NPASS Compound

Structure

NPC470268 OpenBabel07101718312D 35 35 0 0 1 0 0 0 0 0999 V2000 19.5981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.0981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.0981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.5981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7321 -5.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2321 -4.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7321 -5.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2321 -4.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2321 -6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.5981 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7321 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2321 -6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.0981 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7321 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7321 -7.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2321 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -12.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2321 -7.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -11.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7321 -8.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.0981 -2.2321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 14.2321 -2.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.3660 -12.1603 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7321 -8.7942 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.7321 -7.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -13.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -12.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2321 -9.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2321 -6.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -8.6603 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 1.2321 -9.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2321 -7.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -10.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -9.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -9.6603 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 16 21 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 24 1 0 0 0 0 18 32 1 0 0 0 0 19 23 1 0 0 0 0 19 33 1 0 0 0 0 20 24 1 0 0 0 0 20 34 1 0 0 0 0 21 22 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 2 0 0 0 0 25 32 1 0 0 0 0 30 35 1 0 0 0 0 31 35 2 0 0 0 0 33 35 1 0 0 0 0 34 35 1 0 0 0 0 M CHG 1 30 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	523.3
Volume:	527.384
LogP:	3.974
LogD:	2.079
LogS:	-3.676
# Rotatable Bonds:	25
TPSA:	145.58
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	4.338
Fsp3:	0.96
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.4
MDCK Permeability:	3.8003450754331425e-05
Pgp-inhibitor:	0.792
Pgp-substrate:	0.727
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.316

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	97.49437713623047%
Volume Distribution (VD):	0.83
Pgp-substrate:	2.31904673576355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.303
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	1.44
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.322
Human Hepatotoxicity (H-HT):	0.314
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.963
Carcinogencity:	0.338
Eye Corrosion:	0.004
Eye Irritation:	0.089
Respiratory Toxicity:	0.934

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC470268

Natural Product ID:	NPC470268
*Common Name:**	Sodium 1-O-(Cis-11,12-Methyleneoctadecanoyl)-Syn-Glycero-3-Phosphoglycerol
IUPAC Name:	sodium;2,3-dihydroxypropyl [(2R)-3-[10-[(1R,2S)-2-hexylcyclopropyl]decanoyloxy]-2-hydroxypropyl] phosphate
Synonyms:
Standard InCHIKey:	VPFWJPGDIDFJDH-FKUFVTGZSA-M
Standard InCHI:	InChI=1S/C25H49O9P.Na/c1-2-3-4-10-13-21-16-22(21)14-11-8-6-5-7-9-12-15-25(29)32-18-24(28)20-34-35(30,31)33-19-23(27)17-26;/h21-24,26-28H,2-20H2,1H3,(H,30,31);/q;+1/p-1/t21-,22+,23?,24+;/m0./s1
SMILES:	CCCCCCC1CC1CCCCCCCCCC(=O)OCC(COP(=O)([O-])OCC(CO)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1938696
PubChem CID:	57392448
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000256] Glycerophospholipids [CHEMONTID:0002216] Glycerophosphoglycerols [CHEMONTID:0000297] Lysophosphatidylglycerols

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

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]

☑ 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	NP ID	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
IC50	2
MIC	4
Others	1

Activity Type	# Activity
Cell Line	1
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	4000.0	nM	PMID[454517]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	13.0	ug.mL-1	PMID[454517]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	100.0	ug.mL-1	PMID[454517]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	100.0	ug.mL-1	PMID[454517]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[454517]
NPT2	Others	Unspecified		IC50	=	87000.0	nM	PMID[454517]
NPT2	Others	Unspecified		IC50	=	4000.0	nM	PMID[454517]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC470268 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	628
0.1-0.2	4704
0.2-0.3	16367
0.3-0.4	10762
0.4-0.5	8597
0.5-0.6	1516
0.6-0.7	113
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC470363
0.84	Intermediate Similarity	NPC474702
0.8	Intermediate Similarity	NPC330017
0.7808	Intermediate Similarity	NPC321873
0.7692	Intermediate Similarity	NPC320588
0.7692	Intermediate Similarity	NPC53463
0.7692	Intermediate Similarity	NPC469937
0.7692	Intermediate Similarity	NPC23155
0.7639	Intermediate Similarity	NPC469925
0.7534	Intermediate Similarity	NPC82315
0.7397	Intermediate Similarity	NPC286842
0.7333	Intermediate Similarity	NPC324165
0.7333	Intermediate Similarity	NPC114640
0.7333	Intermediate Similarity	NPC126366
0.7333	Intermediate Similarity	NPC169976
0.7333	Intermediate Similarity	NPC170963
0.7333	Intermediate Similarity	NPC33267
0.7324	Intermediate Similarity	NPC235788
0.7222	Intermediate Similarity	NPC314103
0.7179	Intermediate Similarity	NPC228411
0.7143	Intermediate Similarity	NPC473775
0.7143	Intermediate Similarity	NPC473699
0.7143	Intermediate Similarity	NPC475260
0.7143	Intermediate Similarity	NPC51249
0.7143	Intermediate Similarity	NPC475232
0.7143	Intermediate Similarity	NPC474100
0.7123	Intermediate Similarity	NPC476330
0.7	Intermediate Similarity	NPC474003
0.6923	Remote Similarity	NPC26253
0.6914	Remote Similarity	NPC475616
0.6849	Remote Similarity	NPC474552
0.6842	Remote Similarity	NPC320663
0.6842	Remote Similarity	NPC224700
0.6818	Remote Similarity	NPC55678
0.6795	Remote Similarity	NPC54460
0.6795	Remote Similarity	NPC185419
0.6795	Remote Similarity	NPC184550
0.6769	Remote Similarity	NPC106872
0.6769	Remote Similarity	NPC477878
0.6769	Remote Similarity	NPC324793
0.6753	Remote Similarity	NPC28526
0.6711	Remote Similarity	NPC206601
0.6709	Remote Similarity	NPC308096
0.6709	Remote Similarity	NPC291228
0.6707	Remote Similarity	NPC11796
0.6707	Remote Similarity	NPC218817
0.6707	Remote Similarity	NPC470014
0.6667	Remote Similarity	NPC226602
0.6667	Remote Similarity	NPC469926
0.6667	Remote Similarity	NPC475821
0.6667	Remote Similarity	NPC238646
0.6667	Remote Similarity	NPC472019
0.6667	Remote Similarity	NPC472020
0.6623	Remote Similarity	NPC209327
0.6623	Remote Similarity	NPC273508
0.6615	Remote Similarity	NPC324004
0.6615	Remote Similarity	NPC328497
0.6615	Remote Similarity	NPC249754
0.6615	Remote Similarity	NPC21844
0.6575	Remote Similarity	NPC472021
0.6567	Remote Similarity	NPC90904
0.6548	Remote Similarity	NPC103634
0.6543	Remote Similarity	NPC179858
0.6538	Remote Similarity	NPC241265
0.6538	Remote Similarity	NPC285003
0.6522	Remote Similarity	NPC72722
0.6512	Remote Similarity	NPC259173
0.6506	Remote Similarity	NPC473984
0.6494	Remote Similarity	NPC104537
0.6494	Remote Similarity	NPC22101
0.6494	Remote Similarity	NPC148192
0.6494	Remote Similarity	NPC330426
0.6494	Remote Similarity	NPC271921
0.6494	Remote Similarity	NPC127091
0.6486	Remote Similarity	NPC469923
0.6477	Remote Similarity	NPC235196
0.6477	Remote Similarity	NPC228593
0.6471	Remote Similarity	NPC100096
0.6471	Remote Similarity	NPC287811
0.6471	Remote Similarity	NPC314084
0.6463	Remote Similarity	NPC474020
0.6462	Remote Similarity	NPC308301
0.6462	Remote Similarity	NPC30195
0.6462	Remote Similarity	NPC314679
0.6462	Remote Similarity	NPC12438
0.6438	Remote Similarity	NPC469924
0.6438	Remote Similarity	NPC174485
0.6437	Remote Similarity	NPC151176
0.6437	Remote Similarity	NPC475963
0.6437	Remote Similarity	NPC473791
0.6437	Remote Similarity	NPC3464
0.6429	Remote Similarity	NPC294748
0.6429	Remote Similarity	NPC477346
0.6429	Remote Similarity	NPC146992
0.6429	Remote Similarity	NPC477344
0.6429	Remote Similarity	NPC22742
0.6429	Remote Similarity	NPC289979
0.6429	Remote Similarity	NPC85759
0.6429	Remote Similarity	NPC158302
0.641	Remote Similarity	NPC473559
0.641	Remote Similarity	NPC50228
0.641	Remote Similarity	NPC141481
0.641	Remote Similarity	NPC48218
0.641	Remote Similarity	NPC97736
0.641	Remote Similarity	NPC324981
0.641	Remote Similarity	NPC319007
0.6404	Remote Similarity	NPC314364
0.6404	Remote Similarity	NPC51662
0.6395	Remote Similarity	NPC164289
0.6395	Remote Similarity	NPC242771
0.6395	Remote Similarity	NPC100366
0.6395	Remote Similarity	NPC212340
0.6395	Remote Similarity	NPC311642
0.6389	Remote Similarity	NPC322148
0.6386	Remote Similarity	NPC83108
0.6386	Remote Similarity	NPC214030
0.6364	Remote Similarity	NPC241949
0.6364	Remote Similarity	NPC135043
0.6364	Remote Similarity	NPC473899
0.6364	Remote Similarity	NPC315525
0.6364	Remote Similarity	NPC476715
0.6353	Remote Similarity	NPC200446
0.6341	Remote Similarity	NPC217725
0.6341	Remote Similarity	NPC81052
0.6333	Remote Similarity	NPC201046
0.6333	Remote Similarity	NPC476379
0.6333	Remote Similarity	NPC470009
0.6329	Remote Similarity	NPC211428
0.6324	Remote Similarity	NPC305182
0.6322	Remote Similarity	NPC474266
0.6322	Remote Similarity	NPC472744
0.6322	Remote Similarity	NPC196102
0.6322	Remote Similarity	NPC178758
0.631	Remote Similarity	NPC252483
0.631	Remote Similarity	NPC191345
0.6308	Remote Similarity	NPC55023
0.6308	Remote Similarity	NPC47363
0.6308	Remote Similarity	NPC287231
0.6296	Remote Similarity	NPC206823
0.6296	Remote Similarity	NPC163812
0.6292	Remote Similarity	NPC92139
0.6292	Remote Similarity	NPC470657
0.6282	Remote Similarity	NPC473829
0.6282	Remote Similarity	NPC475443
0.6279	Remote Similarity	NPC475270
0.6279	Remote Similarity	NPC44782
0.6279	Remote Similarity	NPC475667
0.6279	Remote Similarity	NPC126685
0.6279	Remote Similarity	NPC169345
0.6279	Remote Similarity	NPC115013
0.6279	Remote Similarity	NPC307400
0.6279	Remote Similarity	NPC224953
0.6279	Remote Similarity	NPC143421
0.6279	Remote Similarity	NPC477319
0.6279	Remote Similarity	NPC211049
0.6279	Remote Similarity	NPC476087
0.6279	Remote Similarity	NPC259294
0.6279	Remote Similarity	NPC238056
0.6279	Remote Similarity	NPC472203
0.6279	Remote Similarity	NPC184915
0.6279	Remote Similarity	NPC475327
0.6279	Remote Similarity	NPC472204
0.6279	Remote Similarity	NPC472200
0.6279	Remote Similarity	NPC12933
0.6279	Remote Similarity	NPC173328
0.6279	Remote Similarity	NPC89843
0.6279	Remote Similarity	NPC183888
0.6279	Remote Similarity	NPC477331
0.6279	Remote Similarity	NPC477318
0.6279	Remote Similarity	NPC27289
0.6279	Remote Similarity	NPC472201
0.6279	Remote Similarity	NPC269318
0.6279	Remote Similarity	NPC123204
0.6279	Remote Similarity	NPC477347
0.6279	Remote Similarity	NPC186992
0.6279	Remote Similarity	NPC477317
0.6279	Remote Similarity	NPC119583
0.6279	Remote Similarity	NPC290012
0.6279	Remote Similarity	NPC472205
0.6279	Remote Similarity	NPC297768
0.6279	Remote Similarity	NPC472202
0.6269	Remote Similarity	NPC131770
0.6269	Remote Similarity	NPC200618
0.6265	Remote Similarity	NPC470899
0.625	Remote Similarity	NPC9868
0.625	Remote Similarity	NPC474780
0.625	Remote Similarity	NPC476660
0.6235	Remote Similarity	NPC209995
0.6234	Remote Similarity	NPC306805
0.6234	Remote Similarity	NPC215987
0.6222	Remote Similarity	NPC31349
0.622	Remote Similarity	NPC472945
0.622	Remote Similarity	NPC472944
0.6207	Remote Similarity	NPC148740
0.6207	Remote Similarity	NPC102156
0.6207	Remote Similarity	NPC477936
0.6207	Remote Similarity	NPC477935
0.6207	Remote Similarity	NPC475849
0.6196	Remote Similarity	NPC478004
0.6196	Remote Similarity	NPC313670

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	843
0.1-0.2	4135
0.2-0.3	2800
0.3-0.4	906
0.4-0.5	388
0.5-0.6	67
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
0.7692	Intermediate Similarity	NPD3728	Approved
0.7692	Intermediate Similarity	NPD3730	Approved
0.7465	Intermediate Similarity	NPD7909	Approved
0.7164	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8277	Approved
0.6901	Remote Similarity	NPD3198	Approved
0.6866	Remote Similarity	NPD3186	Phase 1
0.6842	Remote Similarity	NPD8278	Approved
0.6769	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD634	Phase 3
0.6374	Remote Similarity	NPD46	Approved
0.6374	Remote Similarity	NPD6698	Approved
0.6308	Remote Similarity	NPD2699	Approved
0.6129	Remote Similarity	NPD7983	Approved
0.6049	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD2266	Phase 2
0.6023	Remote Similarity	NPD6435	Approved
0.5972	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7154	Phase 3
0.593	Remote Similarity	NPD4802	Phase 2
0.593	Remote Similarity	NPD4238	Approved
0.5882	Remote Similarity	NPD6117	Approved
0.5846	Remote Similarity	NPD2270	Approved
0.5843	Remote Similarity	NPD7345	Approved
0.5833	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6116	Phase 1
0.5795	Remote Similarity	NPD5368	Approved
0.5747	Remote Similarity	NPD6114	Approved
0.5747	Remote Similarity	NPD6115	Approved
0.5747	Remote Similarity	NPD6118	Approved
0.5747	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6697	Approved
0.573	Remote Similarity	NPD5369	Approved
0.5696	Remote Similarity	NPD3197	Phase 1
0.5692	Remote Similarity	NPD7536	Approved
0.5684	Remote Similarity	NPD7838	Discovery
0.5641	Remote Similarity	NPD4283	Discontinued
0.5618	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD5362	Discontinued
0.56	Remote Similarity	NPD73	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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