NPASS Compound

Structure

CID310746 OpenBabel06191716122D 23 22 0 0 0 0 0 0 0 0999 V2000 -13.8564 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 2 0 0 0 0 3 5 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 2 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.3
Volume:	384.08
LogP:	8.577
LogD:	4.432
LogS:	-6.941
# Rotatable Bonds:	19
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	0
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.154
Synthetic Accessibility Score:	2.035
Fsp3:	0.857
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:	-4.863
MDCK Permeability:	1.5781255569891073e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.476
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.154
Plasma Protein Binding (PPB):	99.43873596191406%
Volume Distribution (VD):	1.187
Pgp-substrate:	0.9275582432746887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.29
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.394
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.131
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.362
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.598
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	5.11
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.967
Carcinogencity:	0.16
Eye Corrosion:	0.911
Eye Irritation:	0.978
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC310746

Natural Product ID:	NPC310746
*Common Name:**	Allyl Octadecanoate
IUPAC Name:	prop-2-enyl octadecanoate
Synonyms:
Standard InCHIKey:	HPCIWDZYMSZAEZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H40O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(22)23-20-4-2/h4H,2-3,5-20H2,1H3
SMILES:	CCCCCCCCCCCCCCCCCC(=O)OCC=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229590
PubChem CID:	80500
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	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
Others	13

Activity Type	# Activity
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1637	Organism	Cydia pomonella	Cydia pomonella	LC90	=	7.33	mg/ml	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	43.3	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	13.3	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	LC50	=	2690.0	ug.mL-1	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	0.0	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	11.9	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	17.3	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	32.1	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	41.6	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	82.2	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	87.2	%	PMID[553329]
NPT1637	Organism	Cydia pomonella	Cydia pomonella	mortality	=	100.0	%	PMID[553329]

☑ 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 NPC310746 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	298
0.1-0.2	4809
0.2-0.3	18979
0.3-0.4	11666
0.4-0.5	5125
0.5-0.6	1503
0.6-0.7	254
0.7-0.8	52
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC250919
0.875	High Similarity	NPC172042
0.8571	High Similarity	NPC45097
0.8333	Intermediate Similarity	NPC10316
0.8333	Intermediate Similarity	NPC223677
0.8333	Intermediate Similarity	NPC128061
0.8333	Intermediate Similarity	NPC28779
0.8333	Intermediate Similarity	NPC200845
0.8125	Intermediate Similarity	NPC203531
0.8125	Intermediate Similarity	NPC236579
0.8039	Intermediate Similarity	NPC216130
0.7963	Intermediate Similarity	NPC39633
0.7963	Intermediate Similarity	NPC139545
0.7963	Intermediate Similarity	NPC71761
0.7963	Intermediate Similarity	NPC309606
0.7885	Intermediate Similarity	NPC223675
0.78	Intermediate Similarity	NPC287231
0.78	Intermediate Similarity	NPC47363
0.7778	Intermediate Similarity	NPC161366
0.7708	Intermediate Similarity	NPC256163
0.7708	Intermediate Similarity	NPC165533
0.7708	Intermediate Similarity	NPC161097
0.7708	Intermediate Similarity	NPC12156
0.7708	Intermediate Similarity	NPC250028
0.7708	Intermediate Similarity	NPC40597
0.7708	Intermediate Similarity	NPC28598
0.7708	Intermediate Similarity	NPC149299
0.7692	Intermediate Similarity	NPC68577
0.7679	Intermediate Similarity	NPC228473
0.7627	Intermediate Similarity	NPC229252
0.7627	Intermediate Similarity	NPC143857
0.7593	Intermediate Similarity	NPC262968
0.7551	Intermediate Similarity	NPC53541
0.75	Intermediate Similarity	NPC223249
0.75	Intermediate Similarity	NPC80234
0.7407	Intermediate Similarity	NPC224227
0.7377	Intermediate Similarity	NPC54925
0.7344	Intermediate Similarity	NPC218477
0.7308	Intermediate Similarity	NPC30195
0.7308	Intermediate Similarity	NPC12438
0.7292	Intermediate Similarity	NPC305660
0.7292	Intermediate Similarity	NPC22903
0.7292	Intermediate Similarity	NPC201622
0.7292	Intermediate Similarity	NPC54980
0.7258	Intermediate Similarity	NPC68343
0.7258	Intermediate Similarity	NPC328089
0.7255	Intermediate Similarity	NPC317128
0.7222	Intermediate Similarity	NPC26253
0.7222	Intermediate Similarity	NPC207815
0.7222	Intermediate Similarity	NPC163345
0.7213	Intermediate Similarity	NPC201939
0.7193	Intermediate Similarity	NPC87564
0.7193	Intermediate Similarity	NPC32467
0.7193	Intermediate Similarity	NPC261831
0.7193	Intermediate Similarity	NPC290563
0.7193	Intermediate Similarity	NPC85813
0.7193	Intermediate Similarity	NPC281972
0.7193	Intermediate Similarity	NPC6095
0.7193	Intermediate Similarity	NPC154245
0.7193	Intermediate Similarity	NPC25417
0.7193	Intermediate Similarity	NPC88966
0.7193	Intermediate Similarity	NPC424
0.7164	Intermediate Similarity	NPC474705
0.7143	Intermediate Similarity	NPC31551
0.7143	Intermediate Similarity	NPC219536
0.7115	Intermediate Similarity	NPC312547
0.7091	Intermediate Similarity	NPC55678
0.7083	Intermediate Similarity	NPC128996
0.7049	Intermediate Similarity	NPC299730
0.7049	Intermediate Similarity	NPC243532
0.7037	Intermediate Similarity	NPC106872
0.7037	Intermediate Similarity	NPC180534
0.7018	Intermediate Similarity	NPC294548
0.7018	Intermediate Similarity	NPC36061
0.7018	Intermediate Similarity	NPC1813
0.7018	Intermediate Similarity	NPC70387
0.7018	Intermediate Similarity	NPC321062
0.7018	Intermediate Similarity	NPC139029
0.7015	Intermediate Similarity	NPC84038
0.6984	Remote Similarity	NPC34883
0.6981	Remote Similarity	NPC52700
0.6981	Remote Similarity	NPC105329
0.6981	Remote Similarity	NPC63182
0.6981	Remote Similarity	NPC145045
0.6964	Remote Similarity	NPC287811
0.6957	Remote Similarity	NPC228978
0.6949	Remote Similarity	NPC18951
0.6949	Remote Similarity	NPC477201
0.6935	Remote Similarity	NPC328776
0.6935	Remote Similarity	NPC320305
0.6923	Remote Similarity	NPC271921
0.6923	Remote Similarity	NPC330426
0.6923	Remote Similarity	NPC473829
0.6923	Remote Similarity	NPC148192
0.6923	Remote Similarity	NPC127091
0.6923	Remote Similarity	NPC22101
0.6923	Remote Similarity	NPC475443
0.6923	Remote Similarity	NPC104537
0.6885	Remote Similarity	NPC474267
0.6875	Remote Similarity	NPC80396
0.6875	Remote Similarity	NPC318420
0.6875	Remote Similarity	NPC80641
0.6875	Remote Similarity	NPC326268
0.6875	Remote Similarity	NPC136164
0.6875	Remote Similarity	NPC255863
0.6875	Remote Similarity	NPC154642
0.6875	Remote Similarity	NPC245947
0.6863	Remote Similarity	NPC307783
0.6863	Remote Similarity	NPC171736
0.6863	Remote Similarity	NPC196924
0.6863	Remote Similarity	NPC209970
0.6863	Remote Similarity	NPC216630
0.6863	Remote Similarity	NPC149184
0.6852	Remote Similarity	NPC326957
0.6852	Remote Similarity	NPC328497
0.6852	Remote Similarity	NPC249754
0.6852	Remote Similarity	NPC324004
0.6842	Remote Similarity	NPC281245
0.6842	Remote Similarity	NPC92114
0.6842	Remote Similarity	NPC18357
0.6818	Remote Similarity	NPC473559
0.6818	Remote Similarity	NPC324981
0.6818	Remote Similarity	NPC48218
0.6818	Remote Similarity	NPC141481
0.6792	Remote Similarity	NPC273545
0.6769	Remote Similarity	NPC284447
0.6765	Remote Similarity	NPC186531
0.6731	Remote Similarity	NPC67462
0.6719	Remote Similarity	NPC226592
0.6719	Remote Similarity	NPC470320
0.6716	Remote Similarity	NPC473772
0.6716	Remote Similarity	NPC317583
0.6714	Remote Similarity	NPC329826
0.6714	Remote Similarity	NPC469414
0.6667	Remote Similarity	NPC470410
0.6667	Remote Similarity	NPC308301
0.6667	Remote Similarity	NPC223374
0.6667	Remote Similarity	NPC301398
0.6667	Remote Similarity	NPC187777
0.6667	Remote Similarity	NPC470412
0.6667	Remote Similarity	NPC179764
0.6667	Remote Similarity	NPC156630
0.6667	Remote Similarity	NPC99619
0.6667	Remote Similarity	NPC86545
0.6667	Remote Similarity	NPC196442
0.6667	Remote Similarity	NPC135703
0.6667	Remote Similarity	NPC26500
0.6618	Remote Similarity	NPC42526
0.6618	Remote Similarity	NPC476660
0.6613	Remote Similarity	NPC478095
0.6613	Remote Similarity	NPC274927
0.6613	Remote Similarity	NPC106851
0.661	Remote Similarity	NPC320588
0.661	Remote Similarity	NPC469937
0.661	Remote Similarity	NPC23155
0.661	Remote Similarity	NPC53463
0.6604	Remote Similarity	NPC74845
0.6571	Remote Similarity	NPC140287
0.6571	Remote Similarity	NPC92558
0.6557	Remote Similarity	NPC225929
0.6522	Remote Similarity	NPC163003
0.65	Remote Similarity	NPC52264
0.65	Remote Similarity	NPC274290
0.65	Remote Similarity	NPC473863
0.65	Remote Similarity	NPC54766
0.6491	Remote Similarity	NPC90904
0.6491	Remote Similarity	NPC305182
0.6491	Remote Similarity	NPC59051
0.6481	Remote Similarity	NPC8219
0.6471	Remote Similarity	NPC301585
0.6471	Remote Similarity	NPC113928
0.6471	Remote Similarity	NPC154186
0.6471	Remote Similarity	NPC301696
0.6471	Remote Similarity	NPC261080
0.6471	Remote Similarity	NPC81263
0.6471	Remote Similarity	NPC201844
0.6471	Remote Similarity	NPC14227
0.6471	Remote Similarity	NPC279026
0.6458	Remote Similarity	NPC154396
0.6458	Remote Similarity	NPC63354
0.6458	Remote Similarity	NPC286498
0.6452	Remote Similarity	NPC478096
0.6429	Remote Similarity	NPC470237
0.6415	Remote Similarity	NPC176500
0.6406	Remote Similarity	NPC321838
0.6389	Remote Similarity	NPC49392
0.6389	Remote Similarity	NPC190400
0.6379	Remote Similarity	NPC314084
0.6377	Remote Similarity	NPC475310
0.6364	Remote Similarity	NPC133904
0.6351	Remote Similarity	NPC469690
0.6349	Remote Similarity	NPC159650
0.6349	Remote Similarity	NPC22897
0.6338	Remote Similarity	NPC474321
0.6338	Remote Similarity	NPC476355
0.6333	Remote Similarity	NPC137538
0.6333	Remote Similarity	NPC269615
0.6316	Remote Similarity	NPC5413
0.6316	Remote Similarity	NPC135698
0.6316	Remote Similarity	NPC149821

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 NPC310746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	4312
0.2-0.3	3092
0.3-0.4	1063
0.4-0.5	195
0.5-0.6	47
0.6-0.7	28
0.7-0.8	2
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
0.78	Intermediate Similarity	NPD2699	Approved
0.7593	Intermediate Similarity	NPD29	Approved
0.7593	Intermediate Similarity	NPD28	Approved
0.7292	Intermediate Similarity	NPD3206	Approved
0.7193	Intermediate Similarity	NPD4266	Approved
0.7193	Intermediate Similarity	NPD3196	Approved
0.7193	Intermediate Similarity	NPD3194	Approved
0.7193	Intermediate Similarity	NPD3195	Phase 2
0.7037	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5343	Approved
0.7037	Intermediate Similarity	NPD622	Approved
0.7018	Intermediate Similarity	NPD3172	Approved
0.6957	Remote Similarity	NPD8039	Approved
0.6863	Remote Similarity	NPD2270	Approved
0.6719	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD3174	Discontinued
0.6667	Remote Similarity	NPD6927	Phase 3
0.6667	Remote Similarity	NPD3205	Discontinued
0.661	Remote Similarity	NPD3730	Approved
0.661	Remote Similarity	NPD3728	Approved
0.6481	Remote Similarity	NPD6097	Approved
0.6481	Remote Similarity	NPD6096	Approved
0.6481	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD9448	Phase 2
0.6471	Remote Similarity	NPD633	Phase 3
0.6316	Remote Similarity	NPD3173	Approved
0.625	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9655	Approved
0.6111	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD2266	Phase 2
0.5823	Remote Similarity	NPD7154	Phase 3
0.5797	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD634	Phase 3
0.5789	Remote Similarity	NPD39	Approved
0.5789	Remote Similarity	NPD4222	Approved
0.5738	Remote Similarity	NPD3186	Phase 1
0.5735	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD6435	Approved
0.5692	Remote Similarity	NPD6109	Phase 1
0.5641	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5362	Discontinued
0.5606	Remote Similarity	NPD3198	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