NPASS Compound

Natural Product: NPC510520

Natural Product ID	NPC510520
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,9-Octadecadienoic acid
IUPAC Name	octadeca-5,9-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 52 51 0 0 0 0 0 0 0 0999 V2000 6.3283 1.8315 -0.9529 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0719 0.6172 -1.7815 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6775 0.1236 -1.6466 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2696 -0.3703 -0.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2892 0.5146 0.8565 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7929 -0.2478 2.0703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4019 -0.7662 1.8820 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4640 0.3603 1.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0583 -0.1621 1.4429 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2093 -1.4339 1.5556 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5985 -1.9322 1.3932 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4945 -0.7622 1.0829 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9102 -1.1807 0.9275 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6414 -1.0348 -0.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2379 -0.4478 -1.4062 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8822 0.7800 -1.9172 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3487 0.6843 -2.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0790 0.5890 -0.8045 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5682 0.8749 0.3012 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4059 0.1620 -0.8136 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0450 1.6752 -0.1176 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3666 2.2888 -0.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8445 2.5914 -1.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7985 -0.1961 -1.5010 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2349 0.8850 -2.8666 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6086 -0.7532 -2.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9341 0.8776 -2.0432 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8780 -1.2821 -0.0460 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1936 -0.7426 -0.4172 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6560 1.4161 0.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3469 0.8459 1.1284 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8984 0.3663 2.9899 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5129 -1.1055 2.2307 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3637 -1.5605 1.1137 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0783 -1.3263 2.8276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4412 1.1238 2.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 0.8642 0.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6731 0.6199 1.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5763 -2.1512 1.7714 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9513 -2.5081 2.2700 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5698 -2.5931 0.4760 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4562 -0.0972 1.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1457 -0.2110 0.2101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3871 -1.6602 1.8122 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6704 -1.4598 -0.0874 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1224 -0.2812 -1.4519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4738 -1.2493 -2.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4687 1.0206 -2.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5679 1.6970 -1.3319 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6800 1.5644 -2.6850 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5596 -0.1952 -2.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8091 -0.2293 0.0305 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 1 0 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 3 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 6 33 1 0 7 34 1 0 7 35 1 0 8 36 1 0 8 37 1 0 9 38 1 0 10 39 1 0 11 40 1 0 11 41 1 0 12 42 1 0 12 43 1 0 13 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 17 50 1 0 17 51 1 0 20 52 1 0 M END

Standard InCHIKey	DFJAXEWDHVOILU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10,13-14H,2-8,11-12,15-17H2,1H3,(H,19,20)
SMILES	CCCCCCCCC=CCCC=CCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	280.24	Volume:	329.555 ? Van der Waals volume.
Dense:	0.85	LogP:	6.908 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.625 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.486 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	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:	0.318	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.352	Fsp³:	0.722
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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.064	Fluc inhibitor:	0.231 ? 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:	0.996	Promiscuous compounds:	0.882

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.124	MDCK Permeability:	-4.807
Pgp-inhibitor:	0.0	Pgp-substrate:	0.004
PAMPA:	0.232 ? 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):	0.4
20% Bioavailability (F20%):	0.148	30% Bioavailability (F30%):	0.65
50% Bioavailability (F50%):	0.199

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048	MRP1:	0.982
Plasma Protein Binding (PPB):	98.221%	Volume Distribution (VD):	-0.644
Fu:	0.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.476
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.035
BSEP inhibitor:	0.387

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.987
CYP2C19-inhibitor:	0.022	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.917	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.998	CYP2C8-inhibitor:	0.999
HLM stability:	0.002 ? 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):

5.434

Half-life (T1/2):

0.401

ADMET: Toxicity

hERG Blockers:	0.134	hERG Blockers (10um):	0.301
Human Hepatotoxicity (H-HT):	0.291	Drug-induced Liver Injury (DILI):	0.005
AMES Toxicity:	0.113	Rat Oral Acute Toxicity:	0.091
Maximum Recommended Daily Dose:	0.168	Skin Sensitization:	0.998
Carcinogencity:	0.102	Eye Corrosion:	0.996
Eye Irritation:	0.996	Respiratory Toxicity:	0.697
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.297
Hematotoxicity:	0.075	Drug-induced Nephrotoxicity:	0.384
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.041
A549 Cytotoxicity:	0.204	Hek293 Cytotoxicity:	0.08
BCF:	1.12 ? 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:	4.028 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.459 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.609 ? 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
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21953622]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32520551]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10906	Pinus koraiensis	Species	Pinaceae	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 NPC510520 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	37837
0.1-0.2	10190
0.2-0.3	1404
0.3-0.4	225
0.4-0.5	94
0.5-0.6	55
0.6-0.7	27
0.7-0.8	2
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC59051
0.8333	Intermediate Similarity	NPC91495
0.8276	Intermediate Similarity	NPC424
0.8276	Intermediate Similarity	NPC36061
0.8276	Intermediate Similarity	NPC69510
0.8276	Intermediate Similarity	NPC77272
0.8276	Intermediate Similarity	NPC290563
0.8276	Intermediate Similarity	NPC139029
0.8276	Intermediate Similarity	NPC281972
0.8276	Intermediate Similarity	NPC92114
0.8276	Intermediate Similarity	NPC261831
0.8276	Intermediate Similarity	NPC87564
0.7931	Intermediate Similarity	NPC281245
0.75	Intermediate Similarity	NPC154245
0.75	Intermediate Similarity	NPC85813
0.75	Intermediate Similarity	NPC223697
0.75	Intermediate Similarity	NPC6095
0.7419	Intermediate Similarity	NPC95145
0.7419	Intermediate Similarity	NPC325642
0.7419	Intermediate Similarity	NPC65174
0.7188	Intermediate Similarity	NPC321062
0.7188	Intermediate Similarity	NPC48162
0.7188	Intermediate Similarity	NPC5413
0.6471	Remote Similarity	NPC52955
0.6471	Remote Similarity	NPC88966
0.6471	Remote Similarity	NPC25417
0.6471	Remote Similarity	NPC1813
0.641	Remote Similarity	NPC323597
0.641	Remote Similarity	NPC211752
0.641	Remote Similarity	NPC323498
0.6316	Remote Similarity	NPC477201
0.625	Remote Similarity	NPC117572
0.6216	Remote Similarity	NPC487561
0.6207	Remote Similarity	NPC171736
0.6207	Remote Similarity	NPC301585
0.6207	Remote Similarity	NPC261080
0.6207	Remote Similarity	NPC132565
0.6207	Remote Similarity	NPC209970
0.6207	Remote Similarity	NPC216630
0.6207	Remote Similarity	NPC201844
0.6207	Remote Similarity	NPC301696
0.6207	Remote Similarity	NPC196924
0.6207	Remote Similarity	NPC307783
0.6207	Remote Similarity	NPC154186
0.6207	Remote Similarity	NPC149184
0.6207	Remote Similarity	NPC279026
0.6207	Remote Similarity	NPC113928
0.6207	Remote Similarity	NPC14227
0.6176	Remote Similarity	NPC70387
0.6	Remote Similarity	NPC243532
0.5897	Remote Similarity	NPC106851
0.5897	Remote Similarity	NPC282788
0.5897	Remote Similarity	NPC274927
0.5882	Remote Similarity	NPC149821
0.5862	Remote Similarity	NPC155263
0.5854	Remote Similarity	NPC68343
0.5854	Remote Similarity	NPC328089
0.5814	Remote Similarity	NPC322461
0.5789	Remote Similarity	NPC606120
0.575	Remote Similarity	NPC179764
0.5682	Remote Similarity	NPC605544
0.5682	Remote Similarity	NPC607260
0.5625	Remote Similarity	NPC180534
0.5625	Remote Similarity	NPC611531
0.561	Remote Similarity	NPC251042
0.561	Remote Similarity	NPC255863
0.561	Remote Similarity	NPC473863
0.561	Remote Similarity	NPC174447
0.561	Remote Similarity	NPC136164
0.561	Remote Similarity	NPC122521
0.561	Remote Similarity	NPC245947
0.5556	Remote Similarity	NPC329249
0.5556	Remote Similarity	NPC174368
0.5517	Remote Similarity	NPC175342
0.5476	Remote Similarity	NPC320305
0.5476	Remote Similarity	NPC317583
0.5476	Remote Similarity	NPC321838
0.5476	Remote Similarity	NPC318420
0.5476	Remote Similarity	NPC326268
0.5429	Remote Similarity	NPC207292
0.5385	Remote Similarity	NPC225929
0.5349	Remote Similarity	NPC325977
0.5349	Remote Similarity	NPC320642
0.5349	Remote Similarity	NPC327112
0.5349	Remote Similarity	NPC329550
0.5294	Remote Similarity	NPC34416
0.5294	Remote Similarity	NPC262968
0.5278	Remote Similarity	NPC87394
0.5238	Remote Similarity	NPC318814
0.5238	Remote Similarity	NPC320669
0.5227	Remote Similarity	NPC328311
0.5227	Remote Similarity	NPC323045
0.5227	Remote Similarity	NPC49863
0.5227	Remote Similarity	NPC317881
0.5208	Remote Similarity	NPC322457
0.5172	Remote Similarity	NPC214610
0.5172	Remote Similarity	NPC118968
0.5172	Remote Similarity	NPC183424
0.5172	Remote Similarity	NPC294085
0.5143	Remote Similarity	NPC129972
0.5143	Remote Similarity	NPC8219
0.5143	Remote Similarity	NPC301528
0.5143	Remote Similarity	NPC71317
0.5143	Remote Similarity	NPC163746
0.5143	Remote Similarity	NPC103286

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC510520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6765
0.1-0.2	2117
0.2-0.3	197
0.3-0.4	42
0.4-0.5	11
0.5-0.6	7
0.6-0.7	7
0.7-0.8	2
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD3195	Phase 2
0.8276	Intermediate Similarity	NPD3196	Approved
0.75	Intermediate Similarity	NPD4266	Phase 2
0.7188	Intermediate Similarity	NPD3173	Phase 4
0.6667	Remote Similarity	NPD3194	Phase 4
0.6667	Remote Similarity	NPD39	Phase 4
0.6471	Remote Similarity	NPD3172	Approved
0.625	Remote Similarity	NPD4222	Phase 3
0.6207	Remote Similarity	NPD2270	Pre-clinical
0.6207	Remote Similarity	NPD633	Phase 3
0.6207	Remote Similarity	NPD9448	Phase 2
0.5625	Remote Similarity	NPD622	Pre-clinical
0.5349	Remote Similarity	NPD4246	Phase 2
0.5294	Remote Similarity	NPD28	Approved
0.5294	Remote Similarity	NPD29	Phase 4
0.5278	Remote Similarity	NPD3197	Phase 1
0.5227	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5172	Remote Similarity	NPD9655	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