NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	302.25
Volume:	335.113
LogP:	4.787
LogD:	3.568
LogS:	-3.933
# Rotatable Bonds:	16
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	0
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	2.465
Fsp3:	0.941
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	3.5077504435321316e-05
Pgp-inhibitor:	0.288
Pgp-substrate:	0.79
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.325
Plasma Protein Binding (PPB):	95.92472076416016%
Volume Distribution (VD):	0.694
Pgp-substrate:	2.435723066329956%

ADMET: Metabolism

CYP1A2-inhibitor:	0.613
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.322
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.354
CYP2C9-substrate:	0.852
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	8.852
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.905
Carcinogencity:	0.12
Eye Corrosion:	0.007
Eye Irritation:	0.122
Respiratory Toxicity:	0.215

Download Data

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

Natural Product: NPC320588

Natural Product ID:	NPC320588
*Common Name:**	2,3-Dihydroxypropyl Tetradecanoate
IUPAC Name:	2,3-dihydroxypropyl tetradecanoate
Synonyms:	1-Monomyristin
Standard InCHIKey:	DCBSHORRWZKAKO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H34O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(20)21-15-16(19)14-18/h16,18-19H,2-15H2,1H3
SMILES:	CCCCCCCCCCCCCC(=O)OCC(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463092
PubChem CID:	79050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0003808] Monoradylglycerols [CHEMONTID:0001133] Monoacylglycerols [CHEMONTID:0001597] 1-monoacylglycerols

*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
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15690045]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16529801]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17558398]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18650807]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18791072]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19346493]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19549143]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22235948]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22239548]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[222395484]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23163760]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23475189]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23894595]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24411940]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24453122]
NPO10650	Serenoa repens	Species	Arecaceae	Eukaryota	Berries	n.a.	n.a.	PMID[9134750]
NPO10650	Serenoa repens	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13691	Caenorhabditis elegans	Species	Rhabditidae	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	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
ED50	3
Others	1
Potency	15

Activity Type	# Activity
Cell Line	3
Organism	1
Others	15

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT376	Cell Line	A498	Homo sapiens	ED50	=	3.58	ug ml-1	PMID[524197]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	8.84	ug ml-1	PMID[524197]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	1.87	ug ml-1	PMID[524197]
NPT140	Organism	Artemia	Artemia	LC50	=	53.3	ug.mL-1	PMID[524197]
NPT2	Others	Unspecified		Potency	n.a.	87.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	346.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	38570.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	968.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	6113.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set

☑ 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 NPC320588 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	792
0.1-0.2	5859
0.2-0.3	16934
0.3-0.4	10141
0.4-0.5	7016
0.5-0.6	1574
0.6-0.7	255
0.7-0.8	99
0.8-0.85	15
0.85-0.9	3
0.9-0.95	1
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469937
1.0	High Similarity	NPC53463
1.0	High Similarity	NPC23155
0.9091	High Similarity	NPC470363
0.9	High Similarity	NPC26253
0.8824	High Similarity	NPC55678
0.88	High Similarity	NPC106872
0.86	High Similarity	NPC324004
0.86	High Similarity	NPC328497
0.8462	Intermediate Similarity	NPC90904
0.84	Intermediate Similarity	NPC30195
0.84	Intermediate Similarity	NPC12438
0.8302	Intermediate Similarity	NPC100096
0.8302	Intermediate Similarity	NPC287811
0.82	Intermediate Similarity	NPC287231
0.82	Intermediate Similarity	NPC47363
0.8182	Intermediate Similarity	NPC289979
0.8077	Intermediate Similarity	NPC200618
0.8077	Intermediate Similarity	NPC131770
0.8065	Intermediate Similarity	NPC206601
0.8065	Intermediate Similarity	NPC271921
0.8065	Intermediate Similarity	NPC22101
0.8065	Intermediate Similarity	NPC104537
0.8065	Intermediate Similarity	NPC127091
0.8065	Intermediate Similarity	NPC148192
0.8065	Intermediate Similarity	NPC469925
0.8065	Intermediate Similarity	NPC330426
0.7937	Intermediate Similarity	NPC48218
0.7937	Intermediate Similarity	NPC141481
0.7937	Intermediate Similarity	NPC473559
0.7937	Intermediate Similarity	NPC324981
0.7925	Intermediate Similarity	NPC304162
0.7843	Intermediate Similarity	NPC469781
0.7812	Intermediate Similarity	NPC285003
0.7812	Intermediate Similarity	NPC241265
0.78	Intermediate Similarity	NPC236579
0.78	Intermediate Similarity	NPC203531
0.7778	Intermediate Similarity	NPC473829
0.7778	Intermediate Similarity	NPC475443
0.7705	Intermediate Similarity	NPC235788
0.7705	Intermediate Similarity	NPC325773
0.7692	Intermediate Similarity	NPC470268
0.7692	Intermediate Similarity	NPC321873
0.7692	Intermediate Similarity	NPC476660
0.7656	Intermediate Similarity	NPC50228
0.7656	Intermediate Similarity	NPC82315
0.7656	Intermediate Similarity	NPC97736
0.7647	Intermediate Similarity	NPC74845
0.76	Intermediate Similarity	NPC209970
0.76	Intermediate Similarity	NPC149184
0.76	Intermediate Similarity	NPC307783
0.76	Intermediate Similarity	NPC171736
0.76	Intermediate Similarity	NPC196924
0.76	Intermediate Similarity	NPC53541
0.76	Intermediate Similarity	NPC216630
0.7581	Intermediate Similarity	NPC314103
0.7576	Intermediate Similarity	NPC185419
0.7576	Intermediate Similarity	NPC184550
0.7538	Intermediate Similarity	NPC473772
0.7538	Intermediate Similarity	NPC211428
0.75	Intermediate Similarity	NPC286842
0.75	Intermediate Similarity	NPC17935
0.7463	Intermediate Similarity	NPC308096
0.7463	Intermediate Similarity	NPC291228
0.7463	Intermediate Similarity	NPC163812
0.7463	Intermediate Similarity	NPC206823
0.7451	Intermediate Similarity	NPC67462
0.7424	Intermediate Similarity	NPC114640
0.7424	Intermediate Similarity	NPC170963
0.7424	Intermediate Similarity	NPC42526
0.7424	Intermediate Similarity	NPC33267
0.7424	Intermediate Similarity	NPC126366
0.7424	Intermediate Similarity	NPC324165
0.7424	Intermediate Similarity	NPC169976
0.74	Intermediate Similarity	NPC161097
0.74	Intermediate Similarity	NPC40597
0.74	Intermediate Similarity	NPC149299
0.74	Intermediate Similarity	NPC256163
0.74	Intermediate Similarity	NPC165533
0.74	Intermediate Similarity	NPC250028
0.74	Intermediate Similarity	NPC12156
0.74	Intermediate Similarity	NPC28598
0.7358	Intermediate Similarity	NPC105329
0.7358	Intermediate Similarity	NPC145045
0.7358	Intermediate Similarity	NPC63182
0.7358	Intermediate Similarity	NPC52700
0.7353	Intermediate Similarity	NPC474321
0.7308	Intermediate Similarity	NPC317128
0.7246	Intermediate Similarity	NPC228411
0.7222	Intermediate Similarity	NPC326957
0.7206	Intermediate Similarity	NPC475260
0.7206	Intermediate Similarity	NPC39266
0.7206	Intermediate Similarity	NPC475232
0.7206	Intermediate Similarity	NPC473699
0.7206	Intermediate Similarity	NPC474100
0.7206	Intermediate Similarity	NPC169085
0.7206	Intermediate Similarity	NPC473775
0.7206	Intermediate Similarity	NPC51249
0.7206	Intermediate Similarity	NPC225748
0.7206	Intermediate Similarity	NPC9763
0.72	Intermediate Similarity	NPC14227
0.72	Intermediate Similarity	NPC279026
0.72	Intermediate Similarity	NPC261080
0.72	Intermediate Similarity	NPC214610
0.72	Intermediate Similarity	NPC301696
0.72	Intermediate Similarity	NPC113928
0.72	Intermediate Similarity	NPC154186
0.72	Intermediate Similarity	NPC219536
0.72	Intermediate Similarity	NPC294085
0.72	Intermediate Similarity	NPC223249
0.72	Intermediate Similarity	NPC201844
0.72	Intermediate Similarity	NPC80234
0.72	Intermediate Similarity	NPC183424
0.72	Intermediate Similarity	NPC31551
0.72	Intermediate Similarity	NPC301585
0.72	Intermediate Similarity	NPC118968
0.7188	Intermediate Similarity	NPC476657
0.7188	Intermediate Similarity	NPC76881
0.7188	Intermediate Similarity	NPC12040
0.7188	Intermediate Similarity	NPC476655
0.7188	Intermediate Similarity	NPC476654
0.7188	Intermediate Similarity	NPC476330
0.717	Intermediate Similarity	NPC62014
0.717	Intermediate Similarity	NPC273545
0.717	Intermediate Similarity	NPC8219
0.7143	Intermediate Similarity	NPC54925
0.7143	Intermediate Similarity	NPC477350
0.7097	Intermediate Similarity	NPC321919
0.7097	Intermediate Similarity	NPC81896
0.7077	Intermediate Similarity	NPC476656
0.7077	Intermediate Similarity	NPC476659
0.7059	Intermediate Similarity	NPC152008
0.7042	Intermediate Similarity	NPC216883
0.7042	Intermediate Similarity	NPC476781
0.7042	Intermediate Similarity	NPC476782
0.7042	Intermediate Similarity	NPC476783
0.7	Intermediate Similarity	NPC201622
0.7	Intermediate Similarity	NPC305660
0.7	Intermediate Similarity	NPC22903
0.7	Intermediate Similarity	NPC197039
0.7	Intermediate Similarity	NPC54980
0.7	Intermediate Similarity	NPC268826
0.6984	Remote Similarity	NPC321838
0.6984	Remote Similarity	NPC201939
0.6981	Remote Similarity	NPC76051
0.6981	Remote Similarity	NPC19305
0.6981	Remote Similarity	NPC255837
0.697	Remote Similarity	NPC99619
0.697	Remote Similarity	NPC26500
0.6944	Remote Similarity	NPC146380
0.6944	Remote Similarity	NPC477320
0.6944	Remote Similarity	NPC477330
0.6944	Remote Similarity	NPC477326
0.6944	Remote Similarity	NPC113745
0.6944	Remote Similarity	NPC281563
0.6944	Remote Similarity	NPC477328
0.6944	Remote Similarity	NPC109887
0.6944	Remote Similarity	NPC475425
0.6944	Remote Similarity	NPC477329
0.6944	Remote Similarity	NPC477323
0.6944	Remote Similarity	NPC477325
0.6923	Remote Similarity	NPC469926
0.6923	Remote Similarity	NPC471761
0.6923	Remote Similarity	NPC190418
0.6923	Remote Similarity	NPC471760
0.6909	Remote Similarity	NPC21844
0.6909	Remote Similarity	NPC8597
0.6909	Remote Similarity	NPC249754
0.6901	Remote Similarity	NPC330017
0.6875	Remote Similarity	NPC474552
0.6866	Remote Similarity	NPC250619
0.6866	Remote Similarity	NPC209327
0.6866	Remote Similarity	NPC273508
0.6849	Remote Similarity	NPC294748
0.6849	Remote Similarity	NPC477346
0.6849	Remote Similarity	NPC146992
0.6849	Remote Similarity	NPC477344
0.6849	Remote Similarity	NPC85759
0.6849	Remote Similarity	NPC158302
0.6849	Remote Similarity	NPC22742
0.6825	Remote Similarity	NPC243532
0.6806	Remote Similarity	NPC474003
0.68	Remote Similarity	NPC128996
0.6792	Remote Similarity	NPC71317
0.6792	Remote Similarity	NPC129972
0.6792	Remote Similarity	NPC301528
0.6792	Remote Similarity	NPC176500
0.6786	Remote Similarity	NPC477878
0.6786	Remote Similarity	NPC324793
0.6769	Remote Similarity	NPC68343
0.6769	Remote Similarity	NPC476658
0.6769	Remote Similarity	NPC328089
0.6765	Remote Similarity	NPC28526
0.6757	Remote Similarity	NPC267592
0.6757	Remote Similarity	NPC47653
0.6727	Remote Similarity	NPC308301
0.6724	Remote Similarity	NPC314084
0.6721	Remote Similarity	NPC148424
0.6719	Remote Similarity	NPC469923
0.6712	Remote Similarity	NPC473984

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 NPC320588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1155
0.1-0.2	4372
0.2-0.3	2294
0.3-0.4	812
0.4-0.5	353
0.5-0.6	134
0.6-0.7	19
0.7-0.8	7
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3730	Approved
1.0	High Similarity	NPD3728	Approved
0.88	High Similarity	NPD6125	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2699	Approved
0.7857	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2270	Approved
0.7302	Intermediate Similarity	NPD7909	Approved
0.72	Intermediate Similarity	NPD9448	Phase 2
0.72	Intermediate Similarity	NPD9655	Approved
0.72	Intermediate Similarity	NPD633	Phase 3
0.717	Intermediate Similarity	NPD3199	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7536	Approved
0.7031	Intermediate Similarity	NPD3197	Phase 1
0.7	Intermediate Similarity	NPD3206	Approved
0.6935	Remote Similarity	NPD3198	Approved
0.6786	Remote Similarity	NPD2266	Phase 2
0.6765	Remote Similarity	NPD8277	Approved
0.6721	Remote Similarity	NPD73	Approved
0.6618	Remote Similarity	NPD8278	Approved
0.6613	Remote Similarity	NPD8959	Approved
0.6429	Remote Similarity	NPD634	Phase 3
0.6333	Remote Similarity	NPD9007	Approved
0.6333	Remote Similarity	NPD9009	Approved
0.6333	Remote Similarity	NPD9010	Approved
0.6333	Remote Similarity	NPD8960	Approved
0.6333	Remote Similarity	NPD3186	Phase 1
0.6333	Remote Similarity	NPD64	Approved
0.6333	Remote Similarity	NPD9008	Approved
0.6333	Remote Similarity	NPD66	Approved
0.6333	Remote Similarity	NPD9011	Approved
0.6333	Remote Similarity	NPD72	Approved
0.6333	Remote Similarity	NPD65	Approved
0.6232	Remote Similarity	NPD897	Approved
0.6232	Remote Similarity	NPD896	Approved
0.6232	Remote Similarity	NPD898	Approved
0.619	Remote Similarity	NPD2267	Suspended
0.6129	Remote Similarity	NPD4266	Approved
0.6129	Remote Similarity	NPD3195	Phase 2
0.6129	Remote Similarity	NPD3194	Approved
0.6129	Remote Similarity	NPD3196	Approved
0.6119	Remote Similarity	NPD8961	Approved
0.6	Remote Similarity	NPD5383	Approved
0.6	Remote Similarity	NPD2272	Approved
0.6	Remote Similarity	NPD6109	Phase 1
0.5974	Remote Similarity	NPD7329	Approved
0.5972	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD3172	Approved
0.5952	Remote Similarity	NPD46	Approved
0.5952	Remote Similarity	NPD6698	Approved
0.5949	Remote Similarity	NPD6435	Approved
0.5932	Remote Similarity	NPD622	Approved
0.5902	Remote Similarity	NPD9638	Phase 2
0.5893	Remote Similarity	NPD387	Clinical (unspecified phase)
0.589	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7983	Approved
0.5875	Remote Similarity	NPD7154	Phase 3
0.5873	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD376	Approved
0.5867	Remote Similarity	NPD11	Approved
0.5862	Remote Similarity	NPD9430	Approved
0.5862	Remote Similarity	NPD9431	Approved
0.5844	Remote Similarity	NPD4238	Approved
0.5844	Remote Similarity	NPD4802	Phase 2
0.5833	Remote Similarity	NPD8964	Approved
0.5821	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD3181	Approved
0.5806	Remote Similarity	NPD2269	Approved
0.58	Remote Similarity	NPD9636	Phase 2
0.5789	Remote Similarity	NPD9006	Approved
0.5789	Remote Similarity	NPD6117	Approved
0.575	Remote Similarity	NPD7345	Approved
0.5733	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD618	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6116	Phase 1
0.5696	Remote Similarity	NPD5368	Approved
0.5696	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD9005	Phase 3
0.5667	Remote Similarity	NPD9003	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD9004	Approved
0.5645	Remote Similarity	NPD905	Approved
0.5645	Remote Similarity	NPD28	Approved
0.5645	Remote Similarity	NPD1400	Approved
0.5645	Remote Similarity	NPD29	Approved
0.5645	Remote Similarity	NPD9002	Approved
0.5645	Remote Similarity	NPD904	Phase 3
0.5645	Remote Similarity	NPD1399	Approved
0.5645	Remote Similarity	NPD9001	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6114	Approved
0.5641	Remote Similarity	NPD6697	Approved
0.5641	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6115	Approved
0.5641	Remote Similarity	NPD6118	Approved
0.5636	Remote Similarity	NPD9450	Approved
0.5636	Remote Similarity	NPD77	Approved
0.5634	Remote Similarity	NPD3704	Approved
0.5625	Remote Similarity	NPD5369	Approved
0.5614	Remote Similarity	NPD8957	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