NPASS Compound

Natural Product: NPC285186

Natural Product ID	NPC285186
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VYCOKDKHCLSBAE-LGJCAXMNSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101457888
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

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 78 83 0 0 0 0 0 0 0 0999 V2000 1.8194 -2.8966 -1.3486 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3372 -2.5725 -1.2061 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4901 -3.6204 -1.3369 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9923 -3.4734 -1.2279 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1891 -2.0229 -1.7459 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5841 -1.1526 -0.7506 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0771 -1.1769 -0.9561 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3478 -0.4265 -2.1893 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4887 -0.6345 0.3020 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0121 0.7587 0.6300 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2676 1.2160 0.0757 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0732 2.4620 -0.8144 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1724 0.2091 -0.5708 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7931 0.7366 -1.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 0.0635 0.3815 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4600 -0.8096 -0.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5775 -0.3973 0.9091 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6009 -1.2977 2.1123 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5974 -0.7991 2.9535 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4775 0.5594 2.7288 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9563 1.3738 3.5197 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0526 0.9292 1.4155 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0256 1.2853 0.5522 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9366 1.8569 1.1748 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0398 1.6397 0.1541 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8548 2.3824 0.9561 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6884 2.2834 2.2100 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8963 3.2754 0.4697 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0742 3.3794 -0.8914 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0501 4.2153 -1.3951 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8225 4.9265 -0.4932 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6173 4.7971 0.8295 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6806 3.9948 1.3142 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8921 -0.6906 0.2887 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6445 -1.3904 1.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0241 -1.9950 2.1234 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0963 -1.4305 1.1897 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8556 -0.7899 0.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2477 -0.8855 0.2791 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8789 -1.6075 1.2571 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1208 -2.2254 2.1792 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7604 -2.1474 2.1582 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4337 -2.0309 -1.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1164 -3.5518 -0.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9444 -3.5299 -2.2902 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0544 -4.5796 -1.5235 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4960 -4.1982 -1.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2245 -3.5292 -0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2245 -1.9630 -2.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6111 -2.0117 -2.7171 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -1.6437 0.2708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4493 0.0015 -2.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0064 0.4146 -1.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9935 -1.0138 -2.8618 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1459 -1.2963 1.1350 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0740 0.8530 1.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0187 3.0098 -0.9511 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4622 3.1471 -0.1470 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 2.2979 -1.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8431 -0.0730 -2.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8167 1.1433 -1.7105 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2217 1.5424 -2.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9741 -0.3244 1.3418 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8860 -0.5542 -1.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3338 -1.8912 0.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5522 -0.3295 0.4268 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4264 -2.3626 1.8152 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5935 -1.2056 2.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8426 1.6851 1.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3052 2.4982 1.5552 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4705 2.8229 -1.6049 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1765 4.2856 -2.4485 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5917 5.5875 -0.8369 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5307 3.9042 2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3610 -0.2234 -0.5317 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8721 -0.3883 -0.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9536 -1.7084 1.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2604 -2.6866 2.9523 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 11 24 1 1 10 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 9 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 2 0 7 2 1 0 23 15 1 0 33 28 1 0 42 37 1 0 13 6 1 0 22 17 1 0 1 43 1 0 1 44 1 0 1 45 1 0 3 46 1 0 4 47 1 0 4 48 1 0 5 49 1 0 5 50 1 0 6 51 1 1 8 52 1 0 8 53 1 0 8 54 1 0 9 55 1 1 10 56 1 0 12 57 1 0 12 58 1 0 12 59 1 0 14 60 1 0 14 61 1 0 14 62 1 0 15 63 1 1 16 64 1 0 16 65 1 0 17 66 1 0 18 67 1 0 18 68 1 0 22 69 1 0 24 70 1 0 29 71 1 0 30 72 1 0 31 73 1 0 33 74 1 0 38 75 1 0 39 76 1 0 40 77 1 0 42 78 1 0 M END

Standard InCHIKey	VYCOKDKHCLSBAE-LGJCAXMNSA-N
Standard InCHI	InChI=1S/C32H36N2O8/c1-18-8-5-11-22-30(18,2)25(41-27(35)19-9-6-12-33-15-19)26(42-28(36)20-10-7-13-34-16-20)32(4,38)31(22,3)23-14-21-17-39-29(37)24(21)40-23/h6-10,12-13,15-16,21-26,38H,5,11,14,17H2,1-4H3/t21?,22-,23-,24?,25-,26?,30?,31-,32-/m0/s1
SMILES	CC1=CCC[C@H]2C1(C)[C@H](C([C@@](C)([C@]2(C)[C@@H]1CC2COC(=O)C2O1)O)OC(=O)c1cccnc1)OC(=O)c1cccnc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	576.25	Volume:	576.64 ? Van der Waals volume.
Dense:	0.999	LogP:	2.197 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.426 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.011 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	35.0
TPSA:	134.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.319	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.151	Fsp³:	0.531
MCE-18:	137.694 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.107	Fluc inhibitor:	0.048 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.203 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.027	Promiscuous compounds:	0.024

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.384	MDCK Permeability:	-4.994
Pgp-inhibitor:	0.381	Pgp-substrate:	0.074
PAMPA:	0.914 ? 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%):	0.214	30% Bioavailability (F30%):	0.042
50% Bioavailability (F50%):	0.398

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02	MRP1:	1.0
Plasma Protein Binding (PPB):	77.836%	Volume Distribution (VD):	-0.113
Fu:	15.78% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.721
OATP1B3 inhibitor:	0.313	BCRP inhibitor:	0.002
BSEP inhibitor:	0.985

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.767	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.985
CYP3A4-inhibitor:	0.045	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.894 ? 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):

3.628

Half-life (T1/2):

1.12

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.26
Human Hepatotoxicity (H-HT):	0.213	Drug-induced Liver Injury (DILI):	0.94
AMES Toxicity:	0.211	Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.325	Skin Sensitization:	0.992
Carcinogencity:	0.824	Eye Corrosion:	0.0
Eye Irritation:	0.146	Respiratory Toxicity:	0.095
Drug-induced Neurotoxicity:	0.676	Ototoxicity:	0.624
Hematotoxicity:	0.096	Drug-induced Nephrotoxicity:	0.781
Genotoxicity:	0.65	RPMI-8226 Immunitoxicity:	0.087
A549 Cytotoxicity:	0.11	Hek293 Cytotoxicity:	0.25
BCF:	0.99 ? 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:	3.727 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.824 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.527 ? 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
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16755060]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17666848]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18239311]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19785430]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19962306]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20078074]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	whole plants	Nanning District, Guangxi Province, China	2012-Sep	PMID[25647077]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	aerial parts	Seoul, Korea	n.a.	PMID[26331882]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16039	Scutellaria barbata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16039	Scutellaria barbata	Species	Lamiaceae	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 NPC285186 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	8853
0.1-0.2	38063
0.2-0.3	2769
0.3-0.4	136
0.4-0.5	16
0.5-0.6	14
0.6-0.7	7
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
0.7037	Intermediate Similarity	NPC472555
0.6951	Remote Similarity	NPC477911
0.686	Remote Similarity	NPC148860
0.6588	Remote Similarity	NPC472553
0.6552	Remote Similarity	NPC62367
0.6477	Remote Similarity	NPC477912
0.6341	Remote Similarity	NPC206343
0.6341	Remote Similarity	NPC477908
0.5977	Remote Similarity	NPC472550
0.593	Remote Similarity	NPC304179
0.593	Remote Similarity	NPC48042
0.5909	Remote Similarity	NPC42678
0.5909	Remote Similarity	NPC477907
0.5909	Remote Similarity	NPC477909
0.5814	Remote Similarity	NPC91125
0.5778	Remote Similarity	NPC319128
0.5682	Remote Similarity	NPC26881
0.5604	Remote Similarity	NPC228331
0.5385	Remote Similarity	NPC477910
0.5281	Remote Similarity	NPC477906
0.5114	Remote Similarity	NPC330029
0.5111	Remote Similarity	NPC63041

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC285186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2955
0.1-0.2	6091
0.2-0.3	99
0.3-0.4	5
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