NPASS Compound

Structure

NPC475443 OpenBabel07101719142D 44 43 0 0 1 0 0 0 0 0999 V2000 -15.5885 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 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 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -0.0000 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 -11.2583 0.5000 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 -10.3923 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -3.4641 -0.0000 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 -1.7321 2.0000 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 -0.8660 1.5000 0.0000 C 0 0 3 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 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 -2.5981 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 1 0 0 0 0 3 5 1 0 0 0 0 4 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 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 18 20 2 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 29 31 1 0 0 0 0 30 32 1 0 0 0 0 31 33 1 0 0 0 0 32 34 1 0 0 0 0 33 38 1 0 0 0 0 34 39 1 0 0 0 0 35 37 1 0 0 0 0 35 43 1 0 0 0 0 36 37 1 0 0 0 0 36 44 1 0 0 0 0 37 40 1 0 0 0 0 38 41 2 0 0 0 0 38 43 1 0 0 0 0 39 42 2 0 0 0 0 39 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.52
Volume:	713.869
LogP:	9.918
LogD:	6.16
LogS:	-2.399
# Rotatable Bonds:	35
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.045
Synthetic Accessibility Score:	3.275
Fsp3:	0.795
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.064
MDCK Permeability:	2.8202452085679397e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.465
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.04889678955078%
Volume Distribution (VD):	2.638
Pgp-substrate:	0.2433127760887146%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.041
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.499
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.592
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	3.636
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.48
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.121
Skin Sensitization:	0.987
Carcinogencity:	0.062
Eye Corrosion:	0.004
Eye Irritation:	0.08
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC475443

Natural Product ID:	NPC475443
*Common Name:**	1-O-(9Z,12Z-Octadecadienoyl)-3-O-(9Z-Octadecenoyl)Glycerol
IUPAC Name:	[2-hydroxy-3-[(9E,12Z)-octadeca-9,12-dienoyl]oxypropyl] (Z)-octadec-9-enoate
Synonyms:
Standard InCHIKey:	GREDRAMJRDQWEJ-DEDKAWTBSA-N
Standard InCHI:	InChI=1S/C39H70O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,37,40H,3-10,12,14-16,21-36H2,1-2H3/b13-11-,19-17+,20-18-
SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCC/C=C/C/C=CCCCCC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505746
PubChem CID:	44584139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

*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
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	100000.0	nM	PMID[533103]

☑ 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 NPC475443 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	173
0.1-0.2	2090
0.2-0.3	8386
0.3-0.4	16766
0.4-0.5	8610
0.5-0.6	5285
0.6-0.7	1073
0.7-0.8	269
0.8-0.85	14
0.85-0.9	14
0.9-0.95	1
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473829
0.9841	High Similarity	NPC473559
0.9841	High Similarity	NPC48218
0.9841	High Similarity	NPC141481
0.9841	High Similarity	NPC324981
0.9688	High Similarity	NPC473772
0.9683	High Similarity	NPC104537
0.9683	High Similarity	NPC127091
0.9683	High Similarity	NPC148192
0.9683	High Similarity	NPC271921
0.9683	High Similarity	NPC22101
0.9683	High Similarity	NPC330426
0.9538	High Similarity	NPC476660
0.9355	High Similarity	NPC54925
0.8955	High Similarity	NPC42526
0.8923	High Similarity	NPC476659
0.8923	High Similarity	NPC476656
0.8841	High Similarity	NPC474321
0.8769	High Similarity	NPC476657
0.8769	High Similarity	NPC476654
0.8769	High Similarity	NPC476655
0.873	High Similarity	NPC81896
0.873	High Similarity	NPC321919
0.8615	High Similarity	NPC476658
0.8594	High Similarity	NPC201939
0.8594	High Similarity	NPC321838
0.8507	High Similarity	NPC99619
0.8507	High Similarity	NPC26500
0.8438	Intermediate Similarity	NPC243532
0.8382	Intermediate Similarity	NPC209327
0.8382	Intermediate Similarity	NPC273508
0.8333	Intermediate Similarity	NPC328089
0.8333	Intermediate Similarity	NPC68343
0.8267	Intermediate Similarity	NPC21693
0.8267	Intermediate Similarity	NPC236649
0.8226	Intermediate Similarity	NPC128061
0.8226	Intermediate Similarity	NPC200845
0.8226	Intermediate Similarity	NPC10316
0.8226	Intermediate Similarity	NPC223677
0.8226	Intermediate Similarity	NPC28779
0.8209	Intermediate Similarity	NPC176215
0.8209	Intermediate Similarity	NPC296436
0.8108	Intermediate Similarity	NPC218817
0.8108	Intermediate Similarity	NPC11796
0.8088	Intermediate Similarity	NPC83965
0.8082	Intermediate Similarity	NPC49392
0.8082	Intermediate Similarity	NPC190400
0.8052	Intermediate Similarity	NPC473500
0.8052	Intermediate Similarity	NPC470313
0.8052	Intermediate Similarity	NPC38295
0.8052	Intermediate Similarity	NPC156089
0.803	Intermediate Similarity	NPC328776
0.803	Intermediate Similarity	NPC320305
0.7971	Intermediate Similarity	NPC473357
0.7971	Intermediate Similarity	NPC25298
0.7971	Intermediate Similarity	NPC193029
0.7969	Intermediate Similarity	NPC323436
0.7941	Intermediate Similarity	NPC255863
0.7941	Intermediate Similarity	NPC318420
0.7941	Intermediate Similarity	NPC326268
0.7941	Intermediate Similarity	NPC136164
0.7941	Intermediate Similarity	NPC245947
0.7917	Intermediate Similarity	NPC470435
0.7903	Intermediate Similarity	NPC39633
0.7903	Intermediate Similarity	NPC139545
0.7903	Intermediate Similarity	NPC71761
0.7903	Intermediate Similarity	NPC309606
0.7879	Intermediate Similarity	NPC229252
0.7879	Intermediate Similarity	NPC143857
0.7821	Intermediate Similarity	NPC196102
0.7821	Intermediate Similarity	NPC178758
0.7821	Intermediate Similarity	NPC253801
0.7812	Intermediate Similarity	NPC477201
0.7794	Intermediate Similarity	NPC470320
0.7778	Intermediate Similarity	NPC23155
0.7778	Intermediate Similarity	NPC32467
0.7778	Intermediate Similarity	NPC281972
0.7778	Intermediate Similarity	NPC85813
0.7778	Intermediate Similarity	NPC290563
0.7778	Intermediate Similarity	NPC469937
0.7778	Intermediate Similarity	NPC53463
0.7778	Intermediate Similarity	NPC25417
0.7778	Intermediate Similarity	NPC261831
0.7778	Intermediate Similarity	NPC88966
0.7778	Intermediate Similarity	NPC6095
0.7778	Intermediate Similarity	NPC154245
0.7778	Intermediate Similarity	NPC320588
0.7778	Intermediate Similarity	NPC424
0.7778	Intermediate Similarity	NPC87564
0.7763	Intermediate Similarity	NPC469747
0.7763	Intermediate Similarity	NPC263574
0.7746	Intermediate Similarity	NPC317583
0.7746	Intermediate Similarity	NPC470436
0.7746	Intermediate Similarity	NPC130618
0.7733	Intermediate Similarity	NPC110813
0.7722	Intermediate Similarity	NPC163093
0.7714	Intermediate Similarity	NPC478100
0.7692	Intermediate Similarity	NPC473529
0.7692	Intermediate Similarity	NPC94875
0.7692	Intermediate Similarity	NPC473780
0.7692	Intermediate Similarity	NPC65930
0.7692	Intermediate Similarity	NPC180363
0.7692	Intermediate Similarity	NPC145914
0.7692	Intermediate Similarity	NPC131002
0.7692	Intermediate Similarity	NPC11332
0.7692	Intermediate Similarity	NPC73310
0.7692	Intermediate Similarity	NPC475159
0.7692	Intermediate Similarity	NPC329829
0.7692	Intermediate Similarity	NPC473712
0.7671	Intermediate Similarity	NPC325627
0.7662	Intermediate Similarity	NPC200446
0.7662	Intermediate Similarity	NPC103634
0.7656	Intermediate Similarity	NPC228473
0.7656	Intermediate Similarity	NPC52264
0.7632	Intermediate Similarity	NPC133377
0.7625	Intermediate Similarity	NPC475206
0.7625	Intermediate Similarity	NPC477014
0.7625	Intermediate Similarity	NPC120398
0.7625	Intermediate Similarity	NPC471567
0.7625	Intermediate Similarity	NPC322529
0.7625	Intermediate Similarity	NPC477013
0.7619	Intermediate Similarity	NPC36061
0.7619	Intermediate Similarity	NPC70387
0.7619	Intermediate Similarity	NPC321062
0.7619	Intermediate Similarity	NPC294548
0.7619	Intermediate Similarity	NPC139029
0.7619	Intermediate Similarity	NPC1813
0.76	Intermediate Similarity	NPC470899
0.7595	Intermediate Similarity	NPC144415
0.7581	Intermediate Similarity	NPC262968
0.7571	Intermediate Similarity	NPC478101
0.7538	Intermediate Similarity	NPC18951
0.7536	Intermediate Similarity	NPC226592
0.7534	Intermediate Similarity	NPC320119
0.7532	Intermediate Similarity	NPC209995
0.7531	Intermediate Similarity	NPC279267
0.7531	Intermediate Similarity	NPC69082
0.7531	Intermediate Similarity	NPC477015
0.7531	Intermediate Similarity	NPC309211
0.75	Intermediate Similarity	NPC143396
0.75	Intermediate Similarity	NPC156804
0.75	Intermediate Similarity	NPC66460
0.75	Intermediate Similarity	NPC137538
0.75	Intermediate Similarity	NPC325929
0.75	Intermediate Similarity	NPC113293
0.75	Intermediate Similarity	NPC271282
0.747	Intermediate Similarity	NPC39290
0.747	Intermediate Similarity	NPC159369
0.7468	Intermediate Similarity	NPC474252
0.7465	Intermediate Similarity	NPC478097
0.7463	Intermediate Similarity	NPC274927
0.7463	Intermediate Similarity	NPC106851
0.746	Intermediate Similarity	NPC92114
0.746	Intermediate Similarity	NPC281245
0.7439	Intermediate Similarity	NPC178215
0.7432	Intermediate Similarity	NPC326024
0.7424	Intermediate Similarity	NPC323498
0.7424	Intermediate Similarity	NPC211752
0.7424	Intermediate Similarity	NPC323597
0.7419	Intermediate Similarity	NPC55678
0.7419	Intermediate Similarity	NPC224227
0.7407	Intermediate Similarity	NPC231009
0.7407	Intermediate Similarity	NPC329615
0.7407	Intermediate Similarity	NPC82795
0.7407	Intermediate Similarity	NPC107986
0.7407	Intermediate Similarity	NPC132496
0.7407	Intermediate Similarity	NPC283085
0.7407	Intermediate Similarity	NPC1083
0.7407	Intermediate Similarity	NPC473669
0.7407	Intermediate Similarity	NPC473671
0.7407	Intermediate Similarity	NPC286338
0.7407	Intermediate Similarity	NPC475268
0.7407	Intermediate Similarity	NPC473156
0.7407	Intermediate Similarity	NPC202055
0.7407	Intermediate Similarity	NPC103284
0.7407	Intermediate Similarity	NPC39279
0.7407	Intermediate Similarity	NPC25764
0.7407	Intermediate Similarity	NPC223871
0.7407	Intermediate Similarity	NPC77871
0.7407	Intermediate Similarity	NPC66346
0.7407	Intermediate Similarity	NPC9678
0.7407	Intermediate Similarity	NPC329838
0.7407	Intermediate Similarity	NPC39167
0.7407	Intermediate Similarity	NPC473651
0.7407	Intermediate Similarity	NPC477018
0.7407	Intermediate Similarity	NPC473478
0.7407	Intermediate Similarity	NPC470400
0.7407	Intermediate Similarity	NPC110710
0.7407	Intermediate Similarity	NPC235809
0.7407	Intermediate Similarity	NPC292809
0.7407	Intermediate Similarity	NPC319036
0.7407	Intermediate Similarity	NPC100921
0.7407	Intermediate Similarity	NPC182383
0.7403	Intermediate Similarity	NPC469495
0.7391	Intermediate Similarity	NPC29697
0.7381	Intermediate Similarity	NPC478004
0.7381	Intermediate Similarity	NPC158388
0.7381	Intermediate Similarity	NPC478003
0.7381	Intermediate Similarity	NPC313670
0.7353	Intermediate Similarity	NPC327112

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 NPC475443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	2855
0.2-0.3	3762
0.3-0.4	1604
0.4-0.5	588
0.5-0.6	150
0.6-0.7	37
0.7-0.8	14
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8615	High Similarity	NPD3197	Phase 1
0.7778	Intermediate Similarity	NPD3195	Phase 2
0.7778	Intermediate Similarity	NPD4266	Approved
0.7778	Intermediate Similarity	NPD3196	Approved
0.7778	Intermediate Similarity	NPD3730	Approved
0.7778	Intermediate Similarity	NPD3194	Approved
0.7778	Intermediate Similarity	NPD3728	Approved
0.7619	Intermediate Similarity	NPD3172	Approved
0.7581	Intermediate Similarity	NPD28	Approved
0.7581	Intermediate Similarity	NPD29	Approved
0.7576	Intermediate Similarity	NPD6109	Phase 1
0.7353	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7983	Approved
0.725	Intermediate Similarity	NPD6435	Approved
0.716	Intermediate Similarity	NPD7154	Phase 3
0.7097	Intermediate Similarity	NPD6125	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5343	Approved
0.7	Intermediate Similarity	NPD5368	Approved
0.7	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD3173	Approved
0.6977	Remote Similarity	NPD6698	Approved
0.6977	Remote Similarity	NPD46	Approved
0.6914	Remote Similarity	NPD5369	Approved
0.6825	Remote Similarity	NPD622	Approved
0.6774	Remote Similarity	NPD3174	Discontinued
0.675	Remote Similarity	NPD4268	Approved
0.675	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4271	Approved
0.6747	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6627	Remote Similarity	NPD4270	Approved
0.6627	Remote Similarity	NPD4269	Approved
0.6613	Remote Similarity	NPD2699	Approved
0.6613	Remote Similarity	NPD6097	Approved
0.6613	Remote Similarity	NPD6096	Approved
0.6591	Remote Similarity	NPD7838	Discovery
0.6585	Remote Similarity	NPD4820	Approved
0.6585	Remote Similarity	NPD4822	Approved
0.6585	Remote Similarity	NPD4819	Approved
0.6585	Remote Similarity	NPD4821	Approved
0.6585	Remote Similarity	NPD4252	Approved
0.6582	Remote Similarity	NPD8039	Approved
0.6543	Remote Similarity	NPD3732	Approved
0.6517	Remote Similarity	NPD6411	Approved
0.6512	Remote Similarity	NPD5786	Approved
0.6508	Remote Similarity	NPD39	Approved
0.6508	Remote Similarity	NPD4222	Approved
0.6444	Remote Similarity	NPD5778	Approved
0.6444	Remote Similarity	NPD5779	Approved
0.6437	Remote Similarity	NPD4250	Approved
0.6437	Remote Similarity	NPD4251	Approved
0.6413	Remote Similarity	NPD7839	Suspended
0.6395	Remote Similarity	NPD5363	Approved
0.6322	Remote Similarity	NPD4249	Approved
0.6322	Remote Similarity	NPD6422	Discontinued
0.6232	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5785	Approved
0.622	Remote Similarity	NPD4756	Discovery
0.619	Remote Similarity	NPD5326	Phase 3
0.6184	Remote Similarity	NPD3704	Approved
0.6184	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD5331	Approved
0.6163	Remote Similarity	NPD5332	Approved
0.6133	Remote Similarity	NPD7909	Approved
0.6118	Remote Similarity	NPD4790	Discontinued
0.6111	Remote Similarity	NPD5370	Suspended
0.6098	Remote Similarity	NPD819	Approved
0.6098	Remote Similarity	NPD818	Approved
0.6078	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6927	Phase 3
0.6023	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD7331	Phase 2
0.5957	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD8277	Approved
0.5941	Remote Similarity	NPD6686	Approved
0.5938	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6399	Phase 3
0.589	Remote Similarity	NPD585	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7798	Approved
0.5873	Remote Similarity	NPD2270	Approved
0.5865	Remote Similarity	NPD8297	Approved
0.5844	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6084	Phase 2
0.5833	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD7902	Approved
0.5825	Remote Similarity	NPD6421	Discontinued
0.5825	Remote Similarity	NPD6371	Approved
0.5823	Remote Similarity	NPD8278	Approved
0.5814	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7515	Phase 2
0.5806	Remote Similarity	NPD7637	Suspended
0.5778	Remote Similarity	NPD7521	Approved
0.5778	Remote Similarity	NPD6684	Approved
0.5778	Remote Similarity	NPD7334	Approved
0.5778	Remote Similarity	NPD7146	Approved
0.5778	Remote Similarity	NPD6409	Approved
0.5778	Remote Similarity	NPD5330	Approved
0.5773	Remote Similarity	NPD4225	Approved
0.5745	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.573	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7536	Approved
0.5699	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6412	Phase 2
0.5684	Remote Similarity	NPD7900	Approved
0.5684	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5209	Approved
0.5657	Remote Similarity	NPD5344	Discontinued
0.5652	Remote Similarity	NPD6903	Approved
0.5652	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6672	Approved
0.5652	Remote Similarity	NPD5737	Approved
0.5648	Remote Similarity	NPD7115	Discovery
0.5648	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6935	Phase 3
0.5645	Remote Similarity	NPD3206	Approved
0.5631	Remote Similarity	NPD6899	Approved
0.5631	Remote Similarity	NPD6881	Approved
0.5625	Remote Similarity	NPD5695	Phase 3
0.5619	Remote Similarity	NPD8130	Phase 1
0.5618	Remote Similarity	NPD6110	Phase 1
0.5606	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.56	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