remote Similarity	NPC471224
0.5068	Remote Similarity	NPC470375
0.5068	Remote Similarity	NPC470376

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC125399 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7499
0.1-0.2	1550
0.2-0.3	97
0.3-0.4	3
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