NPASS Compound

Natural Product: NPC21543

Natural Product ID	NPC21543
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IJTNSXPMYKJZPR-OAUSVTMXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10378843
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 48 47 0 0 0 0 0 0 0 0999 V2000 8.5236 -1.7151 -0.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5246 -1.6776 0.7555 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3257 -0.2811 1.1886 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1545 0.2842 1.1270 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9685 -0.3742 0.6438 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7973 0.2794 0.6116 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6030 -0.3871 0.1198 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4202 0.2680 0.0850 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2472 -0.3841 -0.3975 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9306 0.2165 -0.4549 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0986 1.6007 -0.0226 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0465 1.8932 1.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4761 1.8782 0.8828 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2843 0.7961 0.2796 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2449 0.6643 -1.2032 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9755 -0.4846 -1.8074 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4457 -0.5587 -1.6492 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9908 -0.6413 -0.2956 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8589 0.2036 0.0899 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5795 -1.6229 0.5724 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2817 -2.5153 -0.2823 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0571 -1.7765 -1.3730 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1129 -0.7550 -0.3486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6519 -2.2894 0.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0986 -2.1609 1.6206 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2069 0.2942 1.5762 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0728 1.3390 1.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0033 -1.3809 0.3041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8065 1.2955 0.9645 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5975 -1.4019 -0.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4567 1.2603 0.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3513 -1.4257 -0.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7409 -0.3863 -0.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4251 2.1424 -1.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1377 2.1484 0.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7453 2.9230 1.5318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8311 1.1835 1.9598 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8436 2.8583 0.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9868 2.1043 1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9753 -0.1857 0.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3703 0.8841 0.5961 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9150 1.6012 -1.5379 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3083 0.9048 -1.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4583 -1.4145 -1.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7114 -0.4733 -2.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8135 -1.4444 -2.2681 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8901 0.3410 -2.2002 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1775 -1.8751 1.3415 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 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 4 27 1 0 5 28 1 0 6 29 1 0 7 30 1 0 8 31 1 0 9 32 1 0 10 33 1 0 11 34 1 0 11 35 1 0 12 36 1 0 12 37 1 0 13 38 1 0 13 39 1 0 14 40 1 0 14 41 1 0 15 42 1 0 15 43 1 0 16 44 1 0 16 45 1 0 17 46 1 0 17 47 1 0 20 48 1 0 M ISO 1 18 14 M END

Standard InCHIKey	IJTNSXPMYKJZPR-OAUSVTMXSA-N
Standard InCHI	InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-10H,2,11-17H2,1H3,(H,19,20)/b4-3-,6-5+,8-7+,10-9-/i18+2
SMILES	CC/C=CC=CC=CC=C/CCCCCCC[14C](=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	278.21	Volume:	324.282 ? Van der Waals volume.
Dense:	0.858	LogP:	5.147 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.391 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.027 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	5.0
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:	0.381	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.85	Fsp³:	0.5
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:	0.11	Fluc inhibitor:	0.698 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.155 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.995	Promiscuous compounds:	0.571

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.102	MDCK Permeability:	-4.877
Pgp-inhibitor:	0.002	Pgp-substrate:	0.008
PAMPA:	0.692 ? 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):	0.033
20% Bioavailability (F20%):	0.022	30% Bioavailability (F30%):	0.202
50% Bioavailability (F50%):	0.223

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.807
Plasma Protein Binding (PPB):	95.662%	Volume Distribution (VD):	-0.538
Fu:	3.727% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.01
OATP1B3 inhibitor:	0.308	BCRP inhibitor:	0.037
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.102	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.998
CYP2B6-substrate:	0.414	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

4.427

Half-life (T1/2):

0.775

ADMET: Toxicity

hERG Blockers:	0.091	hERG Blockers (10um):	0.214
Human Hepatotoxicity (H-HT):	0.44	Drug-induced Liver Injury (DILI):	0.041
AMES Toxicity:	0.464	Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.685	Skin Sensitization:	0.997
Carcinogencity:	0.361	Eye Corrosion:	0.695
Eye Irritation:	0.973	Respiratory Toxicity:	0.78
Drug-induced Neurotoxicity:	0.043	Ototoxicity:	0.592
Hematotoxicity:	0.169	Drug-induced Nephrotoxicity:	0.33
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.032	Hek293 Cytotoxicity:	0.098
BCF:	1.223 ? 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:	4.095 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.414 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.794 ? 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
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[12033510]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28165740]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	Pericarp	n.a.	n.a.	PMID[9748380]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30941	Holarrhena antidysenterica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30941	Holarrhena antidysenterica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30941	Holarrhena antidysenterica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11196	Impatiens balsamina	Species	Balsaminaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO765	Holarrhena pubescens	Species	Apocynaceae	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 NPC21543 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	39017
0.1-0.2	9483
0.2-0.3	1034
0.3-0.4	157
0.4-0.5	80
0.5-0.6	29
0.6-0.7	41
0.7-0.8	3
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC95145
0.8333	Intermediate Similarity	NPC325642
0.8333	Intermediate Similarity	NPC65174
0.7667	Intermediate Similarity	NPC281245
0.7419	Intermediate Similarity	NPC424
0.7419	Intermediate Similarity	NPC36061
0.7419	Intermediate Similarity	NPC69510
0.7419	Intermediate Similarity	NPC77272
0.7419	Intermediate Similarity	NPC290563
0.7419	Intermediate Similarity	NPC139029
0.7419	Intermediate Similarity	NPC281972
0.7419	Intermediate Similarity	NPC261831
0.7419	Intermediate Similarity	NPC87564
0.7273	Intermediate Similarity	NPC52955
0.7273	Intermediate Similarity	NPC88966
0.7273	Intermediate Similarity	NPC25417
0.7273	Intermediate Similarity	NPC1813
0.697	Remote Similarity	NPC70387
0.6875	Remote Similarity	NPC92114
0.6765	Remote Similarity	NPC154245
0.6765	Remote Similarity	NPC85813
0.6765	Remote Similarity	NPC223697
0.6765	Remote Similarity	NPC6095
0.6471	Remote Similarity	NPC321062
0.6452	Remote Similarity	NPC180534
0.6452	Remote Similarity	NPC611531
0.625	Remote Similarity	NPC251042
0.625	Remote Similarity	NPC255863
0.625	Remote Similarity	NPC174447
0.625	Remote Similarity	NPC136164
0.625	Remote Similarity	NPC122521
0.625	Remote Similarity	NPC245947
0.6176	Remote Similarity	NPC149821
0.6098	Remote Similarity	NPC318420
0.6098	Remote Similarity	NPC326268
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	NPC225929
0.6053	Remote Similarity	NPC606120
0.6	Remote Similarity	NPC171736
0.6	Remote Similarity	NPC301585
0.6	Remote Similarity	NPC261080
0.6	Remote Similarity	NPC132565
0.6	Remote Similarity	NPC209970
0.6	Remote Similarity	NPC216630
0.6	Remote Similarity	NPC201844
0.6	Remote Similarity	NPC301696
0.6	Remote Similarity	NPC5413
0.6	Remote Similarity	NPC196924
0.6	Remote Similarity	NPC307783
0.6	Remote Similarity	NPC154186
0.6	Remote Similarity	NPC149184
0.6	Remote Similarity	NPC279026
0.6	Remote Similarity	NPC113928
0.6	Remote Similarity	NPC14227
0.5833	Remote Similarity	NPC59051
0.575	Remote Similarity	NPC106851
0.575	Remote Similarity	NPC282788
0.575	Remote Similarity	NPC274927
0.575	Remote Similarity	NPC477201
0.5714	Remote Similarity	NPC268826
0.5667	Remote Similarity	NPC155263
0.561	Remote Similarity	NPC179764
0.5556	Remote Similarity	NPC91495
0.5476	Remote Similarity	NPC243532
0.5455	Remote Similarity	NPC120776
0.5455	Remote Similarity	NPC55023
0.5455	Remote Similarity	NPC240170
0.5455	Remote Similarity	NPC21844
0.5429	Remote Similarity	NPC184171
0.5405	Remote Similarity	NPC174560
0.5405	Remote Similarity	NPC125312
0.5349	Remote Similarity	NPC68343
0.5349	Remote Similarity	NPC328089
0.5333	Remote Similarity	NPC175342
0.5312	Remote Similarity	NPC604140
0.5278	Remote Similarity	NPC207292
0.525	Remote Similarity	NPC487561
0.5172	Remote Similarity	NPC134782
0.5143	Remote Similarity	NPC314679
0.5143	Remote Similarity	NPC117572
0.5135	Remote Similarity	NPC48162
0.5116	Remote Similarity	NPC187777
0.5116	Remote Similarity	NPC473863

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC21543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6881
0.1-0.2	2028
0.2-0.3	192
0.3-0.4	28
0.4-0.5	8
0.5-0.6	2
0.6-0.7	8
0.7-0.8	3
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
0.7419	Intermediate Similarity	NPD3195	Phase 2
0.7419	Intermediate Similarity	NPD3196	Approved
0.7273	Intermediate Similarity	NPD3172	Approved
0.6765	Remote Similarity	NPD4266	Phase 2
0.6452	Remote Similarity	NPD622	Pre-clinical
0.6071	Remote Similarity	NPD9655	Phase 4
0.6053	Remote Similarity	NPD3194	Phase 4
0.6	Remote Similarity	NPD2270	Pre-clinical
0.6	Remote Similarity	NPD3173	Phase 4
0.6	Remote Similarity	NPD633	Phase 3
0.6	Remote Similarity	NPD9448	Phase 2
0.5714	Remote Similarity	NPD39	Phase 4
0.5143	Remote Similarity	NPD4222	Phase 3

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