NPASS Compound

Natural Product: NPC474674

Natural Product ID	NPC474674
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-(2'-Methoxy-4'z-Hexadecenyl)-Sn-Glycero-3-Phosphocholine
IUPAC Name	[(2S)-2-hydroxy-3-[(Z)-2-methoxyhexadec-4-enoxy]propyl] 2-(trimethylazaniumyl)ethyl phosphate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479108
PubChem CID	44584786
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000256] Glycerophospholipids [CHEMONTID:0002213] Glycerophosphocholines [CHEMONTID:0001414] Monoalkylglycerophosphocholines

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 86 85 0 0 0 0 0 0 0 0999 V2000 8.6184 -0.0521 -2.2529 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4167 -1.0011 -1.4340 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3247 -0.3222 -0.4612 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5881 0.4999 0.5488 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6588 -0.3671 1.3593 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9212 0.3475 2.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0597 1.4913 2.1422 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8729 1.4111 1.2976 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0365 1.0576 -0.1255 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7056 1.0876 -0.8849 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7175 0.1002 -0.3033 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4516 0.1428 -1.0556 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2993 0.4513 -0.5143 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 0.8030 0.8772 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0747 -0.1597 1.5558 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2520 -0.1876 0.8493 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1803 -0.7364 -0.4051 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3899 -0.7619 -1.0812 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4593 -1.5705 -0.3771 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6779 -1.5141 -1.2537 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7338 -2.2874 -0.8238 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9951 -2.3972 -1.9037 P 0 0 0 0 0 0 0 0 0 0 0 0 -7.0182 -3.8290 -2.4330 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7198 -1.4351 -3.2960 O 0 0 0 0 0 1 0 0 0 0 0 0 -8.4982 -2.0312 -1.3275 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7250 -0.6978 -1.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1398 -0.4112 -0.6409 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3978 0.9599 -0.3681 N 0 0 0 0 0 4 0 0 0 0 0 0 -10.3507 1.1676 1.0693 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4626 1.8862 -0.9654 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7335 1.3912 -0.7911 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9499 -2.8662 -0.2734 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1041 0.3645 2.8641 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4338 -0.5741 3.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5898 -0.4608 -2.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0584 -0.0150 -3.2773 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5853 0.9652 -1.8438 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7384 -1.7288 -0.9232 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0231 -1.6730 -2.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0392 0.3625 -0.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8948 -1.0961 0.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0495 1.3202 0.0408 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2946 0.9915 1.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0074 -1.0181 0.7884 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4069 -1.0438 1.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6450 0.5882 3.2811 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2661 -0.4463 2.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6871 1.8760 3.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6755 2.4084 1.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3501 2.4083 1.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1917 0.6317 1.7585 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6755 1.8112 -0.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5161 0.0846 -0.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2737 2.1001 -0.8811 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9359 0.7538 -1.9186 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1145 -0.9577 -0.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5219 0.2481 0.7584 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5204 -0.1024 -2.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4468 0.4582 -1.2451 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5499 1.8462 0.9305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8931 0.8917 1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5791 -1.1431 1.5785 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9438 -0.7444 1.5271 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6234 0.8658 0.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 0.3040 -1.2184 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1973 -1.1566 -2.1052 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6792 -1.0864 0.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3647 -1.7567 -2.3022 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0194 -0.4597 -1.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5627 -0.1535 -2.0384 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9717 -0.3262 -0.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3953 -1.0750 0.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8471 -0.7093 -1.4687 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3025 0.9509 1.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6809 2.1811 1.3593 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9641 0.3706 1.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3701 1.7461 -2.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9149 2.9071 -0.8412 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4875 1.9279 -0.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5010 0.6143 -0.6046 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9454 2.3081 -0.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7263 1.7093 -1.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4989 -3.0589 -1.1370 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1387 -1.5165 3.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4238 -0.2587 4.7847 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4689 -0.7589 3.4033 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 1 0 10 11 1 0 11 12 1 0 12 13 2 3 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 1 0 21 22 1 0 22 23 2 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 28 31 1 0 19 32 1 0 15 33 1 0 33 34 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 0 2 39 1 0 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 6 46 1 0 6 47 1 0 7 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 9 52 1 0 9 53 1 0 10 54 1 0 10 55 1 0 11 56 1 0 11 57 1 0 12 58 1 0 13 59 1 0 14 60 1 0 14 61 1 0 15 62 1 0 16 63 1 0 16 64 1 0 18 65 1 0 18 66 1 0 19 67 1 0 20 68 1 0 20 69 1 0 26 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 29 74 1 0 29 75 1 0 29 76 1 0 30 77 1 0 30 78 1 0 30 79 1 0 31 80 1 0 31 81 1 0 31 82 1 0 32 83 1 0 34 84 1 0 34 85 1 0 34 86 1 0 M CHG 2 24 -1 28 1 M END

Standard InCHIKey	NYFGVUCTLCDUFF-VTYVONMNSA-N
Standard InCHI	InChI=1S/C25H52NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-25(30-5)23-31-21-24(27)22-33-34(28,29)32-20-19-26(2,3)4/h16-17,24-25,27H,6-15,18-23H2,1-5H3/b17-16-/t24-,25?/m0/s1
SMILES	CCCCCCCCCCCC=CCC(COCC(COP(=O)([O-])OCC[N+](C)(C)C)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	509.35	Volume:	530.675 ? Van der Waals volume.
Dense:	0.96	LogP:	1.611 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.576 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.593 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	2.0
TPSA:	97.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.089	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.319	Fsp³:	0.92
MCE-18:	8.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.333	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.1	Promiscuous compounds:	0.138

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.571	MDCK Permeability:	-4.922
Pgp-inhibitor:	0.003	Pgp-substrate:	0.0
PAMPA:	0.004 ? 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):	0.787
20% Bioavailability (F20%):	0.109	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.855
Plasma Protein Binding (PPB):	95.945%	Volume Distribution (VD):	0.118
Fu:	4.384% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.072
BSEP inhibitor:	0.995

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.117	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.977	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.999	CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.991
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.642
HLM stability:	0.0 ? 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):

5.253

Half-life (T1/2):

0.604

ADMET: Toxicity

hERG Blockers:	0.189	hERG Blockers (10um):	0.423
Human Hepatotoxicity (H-HT):	0.926	Drug-induced Liver Injury (DILI):	0.013
AMES Toxicity:	0.085	Rat Oral Acute Toxicity:	0.419
Maximum Recommended Daily Dose:	0.991	Skin Sensitization:	1.0
Carcinogencity:	0.596	Eye Corrosion:	0.996
Eye Irritation:	0.997	Respiratory Toxicity:	0.99
Drug-induced Neurotoxicity:	0.178	Ototoxicity:	0.007
Hematotoxicity:	0.026	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.666	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.021
BCF:	1.141 ? 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:	4.57 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.096 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.751 ? 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
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579872]
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325244]
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088447]
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22182501]
NPO85	Spirastrella abata	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

Activity Type	# Activity
ED50	5

Activity Type	# Activity
Cell line	5

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	6.3	ug ml-1	PMID[21513293]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	=	5.9	ug ml-1	PMID[22209564]
NPT2358	Cell line	SK-MEL3	Homo sapiens	ED50	=	3.8	ug ml-1	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[9584409]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[22037378]

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 NPC474674 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	19138
0.1-0.2	29532
0.2-0.3	1130
0.3-0.4	33
0.4-0.5	7
0.5-0.6	7
0.6-0.7	5
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
0.7736	Intermediate Similarity	NPC474627
0.7143	Intermediate Similarity	NPC305223
0.7143	Intermediate Similarity	NPC137620
0.7143	Intermediate Similarity	NPC474675
0.7143	Intermediate Similarity	NPC127145
0.7143	Intermediate Similarity	NPC475930
0.6441	Remote Similarity	NPC178758
0.6441	Remote Similarity	NPC192326
0.6441	Remote Similarity	NPC322769
0.6071	Remote Similarity	NPC328786
0.6071	Remote Similarity	NPC201338
0.5758	Remote Similarity	NPC82799
0.5424	Remote Similarity	NPC170963
0.5424	Remote Similarity	NPC324165
0.5424	Remote Similarity	NPC114640
0.5424	Remote Similarity	NPC126366
0.5424	Remote Similarity	NPC608333
0.5246	Remote Similarity	NPC238646

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6230
0.1-0.2	2830
0.2-0.3	78
0.3-0.4	7
0.4-0.5	4
0.5-0.6	1
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
0.5254	Remote Similarity	NPD6950	Phase 2

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