NPASS Compound

Natural Product: NPC329417

Natural Product ID	NPC329417
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Polyporoid C
IUPAC Name	(2S,3R,5R,9R,10R,13R,14S,16S,17R)-17-[(2R,3R)-2,3-dihydroxy-5,6-dimethylheptan-2-yl]-2,3,14,16-tetrahydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms	Polyporoid C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL411238
PubChem CID	44449996
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives

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 81 84 0 0 0 0 0 0 0 0999 V2000 8.0900 -0.4745 -0.6745 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5454 -0.6267 -0.6442 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0136 -0.1316 -1.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0872 0.1666 0.5243 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3894 1.6475 0.4355 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7701 -0.1862 1.1121 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5769 -0.1047 0.2407 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2572 -0.4287 0.9217 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2505 -1.8370 1.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1968 -0.1656 -0.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3152 1.3017 -0.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1203 1.8393 -0.6124 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8887 0.5846 -0.7517 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2008 -0.2843 0.3202 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 -1.6368 0.2493 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3041 -1.6264 0.4500 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9933 -0.6628 -0.4925 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3071 0.6523 -0.3504 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9322 1.7221 0.0856 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3540 1.6851 0.4632 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0497 2.7171 0.5510 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9260 0.3628 0.7362 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4561 -0.6102 -0.2999 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1143 -0.4165 -1.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1033 0.6973 -1.7020 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0376 0.7790 -0.5414 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4279 0.4210 0.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5718 2.0883 -0.5251 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9037 0.4679 -2.8480 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8965 -2.0087 0.1712 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4668 0.2899 1.6869 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6737 0.0498 -1.9950 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8466 1.4530 -1.8150 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1142 0.4435 1.9881 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6968 -1.0645 -0.7988 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3310 0.3854 -1.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4499 -0.3265 0.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4910 -1.4304 -1.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2637 -1.6742 -0.5297 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6860 -0.9886 -2.5841 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9077 0.2757 -2.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3340 0.7156 -1.9135 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8483 -0.1590 1.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1165 2.0675 -0.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8626 2.1416 1.2783 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4700 1.8598 0.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5756 0.4122 2.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9101 -1.2315 1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5220 0.8622 -0.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8830 -2.5402 0.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6634 -2.0093 2.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2590 -2.2098 1.6005 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4122 -0.8387 -0.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8430 1.9095 0.1855 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3522 2.4795 0.2347 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2685 2.4640 -1.5342 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4951 -2.2433 -0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4117 -2.2213 1.1335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6692 -2.6459 0.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5184 -1.4417 1.5048 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8086 -1.0748 -1.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3760 2.6431 0.1625 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6043 -0.0465 1.7233 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6166 -1.3331 -2.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3398 -0.1898 -2.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6172 1.6927 -1.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9162 0.1083 -0.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8821 -0.4951 1.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6930 1.2356 1.5067 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8834 2.2127 0.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4180 1.2729 -3.0893 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5675 -2.7868 -0.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6059 -2.1907 1.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0211 -2.0154 0.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 0.3462 1.7895 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0572 1.2833 1.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 -0.4274 2.4382 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8631 -0.8930 -2.1105 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7053 0.6767 -2.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7019 1.2313 1.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8443 -1.9666 -0.4089 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 25 29 1 0 23 30 1 0 14 31 1 0 13 32 1 0 11 33 1 0 8 34 1 0 7 35 1 0 14 10 1 0 18 13 1 0 23 17 1 0 27 22 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 5 46 1 0 6 47 1 0 6 48 1 0 7 49 1 0 9 50 1 0 9 51 1 0 9 52 1 0 10 53 1 0 11 54 1 0 12 55 1 0 12 56 1 0 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 19 62 1 0 22 63 1 0 24 64 1 0 24 65 1 0 25 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 32 78 1 0 33 79 1 0 34 80 1 0 35 81 1 0 M END

Standard InCHIKey	RVRAYMBCPTYQKZ-UFOPSCFWSA-N
Standard InCHI	InChI=1S/C28H46O7/c1-14(2)15(3)9-23(33)27(6,34)24-22(32)13-28(35)17-10-19(29)18-11-20(30)21(31)12-25(18,4)16(17)7-8-26(24,28)5/h10,14-16,18,20-24,30-35H,7-9,11-13H2,1-6H3/t15?,16-,18-,20+,21-,22-,23+,24-,25+,26+,27-,28+/m0/s1
SMILES	CC(C)C(C)CC(C(C)(C1C(CC2(C1(CCC3C2=CC(=O)C4C3(CC(C(C4)O)O)C)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	494.32	Volume:	514.877 ? Van der Waals volume.
Dense:	0.96	LogP:	2.569 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.002 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	138.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.343	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.421	Fsp³:	0.893
MCE-18:	88.491 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.06	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.103 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.235	Promiscuous compounds:	0.044

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.377	MDCK Permeability:	-4.891
Pgp-inhibitor:	0.0	Pgp-substrate:	0.706
PAMPA:	0.999 ? 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):	0.006
20% Bioavailability (F20%):	0.004	30% Bioavailability (F30%):	0.011
50% Bioavailability (F50%):	0.877

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.4	MRP1:	0.999
Plasma Protein Binding (PPB):	67.053%	Volume Distribution (VD):	-0.163
Fu:	35.729% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.004
OATP1B3 inhibitor:	0.613	BCRP inhibitor:	0.001
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.099	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.202
HLM stability:	0.0 ? 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):

8.419

Half-life (T1/2):

3.183

ADMET: Toxicity

hERG Blockers:	0.124	hERG Blockers (10um):	0.644
Human Hepatotoxicity (H-HT):	0.517	Drug-induced Liver Injury (DILI):	0.016
AMES Toxicity:	0.092	Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.923	Skin Sensitization:	0.027
Carcinogencity:	0.211	Eye Corrosion:	0.0
Eye Irritation:	0.007	Respiratory Toxicity:	0.351
Drug-induced Neurotoxicity:	0.294	Ototoxicity:	0.992
Hematotoxicity:	0.041	Drug-induced Nephrotoxicity:	0.201
Genotoxicity:	0.022	RPMI-8226 Immunitoxicity:	0.077
A549 Cytotoxicity:	0.054	Hek293 Cytotoxicity:	0.308
BCF:	0.622 ? 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:	3.577 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.528 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.243 ? 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
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO17579	Polyporus umbellatus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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
ID50	1

Activity Type	# Activity
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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.184	uM	PMID[18439824]

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 NPC329417 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	19453
0.1-0.2	27765
0.2-0.3	2573
0.3-0.4	17
0.4-0.5	15
0.5-0.6	16
0.6-0.7	18
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
0.7419	Intermediate Similarity	NPC85829
0.6462	Remote Similarity	NPC204833
0.6462	Remote Similarity	NPC209502
0.6364	Remote Similarity	NPC214264
0.6364	Remote Similarity	NPC475060
0.6269	Remote Similarity	NPC296945
0.6269	Remote Similarity	NPC601682
0.6119	Remote Similarity	NPC50692
0.6119	Remote Similarity	NPC260268
0.6119	Remote Similarity	NPC48733
0.6119	Remote Similarity	NPC171137
0.6119	Remote Similarity	NPC152695
0.6119	Remote Similarity	NPC319077
0.6119	Remote Similarity	NPC83744
0.6119	Remote Similarity	NPC76084
0.6119	Remote Similarity	NPC97202
0.6119	Remote Similarity	NPC601752
0.6029	Remote Similarity	NPC220229
0.6	Remote Similarity	NPC476027
0.5857	Remote Similarity	NPC202167
0.5857	Remote Similarity	NPC49958
0.5833	Remote Similarity	NPC49492
0.5833	Remote Similarity	NPC326542
0.5833	Remote Similarity	NPC266728
0.5821	Remote Similarity	NPC150531
0.5781	Remote Similarity	NPC603391
0.5775	Remote Similarity	NPC317210
0.5735	Remote Similarity	NPC302607
0.5735	Remote Similarity	NPC477915
0.5652	Remote Similarity	NPC149047
0.5541	Remote Similarity	NPC600136
0.5479	Remote Similarity	NPC207251
0.5395	Remote Similarity	NPC109973
0.5128	Remote Similarity	NPC475041
0.5128	Remote Similarity	NPC600372

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC329417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6983
0.1-0.2	2044
0.2-0.3	123
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