NPASS Compound

Natural Product: NPC20408

Natural Product ID	NPC20408
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DQGMPXYVZZCNDQ-KDQYYBQISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5282817
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids 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 50 49 0 0 0 0 0 0 0 0999 V2000 -5.7441 1.3370 -1.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5389 0.1001 -0.7554 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8700 -0.1114 0.6963 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6560 -0.2323 1.5643 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7749 -1.4047 1.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6290 -1.4003 2.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4020 -1.2669 1.6694 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0733 -1.1148 0.2790 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7778 -0.9786 -0.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4394 -0.8260 -1.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7893 -0.6943 -1.9132 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9349 -0.6925 -0.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6204 0.6521 -1.1519 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8216 0.8086 -0.2500 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8745 -0.2312 -0.5023 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0661 -0.0640 0.4006 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7191 1.2824 0.2065 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8818 1.4269 1.0954 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1864 0.4897 1.8626 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6660 2.5704 1.1216 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7218 1.0076 -1.3631 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6769 2.0276 -0.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1842 1.9358 -1.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5234 0.1735 -1.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0664 -0.8242 -1.1476 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4732 0.7249 1.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4557 -1.0371 0.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0040 -0.4227 2.6013 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0259 0.6571 1.5914 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4013 -2.3280 1.2941 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5434 -1.3527 0.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8491 -1.5166 3.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6351 -1.2796 2.4626 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7530 -1.0907 -0.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0727 -0.9967 0.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2116 -0.8161 -2.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0154 -0.5773 -3.0041 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6659 -1.4871 -1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7261 -0.9319 0.0537 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9121 1.4626 -0.9364 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9774 0.7991 -2.1870 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4507 0.8105 0.7862 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2257 1.8316 -0.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2346 -0.1071 -1.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4626 -1.2437 -0.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8109 -0.2675 1.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8036 -0.8529 0.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9853 2.0635 0.5143 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0056 1.4563 -0.8333 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6672 2.5316 1.2675 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 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 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 18 20 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 0 2 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 5 30 1 0 5 31 1 0 6 32 1 0 7 33 1 0 8 34 1 0 9 35 1 0 10 36 1 0 11 37 1 0 12 38 1 0 12 39 1 0 13 40 1 0 13 41 1 0 14 42 1 0 14 43 1 0 15 44 1 0 15 45 1 0 16 46 1 0 16 47 1 0 17 48 1 0 17 49 1 0 20 50 1 0 M END

Standard InCHIKey	DQGMPXYVZZCNDQ-KDQYYBQISA-N
Standard InCHI	InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10-
SMILES	CCCCC/C=CC=CC=C/CCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	278.22	Volume:	326.919 ? Van der Waals volume.
Dense:	0.851	LogP:	6.001 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.563 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.759 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	4.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.348	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.51	Fsp³:	0.611
MCE-18:	0.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.292	Fluc inhibitor:	0.589 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.18 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.995	Promiscuous compounds:	0.707

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052	MDCK Permeability:	-4.817
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
PAMPA:	0.595 ? 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):	0.013
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.051
50% Bioavailability (F50%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.922
Plasma Protein Binding (PPB):	97.133%	Volume Distribution (VD):	-0.454
Fu:	2.804% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.013
OATP1B3 inhibitor:	0.212	BCRP inhibitor:	0.006
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.697
CYP2C19-inhibitor:	0.083	CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.265	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.014 ? 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):

3.893

Half-life (T1/2):

0.855

ADMET: Toxicity

hERG Blockers:	0.211	hERG Blockers (10um):	0.317
Human Hepatotoxicity (H-HT):	0.466	Drug-induced Liver Injury (DILI):	0.015
AMES Toxicity:	0.205	Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.605	Skin Sensitization:	1.0
Carcinogencity:	0.075	Eye Corrosion:	0.906
Eye Irritation:	0.981	Respiratory Toxicity:	0.679
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.532
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.549
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.229	Hek293 Cytotoxicity:	0.255
BCF:	1.214 ? 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:	4.098 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.38 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.246 ? 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
NPO5498	Penicillium griseofulvum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16345795]
NPO5498	Penicillium griseofulvum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125229]
NPO5498	Penicillium griseofulvum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[241643]
NPO14961	Francoeuria crispa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5498	Penicillium griseofulvum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12530	Phorbia falcata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11671	Vochysia guianensis	Species	Vochysiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12530	Phorbia falcata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11671	Vochysia guianensis	Species	Vochysiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5498	Penicillium griseofulvum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14961	Francoeuria crispa	Species	Asteraceae	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 NPC20408 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	38085
0.1-0.2	10001
0.2-0.3	1358
0.3-0.4	215
0.4-0.5	82
0.5-0.6	47
0.6-0.7	29
0.7-0.8	4
0.8-0.85	2
0.85-0.9	9
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC95145
0.9643	High Similarity	NPC325642
0.9643	High Similarity	NPC65174
0.8621	High Similarity	NPC424
0.8621	High Similarity	NPC36061
0.8621	High Similarity	NPC69510
0.8621	High Similarity	NPC77272
0.8621	High Similarity	NPC290563
0.8621	High Similarity	NPC139029
0.8621	High Similarity	NPC281972
0.8621	High Similarity	NPC261831
0.8621	High Similarity	NPC87564
0.8276	Intermediate Similarity	NPC281245
0.8	Intermediate Similarity	NPC92114
0.7812	Intermediate Similarity	NPC154245
0.7812	Intermediate Similarity	NPC85813
0.7812	Intermediate Similarity	NPC223697
0.7812	Intermediate Similarity	NPC6095
0.75	Intermediate Similarity	NPC321062
0.7143	Intermediate Similarity	NPC171736
0.7143	Intermediate Similarity	NPC301585
0.7143	Intermediate Similarity	NPC261080
0.7143	Intermediate Similarity	NPC132565
0.7143	Intermediate Similarity	NPC209970
0.7143	Intermediate Similarity	NPC216630
0.7143	Intermediate Similarity	NPC201844
0.7143	Intermediate Similarity	NPC301696
0.7143	Intermediate Similarity	NPC196924
0.7143	Intermediate Similarity	NPC307783
0.7143	Intermediate Similarity	NPC154186
0.7143	Intermediate Similarity	NPC149184
0.7143	Intermediate Similarity	NPC279026
0.7143	Intermediate Similarity	NPC113928
0.7143	Intermediate Similarity	NPC14227
0.7105	Intermediate Similarity	NPC251042
0.7105	Intermediate Similarity	NPC255863
0.7105	Intermediate Similarity	NPC174447
0.7105	Intermediate Similarity	NPC136164
0.7105	Intermediate Similarity	NPC122521
0.7105	Intermediate Similarity	NPC245947
0.697	Remote Similarity	NPC5413
0.6923	Remote Similarity	NPC318420
0.6923	Remote Similarity	NPC326268
0.6786	Remote Similarity	NPC155263
0.6765	Remote Similarity	NPC52955
0.6765	Remote Similarity	NPC88966
0.6765	Remote Similarity	NPC25417
0.6765	Remote Similarity	NPC1813
0.6765	Remote Similarity	NPC59051
0.6579	Remote Similarity	NPC106851
0.6579	Remote Similarity	NPC282788
0.6579	Remote Similarity	NPC274927
0.6579	Remote Similarity	NPC477201
0.6471	Remote Similarity	NPC91495
0.6471	Remote Similarity	NPC70387
0.6452	Remote Similarity	NPC180534
0.6452	Remote Similarity	NPC611531
0.641	Remote Similarity	NPC179764
0.625	Remote Similarity	NPC243532
0.6098	Remote Similarity	NPC68343
0.6098	Remote Similarity	NPC328089
0.6071	Remote Similarity	NPC214610
0.6071	Remote Similarity	NPC118968
0.6071	Remote Similarity	NPC183424
0.6071	Remote Similarity	NPC294085
0.6061	Remote Similarity	NPC34416
0.6053	Remote Similarity	NPC487561
0.6053	Remote Similarity	NPC225929
0.6053	Remote Similarity	NPC606120
0.5882	Remote Similarity	NPC8219
0.5882	Remote Similarity	NPC184171
0.5862	Remote Similarity	NPC175342
0.5854	Remote Similarity	NPC473863
0.5714	Remote Similarity	NPC18712
0.5714	Remote Similarity	NPC149821
0.5714	Remote Similarity	NPC74845
0.5714	Remote Similarity	NPC268826
0.5581	Remote Similarity	NPC320642
0.5581	Remote Similarity	NPC329550
0.5556	Remote Similarity	NPC87394
0.5556	Remote Similarity	NPC324004
0.5556	Remote Similarity	NPC328497
0.5556	Remote Similarity	NPC602547
0.5526	Remote Similarity	NPC40082
0.5476	Remote Similarity	NPC187777
0.5476	Remote Similarity	NPC318814
0.5476	Remote Similarity	NPC320669
0.5455	Remote Similarity	NPC55023
0.5455	Remote Similarity	NPC21844
0.5455	Remote Similarity	NPC323045
0.5455	Remote Similarity	NPC49863
0.5455	Remote Similarity	NPC317881
0.5435	Remote Similarity	NPC92558
0.5429	Remote Similarity	NPC129972
0.5429	Remote Similarity	NPC301528
0.5429	Remote Similarity	NPC71317
0.5429	Remote Similarity	NPC163746
0.5429	Remote Similarity	NPC103286
0.5405	Remote Similarity	NPC174560
0.5405	Remote Similarity	NPC125312
0.5357	Remote Similarity	NPC174368
0.5333	Remote Similarity	NPC322461
0.5312	Remote Similarity	NPC604140
0.5278	Remote Similarity	NPC207292
0.5238	Remote Similarity	NPC274290
0.5217	Remote Similarity	NPC605544
0.5217	Remote Similarity	NPC607260
0.5172	Remote Similarity	NPC134782
0.5143	Remote Similarity	NPC314679
0.5143	Remote Similarity	NPC262968
0.5135	Remote Similarity	NPC48162
0.5116	Remote Similarity	NPC323597
0.5116	Remote Similarity	NPC211752
0.5116	Remote Similarity	NPC323498
0.5116	Remote Similarity	NPC99619
0.5106	Remote Similarity	NPC329249

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6787
0.1-0.2	2107
0.2-0.3	195
0.3-0.4	34
0.4-0.5	11
0.5-0.6	4
0.6-0.7	6
0.7-0.8	4
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD3195	Phase 2
0.8621	High Similarity	NPD3196	Approved
0.7812	Intermediate Similarity	NPD4266	Phase 2
0.7143	Intermediate Similarity	NPD2270	Pre-clinical
0.7143	Intermediate Similarity	NPD633	Phase 3
0.7143	Intermediate Similarity	NPD9448	Phase 2
0.697	Remote Similarity	NPD3173	Phase 4
0.6944	Remote Similarity	NPD3194	Phase 4
0.6765	Remote Similarity	NPD3172	Approved
0.6452	Remote Similarity	NPD622	Pre-clinical
0.6098	Remote Similarity	NPD39	Phase 4
0.6071	Remote Similarity	NPD9655	Phase 4
0.5556	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5455	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5143	Remote Similarity	NPD28	Approved
0.5143	Remote Similarity	NPD29	Phase 4

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