NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.08
Volume:	197.524
LogP:	1.604
LogD:	1.608
LogS:	-2.507
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.74
Synthetic Accessibility Score:	2.962
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.574
MDCK Permeability:	2.1131563698872924e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.197
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.587
Plasma Protein Binding (PPB):	36.40549087524414%
Volume Distribution (VD):	0.661
Pgp-substrate:	54.53510284423828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.75
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.749
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	11.572
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.429
AMES Toxicity:	0.749
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.709
Carcinogencity:	0.842
Eye Corrosion:	0.058
Eye Irritation:	0.733
Respiratory Toxicity:	0.604

Download Data

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

Natural Product: NPC217756

Natural Product ID:	NPC217756
*Common Name:**	(S)-5-Hydroxy-4-Methoxy-3,4-Dihydronaphthalen-1(2H)-One
IUPAC Name:	(4S)-5-hydroxy-4-methoxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	DLAOANUIPRSQCX-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C11H12O3/c1-14-10-6-5-8(12)7-3-2-4-9(13)11(7)10/h2-4,10,13H,5-6H2,1H3/t10-/m0/s1
SMILES:	CO[C@H]1CCC(=O)c2c1c(O)ccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797382
PubChem CID:	11355988
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
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26892.1	Juglans mandshurica var. sieboldiana	Varieties	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	6.25	ug.mL-1	PMID[522211]

☑ 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 NPC217756 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	272
0.1-0.2	1374
0.2-0.3	3496
0.3-0.4	9010
0.4-0.5	9886
0.5-0.6	4154
0.6-0.7	9838
0.7-0.8	4346
0.8-0.85	280
0.85-0.9	39
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8952	High Similarity	NPC470841
0.8917	High Similarity	NPC473662
0.8917	High Similarity	NPC216297
0.8917	High Similarity	NPC7151
0.8852	High Similarity	NPC46634
0.876	High Similarity	NPC274876
0.871	High Similarity	NPC74507
0.871	High Similarity	NPC91475
0.871	High Similarity	NPC234890
0.871	High Similarity	NPC265910
0.8682	High Similarity	NPC43627
0.8672	High Similarity	NPC470831
0.8672	High Similarity	NPC214702
0.8672	High Similarity	NPC7012
0.8615	High Similarity	NPC474097
0.8609	High Similarity	NPC34715
0.8607	High Similarity	NPC206778
0.8607	High Similarity	NPC285829
0.8605	High Similarity	NPC477406
0.8583	High Similarity	NPC108288
0.8571	High Similarity	NPC81808
0.856	High Similarity	NPC68756
0.856	High Similarity	NPC152525
0.855	High Similarity	NPC27407
0.8538	High Similarity	NPC472591
0.8512	High Similarity	NPC125252
0.8507	High Similarity	NPC473499
0.8504	High Similarity	NPC181715
0.8462	Intermediate Similarity	NPC477407
0.8455	Intermediate Similarity	NPC233282
0.8448	Intermediate Similarity	NPC211439
0.8448	Intermediate Similarity	NPC141523
0.8443	Intermediate Similarity	NPC94637
0.843	Intermediate Similarity	NPC477453
0.843	Intermediate Similarity	NPC128825
0.8425	Intermediate Similarity	NPC51037
0.8409	Intermediate Similarity	NPC142027
0.8403	Intermediate Similarity	NPC231717
0.84	Intermediate Similarity	NPC307174
0.84	Intermediate Similarity	NPC300274
0.8385	Intermediate Similarity	NPC93015
0.8374	Intermediate Similarity	NPC90522
0.8374	Intermediate Similarity	NPC328459
0.8358	Intermediate Similarity	NPC197666
0.8358	Intermediate Similarity	NPC126739
0.8358	Intermediate Similarity	NPC61590
0.8347	Intermediate Similarity	NPC240163
0.8347	Intermediate Similarity	NPC161304
0.8346	Intermediate Similarity	NPC141934
0.8346	Intermediate Similarity	NPC291454
0.8346	Intermediate Similarity	NPC240744
0.8346	Intermediate Similarity	NPC167055
0.8346	Intermediate Similarity	NPC472592
0.8333	Intermediate Similarity	NPC135062
0.8333	Intermediate Similarity	NPC375356
0.8333	Intermediate Similarity	NPC182646
0.8321	Intermediate Similarity	NPC470160
0.832	Intermediate Similarity	NPC198336
0.8308	Intermediate Similarity	NPC147757
0.8308	Intermediate Similarity	NPC31799
0.8306	Intermediate Similarity	NPC72977
0.8296	Intermediate Similarity	NPC295339
0.8295	Intermediate Similarity	NPC165257
0.8295	Intermediate Similarity	NPC247250
0.8295	Intermediate Similarity	NPC237225
0.8295	Intermediate Similarity	NPC767
0.8293	Intermediate Similarity	NPC41567
0.8284	Intermediate Similarity	NPC301915
0.8284	Intermediate Similarity	NPC261292
0.8281	Intermediate Similarity	NPC160499
0.8281	Intermediate Similarity	NPC3224
0.8273	Intermediate Similarity	NPC202112
0.8273	Intermediate Similarity	NPC51513
0.8271	Intermediate Similarity	NPC22222
0.8271	Intermediate Similarity	NPC281513
0.8268	Intermediate Similarity	NPC310540
0.8268	Intermediate Similarity	NPC4012
0.8268	Intermediate Similarity	NPC142956
0.8268	Intermediate Similarity	NPC117794
0.8261	Intermediate Similarity	NPC193703
0.8261	Intermediate Similarity	NPC21599
0.8261	Intermediate Similarity	NPC48762
0.8258	Intermediate Similarity	NPC263817
0.8258	Intermediate Similarity	NPC59459
0.8254	Intermediate Similarity	NPC244351
0.8254	Intermediate Similarity	NPC283514
0.8248	Intermediate Similarity	NPC49108
0.8248	Intermediate Similarity	NPC103752
0.8244	Intermediate Similarity	NPC205360
0.824	Intermediate Similarity	NPC222876
0.824	Intermediate Similarity	NPC244994
0.824	Intermediate Similarity	NPC165197
0.824	Intermediate Similarity	NPC115188
0.824	Intermediate Similarity	NPC26433
0.824	Intermediate Similarity	NPC292665
0.824	Intermediate Similarity	NPC35856
0.824	Intermediate Similarity	NPC272454
0.824	Intermediate Similarity	NPC159760
0.824	Intermediate Similarity	NPC179092
0.824	Intermediate Similarity	NPC178395
0.824	Intermediate Similarity	NPC301987
0.824	Intermediate Similarity	NPC190971
0.8226	Intermediate Similarity	NPC233165
0.8226	Intermediate Similarity	NPC184579
0.8226	Intermediate Similarity	NPC232178
0.8222	Intermediate Similarity	NPC221104
0.8222	Intermediate Similarity	NPC478200
0.8222	Intermediate Similarity	NPC33144
0.822	Intermediate Similarity	NPC224584
0.8217	Intermediate Similarity	NPC71525
0.8211	Intermediate Similarity	NPC269414
0.8211	Intermediate Similarity	NPC240664
0.8209	Intermediate Similarity	NPC235115
0.8203	Intermediate Similarity	NPC4164
0.8203	Intermediate Similarity	NPC103540
0.8201	Intermediate Similarity	NPC34482
0.8201	Intermediate Similarity	NPC478019
0.8189	Intermediate Similarity	NPC275145
0.8188	Intermediate Similarity	NPC3732
0.8188	Intermediate Similarity	NPC66593
0.8188	Intermediate Similarity	NPC476473
0.8182	Intermediate Similarity	NPC242358
0.8182	Intermediate Similarity	NPC110609
0.8182	Intermediate Similarity	NPC17843
0.8182	Intermediate Similarity	NPC478190
0.8182	Intermediate Similarity	NPC246693
0.8175	Intermediate Similarity	NPC120545
0.8175	Intermediate Similarity	NPC257003
0.8175	Intermediate Similarity	NPC472035
0.8175	Intermediate Similarity	NPC25168
0.8175	Intermediate Similarity	NPC478201
0.8175	Intermediate Similarity	NPC470842
0.8175	Intermediate Similarity	NPC130485
0.8168	Intermediate Similarity	NPC199253
0.8168	Intermediate Similarity	NPC136588
0.8168	Intermediate Similarity	NPC475741
0.8162	Intermediate Similarity	NPC256463
0.8162	Intermediate Similarity	NPC268052
0.8162	Intermediate Similarity	NPC306835
0.8162	Intermediate Similarity	NPC1268
0.8162	Intermediate Similarity	NPC471602
0.8162	Intermediate Similarity	NPC92655
0.8162	Intermediate Similarity	NPC476477
0.8162	Intermediate Similarity	NPC216312
0.8162	Intermediate Similarity	NPC111422
0.8162	Intermediate Similarity	NPC52358
0.8162	Intermediate Similarity	NPC86744
0.8162	Intermediate Similarity	NPC477408
0.8162	Intermediate Similarity	NPC29771
0.8162	Intermediate Similarity	NPC299405
0.8154	Intermediate Similarity	NPC95537
0.8154	Intermediate Similarity	NPC282923
0.8154	Intermediate Similarity	NPC48248
0.8143	Intermediate Similarity	NPC300540
0.8143	Intermediate Similarity	NPC470570
0.814	Intermediate Similarity	NPC96915
0.814	Intermediate Similarity	NPC231774
0.814	Intermediate Similarity	NPC306765
0.8129	Intermediate Similarity	NPC475201
0.8125	Intermediate Similarity	NPC193805
0.8125	Intermediate Similarity	NPC173978
0.8125	Intermediate Similarity	NPC236189
0.812	Intermediate Similarity	NPC163734
0.812	Intermediate Similarity	NPC295406
0.812	Intermediate Similarity	NPC200422
0.812	Intermediate Similarity	NPC289572
0.812	Intermediate Similarity	NPC153783
0.812	Intermediate Similarity	NPC157478
0.8116	Intermediate Similarity	NPC18714
0.8116	Intermediate Similarity	NPC474300
0.8115	Intermediate Similarity	NPC470837
0.811	Intermediate Similarity	NPC477151
0.811	Intermediate Similarity	NPC282577
0.811	Intermediate Similarity	NPC132518
0.811	Intermediate Similarity	NPC297193
0.811	Intermediate Similarity	NPC91478
0.8106	Intermediate Similarity	NPC219892
0.8106	Intermediate Similarity	NPC189823
0.8102	Intermediate Similarity	NPC241349
0.8102	Intermediate Similarity	NPC220496
0.8102	Intermediate Similarity	NPC147542
0.8102	Intermediate Similarity	NPC32749
0.8102	Intermediate Similarity	NPC42262
0.8102	Intermediate Similarity	NPC155205
0.8102	Intermediate Similarity	NPC37992
0.8102	Intermediate Similarity	NPC156872
0.8102	Intermediate Similarity	NPC327916
0.8092	Intermediate Similarity	NPC146647
0.8092	Intermediate Similarity	NPC99731
0.8092	Intermediate Similarity	NPC92624
0.8092	Intermediate Similarity	NPC34414
0.8088	Intermediate Similarity	NPC191835
0.8088	Intermediate Similarity	NPC173980
0.8085	Intermediate Similarity	NPC77903
0.8085	Intermediate Similarity	NPC81835
0.8085	Intermediate Similarity	NPC17101
0.808	Intermediate Similarity	NPC473767
0.808	Intermediate Similarity	NPC472593
0.8077	Intermediate Similarity	NPC45537
0.8065	Intermediate Similarity	NPC160199

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 NPC217756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	935
0.2-0.3	1344
0.3-0.4	2478
0.4-0.5	2135
0.5-0.6	1302
0.6-0.7	574
0.7-0.8	111
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8583	High Similarity	NPD405	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD9493	Approved
0.8203	Intermediate Similarity	NPD1470	Approved
0.8175	Intermediate Similarity	NPD1201	Approved
0.791	Intermediate Similarity	NPD1240	Approved
0.7883	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD9545	Approved
0.781	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1510	Phase 2
0.7794	Intermediate Similarity	NPD1607	Approved
0.7786	Intermediate Similarity	NPD1203	Approved
0.777	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD9266	Approved
0.7769	Intermediate Similarity	NPD74	Approved
0.7761	Intermediate Similarity	NPD3764	Approved
0.7752	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2798	Approved
0.771	Intermediate Similarity	NPD1876	Approved
0.7698	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD9717	Approved
0.7686	Intermediate Similarity	NPD9264	Approved
0.7686	Intermediate Similarity	NPD9267	Approved
0.7686	Intermediate Similarity	NPD9263	Approved
0.7669	Intermediate Similarity	NPD9494	Approved
0.766	Intermediate Similarity	NPD3750	Approved
0.766	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1164	Approved
0.7647	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD1549	Phase 2
0.7603	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1241	Discontinued
0.7591	Intermediate Similarity	NPD230	Phase 1
0.7591	Intermediate Similarity	NPD447	Suspended
0.7583	Intermediate Similarity	NPD1237	Approved
0.7576	Intermediate Similarity	NPD1283	Approved
0.7571	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2344	Approved
0.7571	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2797	Approved
0.7519	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7483	Intermediate Similarity	NPD2651	Approved
0.7483	Intermediate Similarity	NPD2649	Approved
0.7481	Intermediate Similarity	NPD6832	Phase 2
0.7464	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2932	Approved
0.7462	Intermediate Similarity	NPD3019	Approved
0.7447	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD164	Approved
0.7429	Intermediate Similarity	NPD4308	Phase 3
0.7429	Intermediate Similarity	NPD2799	Discontinued
0.7424	Intermediate Similarity	NPD3972	Approved
0.7413	Intermediate Similarity	NPD7003	Approved
0.74	Intermediate Similarity	NPD7819	Suspended
0.7385	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5406	Approved
0.7376	Intermediate Similarity	NPD5405	Approved
0.7376	Intermediate Similarity	NPD5408	Approved
0.7376	Intermediate Similarity	NPD5404	Approved
0.7376	Intermediate Similarity	NPD2796	Approved
0.7372	Intermediate Similarity	NPD3268	Approved
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD3226	Approved
0.7361	Intermediate Similarity	NPD2309	Approved
0.7355	Intermediate Similarity	NPD9261	Approved
0.7348	Intermediate Similarity	NPD1281	Approved
0.7339	Intermediate Similarity	NPD2182	Approved
0.7333	Intermediate Similarity	NPD1934	Approved
0.7328	Intermediate Similarity	NPD4626	Approved
0.7305	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3748	Approved
0.7303	Intermediate Similarity	NPD3882	Suspended
0.7293	Intermediate Similarity	NPD1608	Approved
0.7285	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6273	Approved
0.7266	Intermediate Similarity	NPD9281	Approved
0.726	Intermediate Similarity	NPD1511	Approved
0.7258	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD1238	Approved
0.7239	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD288	Approved
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2533	Approved
0.7211	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2532	Approved
0.7211	Intermediate Similarity	NPD2534	Approved
0.7206	Intermediate Similarity	NPD1019	Discontinued
0.72	Intermediate Similarity	NPD4380	Phase 2
0.7197	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6663	Approved
0.7194	Intermediate Similarity	NPD520	Approved
0.719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7008	Discontinued
0.7172	Intermediate Similarity	NPD8166	Discontinued
0.7172	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD2801	Approved
0.7162	Intermediate Similarity	NPD1512	Approved
0.7153	Intermediate Similarity	NPD5736	Approved
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7132	Intermediate Similarity	NPD3266	Approved
0.7132	Intermediate Similarity	NPD3267	Approved
0.7124	Intermediate Similarity	NPD5402	Approved
0.7124	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5691	Approved
0.7115	Intermediate Similarity	NPD6959	Discontinued
0.7111	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7078	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD709	Approved
0.707	Intermediate Similarity	NPD6232	Discontinued
0.7068	Intermediate Similarity	NPD1778	Approved
0.7068	Intermediate Similarity	NPD17	Approved
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7473	Discontinued
0.7037	Intermediate Similarity	NPD9269	Phase 2
0.7032	Intermediate Similarity	NPD3749	Approved
0.7032	Intermediate Similarity	NPD7075	Discontinued
0.7027	Intermediate Similarity	NPD6799	Approved
0.7021	Intermediate Similarity	NPD4060	Phase 1
0.702	Intermediate Similarity	NPD7458	Discontinued
0.702	Intermediate Similarity	NPD3455	Phase 2
0.7015	Intermediate Similarity	NPD3496	Discontinued
0.7014	Intermediate Similarity	NPD4476	Approved
0.7014	Intermediate Similarity	NPD4477	Approved
0.7008	Intermediate Similarity	NPD4750	Phase 3
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5951	Approved
0.6992	Remote Similarity	NPD9268	Approved
0.6985	Remote Similarity	NPD1755	Approved
0.6984	Remote Similarity	NPD290	Approved
0.6984	Remote Similarity	NPD2342	Discontinued
0.698	Remote Similarity	NPD5401	Approved
0.698	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7635	Approved
0.6972	Remote Similarity	NPD1933	Approved
0.6972	Remote Similarity	NPD6355	Discontinued
0.697	Remote Similarity	NPD5536	Phase 2
0.6968	Remote Similarity	NPD7768	Phase 2
0.6967	Remote Similarity	NPD3020	Approved
0.6963	Remote Similarity	NPD1610	Phase 2
0.6963	Remote Similarity	NPD422	Phase 1
0.6959	Remote Similarity	NPD3300	Phase 2
0.6957	Remote Similarity	NPD5844	Phase 1
0.6948	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1465	Phase 2
0.6947	Remote Similarity	NPD6671	Approved
0.6935	Remote Similarity	NPD1929	Approved
0.6935	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD1930	Approved
0.6934	Remote Similarity	NPD3225	Approved
0.6929	Remote Similarity	NPD4625	Phase 3
0.6928	Remote Similarity	NPD7411	Suspended
0.6928	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2933	Approved
0.6917	Remote Similarity	NPD3091	Approved
0.6917	Remote Similarity	NPD2934	Approved
0.6917	Remote Similarity	NPD1548	Phase 1
0.6917	Remote Similarity	NPD1894	Discontinued
0.6912	Remote Similarity	NPD1481	Phase 2
0.6911	Remote Similarity	NPD1242	Phase 1
0.6905	Remote Similarity	NPD968	Approved
0.6901	Remote Similarity	NPD2979	Phase 3
0.6899	Remote Similarity	NPD228	Approved
0.6897	Remote Similarity	NPD2438	Suspended
0.6894	Remote Similarity	NPD3818	Discontinued
0.6892	Remote Similarity	NPD6190	Approved
0.6889	Remote Similarity	NPD3023	Approved
0.6889	Remote Similarity	NPD3026	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD6166	Phase 2
0.6875	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2800	Approved
0.687	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4662	Approved
0.6867	Remote Similarity	NPD4661	Approved
0.6866	Remote Similarity	NPD3024	Approved
0.6866	Remote Similarity	NPD3025	Approved
0.6866	Remote Similarity	NPD5585	Approved
0.6864	Remote Similarity	NPD9258	Approved
0.6864	Remote Similarity	NPD9256	Approved
0.6863	Remote Similarity	NPD6599	Discontinued
0.686	Remote Similarity	NPD2859	Approved
0.686	Remote Similarity	NPD2860	Approved
0.6855	Remote Similarity	NPD940	Approved
0.6855	Remote Similarity	NPD846	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data