NPASS Compound

Natural Product: NPC551062

Natural Product ID	NPC551062
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	10,14-icosadienoic acid
IUPAC Name	icosa-10,14-dienoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 58 57 0 0 0 0 0 0 0 0999 V2000 9.9632 -1.1834 1.5487 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4426 -1.2708 1.3558 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1627 -0.5375 0.0680 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6975 -0.5799 -0.2343 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9226 0.0913 0.8732 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4871 0.0242 0.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8091 1.1435 0.3215 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3703 1.1681 -0.0732 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9039 -0.2398 -0.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4534 -0.2190 -0.6406 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1751 0.9285 -0.7859 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6284 0.8992 -1.1889 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3863 1.5782 -0.0918 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8550 1.6197 -0.4005 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4001 0.2409 -0.5408 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8954 0.2463 -0.8401 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3062 -1.2156 -0.9552 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7608 -1.3718 -1.2496 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6759 -0.7905 -0.2254 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5273 -1.3676 1.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6926 -2.2759 1.3284 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3010 -0.9300 2.1706 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1681 -0.1862 1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3983 -1.3528 0.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2296 -1.9774 2.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9483 -0.8516 2.2359 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2197 -2.3438 1.2605 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4675 0.5483 0.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7290 -0.9804 -0.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4111 -1.6637 -0.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4609 -0.1359 -1.2284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0871 -0.4341 1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1921 1.1609 0.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0395 -0.9396 0.3272 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2706 2.1200 0.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7921 1.7356 0.6850 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2964 1.7004 -1.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4462 -0.7189 -1.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0357 -0.8361 0.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0858 -1.1530 -0.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2602 1.9008 -0.6417 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7287 1.4176 -2.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9625 -0.1354 -1.3449 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1872 1.0405 0.8816 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9784 2.6096 0.1073 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3522 2.1676 0.4542 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0558 2.2662 -1.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2890 -0.2709 0.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9221 -0.3675 -1.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4414 0.6833 0.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1345 0.8150 -1.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7574 -1.6034 -1.8635 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9263 -1.8059 -0.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9812 -2.4330 -1.4806 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9441 -0.8319 -2.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7254 -0.9645 -0.6034 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5699 0.3206 -0.2208 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0183 -1.1775 3.1061 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 3 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 3 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 1 0 19 20 1 0 20 21 2 0 20 22 1 0 1 23 1 0 1 24 1 0 1 25 1 0 2 26 1 0 2 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 6 34 1 0 7 35 1 0 8 36 1 0 8 37 1 0 9 38 1 0 9 39 1 0 10 40 1 0 11 41 1 0 12 42 1 0 12 43 1 0 13 44 1 0 13 45 1 0 14 46 1 0 14 47 1 0 15 48 1 0 15 49 1 0 16 50 1 0 16 51 1 0 17 52 1 0 17 53 1 0 18 54 1 0 18 55 1 0 19 56 1 0 19 57 1 0 22 58 1 0 M END

Standard InCHIKey	LZHSQQHUCUUTJU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,10-11H,2-5,8-9,12-19H2,1H3,(H,21,22)
SMILES	CCCCCC=CCCC=CCCCCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	308.27	Volume:	364.147 ? Van der Waals volume.
Dense:	0.847	LogP:	7.803 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.932 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.358 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	3.0
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:	0.255	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.347	Fsp³:	0.75
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:	0.249	Fluc inhibitor:	0.272 ? 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:	0.011 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.994	Promiscuous compounds:	0.893

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.058	MDCK Permeability:	-4.713
Pgp-inhibitor:	0.001	Pgp-substrate:	0.004
PAMPA:	0.042 ? 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):	0.544
20% Bioavailability (F20%):	0.291	30% Bioavailability (F30%):	0.859
50% Bioavailability (F50%):	0.375

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062	MRP1:	0.987
Plasma Protein Binding (PPB):	97.888%	Volume Distribution (VD):	-0.559
Fu:	0.972% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.201
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.133
BSEP inhibitor:	0.605

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.601
CYP2C19-inhibitor:	0.412	CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.927	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.103 ? 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):

3.986

Half-life (T1/2):

0.559

ADMET: Toxicity

hERG Blockers:	0.22	hERG Blockers (10um):	0.365
Human Hepatotoxicity (H-HT):	0.235	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.061	Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.101	Skin Sensitization:	0.999
Carcinogencity:	0.049	Eye Corrosion:	0.998
Eye Irritation:	0.997	Respiratory Toxicity:	0.766
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.285
Hematotoxicity:	0.045	Drug-induced Nephrotoxicity:	0.343
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.281	Hek293 Cytotoxicity:	0.069
BCF:	0.916 ? 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:	4.003 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.576 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.056 ? 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
NPO24762	Sporothrix flocculosa	Species	Ophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24762	Sporothrix flocculosa	Species	Ophiostomataceae	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 NPC551062 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	37597
0.1-0.2	10364
0.2-0.3	1441
0.3-0.4	242
0.4-0.5	89
0.5-0.6	45
0.6-0.7	30
0.7-0.8	6
0.8-0.85	1
0.85-0.9	8
0.9-0.95	1
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC424
0.963	High Similarity	NPC36061
0.963	High Similarity	NPC69510
0.963	High Similarity	NPC77272
0.963	High Similarity	NPC290563
0.963	High Similarity	NPC139029
0.963	High Similarity	NPC281972
0.963	High Similarity	NPC261831
0.963	High Similarity	NPC87564
0.9259	High Similarity	NPC281245
0.8929	High Similarity	NPC92114
0.8667	High Similarity	NPC154245
0.8667	High Similarity	NPC85813
0.8667	High Similarity	NPC223697
0.8667	High Similarity	NPC6095
0.8621	High Similarity	NPC95145
0.8621	High Similarity	NPC325642
0.8621	High Similarity	NPC65174
0.8333	Intermediate Similarity	NPC321062
0.7742	Intermediate Similarity	NPC5413
0.75	Intermediate Similarity	NPC52955
0.75	Intermediate Similarity	NPC88966
0.75	Intermediate Similarity	NPC25417
0.75	Intermediate Similarity	NPC1813
0.75	Intermediate Similarity	NPC59051
0.7407	Intermediate Similarity	NPC171736
0.7407	Intermediate Similarity	NPC301585
0.7407	Intermediate Similarity	NPC261080
0.7407	Intermediate Similarity	NPC132565
0.7407	Intermediate Similarity	NPC209970
0.7407	Intermediate Similarity	NPC216630
0.7407	Intermediate Similarity	NPC201844
0.7407	Intermediate Similarity	NPC301696
0.7407	Intermediate Similarity	NPC196924
0.7407	Intermediate Similarity	NPC307783
0.7407	Intermediate Similarity	NPC154186
0.7407	Intermediate Similarity	NPC149184
0.7407	Intermediate Similarity	NPC279026
0.7407	Intermediate Similarity	NPC113928
0.7407	Intermediate Similarity	NPC14227
0.7222	Intermediate Similarity	NPC477201
0.7188	Intermediate Similarity	NPC91495
0.7188	Intermediate Similarity	NPC70387
0.7037	Intermediate Similarity	NPC155263
0.6842	Remote Similarity	NPC243532
0.6757	Remote Similarity	NPC106851
0.6757	Remote Similarity	NPC282788
0.6757	Remote Similarity	NPC274927
0.6667	Remote Similarity	NPC180534
0.6667	Remote Similarity	NPC68343
0.6667	Remote Similarity	NPC328089
0.6667	Remote Similarity	NPC606120
0.6667	Remote Similarity	NPC611531
0.6579	Remote Similarity	NPC179764
0.641	Remote Similarity	NPC251042
0.641	Remote Similarity	NPC255863
0.641	Remote Similarity	NPC473863
0.641	Remote Similarity	NPC174447
0.641	Remote Similarity	NPC136164
0.641	Remote Similarity	NPC122521
0.641	Remote Similarity	NPC245947
0.6364	Remote Similarity	NPC149821
0.6296	Remote Similarity	NPC214610
0.6296	Remote Similarity	NPC118968
0.6296	Remote Similarity	NPC183424
0.6296	Remote Similarity	NPC294085
0.625	Remote Similarity	NPC34416
0.625	Remote Similarity	NPC318420
0.625	Remote Similarity	NPC326268
0.6216	Remote Similarity	NPC487561
0.6216	Remote Similarity	NPC225929
0.6176	Remote Similarity	NPC48162
0.6071	Remote Similarity	NPC175342
0.6061	Remote Similarity	NPC8219
0.5926	Remote Similarity	NPC268826
0.5882	Remote Similarity	NPC18712
0.5882	Remote Similarity	NPC74845
0.5882	Remote Similarity	NPC207292
0.5758	Remote Similarity	NPC262968
0.5714	Remote Similarity	NPC320642
0.5714	Remote Similarity	NPC87394
0.5714	Remote Similarity	NPC324004
0.5714	Remote Similarity	NPC328497
0.5714	Remote Similarity	NPC329550
0.5714	Remote Similarity	NPC602547
0.5676	Remote Similarity	NPC40082
0.5625	Remote Similarity	NPC55023
0.5625	Remote Similarity	NPC21844
0.561	Remote Similarity	NPC323597
0.561	Remote Similarity	NPC187777
0.561	Remote Similarity	NPC211752
0.561	Remote Similarity	NPC318814
0.561	Remote Similarity	NPC320669
0.561	Remote Similarity	NPC323498
0.5588	Remote Similarity	NPC129972
0.5588	Remote Similarity	NPC301528
0.5588	Remote Similarity	NPC71317
0.5588	Remote Similarity	NPC163746
0.5588	Remote Similarity	NPC103286
0.5581	Remote Similarity	NPC323045
0.5581	Remote Similarity	NPC49863
0.5581	Remote Similarity	NPC317881
0.5556	Remote Similarity	NPC174368
0.5556	Remote Similarity	NPC174560
0.5556	Remote Similarity	NPC125312
0.5484	Remote Similarity	NPC604140
0.5476	Remote Similarity	NPC317583
0.5455	Remote Similarity	NPC322461
0.5366	Remote Similarity	NPC274290
0.5357	Remote Similarity	NPC134782
0.5333	Remote Similarity	NPC605544
0.5333	Remote Similarity	NPC607260
0.5294	Remote Similarity	NPC314679
0.5294	Remote Similarity	NPC117572
0.5278	Remote Similarity	NPC224227
0.5238	Remote Similarity	NPC99619
0.5217	Remote Similarity	NPC329249
0.5217	Remote Similarity	NPC92558
0.5122	Remote Similarity	NPC28205

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC551062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6723
0.1-0.2	2155
0.2-0.3	200
0.3-0.4	43
0.4-0.5	10
0.5-0.6	6
0.6-0.7	3
0.7-0.8	6
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.963	High Similarity	NPD3195	Phase 2
0.963	High Similarity	NPD3196	Approved
0.8667	High Similarity	NPD4266	Phase 2
0.7742	Intermediate Similarity	NPD3173	Phase 4
0.7647	Intermediate Similarity	NPD3194	Phase 4
0.75	Intermediate Similarity	NPD3172	Approved
0.7407	Intermediate Similarity	NPD2270	Pre-clinical
0.7407	Intermediate Similarity	NPD633	Phase 3
0.7407	Intermediate Similarity	NPD9448	Phase 2
0.6667	Remote Similarity	NPD39	Phase 4
0.6667	Remote Similarity	NPD622	Pre-clinical
0.6296	Remote Similarity	NPD9655	Phase 4
0.5758	Remote Similarity	NPD28	Approved
0.5758	Remote Similarity	NPD29	Phase 4
0.5714	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5581	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5294	Remote Similarity	NPD4222	Phase 3
0.5278	Remote Similarity	NPD3197	Phase 1

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