NPASS Compound

Natural Product: NPC477858

Natural Product ID	NPC477858
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	24-Hydroxycycloart-25-en-3-one
IUPAC Name	(1S,3R,8R,11R,12S,15R,16R)-15-[(2R)-5-hydroxy-6-methylhept-6-en-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	15767709
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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 80 84 0 0 0 0 0 0 0 0999 V2000 4.1645 -1.2174 1.1400 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1429 -0.9974 -0.0045 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7807 -0.1041 -0.9821 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9810 -0.4399 -1.7120 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3207 -0.6977 -1.2365 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0744 0.3394 -0.5243 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1989 0.7954 -1.0866 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7188 0.9532 0.7836 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0873 -0.9249 -2.4554 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8761 -0.5824 0.6392 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9271 0.7165 1.3960 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6620 1.4356 0.9462 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2685 0.2701 0.8625 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5624 -0.6774 -0.0039 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1184 -2.0273 0.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5899 -1.9820 0.3088 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 -0.7458 -0.1487 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6322 0.5236 0.3840 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9291 1.6810 -0.4777 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4517 1.8950 -0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1790 0.8307 0.3269 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7200 -0.5780 -0.0040 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1687 -0.7503 -1.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5979 -1.5933 0.6302 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6257 -1.0307 1.5594 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3813 0.0569 0.8809 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5623 0.1777 1.1555 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6562 0.9296 -0.0884 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0660 2.3655 0.2659 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9338 0.5738 -1.4896 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5597 -0.3441 -1.4289 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3597 -0.2858 2.2728 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 -1.8413 0.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5777 -1.8216 1.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3357 -0.2658 1.6725 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0674 -2.0184 -0.4683 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9944 0.8864 -0.4236 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0623 0.3001 -1.7724 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1043 0.4017 -2.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7308 -1.3061 -2.4561 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4707 -1.7218 -0.7617 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7706 1.5484 -0.5965 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5114 0.3949 -2.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5786 1.5952 1.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8673 1.6225 0.7604 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6679 0.1483 1.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8242 -0.1617 -3.0253 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7837 -1.4072 1.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8351 1.3110 1.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9417 0.5318 2.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3480 2.1989 1.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8330 1.8544 -0.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3187 -2.6343 0.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1814 -2.6125 -0.7790 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9483 -2.3017 1.3320 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0092 -2.8124 -0.3434 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2487 0.7503 1.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3758 2.5644 -0.1074 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6830 1.5706 -1.5437 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5906 2.8517 0.1626 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8641 2.1208 -1.4218 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 1.0217 1.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9450 0.0359 -2.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2687 -1.7585 -1.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1267 -2.1589 -0.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0200 -2.3985 1.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2946 -1.8684 1.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1177 -0.6903 2.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1539 2.3690 0.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8400 3.0727 -0.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5233 2.6894 1.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2419 -0.5121 -1.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8789 1.1159 -1.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1966 0.8254 -2.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8121 0.6773 -1.7232 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2368 -1.0453 -1.9597 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4168 -0.5273 -1.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4525 -0.3490 2.5906 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0216 0.4652 3.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 -1.2766 2.4286 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 2 0 6 8 1 0 5 9 1 0 2 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 17 16 1 1 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 14 31 1 6 13 32 1 1 14 10 1 0 18 13 1 0 22 17 1 0 23 17 1 0 28 21 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 6 3 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 7 42 1 0 7 43 1 0 8 44 1 0 8 45 1 0 8 46 1 0 9 47 1 0 10 48 1 1 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 18 57 1 1 19 58 1 0 19 59 1 0 20 60 1 0 20 61 1 0 21 62 1 1 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 29 69 1 0 29 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 32 79 1 0 32 80 1 0 M END

Standard InCHIKey	TXRLVQNUVQVFJG-KJOMNYIYSA-N
Standard InCHI	InChI=1S/C30H48O2/c1-19(2)22(31)9-8-20(3)21-12-14-28(7)24-11-10-23-26(4,5)25(32)13-15-29(23)18-30(24,29)17-16-27(21,28)6/h20-24,31H,1,8-18H2,2-7H3/t20-,21-,22?,23+,24-,27-,28+,29-,30+/m1/s1
SMILES	C[C@H](CCC(C(=C)C)O)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@@H]2CC[C@@H]5[C@]3(C4)CCC(=O)C5(C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	440.37	Volume:	496.961 ? Van der Waals volume.
Dense:	0.886	LogP:	3.943 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.43 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.63 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.454	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.563	Fsp³:	0.9
MCE-18:	133.07 ? 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:	0.894	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.61	Promiscuous compounds:	0.053

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068	MDCK Permeability:	-4.865
Pgp-inhibitor:	0.003	Pgp-substrate:	0.0
PAMPA:	0.32 ? 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%):	0.016	30% Bioavailability (F30%):	0.356
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.011
Plasma Protein Binding (PPB):	92.592%	Volume Distribution (VD):	0.237
Fu:	8.644% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.645
BSEP inhibitor:	0.265

ADMET: Metabolism

CYP1A2-inhibitor:	0.917	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.943
CYP2B6-substrate:	0.008	CYP2C8-inhibitor:	0.465
HLM stability:	0.052 ? 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):

16.061

Half-life (T1/2):

0.574

ADMET: Toxicity

hERG Blockers:	0.141	hERG Blockers (10um):	0.436
Human Hepatotoxicity (H-HT):	0.563	Drug-induced Liver Injury (DILI):	0.051
AMES Toxicity:	0.228	Rat Oral Acute Toxicity:	0.488
Maximum Recommended Daily Dose:	0.712	Skin Sensitization:	0.453
Carcinogencity:	0.792	Eye Corrosion:	0.002
Eye Irritation:	0.177	Respiratory Toxicity:	0.832
Drug-induced Neurotoxicity:	0.196	Ototoxicity:	0.724
Hematotoxicity:	0.453	Drug-induced Nephrotoxicity:	0.482
Genotoxicity:	0.592	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.158	Hek293 Cytotoxicity:	0.243
BCF:	2.671 ? 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:	5.074 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.314 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.345 ? 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
NPO31363	Rhus sylvestris	Species	Anacardiaceae	Eukaryota	stems and leaves	n.a.	n.a.	PMID[19447618]
NPO31363	Rhus sylvestris	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Inhibition	2
IC50	3

Activity Type	# Activity
Cell line	5

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	Inhibition	=	54.6	%	PMID[19447618]
NPT113	Cell line	RAW264.7	Mus musculus	Inhibition	=	20.9	%	PMID[19447618]
NPT926	Cell line	SK-MEL-1	Homo sapiens	IC50	>	50000	nM	PMID[19447618]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	50000	nM	PMID[19447618]
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	50000	nM	PMID[19447618]

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 NPC477858 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	23580
0.1-0.2	22868
0.2-0.3	2904
0.3-0.4	354
0.4-0.5	103
0.5-0.6	27
0.6-0.7	11
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
0.7885	Intermediate Similarity	NPC282275
0.7455	Intermediate Similarity	NPC479660
0.7308	Intermediate Similarity	NPC477857
0.717	Intermediate Similarity	NPC107704
0.6909	Remote Similarity	NPC264602
0.6852	Remote Similarity	NPC214770
0.6852	Remote Similarity	NPC477856
0.6792	Remote Similarity	NPC331618
0.6792	Remote Similarity	NPC257191
0.6429	Remote Similarity	NPC474123
0.6364	Remote Similarity	NPC255650
0.619	Remote Similarity	NPC23217
0.6066	Remote Similarity	NPC16287
0.6034	Remote Similarity	NPC76518
0.6	Remote Similarity	NPC474962
0.5938	Remote Similarity	NPC476174
0.5909	Remote Similarity	NPC70661
0.5781	Remote Similarity	NPC472745
0.5714	Remote Similarity	NPC472744
0.569	Remote Similarity	NPC273366
0.5469	Remote Similarity	NPC60350
0.5345	Remote Similarity	NPC196358
0.5333	Remote Similarity	NPC168824
0.5323	Remote Similarity	NPC89747
0.5323	Remote Similarity	NPC606508
0.5254	Remote Similarity	NPC200243
0.5254	Remote Similarity	NPC254509
0.5246	Remote Similarity	NPC189917
0.5246	Remote Similarity	NPC96812
0.5246	Remote Similarity	NPC39462
0.5224	Remote Similarity	NPC29152
0.5172	Remote Similarity	NPC299948
0.5172	Remote Similarity	NPC241085
0.5172	Remote Similarity	NPC607543
0.5167	Remote Similarity	NPC472342
0.5167	Remote Similarity	NPC145552
0.5147	Remote Similarity	NPC156546
0.5147	Remote Similarity	NPC611460
0.5082	Remote Similarity	NPC22133
0.5082	Remote Similarity	NPC49168
0.5082	Remote Similarity	NPC5046
0.5077	Remote Similarity	NPC483817

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477858 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7552
0.1-0.2	1488
0.2-0.3	110
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