NPASS Compound

Structure

CID83062 OpenBabel06191715422D 52 53 0 0 0 0 0 0 0 0999 V2000 -29.4449 -4.0000 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 -13.8564 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 -4.0000 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 -16.4545 -4.5000 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 -17.3205 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.9186 -4.5000 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 -20.7846 -4.0000 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 -21.6506 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -22.5167 -4.0000 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 -26.8468 -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 -25.9808 -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 -27.7128 -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 -25.1147 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -23.3827 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -27.7128 -3.0000 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 -26.8468 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -28.5788 -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 -28.5788 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -24.2487 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -29.4449 -1.0000 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 -23.3827 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -29.4449 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -24.2487 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 49 1 0 0 0 0 2 50 1 0 0 0 0 3 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 1 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 1 0 0 0 0 18 20 1 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 33 1 0 0 0 0 24 34 1 0 0 0 0 25 29 2 0 0 0 0 25 37 1 0 0 0 0 26 30 2 0 0 0 0 26 38 1 0 0 0 0 27 31 2 0 0 0 0 27 37 1 0 0 0 0 28 32 2 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 31 43 1 0 0 0 0 32 44 1 0 0 0 0 33 51 1 0 0 0 0 34 52 1 0 0 0 0 35 37 2 0 0 0 0 35 41 1 0 0 0 0 36 38 2 0 0 0 0 36 42 1 0 0 0 0 39 41 2 0 0 0 0 39 45 1 0 0 0 0 40 42 2 0 0 0 0 40 46 1 0 0 0 0 41 49 1 0 0 0 0 42 50 1 0 0 0 0 43 47 2 0 0 0 0 43 51 1 0 0 0 0 44 48 2 0 0 0 0 44 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	722.48
Volume:	796.424
LogP:	11.879
LogD:	4.443
LogS:	-6.207
# Rotatable Bonds:	33
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.045
Synthetic Accessibility Score:	2.742
Fsp3:	0.591
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.369
MDCK Permeability:	8.603349670011085e-06
Pgp-inhibitor:	0.988
Pgp-substrate:	0.809
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	104.3158187866211%
Volume Distribution (VD):	5.719
Pgp-substrate:	0.5409589409828186%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	5.636
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.93
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.227
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.387
Skin Sensitization:	0.993
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.552
Respiratory Toxicity:	0.421

Download Data

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

Natural Product: NPC83062

Natural Product ID:	NPC83062
*Common Name:**	1,24-Tetracosanediol Diferulate
IUPAC Name:	24-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxytetracosyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	1,24-Tetracosanediol Diferulate
Standard InCHIKey:	JVYGWGTXGGTEAZ-WWQQVGJXSA-N
Standard InCHI:	InChI=1S/C44H66O8/c1-49-41-35-37(25-29-39(41)45)27-31-43(47)51-33-23-21-19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-22-24-34-52-44(48)32-28-38-26-30-40(46)42(36-38)50-2/h25-32,35-36,45-46H,3-24,33-34H2,1-2H3/b31-27+,32-28+
SMILES:	COc1cc(/C=C/C(=O)OCCCCCCCCCCCCCCCCCCCCCCCCOC(=O)/C=C/c2ccc(c(c2)OC)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL443415
PubChem CID:	11967021
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric 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[546490]

☑ 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 NPC83062 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	262
0.1-0.2	1354
0.2-0.3	4057
0.3-0.4	10209
0.4-0.5	8109
0.5-0.6	4313
0.6-0.7	9900
0.7-0.8	3752
0.8-0.85	548
0.85-0.9	157
0.9-0.95	26
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9754	High Similarity	NPC213552
0.9754	High Similarity	NPC120225
0.9672	High Similarity	NPC289459
0.959	High Similarity	NPC60517
0.959	High Similarity	NPC146886
0.959	High Similarity	NPC20443
0.959	High Similarity	NPC246704
0.9308	High Similarity	NPC120852
0.9302	High Similarity	NPC135127
0.9286	High Similarity	NPC110313
0.9262	High Similarity	NPC204466
0.9242	High Similarity	NPC106055
0.9242	High Similarity	NPC110699
0.9225	High Similarity	NPC475468
0.9187	High Similarity	NPC70752
0.918	High Similarity	NPC202474
0.9134	High Similarity	NPC478215
0.9106	High Similarity	NPC14007
0.9106	High Similarity	NPC470848
0.9106	High Similarity	NPC269843
0.9106	High Similarity	NPC60962
0.9106	High Similarity	NPC224814
0.9106	High Similarity	NPC470849
0.9106	High Similarity	NPC109083
0.9106	High Similarity	NPC189844
0.9098	High Similarity	NPC263386
0.9098	High Similarity	NPC141791
0.9048	High Similarity	NPC87113
0.9024	High Similarity	NPC2058
0.9016	High Similarity	NPC137537
0.9016	High Similarity	NPC107588
0.9016	High Similarity	NPC70744
0.9016	High Similarity	NPC272471
0.9016	High Similarity	NPC277460
0.9016	High Similarity	NPC164706
0.9016	High Similarity	NPC275519
0.9016	High Similarity	NPC203124
0.9015	High Similarity	NPC90431
0.9008	High Similarity	NPC471110
0.8955	High Similarity	NPC288452
0.8955	High Similarity	NPC289690
0.8947	High Similarity	NPC126206
0.8915	High Similarity	NPC241354
0.8906	High Similarity	NPC123722
0.8906	High Similarity	NPC276466
0.8906	High Similarity	NPC5018
0.8906	High Similarity	NPC151167
0.8906	High Similarity	NPC123228
0.8905	High Similarity	NPC274960
0.8905	High Similarity	NPC143120
0.8905	High Similarity	NPC473909
0.8898	High Similarity	NPC280767
0.8889	High Similarity	NPC18984
0.8889	High Similarity	NPC160900
0.8889	High Similarity	NPC106659
0.8889	High Similarity	NPC229084
0.8881	High Similarity	NPC76032
0.8881	High Similarity	NPC284409
0.8881	High Similarity	NPC132723
0.888	High Similarity	NPC147654
0.8872	High Similarity	NPC471664
0.8872	High Similarity	NPC471665
0.8862	High Similarity	NPC470626
0.8862	High Similarity	NPC309434
0.8828	High Similarity	NPC179777
0.8828	High Similarity	NPC84076
0.8828	High Similarity	NPC303680
0.8828	High Similarity	NPC90128
0.8824	High Similarity	NPC140502
0.8824	High Similarity	NPC67467
0.88	High Similarity	NPC207613
0.879	High Similarity	NPC37858
0.878	High Similarity	NPC293619
0.878	High Similarity	NPC280001
0.8769	High Similarity	NPC304622
0.8768	High Similarity	NPC252292
0.8768	High Similarity	NPC34927
0.8768	High Similarity	NPC100998
0.8768	High Similarity	NPC34587
0.8768	High Similarity	NPC476382
0.874	High Similarity	NPC31344
0.874	High Similarity	NPC317769
0.8731	High Similarity	NPC471988
0.873	High Similarity	NPC324571
0.873	High Similarity	NPC54872
0.873	High Similarity	NPC470212
0.873	High Similarity	NPC312675
0.873	High Similarity	NPC473853
0.873	High Similarity	NPC262156
0.873	High Similarity	NPC113865
0.873	High Similarity	NPC184651
0.873	High Similarity	NPC343720
0.8722	High Similarity	NPC300776
0.8722	High Similarity	NPC119060
0.8722	High Similarity	NPC111635
0.8722	High Similarity	NPC67247
0.8722	High Similarity	NPC249791
0.8722	High Similarity	NPC237594
0.8722	High Similarity	NPC5310
0.8722	High Similarity	NPC4982
0.8722	High Similarity	NPC176814
0.8722	High Similarity	NPC476387
0.8722	High Similarity	NPC68779
0.872	High Similarity	NPC95614
0.872	High Similarity	NPC56214
0.872	High Similarity	NPC242885
0.872	High Similarity	NPC227217
0.872	High Similarity	NPC117780
0.872	High Similarity	NPC165133
0.872	High Similarity	NPC232316
0.8714	High Similarity	NPC102934
0.8714	High Similarity	NPC252402
0.8699	High Similarity	NPC281277
0.8692	High Similarity	NPC109275
0.8689	High Similarity	NPC261453
0.8689	High Similarity	NPC33749
0.8689	High Similarity	NPC294941
0.8689	High Similarity	NPC328593
0.8682	High Similarity	NPC276014
0.8682	High Similarity	NPC118584
0.8672	High Similarity	NPC273686
0.8672	High Similarity	NPC312404
0.8667	High Similarity	NPC281780
0.8661	High Similarity	NPC85488
0.8661	High Similarity	NPC286573
0.8657	High Similarity	NPC113295
0.8657	High Similarity	NPC477301
0.8652	High Similarity	NPC94871
0.8652	High Similarity	NPC470933
0.8652	High Similarity	NPC471062
0.8652	High Similarity	NPC473427
0.8652	High Similarity	NPC475250
0.8652	High Similarity	NPC259347
0.8652	High Similarity	NPC306890
0.8652	High Similarity	NPC476398
0.8652	High Similarity	NPC476386
0.8643	High Similarity	NPC232992
0.864	High Similarity	NPC70084
0.864	High Similarity	NPC281298
0.864	High Similarity	NPC310338
0.8633	High Similarity	NPC271607
0.8633	High Similarity	NPC307205
0.8633	High Similarity	NPC83743
0.8633	High Similarity	NPC53884
0.8633	High Similarity	NPC19862
0.8633	High Similarity	NPC287615
0.8633	High Similarity	NPC216819
0.8633	High Similarity	NPC235195
0.8633	High Similarity	NPC262182
0.8633	High Similarity	NPC280717
0.8633	High Similarity	NPC258671
0.8629	High Similarity	NPC610
0.8629	High Similarity	NPC39793
0.8629	High Similarity	NPC200988
0.8629	High Similarity	NPC145023
0.8629	High Similarity	NPC86947
0.8629	High Similarity	NPC175799
0.8626	High Similarity	NPC48315
0.8623	High Similarity	NPC478239
0.8618	High Similarity	NPC233669
0.8618	High Similarity	NPC474967
0.8607	High Similarity	NPC95381
0.8605	High Similarity	NPC194519
0.8605	High Similarity	NPC257589
0.8605	High Similarity	NPC67951
0.8605	High Similarity	NPC53305
0.8594	High Similarity	NPC257976
0.8594	High Similarity	NPC471693
0.8594	High Similarity	NPC242372
0.8594	High Similarity	NPC4181
0.8594	High Similarity	NPC164778
0.8594	High Similarity	NPC280704
0.8593	High Similarity	NPC471719
0.8593	High Similarity	NPC157554
0.8592	High Similarity	NPC257970
0.8592	High Similarity	NPC470934
0.8592	High Similarity	NPC188393
0.8592	High Similarity	NPC470927
0.8583	High Similarity	NPC127389
0.8583	High Similarity	NPC38996
0.8583	High Similarity	NPC160380
0.8583	High Similarity	NPC290451
0.8583	High Similarity	NPC177291
0.8583	High Similarity	NPC194416
0.8582	High Similarity	NPC473054
0.8571	High Similarity	NPC245120
0.8561	High Similarity	NPC304956
0.8561	High Similarity	NPC160378
0.8561	High Similarity	NPC110063
0.856	High Similarity	NPC86198
0.856	High Similarity	NPC124916
0.8551	High Similarity	NPC157816
0.855	High Similarity	NPC226661
0.854	High Similarity	NPC267291
0.8538	High Similarity	NPC178284
0.8538	High Similarity	NPC92207
0.8538	High Similarity	NPC191037
0.8538	High Similarity	NPC127937
0.8538	High Similarity	NPC58607
0.8537	High Similarity	NPC217472

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 NPC83062 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	860
0.2-0.3	1635
0.3-0.4	2604
0.4-0.5	1867
0.5-0.6	1108
0.6-0.7	701
0.7-0.8	133
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD4379	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD228	Approved
0.8333	Intermediate Similarity	NPD5536	Phase 2
0.8333	Intermediate Similarity	NPD7266	Discontinued
0.8209	Intermediate Similarity	NPD3027	Phase 3
0.8162	Intermediate Similarity	NPD4060	Phase 1
0.816	Intermediate Similarity	NPD5283	Phase 1
0.8115	Intermediate Similarity	NPD1358	Approved
0.7941	Intermediate Similarity	NPD7095	Approved
0.7937	Intermediate Similarity	NPD7843	Approved
0.7926	Intermediate Similarity	NPD9494	Approved
0.7902	Intermediate Similarity	NPD8166	Discontinued
0.7886	Intermediate Similarity	NPD3134	Approved
0.7862	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD3022	Approved
0.784	Intermediate Similarity	NPD3021	Approved
0.7803	Intermediate Similarity	NPD3496	Discontinued
0.777	Intermediate Similarity	NPD1653	Approved
0.7752	Intermediate Similarity	NPD7157	Approved
0.7727	Intermediate Similarity	NPD4626	Approved
0.7724	Intermediate Similarity	NPD6190	Approved
0.7714	Intermediate Similarity	NPD6355	Discontinued
0.7656	Intermediate Similarity	NPD5535	Approved
0.7655	Intermediate Similarity	NPD4110	Phase 3
0.7655	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD4628	Phase 3
0.7652	Intermediate Similarity	NPD5691	Approved
0.7652	Intermediate Similarity	NPD1357	Approved
0.7647	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3620	Phase 2
0.7643	Intermediate Similarity	NPD1613	Approved
0.7643	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6798	Discontinued
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD2684	Approved
0.7609	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3455	Phase 2
0.7589	Intermediate Similarity	NPD4340	Discontinued
0.7571	Intermediate Similarity	NPD6233	Phase 2
0.7571	Intermediate Similarity	NPD4062	Phase 3
0.7537	Intermediate Similarity	NPD3847	Discontinued
0.7536	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7518	Intermediate Similarity	NPD1558	Phase 1
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD2983	Phase 2
0.7482	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3705	Approved
0.7469	Intermediate Similarity	NPD7685	Pre-registration
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7465	Intermediate Similarity	NPD447	Suspended
0.7465	Intermediate Similarity	NPD230	Phase 1
0.7452	Intermediate Similarity	NPD8127	Discontinued
0.7451	Intermediate Similarity	NPD1934	Approved
0.7447	Intermediate Similarity	NPD2674	Phase 3
0.7444	Intermediate Similarity	NPD1894	Discontinued
0.7436	Intermediate Similarity	NPD6234	Discontinued
0.7426	Intermediate Similarity	NPD2981	Phase 2
0.7413	Intermediate Similarity	NPD6653	Approved
0.741	Intermediate Similarity	NPD3018	Phase 2
0.7403	Intermediate Similarity	NPD2801	Approved
0.7394	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD5585	Approved
0.7386	Intermediate Similarity	NPD6386	Approved
0.7386	Intermediate Similarity	NPD6385	Approved
0.7376	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7097	Phase 1
0.7357	Intermediate Similarity	NPD6832	Phase 2
0.7353	Intermediate Similarity	NPD422	Phase 1
0.7353	Intermediate Similarity	NPD1535	Discovery
0.7351	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6671	Approved
0.7347	Intermediate Similarity	NPD3060	Approved
0.7338	Intermediate Similarity	NPD6584	Phase 3
0.7329	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD5762	Approved
0.7323	Intermediate Similarity	NPD968	Approved
0.7319	Intermediate Similarity	NPD1283	Approved
0.7299	Intermediate Similarity	NPD1481	Phase 2
0.729	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD4140	Approved
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7266	Intermediate Similarity	NPD2797	Approved
0.7262	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7075	Discontinued
0.726	Intermediate Similarity	NPD6032	Approved
0.726	Intermediate Similarity	NPD2438	Suspended
0.7254	Intermediate Similarity	NPD3144	Approved
0.7254	Intermediate Similarity	NPD3145	Approved
0.7239	Intermediate Similarity	NPD7074	Phase 3
0.7239	Intermediate Similarity	NPD7472	Approved
0.723	Intermediate Similarity	NPD4162	Approved
0.723	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7222	Intermediate Similarity	NPD1933	Approved
0.7213	Intermediate Similarity	NPD9296	Approved
0.7213	Intermediate Similarity	NPD2933	Approved
0.7213	Intermediate Similarity	NPD2934	Approved
0.7206	Intermediate Similarity	NPD5846	Approved
0.7206	Intermediate Similarity	NPD1778	Approved
0.7206	Intermediate Similarity	NPD6516	Phase 2
0.7205	Intermediate Similarity	NPD6166	Phase 2
0.7205	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1241	Discontinued
0.7197	Intermediate Similarity	NPD4965	Approved
0.7197	Intermediate Similarity	NPD4967	Phase 2
0.7197	Intermediate Similarity	NPD4966	Approved
0.7195	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2799	Discontinued
0.719	Intermediate Similarity	NPD3686	Approved
0.719	Intermediate Similarity	NPD3687	Approved
0.7188	Intermediate Similarity	NPD6232	Discontinued
0.7185	Intermediate Similarity	NPD9545	Approved
0.7183	Intermediate Similarity	NPD5163	Phase 2
0.7179	Intermediate Similarity	NPD7819	Suspended
0.7179	Intermediate Similarity	NPD1465	Phase 2
0.7179	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1608	Approved
0.7172	Intermediate Similarity	NPD2653	Approved
0.7163	Intermediate Similarity	NPD2861	Phase 2
0.7162	Intermediate Similarity	NPD4534	Discontinued
0.7161	Intermediate Similarity	NPD6873	Phase 2
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7154	Intermediate Similarity	NPD2860	Approved
0.7154	Intermediate Similarity	NPD2859	Approved
0.7153	Intermediate Similarity	NPD825	Approved
0.7153	Intermediate Similarity	NPD826	Approved
0.7153	Intermediate Similarity	NPD2979	Phase 3
0.7152	Intermediate Similarity	NPD1511	Approved
0.7152	Intermediate Similarity	NPD6799	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD3111	Phase 1
0.7143	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD5110	Phase 2
0.7133	Intermediate Similarity	NPD5109	Approved
0.7133	Intermediate Similarity	NPD5111	Phase 2
0.7133	Intermediate Similarity	NPD5718	Phase 2
0.7132	Intermediate Similarity	NPD290	Approved
0.7125	Intermediate Similarity	NPD7199	Phase 2
0.7122	Intermediate Similarity	NPD6582	Phase 2
0.7122	Intermediate Similarity	NPD6583	Phase 3
0.7122	Intermediate Similarity	NPD4359	Approved
0.712	Intermediate Similarity	NPD3020	Approved
0.7114	Intermediate Similarity	NPD4236	Phase 3
0.7114	Intermediate Similarity	NPD4237	Approved
0.7113	Intermediate Similarity	NPD4908	Phase 1
0.7109	Intermediate Similarity	NPD9697	Approved
0.7108	Intermediate Similarity	NPD7808	Phase 3
0.7108	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3536	Discontinued
0.7101	Intermediate Similarity	NPD1281	Approved
0.7086	Intermediate Similarity	NPD7440	Discontinued
0.7073	Intermediate Similarity	NPD5844	Phase 1
0.7071	Intermediate Similarity	NPD8651	Approved
0.7071	Intermediate Similarity	NPD3225	Approved
0.7071	Intermediate Similarity	NPD2922	Phase 1
0.707	Intermediate Similarity	NPD2977	Approved
0.707	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2978	Approved
0.707	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6331	Phase 2
0.7059	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1512	Approved
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.7048	Intermediate Similarity	NPD7251	Discontinued
0.7047	Intermediate Similarity	NPD5958	Discontinued
0.7042	Intermediate Similarity	NPD5736	Approved
0.7037	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5451	Approved
0.7021	Intermediate Similarity	NPD987	Approved
0.702	Intermediate Similarity	NPD5241	Discontinued
0.702	Intermediate Similarity	NPD2354	Approved
0.7019	Intermediate Similarity	NPD2821	Approved
0.7014	Intermediate Similarity	NPD3764	Approved
0.7014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD291	Approved
0.7007	Intermediate Similarity	NPD1651	Approved
0.7007	Intermediate Similarity	NPD6896	Approved
0.7007	Intermediate Similarity	NPD6895	Approved
0.7	Intermediate Similarity	NPD6674	Discontinued
0.7	Intermediate Similarity	NPD1652	Phase 2
0.6993	Remote Similarity	NPD4123	Phase 3
0.6993	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4739	Approved
0.6993	Remote Similarity	NPD2614	Approved
0.6992	Remote Similarity	NPD821	Approved
0.6988	Remote Similarity	NPD6797	Phase 2
0.6987	Remote Similarity	NPD4380	Phase 2
0.6987	Remote Similarity	NPD7028	Phase 2

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