NPASS Compound

Natural Product: NPC204833

Natural Product ID	NPC204833
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Polyporusterone D
IUPAC Name	(2S,3R,5R,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-17-[(3R,5S)-3-hydroxy-5,6-dimethylhept-1-en-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms	Polyporusterone D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479518
PubChem CID	44575601
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids [CHEMONTID:0001467] Androgens 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 77 80 0 0 0 0 0 0 0 0999 V2000 6.4384 -0.1264 0.2240 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -0.4072 0.8583 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7140 -1.8408 0.8285 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8026 -2.5766 1.6589 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7747 -2.5055 -0.5267 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0565 0.6250 0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6467 0.9358 -0.7576 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6233 2.0652 -0.7841 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9190 3.0820 -1.5843 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4341 2.0547 0.0829 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8125 3.4333 0.1439 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5821 3.2199 -0.4991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8973 1.9309 0.1711 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3551 1.0865 -0.1991 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3109 0.7743 -1.6742 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2310 -0.1286 0.6253 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9575 -0.9710 0.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2184 -0.1366 0.3324 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0349 1.1770 -0.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8669 1.5836 -1.2483 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9958 0.7242 -1.6695 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9539 1.1955 -2.2897 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9692 -0.7248 -1.3383 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4823 -0.8292 0.0723 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3953 -2.2670 0.5433 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5474 -0.1803 0.9725 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8978 -0.7901 0.8125 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0625 -1.9758 1.5514 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3603 -0.9204 -0.6028 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2982 -1.3698 -1.5492 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4048 -1.8587 -0.6415 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9767 2.0784 1.5190 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1445 -0.1225 -1.4428 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4275 -0.2879 -0.8693 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6449 0.9535 0.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1889 -0.7055 0.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3543 -0.2437 1.9877 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7474 -2.0103 1.2958 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6402 -2.8609 0.9860 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2207 -1.8838 2.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3806 -3.4377 2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2146 -1.9031 -1.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7609 -2.8640 -0.8269 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3856 -3.4497 -0.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1392 0.3077 1.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4607 1.5819 1.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5325 1.3217 -1.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8449 3.0737 -2.1665 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2926 3.9125 -1.7190 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7768 1.7774 1.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3566 4.2566 -0.2589 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5678 3.6280 1.2460 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5188 3.1921 -1.5837 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2566 4.0285 -0.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4680 -0.3089 -1.7979 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6933 0.9656 -2.1146 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0258 1.3163 -2.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0190 0.1278 1.7080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0969 -0.7937 0.6260 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0152 -1.7994 0.9404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8409 -1.4430 -0.7939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2221 0.1179 1.4548 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7448 2.5374 -1.7169 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2412 -1.2657 -2.0084 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5596 -2.8230 0.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3474 -2.2421 1.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3146 -2.8509 0.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5922 0.9013 0.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2276 -0.3555 2.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6168 -0.0666 1.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4098 -1.8063 2.4544 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7909 0.0386 -0.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6535 -1.1317 -2.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1542 -2.4725 -1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2009 -2.5230 0.0694 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1898 2.0351 2.0623 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6324 -0.7796 -0.9719 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 3 5 1 0 2 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 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 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 21 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 13 32 1 1 7 33 1 0 14 10 1 0 24 18 1 0 19 13 1 0 30 23 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 7 47 1 6 9 48 1 0 9 49 1 0 10 50 1 1 11 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 15 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 1 20 63 1 0 23 64 1 6 25 65 1 0 25 66 1 0 25 67 1 0 26 68 1 0 26 69 1 0 27 70 1 1 28 71 1 0 29 72 1 6 30 73 1 0 30 74 1 0 31 75 1 0 32 76 1 0 33 77 1 0 M END

Standard InCHIKey	RHWDQPXMKCQCKR-IWEPWQGWSA-N
Standard InCHI	InChI=1S/C28H44O5/c1-15(2)16(3)11-22(29)17(4)18-8-10-28(33)20-12-23(30)21-13-24(31)25(32)14-26(21,5)19(20)7-9-27(18,28)6/h12,15-16,18-19,21-22,24-25,29,31-33H,4,7-11,13-14H2,1-3,5-6H3/t16-,18+,19-,21-,22+,24+,25-,26+,27+,28+/m0/s1
SMILES	C[C@H](C(C)C)C[C@H](C(=C)[C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	460.32	Volume:	494.66 ? Van der Waals volume.
Dense:	0.931	LogP:	3.336 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.312 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.454 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.468	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.23	Fsp³:	0.821
MCE-18:	81.569 ? 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:	0.676	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.407	Promiscuous compounds:	0.345

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835	MDCK Permeability:	-4.55
Pgp-inhibitor:	0.009	Pgp-substrate:	0.973
PAMPA:	0.992 ? 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%):	0.313	30% Bioavailability (F30%):	0.223
50% Bioavailability (F50%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023	MRP1:	0.375
Plasma Protein Binding (PPB):	69.577%	Volume Distribution (VD):	-0.013
Fu:	28.304% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.968
OATP1B3 inhibitor:	0.691	BCRP inhibitor:	0.381
BSEP inhibitor:	0.477

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.717	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.688
HLM stability:	0.98 ? 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):

7.358

Half-life (T1/2):

2.232

ADMET: Toxicity

hERG Blockers:	0.102	hERG Blockers (10um):	0.262
Human Hepatotoxicity (H-HT):	0.684	Drug-induced Liver Injury (DILI):	0.067
AMES Toxicity:	0.432	Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.967	Skin Sensitization:	0.974
Carcinogencity:	0.906	Eye Corrosion:	0.0
Eye Irritation:	0.117	Respiratory Toxicity:	0.528
Drug-induced Neurotoxicity:	0.431	Ototoxicity:	0.848
Hematotoxicity:	0.274	Drug-induced Nephrotoxicity:	0.939
Genotoxicity:	0.842	RPMI-8226 Immunitoxicity:	0.236
A549 Cytotoxicity:	0.721	Hek293 Cytotoxicity:	0.825
BCF:	1.254 ? 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:	3.905 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.69 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.83 ? 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
IC50	1

Activity Type	# Activity
Cell line	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
NPT137	Cell line	L1210	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[14987072]

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 NPC204833 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	20131
0.1-0.2	26459
0.2-0.3	3182
0.3-0.4	36
0.4-0.5	13
0.5-0.6	9
0.6-0.7	25
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
0.7377	Intermediate Similarity	NPC209502
0.7258	Intermediate Similarity	NPC85829
0.7097	Intermediate Similarity	NPC477915
0.6719	Remote Similarity	NPC76084
0.6667	Remote Similarity	NPC150531
0.6562	Remote Similarity	NPC302607
0.6462	Remote Similarity	NPC329417
0.6462	Remote Similarity	NPC149047
0.6462	Remote Similarity	NPC214264
0.6462	Remote Similarity	NPC475060
0.6462	Remote Similarity	NPC50692
0.6462	Remote Similarity	NPC260268
0.6462	Remote Similarity	NPC48733
0.6462	Remote Similarity	NPC171137
0.6462	Remote Similarity	NPC152695
0.6462	Remote Similarity	NPC319077
0.6462	Remote Similarity	NPC83744
0.6462	Remote Similarity	NPC97202
0.6462	Remote Similarity	NPC601752
0.6364	Remote Similarity	NPC296945
0.6364	Remote Similarity	NPC220229
0.6364	Remote Similarity	NPC601682
0.6324	Remote Similarity	NPC317210
0.6176	Remote Similarity	NPC202167
0.6176	Remote Similarity	NPC49958
0.6129	Remote Similarity	NPC603391
0.6087	Remote Similarity	NPC476027
0.6	Remote Similarity	NPC207251
0.5915	Remote Similarity	NPC49492
0.5915	Remote Similarity	NPC266728
0.5833	Remote Similarity	NPC600136
0.5676	Remote Similarity	NPC109973
0.56	Remote Similarity	NPC475041
0.56	Remote Similarity	NPC600372
0.5479	Remote Similarity	NPC326542
0.5217	Remote Similarity	NPC154072
0.5217	Remote Similarity	NPC477916

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC204833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6808
0.1-0.2	2209
0.2-0.3	133
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