NPASS Compound

Structure

NPC473559 OpenBabel07101719142D 44 43 0 0 1 0 0 0 0 0999 V2000 -8.6603 14.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -1.7321 -0.0000 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 3 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -1.7321 2.0000 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 2 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 40 1 0 0 0 0 36 37 1 0 0 0 0 36 43 1 0 0 0 0 37 44 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:	616.51
Volume:	711.232
LogP:	9.081
LogD:	5.781
LogS:	-2.525
# Rotatable Bonds:	34
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.046
Synthetic Accessibility Score:	3.504
Fsp3:	0.744
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:	-5.081
MDCK Permeability:	4.739396899822168e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.205
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	102.49744415283203%
Volume Distribution (VD):	4.071
Pgp-substrate:	0.25313907861709595%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.152
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.988
CYP2D6-inhibitor:	0.779
CYP2D6-substrate:	0.522
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.055

ADMET: Excretion

Clearance (CL):	3.109
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.417
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.583
Skin Sensitization:	0.986
Carcinogencity:	0.105
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.757

Download Data

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

Natural Product: NPC473559

Natural Product ID:	NPC473559
*Common Name:**	1-O-(9Z,12Z-Octadecadienoyl)-2-O-(9Z,12Z-Octadecadienoyl)Glycerol
IUPAC Name:	[3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] (9E,12E)-octadeca-9,12-dienoate
Synonyms:
Standard InCHIKey:	MQGBAQLIFKSMEM-YIEDHNAISA-N
Standard InCHI:	InChI=1S/C39H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,37,40H,3-10,15-16,21-36H2,1-2H3/b13-11+,14-12-,19-17+,20-18-
SMILES:	CCCCCC=CCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCC=CCCCCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445705
PubChem CID:	44584138
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[479554]

☑ 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 NPC473559 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	176
0.1-0.2	1950
0.2-0.3	7603
0.3-0.4	17028
0.4-0.5	8594
0.5-0.6	5785
0.6-0.7	1204
0.7-0.8	306
0.8-0.85	16
0.85-0.9	14
0.9-0.95	5
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC324981
1.0	High Similarity	NPC141481
1.0	High Similarity	NPC48218
0.9841	High Similarity	NPC475443
0.9841	High Similarity	NPC22101
0.9841	High Similarity	NPC148192
0.9841	High Similarity	NPC473829
0.9841	High Similarity	NPC104537
0.9841	High Similarity	NPC330426
0.9841	High Similarity	NPC271921
0.9841	High Similarity	NPC127091
0.9692	High Similarity	NPC476660
0.9538	High Similarity	NPC473772
0.9206	High Similarity	NPC54925
0.9104	High Similarity	NPC42526
0.9077	High Similarity	NPC476656
0.9077	High Similarity	NPC476659
0.8986	High Similarity	NPC474321
0.8923	High Similarity	NPC476654
0.8923	High Similarity	NPC476657
0.8923	High Similarity	NPC476655
0.8889	High Similarity	NPC321919
0.8889	High Similarity	NPC81896
0.8769	High Similarity	NPC476658
0.875	High Similarity	NPC321838
0.875	High Similarity	NPC201939
0.8657	High Similarity	NPC99619
0.8657	High Similarity	NPC26500
0.8594	High Similarity	NPC243532
0.8529	High Similarity	NPC209327
0.8529	High Similarity	NPC273508
0.8485	Intermediate Similarity	NPC328089
0.8485	Intermediate Similarity	NPC68343
0.84	Intermediate Similarity	NPC21693
0.84	Intermediate Similarity	NPC236649
0.8358	Intermediate Similarity	NPC176215
0.8358	Intermediate Similarity	NPC296436
0.8243	Intermediate Similarity	NPC11796
0.8243	Intermediate Similarity	NPC218817
0.8235	Intermediate Similarity	NPC83965
0.8219	Intermediate Similarity	NPC190400
0.8219	Intermediate Similarity	NPC49392
0.8182	Intermediate Similarity	NPC473500
0.8182	Intermediate Similarity	NPC38295
0.8182	Intermediate Similarity	NPC328776
0.8182	Intermediate Similarity	NPC470313
0.8182	Intermediate Similarity	NPC320305
0.8182	Intermediate Similarity	NPC156089
0.8125	Intermediate Similarity	NPC323436
0.8116	Intermediate Similarity	NPC473357
0.8116	Intermediate Similarity	NPC193029
0.8116	Intermediate Similarity	NPC25298
0.8095	Intermediate Similarity	NPC200845
0.8095	Intermediate Similarity	NPC10316
0.8095	Intermediate Similarity	NPC128061
0.8095	Intermediate Similarity	NPC223677
0.8095	Intermediate Similarity	NPC28779
0.8088	Intermediate Similarity	NPC318420
0.8088	Intermediate Similarity	NPC136164
0.8088	Intermediate Similarity	NPC326268
0.8088	Intermediate Similarity	NPC255863
0.8088	Intermediate Similarity	NPC245947
0.8056	Intermediate Similarity	NPC470435
0.7969	Intermediate Similarity	NPC477201
0.7949	Intermediate Similarity	NPC253801
0.7941	Intermediate Similarity	NPC470320
0.7937	Intermediate Similarity	NPC88966
0.7937	Intermediate Similarity	NPC154245
0.7937	Intermediate Similarity	NPC6095
0.7937	Intermediate Similarity	NPC23155
0.7937	Intermediate Similarity	NPC320588
0.7937	Intermediate Similarity	NPC25417
0.7937	Intermediate Similarity	NPC281972
0.7937	Intermediate Similarity	NPC261831
0.7937	Intermediate Similarity	NPC32467
0.7937	Intermediate Similarity	NPC87564
0.7937	Intermediate Similarity	NPC469937
0.7937	Intermediate Similarity	NPC85813
0.7937	Intermediate Similarity	NPC424
0.7937	Intermediate Similarity	NPC290563
0.7937	Intermediate Similarity	NPC53463
0.7895	Intermediate Similarity	NPC263574
0.7895	Intermediate Similarity	NPC469747
0.7887	Intermediate Similarity	NPC130618
0.7887	Intermediate Similarity	NPC317583
0.7887	Intermediate Similarity	NPC470436
0.7867	Intermediate Similarity	NPC110813
0.7857	Intermediate Similarity	NPC478100
0.7848	Intermediate Similarity	NPC163093
0.7821	Intermediate Similarity	NPC329829
0.7821	Intermediate Similarity	NPC145914
0.7821	Intermediate Similarity	NPC94875
0.7821	Intermediate Similarity	NPC473712
0.7821	Intermediate Similarity	NPC180363
0.7821	Intermediate Similarity	NPC11332
0.7821	Intermediate Similarity	NPC65930
0.7821	Intermediate Similarity	NPC73310
0.7821	Intermediate Similarity	NPC473529
0.7821	Intermediate Similarity	NPC131002
0.7821	Intermediate Similarity	NPC473780
0.7821	Intermediate Similarity	NPC475159
0.7812	Intermediate Similarity	NPC52264
0.7808	Intermediate Similarity	NPC325627
0.7792	Intermediate Similarity	NPC200446
0.7792	Intermediate Similarity	NPC103634
0.7778	Intermediate Similarity	NPC139029
0.7778	Intermediate Similarity	NPC71761
0.7778	Intermediate Similarity	NPC36061
0.7778	Intermediate Similarity	NPC309606
0.7778	Intermediate Similarity	NPC294548
0.7778	Intermediate Similarity	NPC70387
0.7778	Intermediate Similarity	NPC39633
0.7778	Intermediate Similarity	NPC139545
0.7778	Intermediate Similarity	NPC321062
0.7778	Intermediate Similarity	NPC1813
0.7763	Intermediate Similarity	NPC133377
0.7761	Intermediate Similarity	NPC229252
0.7761	Intermediate Similarity	NPC143857
0.775	Intermediate Similarity	NPC475206
0.775	Intermediate Similarity	NPC477013
0.775	Intermediate Similarity	NPC471567
0.775	Intermediate Similarity	NPC477014
0.775	Intermediate Similarity	NPC120398
0.775	Intermediate Similarity	NPC322529
0.7733	Intermediate Similarity	NPC470899
0.7722	Intermediate Similarity	NPC196102
0.7722	Intermediate Similarity	NPC144415
0.7722	Intermediate Similarity	NPC178758
0.7714	Intermediate Similarity	NPC478101
0.7692	Intermediate Similarity	NPC18951
0.7681	Intermediate Similarity	NPC226592
0.7671	Intermediate Similarity	NPC320119
0.7662	Intermediate Similarity	NPC209995
0.7656	Intermediate Similarity	NPC137538
0.7654	Intermediate Similarity	NPC69082
0.7654	Intermediate Similarity	NPC279267
0.7654	Intermediate Similarity	NPC477015
0.7654	Intermediate Similarity	NPC309211
0.7647	Intermediate Similarity	NPC113293
0.7639	Intermediate Similarity	NPC143396
0.7625	Intermediate Similarity	NPC156804
0.7619	Intermediate Similarity	NPC281245
0.7619	Intermediate Similarity	NPC92114
0.7612	Intermediate Similarity	NPC274927
0.7612	Intermediate Similarity	NPC106851
0.7606	Intermediate Similarity	NPC478097
0.7595	Intermediate Similarity	NPC474252
0.759	Intermediate Similarity	NPC39290
0.759	Intermediate Similarity	NPC159369
0.7576	Intermediate Similarity	NPC323597
0.7576	Intermediate Similarity	NPC323498
0.7576	Intermediate Similarity	NPC211752
0.7568	Intermediate Similarity	NPC326024
0.7561	Intermediate Similarity	NPC178215
0.7538	Intermediate Similarity	NPC228473
0.7536	Intermediate Similarity	NPC29697
0.7532	Intermediate Similarity	NPC469495
0.7531	Intermediate Similarity	NPC473671
0.7531	Intermediate Similarity	NPC470400
0.7531	Intermediate Similarity	NPC235809
0.7531	Intermediate Similarity	NPC319036
0.7531	Intermediate Similarity	NPC132496
0.7531	Intermediate Similarity	NPC100921
0.7531	Intermediate Similarity	NPC283085
0.7531	Intermediate Similarity	NPC25764
0.7531	Intermediate Similarity	NPC39167
0.7531	Intermediate Similarity	NPC473651
0.7531	Intermediate Similarity	NPC473156
0.7531	Intermediate Similarity	NPC82795
0.7531	Intermediate Similarity	NPC9678
0.7531	Intermediate Similarity	NPC39279
0.7531	Intermediate Similarity	NPC223871
0.7531	Intermediate Similarity	NPC77871
0.7531	Intermediate Similarity	NPC473669
0.7531	Intermediate Similarity	NPC202055
0.7531	Intermediate Similarity	NPC473478
0.7531	Intermediate Similarity	NPC292809
0.7531	Intermediate Similarity	NPC329838
0.7531	Intermediate Similarity	NPC107986
0.7531	Intermediate Similarity	NPC286338
0.7531	Intermediate Similarity	NPC329615
0.7531	Intermediate Similarity	NPC66346
0.7531	Intermediate Similarity	NPC110710
0.7531	Intermediate Similarity	NPC477018
0.7531	Intermediate Similarity	NPC103284
0.7531	Intermediate Similarity	NPC231009
0.7531	Intermediate Similarity	NPC475268
0.7531	Intermediate Similarity	NPC1083
0.7531	Intermediate Similarity	NPC182383
0.75	Intermediate Similarity	NPC313670
0.75	Intermediate Similarity	NPC478003
0.75	Intermediate Similarity	NPC158388
0.75	Intermediate Similarity	NPC478004
0.75	Intermediate Similarity	NPC328311
0.75	Intermediate Similarity	NPC327112
0.747	Intermediate Similarity	NPC48338
0.747	Intermediate Similarity	NPC320458
0.747	Intermediate Similarity	NPC20339
0.747	Intermediate Similarity	NPC89001
0.747	Intermediate Similarity	NPC40376

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 NPC473559 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	2756
0.2-0.3	3703
0.3-0.4	1719
0.4-0.5	606
0.5-0.6	162
0.6-0.7	44
0.7-0.8	17
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
0.8769	High Similarity	NPD3197	Phase 1
0.7937	Intermediate Similarity	NPD3730	Approved
0.7937	Intermediate Similarity	NPD3195	Phase 2
0.7937	Intermediate Similarity	NPD4266	Approved
0.7937	Intermediate Similarity	NPD3196	Approved
0.7937	Intermediate Similarity	NPD3194	Approved
0.7937	Intermediate Similarity	NPD3728	Approved
0.7778	Intermediate Similarity	NPD3172	Approved
0.7727	Intermediate Similarity	NPD6109	Phase 1
0.75	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD29	Approved
0.746	Intermediate Similarity	NPD28	Approved
0.7412	Intermediate Similarity	NPD7983	Approved
0.7375	Intermediate Similarity	NPD6435	Approved
0.7284	Intermediate Similarity	NPD7154	Phase 3
0.7143	Intermediate Similarity	NPD3173	Approved
0.7125	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5368	Approved
0.7123	Intermediate Similarity	NPD4247	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD46	Approved
0.7093	Intermediate Similarity	NPD6698	Approved
0.7037	Intermediate Similarity	NPD5369	Approved
0.6984	Remote Similarity	NPD5343	Approved
0.6984	Remote Similarity	NPD6125	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD622	Approved
0.6875	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4268	Approved
0.6875	Remote Similarity	NPD4271	Approved
0.6867	Remote Similarity	NPD5362	Discontinued
0.6782	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6101	Approved
0.6747	Remote Similarity	NPD4269	Approved
0.6747	Remote Similarity	NPD4270	Approved
0.6707	Remote Similarity	NPD4820	Approved
0.6707	Remote Similarity	NPD4821	Approved
0.6707	Remote Similarity	NPD4252	Approved
0.6707	Remote Similarity	NPD4822	Approved
0.6707	Remote Similarity	NPD4819	Approved
0.6705	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD3732	Approved
0.6667	Remote Similarity	NPD39	Approved
0.6667	Remote Similarity	NPD4222	Approved
0.6667	Remote Similarity	NPD3174	Discontinued
0.6629	Remote Similarity	NPD6411	Approved
0.6628	Remote Similarity	NPD5786	Approved
0.6556	Remote Similarity	NPD5778	Approved
0.6556	Remote Similarity	NPD5779	Approved
0.6552	Remote Similarity	NPD4250	Approved
0.6552	Remote Similarity	NPD4251	Approved
0.6522	Remote Similarity	NPD7839	Suspended
0.6512	Remote Similarity	NPD5363	Approved
0.6508	Remote Similarity	NPD2699	Approved
0.6508	Remote Similarity	NPD6097	Approved
0.6508	Remote Similarity	NPD6096	Approved
0.65	Remote Similarity	NPD8039	Approved
0.6437	Remote Similarity	NPD4249	Approved
0.6377	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5326	Phase 3
0.6341	Remote Similarity	NPD4756	Discovery
0.6333	Remote Similarity	NPD5785	Approved
0.6316	Remote Similarity	NPD3704	Approved
0.6279	Remote Similarity	NPD5331	Approved
0.6279	Remote Similarity	NPD5332	Approved
0.6267	Remote Similarity	NPD7909	Approved
0.625	Remote Similarity	NPD6422	Discontinued
0.6235	Remote Similarity	NPD4790	Discontinued
0.6222	Remote Similarity	NPD5370	Suspended
0.622	Remote Similarity	NPD819	Approved
0.622	Remote Similarity	NPD818	Approved
0.6176	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7748	Approved
0.6104	Remote Similarity	NPD7331	Phase 2
0.6104	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6686	Approved
0.6032	Remote Similarity	NPD2270	Approved
0.6027	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6399	Phase 3
0.5962	Remote Similarity	NPD8297	Approved
0.5955	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD6927	Phase 3
0.5938	Remote Similarity	NPD6083	Phase 2
0.5938	Remote Similarity	NPD6084	Phase 2
0.5938	Remote Similarity	NPD7902	Approved
0.593	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6421	Discontinued
0.5922	Remote Similarity	NPD6371	Approved
0.5914	Remote Similarity	NPD7637	Suspended
0.5914	Remote Similarity	NPD7515	Phase 2
0.5876	Remote Similarity	NPD4225	Approved
0.5875	Remote Similarity	NPD8277	Approved
0.5851	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7798	Approved
0.5806	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6412	Phase 2
0.5769	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5344	Discontinued
0.5758	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.575	Remote Similarity	NPD8278	Approved
0.5741	Remote Similarity	NPD6935	Phase 3
0.5741	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD7115	Discovery
0.5733	Remote Similarity	NPD3198	Approved
0.573	Remote Similarity	NPD6110	Phase 1
0.5729	Remote Similarity	NPD5695	Phase 3
0.5728	Remote Similarity	NPD6899	Approved
0.5728	Remote Similarity	NPD6881	Approved
0.5714	Remote Similarity	NPD9655	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD633	Phase 3
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD9448	Phase 2
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5688	Remote Similarity	NPD6918	Phase 1
0.5688	Remote Similarity	NPD7641	Discontinued
0.5686	Remote Similarity	NPD6402	Approved
0.5686	Remote Similarity	NPD6675	Approved
0.5686	Remote Similarity	NPD5739	Approved
0.5686	Remote Similarity	NPD7128	Approved
0.5676	Remote Similarity	NPD8517	Approved
0.5676	Remote Similarity	NPD8513	Phase 3
0.5676	Remote Similarity	NPD8444	Approved
0.5676	Remote Similarity	NPD8515	Approved
0.5676	Remote Similarity	NPD8516	Approved
0.5673	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD4786	Approved
0.5631	Remote Similarity	NPD5697	Approved
0.5625	Remote Similarity	NPD7900	Approved
0.5625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7536	Approved
0.5625	Remote Similarity	NPD5282	Discontinued
0.5619	Remote Similarity	NPD7102	Approved
0.5619	Remote Similarity	NPD7290	Approved
0.5619	Remote Similarity	NPD6883	Approved
0.5618	Remote Similarity	NPD3667	Approved
0.5618	Remote Similarity	NPD5209	Approved
0.5618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5616	Remote Similarity	NPD4627	Clinical (unspecified phase)

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