NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	261.669
LogP:	2.213
LogD:	2.367
LogS:	-3.418
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.837
Synthetic Accessibility Score:	3.951
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.739
MDCK Permeability:	2.397495882178191e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	90.78902435302734%
Volume Distribution (VD):	0.427
Pgp-substrate:	5.446560859680176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.6
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.17
CYP2C9-substrate:	0.879
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.291
CYP3A4-inhibitor:	0.348
CYP3A4-substrate:	0.723

ADMET: Excretion

Clearance (CL):	7.9
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.342
Drug-inuced Liver Injury (DILI):	0.305
AMES Toxicity:	0.551
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.178
Skin Sensitization:	0.091
Carcinogencity:	0.895
Eye Corrosion:	0.004
Eye Irritation:	0.064
Respiratory Toxicity:	0.429

Download Data

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

Natural Product: NPC475741

Natural Product ID:	NPC475741
*Common Name:**	Nidemone
IUPAC Name:	8-hydroxy-3'-methoxyspiro[3,4-dihydronaphthalene-2,4'-cyclopent-2-ene]-1,1'-dione
Synonyms:	Nidemone
Standard InCHIKey:	HMYHQSWJLABPMD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-19-12-7-10(16)8-15(12)6-5-9-3-2-4-11(17)13(9)14(15)18/h2-4,7,17H,5-6,8H2,1H3
SMILES:	COC1=CC(=O)CC12CCC3=C(C2=O)C(=CC=C3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513538
PubChem CID:	21574988
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO15918	Nidema boothii	Species	Orchidaceae	Eukaryota	whole plant	n.a.	n.a.	PMID[14987052]
NPO15918	Nidema boothii	Species	Orchidaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3200.0	nM	PMID[510920]

☑ 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 NPC475741 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	305
0.1-0.2	1447
0.2-0.3	2857
0.3-0.4	7677
0.4-0.5	11650
0.5-0.6	5131
0.6-0.7	9332
0.7-0.8	3959
0.8-0.85	277
0.85-0.9	60
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9055	High Similarity	NPC3224
0.8976	High Similarity	NPC103540
0.8947	High Similarity	NPC141934
0.8931	High Similarity	NPC309430
0.8915	High Similarity	NPC282923
0.8915	High Similarity	NPC165257
0.8906	High Similarity	NPC231774
0.8846	High Similarity	NPC99731
0.8819	High Similarity	NPC375356
0.88	High Similarity	NPC285829
0.88	High Similarity	NPC206778
0.8769	High Similarity	NPC237225
0.875	High Similarity	NPC234890
0.875	High Similarity	NPC1268
0.875	High Similarity	NPC74507
0.875	High Similarity	NPC173978
0.874	High Similarity	NPC300274
0.874	High Similarity	NPC307174
0.8722	High Similarity	NPC254603
0.8712	High Similarity	NPC205992
0.8692	High Similarity	NPC471530
0.8667	High Similarity	NPC193358
0.8647	High Similarity	NPC70622
0.8647	High Similarity	NPC110609
0.8647	High Similarity	NPC246693
0.8647	High Similarity	NPC242358
0.8636	High Similarity	NPC198305
0.8615	High Similarity	NPC51037
0.8615	High Similarity	NPC1991
0.8615	High Similarity	NPC306765
0.8615	High Similarity	NPC96915
0.8613	High Similarity	NPC26924
0.8613	High Similarity	NPC114620
0.8613	High Similarity	NPC103337
0.8605	High Similarity	NPC310540
0.8605	High Similarity	NPC152525
0.8605	High Similarity	NPC68756
0.8605	High Similarity	NPC142956
0.8582	High Similarity	NPC115458
0.8561	High Similarity	NPC278928
0.8561	High Similarity	NPC146647
0.8561	High Similarity	NPC34414
0.8551	High Similarity	NPC315578
0.854	High Similarity	NPC61590
0.8529	High Similarity	NPC38158
0.8507	High Similarity	NPC477406
0.8507	High Similarity	NPC58685
0.8504	High Similarity	NPC216297
0.8504	High Similarity	NPC7151
0.8504	High Similarity	NPC473662
0.8496	Intermediate Similarity	NPC136588
0.8496	Intermediate Similarity	NPC199253
0.8489	Intermediate Similarity	NPC124365
0.8485	Intermediate Similarity	NPC48248
0.848	Intermediate Similarity	NPC108288
0.848	Intermediate Similarity	NPC477453
0.8478	Intermediate Similarity	NPC216312
0.8478	Intermediate Similarity	NPC295339
0.8478	Intermediate Similarity	NPC256463
0.8478	Intermediate Similarity	NPC29771
0.8478	Intermediate Similarity	NPC299405
0.8478	Intermediate Similarity	NPC111422
0.8478	Intermediate Similarity	NPC476477
0.8478	Intermediate Similarity	NPC306835
0.8478	Intermediate Similarity	NPC471602
0.8467	Intermediate Similarity	NPC305060
0.8456	Intermediate Similarity	NPC281513
0.8456	Intermediate Similarity	NPC283088
0.8456	Intermediate Similarity	NPC22222
0.8456	Intermediate Similarity	NPC161632
0.8444	Intermediate Similarity	NPC171968
0.8444	Intermediate Similarity	NPC314048
0.8433	Intermediate Similarity	NPC17083
0.8433	Intermediate Similarity	NPC244699
0.8429	Intermediate Similarity	NPC474300
0.8417	Intermediate Similarity	NPC241349
0.8417	Intermediate Similarity	NPC220496
0.8417	Intermediate Similarity	NPC147542
0.8417	Intermediate Similarity	NPC37992
0.8417	Intermediate Similarity	NPC327916
0.8417	Intermediate Similarity	NPC42262
0.8417	Intermediate Similarity	NPC32749
0.84	Intermediate Similarity	NPC161304
0.8394	Intermediate Similarity	NPC272268
0.8394	Intermediate Similarity	NPC474813
0.8392	Intermediate Similarity	NPC476821
0.8385	Intermediate Similarity	NPC135062
0.8382	Intermediate Similarity	NPC12070
0.8382	Intermediate Similarity	NPC44437
0.8382	Intermediate Similarity	NPC1249
0.8382	Intermediate Similarity	NPC288089
0.837	Intermediate Similarity	NPC88864
0.8369	Intermediate Similarity	NPC21873
0.8369	Intermediate Similarity	NPC476473
0.8358	Intermediate Similarity	NPC55949
0.8358	Intermediate Similarity	NPC31799
0.8357	Intermediate Similarity	NPC471444
0.8357	Intermediate Similarity	NPC257003
0.8346	Intermediate Similarity	NPC767
0.8346	Intermediate Similarity	NPC247250
0.8333	Intermediate Similarity	NPC160499
0.8333	Intermediate Similarity	NPC53414
0.8333	Intermediate Similarity	NPC245923
0.8333	Intermediate Similarity	NPC53206
0.8321	Intermediate Similarity	NPC249272
0.831	Intermediate Similarity	NPC274085
0.831	Intermediate Similarity	NPC89664
0.831	Intermediate Similarity	NPC19896
0.831	Intermediate Similarity	NPC477409
0.8309	Intermediate Similarity	NPC52407
0.8309	Intermediate Similarity	NPC114183
0.8309	Intermediate Similarity	NPC225051
0.8309	Intermediate Similarity	NPC53896
0.8309	Intermediate Similarity	NPC193169
0.8296	Intermediate Similarity	NPC205360
0.8296	Intermediate Similarity	NPC474517
0.8296	Intermediate Similarity	NPC72669
0.8286	Intermediate Similarity	NPC156872
0.8281	Intermediate Similarity	NPC232178
0.8273	Intermediate Similarity	NPC416
0.8273	Intermediate Similarity	NPC173980
0.8273	Intermediate Similarity	NPC13715
0.8273	Intermediate Similarity	NPC61398
0.8271	Intermediate Similarity	NPC470841
0.8261	Intermediate Similarity	NPC254847
0.8261	Intermediate Similarity	NPC315275
0.8261	Intermediate Similarity	NPC86524
0.8248	Intermediate Similarity	NPC270899
0.8248	Intermediate Similarity	NPC287604
0.8248	Intermediate Similarity	NPC50924
0.8248	Intermediate Similarity	NPC161964
0.8248	Intermediate Similarity	NPC166480
0.8248	Intermediate Similarity	NPC472262
0.8248	Intermediate Similarity	NPC282780
0.8244	Intermediate Similarity	NPC182646
0.8235	Intermediate Similarity	NPC477407
0.8227	Intermediate Similarity	NPC149533
0.8227	Intermediate Similarity	NPC187843
0.8222	Intermediate Similarity	NPC117609
0.8214	Intermediate Similarity	NPC138099
0.8214	Intermediate Similarity	NPC242994
0.8203	Intermediate Similarity	NPC41567
0.8201	Intermediate Similarity	NPC119542
0.8201	Intermediate Similarity	NPC53001
0.8201	Intermediate Similarity	NPC471905
0.8195	Intermediate Similarity	NPC136342
0.8195	Intermediate Similarity	NPC295202
0.8195	Intermediate Similarity	NPC227741
0.8195	Intermediate Similarity	NPC49647
0.8194	Intermediate Similarity	NPC300540
0.8188	Intermediate Similarity	NPC80035
0.8188	Intermediate Similarity	NPC27407
0.8182	Intermediate Similarity	NPC21599
0.8182	Intermediate Similarity	NPC103910
0.8182	Intermediate Similarity	NPC193703
0.8182	Intermediate Similarity	NPC29932
0.8182	Intermediate Similarity	NPC475201
0.8175	Intermediate Similarity	NPC294226
0.8175	Intermediate Similarity	NPC267205
0.8169	Intermediate Similarity	NPC49108
0.8169	Intermediate Similarity	NPC94076
0.8169	Intermediate Similarity	NPC69755
0.8169	Intermediate Similarity	NPC182255
0.8168	Intermediate Similarity	NPC217756
0.8168	Intermediate Similarity	NPC283514
0.8168	Intermediate Similarity	NPC91478
0.8162	Intermediate Similarity	NPC85342
0.8162	Intermediate Similarity	NPC41847
0.8156	Intermediate Similarity	NPC96421
0.8156	Intermediate Similarity	NPC181560
0.8156	Intermediate Similarity	NPC183345
0.8156	Intermediate Similarity	NPC169452
0.8154	Intermediate Similarity	NPC190971
0.8154	Intermediate Similarity	NPC472046
0.8151	Intermediate Similarity	NPC226578
0.8148	Intermediate Similarity	NPC25736
0.8148	Intermediate Similarity	NPC92624
0.8143	Intermediate Similarity	NPC87723
0.8138	Intermediate Similarity	NPC312929
0.8138	Intermediate Similarity	NPC56433
0.8138	Intermediate Similarity	NPC162751
0.8138	Intermediate Similarity	NPC52161
0.8138	Intermediate Similarity	NPC245584
0.8138	Intermediate Similarity	NPC126767
0.8138	Intermediate Similarity	NPC118027
0.8138	Intermediate Similarity	NPC289042
0.8138	Intermediate Similarity	NPC190648
0.8138	Intermediate Similarity	NPC71055
0.8134	Intermediate Similarity	NPC45537
0.8129	Intermediate Similarity	NPC472308
0.8129	Intermediate Similarity	NPC155211
0.8125	Intermediate Similarity	NPC125252
0.812	Intermediate Similarity	NPC131799
0.8112	Intermediate Similarity	NPC84266
0.811	Intermediate Similarity	NPC240163
0.8102	Intermediate Similarity	NPC17843
0.8099	Intermediate Similarity	NPC106519
0.8099	Intermediate Similarity	NPC305845
0.8099	Intermediate Similarity	NPC204045
0.8099	Intermediate Similarity	NPC91019

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 NPC475741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	924
0.2-0.3	1392
0.3-0.4	2587
0.4-0.5	2244
0.5-0.6	1189
0.6-0.7	456
0.7-0.8	70
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8976	High Similarity	NPD1470	Approved
0.881	High Similarity	NPD1201	Approved
0.848	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3226	Approved
0.7803	Intermediate Similarity	NPD2932	Approved
0.7803	Intermediate Similarity	NPD3019	Approved
0.7762	Intermediate Similarity	NPD2346	Discontinued
0.773	Intermediate Similarity	NPD1607	Approved
0.7714	Intermediate Similarity	NPD943	Approved
0.7714	Intermediate Similarity	NPD1240	Approved
0.7708	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5408	Approved
0.7692	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD5406	Approved
0.7622	Intermediate Similarity	NPD1510	Phase 2
0.7571	Intermediate Similarity	NPD3764	Approved
0.7569	Intermediate Similarity	NPD2935	Discontinued
0.7568	Intermediate Similarity	NPD7390	Discontinued
0.7517	Intermediate Similarity	NPD2532	Approved
0.7517	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2344	Approved
0.7517	Intermediate Similarity	NPD2533	Approved
0.7517	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD9493	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6232	Discontinued
0.7464	Intermediate Similarity	NPD1164	Approved
0.7438	Intermediate Similarity	NPD7473	Discontinued
0.7415	Intermediate Similarity	NPD2800	Approved
0.741	Intermediate Similarity	NPD2798	Approved
0.74	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1471	Phase 3
0.7397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7355	Intermediate Similarity	NPD7819	Suspended
0.7353	Intermediate Similarity	NPD3026	Approved
0.7353	Intermediate Similarity	NPD3023	Approved
0.7347	Intermediate Similarity	NPD1549	Phase 2
0.7333	Intermediate Similarity	NPD3024	Approved
0.7333	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3025	Approved
0.7329	Intermediate Similarity	NPD1551	Phase 2
0.7324	Intermediate Similarity	NPD2313	Discontinued
0.7315	Intermediate Similarity	NPD2309	Approved
0.7287	Intermediate Similarity	NPD9266	Approved
0.7287	Intermediate Similarity	NPD74	Approved
0.7273	Intermediate Similarity	NPD6663	Approved
0.7266	Intermediate Similarity	NPD1283	Approved
0.7266	Intermediate Similarity	NPD1876	Approved
0.7248	Intermediate Similarity	NPD7003	Approved
0.7248	Intermediate Similarity	NPD3750	Approved
0.7244	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5736	Approved
0.7219	Intermediate Similarity	NPD1511	Approved
0.7214	Intermediate Similarity	NPD1203	Approved
0.7211	Intermediate Similarity	NPD6099	Approved
0.7211	Intermediate Similarity	NPD6100	Approved
0.7209	Intermediate Similarity	NPD9263	Approved
0.7209	Intermediate Similarity	NPD9264	Approved
0.7209	Intermediate Similarity	NPD9267	Approved
0.7206	Intermediate Similarity	NPD1651	Approved
0.7188	Intermediate Similarity	NPD6959	Discontinued
0.7179	Intermediate Similarity	NPD1934	Approved
0.7174	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2801	Approved
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4628	Phase 3
0.7132	Intermediate Similarity	NPD9545	Approved
0.7124	Intermediate Similarity	NPD1512	Approved
0.7123	Intermediate Similarity	NPD6651	Approved
0.7122	Intermediate Similarity	NPD3972	Approved
0.7122	Intermediate Similarity	NPD9717	Approved
0.7122	Intermediate Similarity	NPD1608	Approved
0.7107	Intermediate Similarity	NPD3749	Approved
0.709	Intermediate Similarity	NPD5951	Approved
0.7089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD447	Suspended
0.7051	Intermediate Similarity	NPD4380	Phase 2
0.7051	Intermediate Similarity	NPD6599	Discontinued
0.705	Intermediate Similarity	NPD1281	Approved
0.7047	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD288	Approved
0.7029	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD8166	Discontinued
0.7013	Intermediate Similarity	NPD6273	Approved
0.7007	Intermediate Similarity	NPD3091	Approved
0.698	Remote Similarity	NPD2796	Approved
0.6963	Remote Similarity	NPD9281	Approved
0.696	Remote Similarity	NPD844	Approved
0.695	Remote Similarity	NPD1755	Approved
0.6948	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2342	Discontinued
0.694	Remote Similarity	NPD7635	Approved
0.6937	Remote Similarity	NPD7768	Phase 2
0.6933	Remote Similarity	NPD5710	Approved
0.6933	Remote Similarity	NPD5711	Approved
0.6929	Remote Similarity	NPD3092	Approved
0.6923	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD8313	Approved
0.6913	Remote Similarity	NPD3748	Approved
0.6906	Remote Similarity	NPD1778	Approved
0.6906	Remote Similarity	NPD17	Approved
0.6901	Remote Similarity	NPD6696	Suspended
0.6899	Remote Similarity	NPD7411	Suspended
0.6899	Remote Similarity	NPD9261	Approved
0.6897	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7075	Discontinued
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7458	Discontinued
0.6866	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3094	Phase 2
0.6849	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1237	Approved
0.6842	Remote Similarity	NPD4750	Phase 3
0.6839	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6832	Phase 2
0.6824	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD230	Phase 1
0.6821	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5494	Approved
0.6806	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6559	Discontinued
0.6803	Remote Similarity	NPD520	Approved
0.6803	Remote Similarity	NPD8032	Phase 2
0.6802	Remote Similarity	NPD8150	Discontinued
0.68	Remote Similarity	NPD4308	Phase 3
0.6786	Remote Similarity	NPD4059	Approved
0.6786	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3095	Discontinued
0.6781	Remote Similarity	NPD4625	Phase 3
0.6774	Remote Similarity	NPD6799	Approved
0.677	Remote Similarity	NPD5402	Approved
0.677	Remote Similarity	NPD2296	Approved
0.6766	Remote Similarity	NPD3818	Discontinued
0.6759	Remote Similarity	NPD9494	Approved
0.6752	Remote Similarity	NPD920	Approved
0.6747	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6166	Phase 2
0.6747	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2797	Approved
0.6735	Remote Similarity	NPD3268	Approved
0.6732	Remote Similarity	NPD1243	Approved
0.6718	Remote Similarity	NPD164	Approved
0.6714	Remote Similarity	NPD5691	Approved
0.6708	Remote Similarity	NPD5761	Phase 2
0.6708	Remote Similarity	NPD5760	Phase 2
0.6706	Remote Similarity	NPD5029	Approved
0.6706	Remote Similarity	NPD5031	Approved
0.6706	Remote Similarity	NPD5027	Approved
0.6705	Remote Similarity	NPD8434	Phase 2
0.6693	Remote Similarity	NPD1809	Phase 2
0.6689	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD3926	Phase 2
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD36	Approved
0.6667	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD5028	Approved
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD4955	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5034	Approved
0.6667	Remote Similarity	NPD5026	Approved
0.6667	Remote Similarity	NPD4954	Approved
0.6647	Remote Similarity	NPD5953	Discontinued
0.6646	Remote Similarity	NPD6801	Discontinued
0.6646	Remote Similarity	NPD37	Approved
0.6646	Remote Similarity	NPD6844	Discontinued
0.6646	Remote Similarity	NPD5403	Approved
0.6645	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2979	Phase 3
0.6644	Remote Similarity	NPD4060	Phase 1
0.6643	Remote Similarity	NPD9269	Phase 2
0.6642	Remote Similarity	NPD1241	Discontinued
0.6641	Remote Similarity	NPD1929	Approved
0.6641	Remote Similarity	NPD1930	Approved
0.6641	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5844	Phase 1

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