NPASS Compound

Natural Product: NPC58524

Natural Product ID	NPC58524
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CMYFKSGATOJENB-OKYHLYSZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	50994309
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 85 88 0 0 0 0 0 0 0 0999 V2000 7.5370 0.2610 -0.5997 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7607 0.0776 0.6401 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5699 0.5988 0.7782 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9536 1.3860 -0.2892 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4300 1.1313 -0.2019 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2322 -0.3505 -0.3965 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7444 -0.8164 -1.7288 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9850 -0.9124 0.1197 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8093 -2.3964 -0.0916 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2990 -2.6833 -0.1188 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2147 -1.4424 0.5140 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1749 -1.6276 1.9690 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6203 -1.1000 0.3465 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5239 -1.9742 0.7523 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9961 -1.8414 0.6840 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3582 -0.5923 -0.0270 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8195 -0.2633 0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5487 -1.4375 -0.6578 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3942 -0.0289 1.3464 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0664 0.9327 -0.8779 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7886 1.5298 -1.4052 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8888 1.8208 -0.2260 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4542 0.5158 0.4107 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3300 0.6941 1.8812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0948 0.1791 -0.2484 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1362 1.2953 -0.0723 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2536 0.9098 0.3807 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6453 -0.4065 -0.2104 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4473 -0.3933 -1.6782 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7245 1.9405 -0.1637 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1104 2.7530 0.0426 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6301 3.5080 -0.9764 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3483 -0.7130 1.7470 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8622 1.3445 -0.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9503 0.0788 -1.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4843 -0.3334 -0.5887 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0148 0.4491 1.7135 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3129 1.2437 -1.2995 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0158 1.7606 -0.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1679 1.4642 0.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0565 -0.7529 0.3039 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8495 -1.0333 -1.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2005 -1.5809 -2.2549 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7614 0.0562 -2.4728 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0266 -0.6924 1.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1324 -2.6723 -1.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3276 -2.9915 0.6915 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0957 -2.9781 -1.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1709 -3.5839 0.5585 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0836 -2.2539 2.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6028 -2.3849 2.3251 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1513 -0.7344 2.5794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2056 -2.9479 1.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4204 -2.7600 0.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4664 -1.8097 1.6906 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1249 -0.7858 -1.1197 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6070 -2.3047 -0.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5180 -1.1251 -1.0900 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9012 -1.7294 -1.5340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5166 -0.0401 1.2329 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1784 1.0108 1.7284 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1662 -0.7694 2.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7024 0.7078 -1.7641 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0717 2.5026 -1.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3259 0.9291 -2.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0295 2.4404 -0.5511 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4755 2.4477 0.4777 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2798 0.8357 2.2268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7739 -0.0830 2.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8423 1.6567 2.1849 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4442 0.0279 -1.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0892 1.9660 -0.9809 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5482 1.9868 0.7241 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8963 1.7558 0.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 0.9421 1.4871 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1227 -1.3025 -2.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2619 0.4230 -2.0183 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3886 -0.1081 -2.2439 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3887 2.4123 -0.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9927 3.4928 -1.8998 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6712 3.2920 -1.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5572 4.5816 -0.6273 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8396 -1.6257 1.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1755 -0.0710 2.1722 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5800 -0.9078 2.5324 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 1 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 20 30 1 0 4 31 1 0 31 32 1 0 2 33 1 0 28 8 1 0 28 11 1 0 25 13 1 0 23 16 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 4 38 1 6 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 1 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 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 6 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 19 62 1 0 20 63 1 6 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 24 68 1 0 24 69 1 0 24 70 1 0 25 71 1 6 26 72 1 0 26 73 1 0 27 74 1 0 27 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 33 84 1 0 33 85 1 0 M END

Standard InCHIKey	CMYFKSGATOJENB-OKYHLYSZSA-N
Standard InCHI	InChI=1S/C31H52O2/c1-20(2)18-22(33-9)19-21(3)23-12-16-31(8)25-10-11-26-28(4,5)27(32)14-15-29(26,6)24(25)13-17-30(23,31)7/h10,18,21-24,26-27,32H,11-17,19H2,1-9H3/t21-,22-,23-,24-,26-,27-,29+,30-,31+/m0/s1
SMILES	CC(=C[C@@H](C[C@H](C)[C@@H]1CC[C@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)[C@H]3CC[C@@]12C)O)OC)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.4	Volume:	522.814 ? Van der Waals volume.
Dense:	0.873	LogP:	7.082 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.8 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.165 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	29.46 ? 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:	0.425	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.925	Fsp³:	0.871
MCE-18:	80.552 ? 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:	0.849	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? 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:	0.584	Promiscuous compounds:	0.215

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781	MDCK Permeability:	-4.677
Pgp-inhibitor:	0.948	Pgp-substrate:	0.044
PAMPA:	0.414 ? 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%):	0.138	30% Bioavailability (F30%):	0.03
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.883	MRP1:	0.812
Plasma Protein Binding (PPB):	93.232%	Volume Distribution (VD):	-0.077
Fu:	7.544% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.961
BSEP inhibitor:	0.99

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.208
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.968
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.998 ? 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):

15.696

Half-life (T1/2):

0.866

ADMET: Toxicity

hERG Blockers:	0.105	hERG Blockers (10um):	0.379
Human Hepatotoxicity (H-HT):	0.549	Drug-induced Liver Injury (DILI):	0.126
AMES Toxicity:	0.263	Rat Oral Acute Toxicity:	0.353
Maximum Recommended Daily Dose:	0.792	Skin Sensitization:	0.836
Carcinogencity:	0.82	Eye Corrosion:	0.008
Eye Irritation:	0.413	Respiratory Toxicity:	0.725
Drug-induced Neurotoxicity:	0.111	Ototoxicity:	0.546
Hematotoxicity:	0.357	Drug-induced Nephrotoxicity:	0.469
Genotoxicity:	0.219	RPMI-8226 Immunitoxicity:	0.128
A549 Cytotoxicity:	0.371	Hek293 Cytotoxicity:	0.526
BCF:	2.885 ? 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:	4.662 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.468 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.433 ? 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
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	stem	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19594	Cornus walteri	Species	Cornaceae	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

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

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 NPC58524 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	16744
0.1-0.2	27346
0.2-0.3	4982
0.3-0.4	605
0.4-0.5	138
0.5-0.6	18
0.6-0.7	15
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	NPC470049
0.746	Intermediate Similarity	NPC484789
0.746	Intermediate Similarity	NPC484801
0.746	Intermediate Similarity	NPC484786
0.746	Intermediate Similarity	NPC484787
0.746	Intermediate Similarity	NPC484788
0.7167	Intermediate Similarity	NPC30166
0.7097	Intermediate Similarity	NPC470077
0.7097	Intermediate Similarity	NPC125399
0.7097	Intermediate Similarity	NPC486522
0.6984	Remote Similarity	NPC470047
0.6984	Remote Similarity	NPC470046
0.697	Remote Similarity	NPC484791
0.697	Remote Similarity	NPC484790
0.6719	Remote Similarity	NPC486523
0.6567	Remote Similarity	NPC324598
0.6471	Remote Similarity	NPC5358
0.6471	Remote Similarity	NPC216260
0.6418	Remote Similarity	NPC472240
0.6418	Remote Similarity	NPC262858
0.6406	Remote Similarity	NPC470224
0.6324	Remote Similarity	NPC471293
0.6029	Remote Similarity	NPC210268
0.6029	Remote Similarity	NPC190604
0.6	Remote Similarity	NPC328052
0.5692	Remote Similarity	NPC1319
0.5571	Remote Similarity	NPC142361
0.5571	Remote Similarity	NPC474684
0.5417	Remote Similarity	NPC605437
0.5385	Remote Similarity	NPC609156
0.5278	Remote Similarity	NPC470375
0.5278	Remote Similarity	NPC470376
0.5211	Remote Similarity	NPC318390
0.5152	Remote Similarity	NPC100334
0.5143	Remote Similarity	NPC90652
0.5143	Remote Similarity	NPC155255
0.5143	Remote Similarity	NPC196485
0.5143	Remote Similarity	NPC245972
0.5143	Remote Similarity	NPC260992
0.5139	Remote Similarity	NPC486521
0.5139	Remote Similarity	NPC262870
0.5068	Remote Similarity	NPC470050
0.5068	Remote Similarity	NPC470051

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC58524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6697
0.1-0.2	2359
0.2-0.3	89
0.3-0.4	4
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