NPASS Compound

Structure

NPC198014 OpenBabel07101718232D 23 25 0 0 1 0 0 0 0 0999 V2000 2.5981 -3.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -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 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 0.8660 -1.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 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 2.5981 -1.5000 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 4.3301 -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 2 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.26
LogD:	2.987
LogS:	-3.541
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.874
Synthetic Accessibility Score:	3.88
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.719
MDCK Permeability:	1.8500533769838512e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.13
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	95.46015167236328%
Volume Distribution (VD):	0.92
Pgp-substrate:	4.079537868499756%

ADMET: Metabolism

CYP1A2-inhibitor:	0.158
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.175
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.774

ADMET: Excretion

Clearance (CL):	14.305
Half-life (T1/2):	0.793

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.279
Carcinogencity:	0.465
Eye Corrosion:	0.004
Eye Irritation:	0.106
Respiratory Toxicity:	0.845

Download Data

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

Natural Product: NPC198014

Natural Product ID:	NPC198014
*Common Name:**	Trogopteroid D
IUPAC Name:	(1S,4aS,10aR)-7-hydroxy-1-(hydroxymethyl)-1,4a-dimethyl-8-propan-2-yl-4,9,10,10a-tetrahydro-3H-phenanthren-2-one
Synonyms:	Trogopteroid D
Standard InCHIKey:	ZMXPSMLBSFAIOY-NSISKUIASA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)18-13-5-8-16-19(3,14(13)6-7-15(18)22)10-9-17(23)20(16,4)11-21/h6-7,12,16,21-22H,5,8-11H2,1-4H3/t16-,19-,20-/m1/s1
SMILES:	OC[C@@]1(C)C(=O)CC[C@]2([C@H]1CCc1c2ccc(c1C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095306
PubChem CID:	46833406
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids

*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
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[501096]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[501096]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[501096]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[501096]

☑ 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 NPC198014 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	240
0.1-0.2	1300
0.2-0.3	2624
0.3-0.4	7401
0.4-0.5	10994
0.5-0.6	8139
0.6-0.7	9777
0.7-0.8	1987
0.8-0.85	161
0.85-0.9	61
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC71610
0.95	High Similarity	NPC87985
0.9496	High Similarity	NPC471187
0.9492	High Similarity	NPC253627
0.9417	High Similarity	NPC181334
0.925	High Similarity	NPC11250
0.9244	High Similarity	NPC32322
0.9244	High Similarity	NPC259703
0.9138	High Similarity	NPC268160
0.9091	High Similarity	NPC176208
0.906	High Similarity	NPC147179
0.9024	High Similarity	NPC137750
0.9008	High Similarity	NPC154696
0.9008	High Similarity	NPC162935
0.9008	High Similarity	NPC249340
0.9	High Similarity	NPC190501
0.9	High Similarity	NPC318552
0.8983	High Similarity	NPC219112
0.8983	High Similarity	NPC308828
0.8934	High Similarity	NPC121168
0.8926	High Similarity	NPC241001
0.8917	High Similarity	NPC42657
0.8898	High Similarity	NPC35797
0.8898	High Similarity	NPC471851
0.8898	High Similarity	NPC192948
0.888	High Similarity	NPC262936
0.888	High Similarity	NPC30491
0.8833	High Similarity	NPC469609
0.8824	High Similarity	NPC38893
0.8824	High Similarity	NPC308311
0.8824	High Similarity	NPC477137
0.8793	High Similarity	NPC141782
0.876	High Similarity	NPC78307
0.875	High Similarity	NPC476847
0.875	High Similarity	NPC172219
0.875	High Similarity	NPC304510
0.875	High Similarity	NPC477136
0.874	High Similarity	NPC276238
0.873	High Similarity	NPC78364
0.873	High Similarity	NPC176130
0.873	High Similarity	NPC69424
0.873	High Similarity	NPC84672
0.8692	High Similarity	NPC202225
0.8689	High Similarity	NPC478121
0.8678	High Similarity	NPC471671
0.8667	High Similarity	NPC92
0.8667	High Similarity	NPC469663
0.8626	High Similarity	NPC103082
0.8615	High Similarity	NPC477139
0.8607	High Similarity	NPC469644
0.8607	High Similarity	NPC182240
0.8607	High Similarity	NPC473974
0.8607	High Similarity	NPC31296
0.8607	High Similarity	NPC258366
0.8607	High Similarity	NPC79933
0.8594	High Similarity	NPC303910
0.8583	High Similarity	NPC72667
0.8559	High Similarity	NPC260323
0.8559	High Similarity	NPC176279
0.8538	High Similarity	NPC165612
0.8537	High Similarity	NPC135467
0.8537	High Similarity	NPC260832
0.8527	High Similarity	NPC108129
0.8516	High Similarity	NPC3009
0.8504	High Similarity	NPC254492
0.8504	High Similarity	NPC269598
0.85	High Similarity	NPC195922
0.8496	Intermediate Similarity	NPC475957
0.8492	Intermediate Similarity	NPC199273
0.8492	Intermediate Similarity	NPC15127
0.8492	Intermediate Similarity	NPC74507
0.8492	Intermediate Similarity	NPC234890
0.8487	Intermediate Similarity	NPC228425
0.8487	Intermediate Similarity	NPC250323
0.848	Intermediate Similarity	NPC471794
0.8475	Intermediate Similarity	NPC13482
0.8473	Intermediate Similarity	NPC49742
0.8468	Intermediate Similarity	NPC164852
0.8462	Intermediate Similarity	NPC291001
0.845	Intermediate Similarity	NPC171460
0.845	Intermediate Similarity	NPC206028
0.8443	Intermediate Similarity	NPC16030
0.8438	Intermediate Similarity	NPC471530
0.8403	Intermediate Similarity	NPC95716
0.8403	Intermediate Similarity	NPC471188
0.8394	Intermediate Similarity	NPC199936
0.8376	Intermediate Similarity	NPC228737
0.8374	Intermediate Similarity	NPC48342
0.8374	Intermediate Similarity	NPC164649
0.8374	Intermediate Similarity	NPC154030
0.8372	Intermediate Similarity	NPC48248
0.8372	Intermediate Similarity	NPC96024
0.8361	Intermediate Similarity	NPC471668
0.8346	Intermediate Similarity	NPC173978
0.8346	Intermediate Similarity	NPC68756
0.8346	Intermediate Similarity	NPC472804
0.8346	Intermediate Similarity	NPC75432
0.8346	Intermediate Similarity	NPC152525
0.8333	Intermediate Similarity	NPC46940
0.8333	Intermediate Similarity	NPC475457
0.8333	Intermediate Similarity	NPC314048
0.8333	Intermediate Similarity	NPC18982
0.8333	Intermediate Similarity	NPC476282
0.8333	Intermediate Similarity	NPC475346
0.8333	Intermediate Similarity	NPC52407
0.8333	Intermediate Similarity	NPC286222
0.8333	Intermediate Similarity	NPC475627
0.8321	Intermediate Similarity	NPC72669
0.8321	Intermediate Similarity	NPC243305
0.8321	Intermediate Similarity	NPC85342
0.8321	Intermediate Similarity	NPC474517
0.832	Intermediate Similarity	NPC328504
0.832	Intermediate Similarity	NPC21216
0.8319	Intermediate Similarity	NPC252544
0.8319	Intermediate Similarity	NPC321252
0.8319	Intermediate Similarity	NPC132720
0.8308	Intermediate Similarity	NPC99731
0.8308	Intermediate Similarity	NPC131684
0.8305	Intermediate Similarity	NPC11554
0.8305	Intermediate Similarity	NPC317305
0.8264	Intermediate Similarity	NPC715
0.825	Intermediate Similarity	NPC77772
0.825	Intermediate Similarity	NPC177576
0.825	Intermediate Similarity	NPC322753
0.8248	Intermediate Similarity	NPC91019
0.8248	Intermediate Similarity	NPC106519
0.8244	Intermediate Similarity	NPC199253
0.8244	Intermediate Similarity	NPC136588
0.824	Intermediate Similarity	NPC473136
0.8226	Intermediate Similarity	NPC328694
0.822	Intermediate Similarity	NPC151477
0.8214	Intermediate Similarity	NPC143685
0.8211	Intermediate Similarity	NPC477453
0.8211	Intermediate Similarity	NPC474358
0.8211	Intermediate Similarity	NPC257540
0.8211	Intermediate Similarity	NPC474387
0.8211	Intermediate Similarity	NPC154511
0.8211	Intermediate Similarity	NPC247858
0.8211	Intermediate Similarity	NPC137496
0.8209	Intermediate Similarity	NPC283088
0.8209	Intermediate Similarity	NPC153088
0.8203	Intermediate Similarity	NPC231767
0.8203	Intermediate Similarity	NPC142956
0.8197	Intermediate Similarity	NPC471534
0.8195	Intermediate Similarity	NPC115458
0.8195	Intermediate Similarity	NPC111845
0.8189	Intermediate Similarity	NPC300274
0.8189	Intermediate Similarity	NPC478058
0.8189	Intermediate Similarity	NPC282577
0.8188	Intermediate Similarity	NPC308572
0.8188	Intermediate Similarity	NPC85310
0.8188	Intermediate Similarity	NPC477209
0.8182	Intermediate Similarity	NPC93015
0.8182	Intermediate Similarity	NPC41847
0.8182	Intermediate Similarity	NPC244699
0.8175	Intermediate Similarity	NPC471853
0.8168	Intermediate Similarity	NPC474546
0.816	Intermediate Similarity	NPC126002
0.816	Intermediate Similarity	NPC93071
0.816	Intermediate Similarity	NPC151197
0.8148	Intermediate Similarity	NPC472308
0.814	Intermediate Similarity	NPC127975
0.814	Intermediate Similarity	NPC137416
0.8134	Intermediate Similarity	NPC161964
0.8134	Intermediate Similarity	NPC287604
0.8134	Intermediate Similarity	NPC472262
0.813	Intermediate Similarity	NPC469719
0.8129	Intermediate Similarity	NPC477207
0.8129	Intermediate Similarity	NPC478164
0.8125	Intermediate Similarity	NPC375356
0.8125	Intermediate Similarity	NPC273683
0.812	Intermediate Similarity	NPC70622
0.8116	Intermediate Similarity	NPC2681
0.8116	Intermediate Similarity	NPC272907
0.811	Intermediate Similarity	NPC142198
0.811	Intermediate Similarity	NPC31936
0.811	Intermediate Similarity	NPC77569
0.8106	Intermediate Similarity	NPC31799
0.8099	Intermediate Similarity	NPC470770
0.8099	Intermediate Similarity	NPC266937
0.8099	Intermediate Similarity	NPC471189
0.8095	Intermediate Similarity	NPC133389
0.8095	Intermediate Similarity	NPC216297
0.8095	Intermediate Similarity	NPC234337
0.8095	Intermediate Similarity	NPC34634
0.8095	Intermediate Similarity	NPC183339
0.8095	Intermediate Similarity	NPC473662
0.8095	Intermediate Similarity	NPC7151
0.8095	Intermediate Similarity	NPC265454
0.8092	Intermediate Similarity	NPC229894
0.8092	Intermediate Similarity	NPC282923
0.8088	Intermediate Similarity	NPC49911
0.8088	Intermediate Similarity	NPC477592
0.8088	Intermediate Similarity	NPC277559
0.8088	Intermediate Similarity	NPC53001
0.8083	Intermediate Similarity	NPC58865
0.8077	Intermediate Similarity	NPC295202
0.8077	Intermediate Similarity	NPC227741
0.8077	Intermediate Similarity	NPC49647
0.8077	Intermediate Similarity	NPC321822

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 NPC198014 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	913
0.2-0.3	1270
0.3-0.4	2569
0.4-0.5	2264
0.5-0.6	1288
0.6-0.7	520
0.7-0.8	73
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD3019	Approved
0.8843	High Similarity	NPD2932	Approved
0.8374	Intermediate Similarity	NPD3091	Approved
0.8321	Intermediate Similarity	NPD6663	Approved
0.832	Intermediate Similarity	NPD3026	Approved
0.832	Intermediate Similarity	NPD3023	Approved
0.8306	Intermediate Similarity	NPD3025	Approved
0.8306	Intermediate Similarity	NPD3024	Approved
0.8295	Intermediate Similarity	NPD5736	Approved
0.8254	Intermediate Similarity	NPD1201	Approved
0.811	Intermediate Similarity	NPD3092	Approved
0.8	Intermediate Similarity	NPD1470	Approved
0.7953	Intermediate Similarity	NPD3095	Discontinued
0.7863	Intermediate Similarity	NPD3094	Phase 2
0.7812	Intermediate Similarity	NPD4059	Approved
0.7801	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD2342	Discontinued
0.7754	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7635	Approved
0.7734	Intermediate Similarity	NPD1651	Approved
0.773	Intermediate Similarity	NPD8166	Discontinued
0.7698	Intermediate Similarity	NPD5408	Approved
0.7698	Intermediate Similarity	NPD5405	Approved
0.7698	Intermediate Similarity	NPD5406	Approved
0.7698	Intermediate Similarity	NPD5404	Approved
0.7652	Intermediate Similarity	NPD1283	Approved
0.7639	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3020	Approved
0.7626	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7003	Approved
0.7597	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7390	Discontinued
0.7521	Intermediate Similarity	NPD1809	Phase 2
0.7518	Intermediate Similarity	NPD8032	Phase 2
0.7464	Intermediate Similarity	NPD4140	Approved
0.7458	Intermediate Similarity	NPD288	Approved
0.7444	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1281	Approved
0.7417	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4626	Approved
0.7373	Intermediate Similarity	NPD2859	Approved
0.7373	Intermediate Similarity	NPD844	Approved
0.7373	Intermediate Similarity	NPD2860	Approved
0.736	Intermediate Similarity	NPD3022	Approved
0.736	Intermediate Similarity	NPD3021	Approved
0.7357	Intermediate Similarity	NPD4097	Suspended
0.735	Intermediate Similarity	NPD845	Approved
0.7347	Intermediate Similarity	NPD6273	Approved
0.7344	Intermediate Similarity	NPD5951	Approved
0.7338	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7338	Intermediate Similarity	NPD3620	Phase 2
0.7333	Intermediate Similarity	NPD1164	Approved
0.7328	Intermediate Similarity	NPD4093	Discontinued
0.7324	Intermediate Similarity	NPD2935	Discontinued
0.7324	Intermediate Similarity	NPD6099	Approved
0.7324	Intermediate Similarity	NPD6100	Approved
0.7288	Intermediate Similarity	NPD2934	Approved
0.7288	Intermediate Similarity	NPD2933	Approved
0.7279	Intermediate Similarity	NPD4624	Approved
0.7273	Intermediate Similarity	NPD2286	Discontinued
0.7273	Intermediate Similarity	NPD1751	Approved
0.726	Intermediate Similarity	NPD3300	Phase 2
0.7254	Intermediate Similarity	NPD7743	Approved
0.7254	Intermediate Similarity	NPD7742	Approved
0.7244	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4750	Phase 3
0.7214	Intermediate Similarity	NPD2979	Phase 3
0.7209	Intermediate Similarity	NPD2629	Approved
0.72	Intermediate Similarity	NPD7458	Discontinued
0.7197	Intermediate Similarity	NPD5691	Approved
0.7185	Intermediate Similarity	NPD5327	Phase 3
0.7185	Intermediate Similarity	NPD1755	Approved
0.7174	Intermediate Similarity	NPD2606	Approved
0.7174	Intermediate Similarity	NPD2605	Approved
0.7164	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5735	Approved
0.7153	Intermediate Similarity	NPD2346	Discontinued
0.7153	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7132	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3400	Discontinued
0.7122	Intermediate Similarity	NPD5156	Approved
0.7122	Intermediate Similarity	NPD5155	Approved
0.7101	Intermediate Similarity	NPD3635	Approved
0.7101	Intermediate Similarity	NPD3636	Approved
0.7101	Intermediate Similarity	NPD3637	Approved
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4477	Approved
0.7083	Intermediate Similarity	NPD4476	Approved
0.707	Intermediate Similarity	NPD6959	Discontinued
0.7055	Intermediate Similarity	NPD3638	Discontinued
0.705	Intermediate Similarity	NPD3594	Approved
0.705	Intermediate Similarity	NPD3595	Approved
0.7047	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2194	Approved
0.7029	Intermediate Similarity	NPD2195	Approved
0.7029	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3317	Approved
0.7016	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4589	Approved
0.7013	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6353	Approved
0.6985	Remote Similarity	NPD3972	Approved
0.6978	Remote Similarity	NPD4208	Discontinued
0.6974	Remote Similarity	NPD3226	Approved
0.6972	Remote Similarity	NPD943	Approved
0.697	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2531	Phase 2
0.6966	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD2797	Approved
0.6953	Remote Similarity	NPD1792	Phase 2
0.695	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3764	Approved
0.695	Remote Similarity	NPD6798	Discontinued
0.6948	Remote Similarity	NPD37	Approved
0.6939	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD846	Approved
0.6935	Remote Similarity	NPD940	Approved
0.6933	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6355	Discontinued
0.6918	Remote Similarity	NPD6232	Discontinued
0.6903	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1510	Phase 2
0.6892	Remote Similarity	NPD4110	Phase 3
0.6892	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1778	Approved
0.6884	Remote Similarity	NPD1876	Approved
0.6884	Remote Similarity	NPD6696	Suspended
0.6879	Remote Similarity	NPD7095	Approved
0.6879	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7008	Discontinued
0.6879	Remote Similarity	NPD4625	Phase 3
0.6875	Remote Similarity	NPD1607	Approved
0.6871	Remote Similarity	NPD970	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2234	Approved
0.687	Remote Similarity	NPD2228	Approved
0.687	Remote Similarity	NPD2229	Approved
0.6866	Remote Similarity	NPD5304	Approved
0.6866	Remote Similarity	NPD5303	Approved
0.6857	Remote Similarity	NPD2861	Phase 2
0.6853	Remote Similarity	NPD1240	Approved
0.6842	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD7427	Discontinued
0.6835	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3268	Approved
0.6821	Remote Similarity	NPD2533	Approved
0.6821	Remote Similarity	NPD2534	Approved
0.6821	Remote Similarity	NPD2532	Approved
0.6818	Remote Similarity	NPD497	Approved
0.6818	Remote Similarity	NPD7028	Phase 2
0.6818	Remote Similarity	NPD4380	Phase 2
0.6815	Remote Similarity	NPD4966	Approved
0.6815	Remote Similarity	NPD5585	Approved
0.6815	Remote Similarity	NPD4967	Phase 2
0.6815	Remote Similarity	NPD4965	Approved
0.6809	Remote Similarity	NPD4908	Phase 1
0.6803	Remote Similarity	NPD4721	Approved
0.6803	Remote Similarity	NPD4726	Approved
0.6803	Remote Similarity	NPD2344	Approved
0.6803	Remote Similarity	NPD4725	Approved
0.6781	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4628	Phase 3
0.6769	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD255	Approved
0.6767	Remote Similarity	NPD256	Approved
0.6765	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6651	Approved
0.6755	Remote Similarity	NPD7041	Phase 2
0.6755	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8127	Discontinued
0.6744	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD74	Approved
0.6744	Remote Similarity	NPD9266	Approved
0.6742	Remote Similarity	NPD498	Approved
0.6742	Remote Similarity	NPD496	Approved
0.6742	Remote Similarity	NPD495	Approved
0.6741	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1608	Approved
0.673	Remote Similarity	NPD6234	Discontinued
0.672	Remote Similarity	NPD1242	Phase 1
0.6719	Remote Similarity	NPD1444	Approved
0.6719	Remote Similarity	NPD1445	Approved
0.6716	Remote Similarity	NPD7340	Approved
0.6713	Remote Similarity	NPD2313	Discontinued
0.6713	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3645	Discontinued

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