NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.08
Volume:	197.524
LogP:	1.546
LogD:	1.296
LogS:	-2.654
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	3.256
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:	-4.56
MDCK Permeability:	1.2461369806260336e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.123

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.938
Plasma Protein Binding (PPB):	60.01976013183594%
Volume Distribution (VD):	0.938
Pgp-substrate:	37.55029296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.484
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.585
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.202
CYP2D6-substrate:	0.609
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	10.581
Half-life (T1/2):	0.537

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.057
Drug-inuced Liver Injury (DILI):	0.572
AMES Toxicity:	0.426
Rat Oral Acute Toxicity:	0.668
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.335
Carcinogencity:	0.634
Eye Corrosion:	0.004
Eye Irritation:	0.663
Respiratory Toxicity:	0.504

Download Data

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

Natural Product: NPC74507

Natural Product ID:	NPC74507
*Common Name:**	Isoshinanolone
IUPAC Name:	(3S,4S)-4,8-dihydroxy-3-methyl-3,4-dihydro-2H-naphthalen-1-one
Synonyms:	Isoshinanolone
Standard InCHIKey:	YUPNHTWYVBHLMG-KGFZYKRKSA-N
Standard InCHI:	InChI=1S/C11H12O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-4,6,11-12,14H,5H2,1H3/t6-,11-/m0/s1
SMILES:	C[C@H]1CC(=O)c2c(cccc2O)[C@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094242
PubChem CID:	46888858
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
NPO22192	Cribraria cancellata	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695806]
NPO20721	Halichondria panicea	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20695474]
NPO22069	Persea major	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614421]
NPO20721	Halichondria panicea	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27035556]
NPO18256	Aconitum excelsum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23045	Lotus helleri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18256	Aconitum excelsum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23045	Lotus helleri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18921	Athrixia phylicoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22999	Cussonia spicata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13717	Aria elegans	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22069	Persea major	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5057	Ephestia kuehniella	Species	Pyralidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27167	Saguinus oedipus	Species	Cebidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22831	Isodon angustifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26614	Planchonella duclitan	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20094	Loranthus micranthus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29101	Tanacetum larvatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23045	Lotus helleri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19736	Haplopappus glutinosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25804	Vernonia zanzibarensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23517	Heterotropa aspera	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23432	Viguiera oaxacana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18256	Aconitum excelsum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6591	Arthrospira maxima	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17645.1	Orobanche cernua var. cumana	Varieties	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21383	Cnicothamnus lorentzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18387	Sedum formosanum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9038	Aconitum burnatii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23865	Scorzonera veratrifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22196	Kickxia ramosissima	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13113	Ardisia kivuensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20721	Halichondria panicea	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26647	Ammannia baccifera	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22192	Cribraria cancellata	Species	Cribrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27035	Artemisia eriopoda	Species	Asteraceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC50	=	1.26	ug.mL-1	PMID[567268]
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC90	=	4.1	ug ml-1	PMID[567268]

☑ 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 NPC74507 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	267
0.1-0.2	1367
0.2-0.3	2894
0.3-0.4	8107
0.4-0.5	11490
0.5-0.6	5679
0.6-0.7	9476
0.7-0.8	2999
0.8-0.85	296
0.85-0.9	103
0.9-0.95	12
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC234890
0.9664	High Similarity	NPC152525
0.9664	High Similarity	NPC68756
0.9573	High Similarity	NPC7151
0.9573	High Similarity	NPC216297
0.9573	High Similarity	NPC473662
0.9083	High Similarity	NPC285829
0.9083	High Similarity	NPC206778
0.9076	High Similarity	NPC41567
0.9055	High Similarity	NPC246693
0.9055	High Similarity	NPC110609
0.9055	High Similarity	NPC242358
0.9048	High Similarity	NPC136588
0.9048	High Similarity	NPC199253
0.9032	High Similarity	NPC3224
0.9016	High Similarity	NPC307174
0.9016	High Similarity	NPC300274
0.8984	High Similarity	NPC314048
0.896	High Similarity	NPC470841
0.8943	High Similarity	NPC375356
0.8908	High Similarity	NPC477453
0.8906	High Similarity	NPC70622
0.8889	High Similarity	NPC247250
0.8889	High Similarity	NPC767
0.888	High Similarity	NPC295202
0.888	High Similarity	NPC49647
0.888	High Similarity	NPC227741
0.888	High Similarity	NPC96915
0.888	High Similarity	NPC306765
0.888	High Similarity	NPC136342
0.8871	High Similarity	NPC310540
0.8871	High Similarity	NPC142956
0.8871	High Similarity	NPC173978
0.8855	High Similarity	NPC305060
0.8837	High Similarity	NPC52407
0.8824	High Similarity	NPC161304
0.881	High Similarity	NPC471530
0.88	High Similarity	NPC131799
0.88	High Similarity	NPC103540
0.876	High Similarity	NPC477406
0.875	High Similarity	NPC475741
0.875	High Similarity	NPC31799
0.875	High Similarity	NPC108288
0.874	High Similarity	NPC48248
0.874	High Similarity	NPC237225
0.874	High Similarity	NPC282923
0.873	High Similarity	NPC160499
0.873	High Similarity	NPC231774
0.871	High Similarity	NPC217756
0.8682	High Similarity	NPC85342
0.8682	High Similarity	NPC205992
0.8672	High Similarity	NPC34414
0.8672	High Similarity	NPC99731
0.8672	High Similarity	NPC146647
0.8667	High Similarity	NPC240163
0.8651	High Similarity	NPC240744
0.8651	High Similarity	NPC167055
0.8647	High Similarity	NPC173980
0.864	High Similarity	NPC275145
0.8615	High Similarity	NPC17843
0.8605	High Similarity	NPC147757
0.8605	High Similarity	NPC55949
0.8605	High Similarity	NPC198305
0.8583	High Similarity	NPC51037
0.8583	High Similarity	NPC1991
0.8583	High Similarity	NPC472047
0.8583	High Similarity	NPC71610
0.8582	High Similarity	NPC103337
0.8582	High Similarity	NPC114620
0.855	High Similarity	NPC115458
0.8538	High Similarity	NPC244699
0.8538	High Similarity	NPC41847
0.8538	High Similarity	NPC471851
0.8537	High Similarity	NPC232178
0.8527	High Similarity	NPC474546
0.8527	High Similarity	NPC278928
0.8525	High Similarity	NPC125252
0.8525	High Similarity	NPC269414
0.8519	High Similarity	NPC32749
0.8519	High Similarity	NPC147542
0.8519	High Similarity	NPC37992
0.8519	High Similarity	NPC327916
0.8519	High Similarity	NPC42262
0.8519	High Similarity	NPC220496
0.8519	High Similarity	NPC241349
0.8504	High Similarity	NPC472592
0.8496	Intermediate Similarity	NPC272268
0.8496	Intermediate Similarity	NPC315275
0.8492	Intermediate Similarity	NPC198014
0.8485	Intermediate Similarity	NPC202225
0.8473	Intermediate Similarity	NPC478190
0.8473	Intermediate Similarity	NPC58685
0.8462	Intermediate Similarity	NPC31539
0.8444	Intermediate Similarity	NPC111422
0.8444	Intermediate Similarity	NPC477408
0.8444	Intermediate Similarity	NPC306835
0.8444	Intermediate Similarity	NPC299405
0.8444	Intermediate Similarity	NPC471602
0.8444	Intermediate Similarity	NPC476477
0.8444	Intermediate Similarity	NPC29771
0.8444	Intermediate Similarity	NPC256463
0.8444	Intermediate Similarity	NPC216312
0.8425	Intermediate Similarity	NPC199273
0.8425	Intermediate Similarity	NPC117794
0.8425	Intermediate Similarity	NPC181334
0.8425	Intermediate Similarity	NPC236189
0.8421	Intermediate Similarity	NPC22222
0.8421	Intermediate Similarity	NPC281513
0.8421	Intermediate Similarity	NPC161632
0.8413	Intermediate Similarity	NPC244351
0.8413	Intermediate Similarity	NPC282577
0.8413	Intermediate Similarity	NPC283514
0.8409	Intermediate Similarity	NPC53896
0.8409	Intermediate Similarity	NPC78307
0.8409	Intermediate Similarity	NPC171968
0.8409	Intermediate Similarity	NPC225051
0.84	Intermediate Similarity	NPC178395
0.84	Intermediate Similarity	NPC244994
0.84	Intermediate Similarity	NPC472046
0.84	Intermediate Similarity	NPC301987
0.84	Intermediate Similarity	NPC190971
0.84	Intermediate Similarity	NPC159760
0.84	Intermediate Similarity	NPC35856
0.84	Intermediate Similarity	NPC179092
0.84	Intermediate Similarity	NPC222876
0.84	Intermediate Similarity	NPC272454
0.84	Intermediate Similarity	NPC292665
0.84	Intermediate Similarity	NPC26433
0.84	Intermediate Similarity	NPC115188
0.8397	Intermediate Similarity	NPC7012
0.8397	Intermediate Similarity	NPC474517
0.8397	Intermediate Similarity	NPC93015
0.8397	Intermediate Similarity	NPC72669
0.8394	Intermediate Similarity	NPC469520
0.8394	Intermediate Similarity	NPC474300
0.8394	Intermediate Similarity	NPC85310
0.8394	Intermediate Similarity	NPC474961
0.839	Intermediate Similarity	NPC224584
0.8387	Intermediate Similarity	NPC233165
0.8387	Intermediate Similarity	NPC473767
0.8387	Intermediate Similarity	NPC184579
0.8374	Intermediate Similarity	NPC160199
0.837	Intermediate Similarity	NPC141368
0.837	Intermediate Similarity	NPC206207
0.837	Intermediate Similarity	NPC61590
0.8359	Intermediate Similarity	NPC87985
0.8359	Intermediate Similarity	NPC287473
0.8358	Intermediate Similarity	NPC193358
0.8358	Intermediate Similarity	NPC472308
0.8358	Intermediate Similarity	NPC86524
0.8358	Intermediate Similarity	NPC141934
0.8358	Intermediate Similarity	NPC155211
0.8358	Intermediate Similarity	NPC474813
0.8346	Intermediate Similarity	NPC288089
0.8346	Intermediate Similarity	NPC135062
0.8346	Intermediate Similarity	NPC471187
0.8346	Intermediate Similarity	NPC287604
0.8346	Intermediate Similarity	NPC161964
0.8346	Intermediate Similarity	NPC474394
0.8346	Intermediate Similarity	NPC477153
0.8346	Intermediate Similarity	NPC50924
0.8346	Intermediate Similarity	NPC472262
0.8345	Intermediate Similarity	NPC170055
0.8333	Intermediate Similarity	NPC120545
0.8333	Intermediate Similarity	NPC309430
0.8333	Intermediate Similarity	NPC476473
0.8333	Intermediate Similarity	NPC198336
0.8321	Intermediate Similarity	NPC257003
0.8321	Intermediate Similarity	NPC187843
0.8321	Intermediate Similarity	NPC305845
0.8321	Intermediate Similarity	NPC108129
0.8321	Intermediate Similarity	NPC204045
0.8321	Intermediate Similarity	NPC117609
0.8321	Intermediate Similarity	NPC471444
0.8321	Intermediate Similarity	NPC91019
0.8321	Intermediate Similarity	NPC106519
0.8309	Intermediate Similarity	NPC295339
0.8309	Intermediate Similarity	NPC190457
0.8308	Intermediate Similarity	NPC3009
0.8308	Intermediate Similarity	NPC96024
0.8308	Intermediate Similarity	NPC165257
0.8306	Intermediate Similarity	NPC184527
0.8305	Intermediate Similarity	NPC34715
0.8305	Intermediate Similarity	NPC211439
0.8296	Intermediate Similarity	NPC475957
0.8296	Intermediate Similarity	NPC245923
0.8286	Intermediate Similarity	NPC285122
0.8284	Intermediate Similarity	NPC283088
0.8284	Intermediate Similarity	NPC80035
0.8279	Intermediate Similarity	NPC163154
0.8273	Intermediate Similarity	NPC218866
0.8273	Intermediate Similarity	NPC84568
0.8273	Intermediate Similarity	NPC300684
0.8273	Intermediate Similarity	NPC103910
0.8273	Intermediate Similarity	NPC48130
0.8273	Intermediate Similarity	NPC471906
0.8273	Intermediate Similarity	NPC244691
0.8273	Intermediate Similarity	NPC477409
0.8273	Intermediate Similarity	NPC79627
0.8271	Intermediate Similarity	NPC59459

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 NPC74507 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	935
0.2-0.3	1342
0.3-0.4	2574
0.4-0.5	2255
0.5-0.6	1183
0.6-0.7	495
0.7-0.8	89
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8934	High Similarity	NPD1201	Approved
0.88	High Similarity	NPD1470	Approved
0.875	High Similarity	NPD405	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2932	Approved
0.7891	Intermediate Similarity	NPD3019	Approved
0.7842	Intermediate Similarity	NPD2346	Discontinued
0.7832	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3300	Phase 2
0.7803	Intermediate Similarity	NPD1164	Approved
0.7717	Intermediate Similarity	NPD9493	Approved
0.7664	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD5405	Approved
0.7643	Intermediate Similarity	NPD5404	Approved
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7643	Intermediate Similarity	NPD5406	Approved
0.7643	Intermediate Similarity	NPD5408	Approved
0.7642	Intermediate Similarity	NPD74	Approved
0.7642	Intermediate Similarity	NPD9266	Approved
0.7639	Intermediate Similarity	NPD7390	Discontinued
0.7612	Intermediate Similarity	NPD2798	Approved
0.7603	Intermediate Similarity	NPD1237	Approved
0.7571	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD9264	Approved
0.7561	Intermediate Similarity	NPD9267	Approved
0.7561	Intermediate Similarity	NPD9263	Approved
0.7542	Intermediate Similarity	NPD288	Approved
0.754	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6663	Approved
0.7463	Intermediate Similarity	NPD1283	Approved
0.7462	Intermediate Similarity	NPD3091	Approved
0.7447	Intermediate Similarity	NPD2799	Discontinued
0.7447	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1607	Approved
0.7426	Intermediate Similarity	NPD5736	Approved
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1240	Approved
0.7405	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2313	Discontinued
0.7355	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2344	Approved
0.7324	Intermediate Similarity	NPD1510	Phase 2
0.7311	Intermediate Similarity	NPD844	Approved
0.7293	Intermediate Similarity	NPD3023	Approved
0.7293	Intermediate Similarity	NPD3026	Approved
0.728	Intermediate Similarity	NPD2342	Discontinued
0.7273	Intermediate Similarity	NPD1651	Approved
0.7273	Intermediate Similarity	NPD3024	Approved
0.7273	Intermediate Similarity	NPD3025	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3092	Approved
0.7239	Intermediate Similarity	NPD1281	Approved
0.7236	Intermediate Similarity	NPD9261	Approved
0.723	Intermediate Similarity	NPD2534	Approved
0.723	Intermediate Similarity	NPD2533	Approved
0.723	Intermediate Similarity	NPD2532	Approved
0.7222	Intermediate Similarity	NPD4955	Approved
0.7222	Intermediate Similarity	NPD5028	Approved
0.7222	Intermediate Similarity	NPD5034	Approved
0.7222	Intermediate Similarity	NPD36	Approved
0.7222	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5026	Approved
0.7222	Intermediate Similarity	NPD4954	Approved
0.7206	Intermediate Similarity	NPD1876	Approved
0.7192	Intermediate Similarity	NPD7003	Approved
0.7192	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6273	Approved
0.7172	Intermediate Similarity	NPD1549	Phase 2
0.717	Intermediate Similarity	NPD7473	Discontinued
0.716	Intermediate Similarity	NPD5030	Phase 2
0.7154	Intermediate Similarity	NPD5951	Approved
0.7154	Intermediate Similarity	NPD9281	Approved
0.7153	Intermediate Similarity	NPD1203	Approved
0.7153	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7131	Intermediate Similarity	NPD3020	Approved
0.7124	Intermediate Similarity	NPD1934	Approved
0.7114	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD447	Suspended
0.7105	Intermediate Similarity	NPD4380	Phase 2
0.7103	Intermediate Similarity	NPD1471	Phase 3
0.7097	Intermediate Similarity	NPD1929	Approved
0.7097	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1930	Approved
0.709	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4626	Approved
0.709	Intermediate Similarity	NPD3095	Discontinued
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7078	Intermediate Similarity	NPD7819	Suspended
0.7075	Intermediate Similarity	NPD8166	Discontinued
0.7073	Intermediate Similarity	NPD8312	Approved
0.7073	Intermediate Similarity	NPD8313	Approved
0.7068	Intermediate Similarity	NPD9545	Approved
0.7059	Intermediate Similarity	NPD9717	Approved
0.7048	Intermediate Similarity	NPD5037	Approved
0.7048	Intermediate Similarity	NPD5038	Approved
0.7048	Intermediate Similarity	NPD8150	Discontinued
0.7034	Intermediate Similarity	NPD1551	Phase 2
0.7032	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4750	Phase 3
0.7027	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2629	Approved
0.7021	Intermediate Similarity	NPD411	Approved
0.7013	Intermediate Similarity	NPD6844	Discontinued
0.7008	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1755	Approved
0.6993	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5036	Approved
0.6972	Remote Similarity	NPD520	Approved
0.697	Remote Similarity	NPD3317	Approved
0.6934	Remote Similarity	NPD3972	Approved
0.6934	Remote Similarity	NPD4878	Approved
0.6934	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD1511	Approved
0.6929	Remote Similarity	NPD9494	Approved
0.6928	Remote Similarity	NPD2649	Approved
0.6928	Remote Similarity	NPD2651	Approved
0.6923	Remote Similarity	NPD2979	Phase 3
0.6923	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2796	Approved
0.6906	Remote Similarity	NPD2797	Approved
0.6899	Remote Similarity	NPD1792	Phase 2
0.6899	Remote Similarity	NPD3021	Approved
0.6899	Remote Similarity	NPD3022	Approved
0.6894	Remote Similarity	NPD497	Approved
0.6889	Remote Similarity	NPD5691	Approved
0.6885	Remote Similarity	NPD2860	Approved
0.6885	Remote Similarity	NPD2859	Approved
0.6884	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6832	Phase 2
0.6859	Remote Similarity	NPD2801	Approved
0.6857	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2066	Phase 3
0.6848	Remote Similarity	NPD5029	Approved
0.6848	Remote Similarity	NPD5027	Approved
0.6848	Remote Similarity	NPD5031	Approved
0.6846	Remote Similarity	NPD3750	Approved
0.6846	Remote Similarity	NPD4628	Phase 3
0.6846	Remote Similarity	NPD3400	Discontinued
0.6846	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1512	Approved
0.6838	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4059	Approved
0.6831	Remote Similarity	NPD7008	Discontinued
0.6825	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD1241	Discontinued
0.6818	Remote Similarity	NPD498	Approved
0.6818	Remote Similarity	NPD496	Approved
0.6818	Remote Similarity	NPD495	Approved
0.6815	Remote Similarity	NPD5402	Approved
0.6806	Remote Similarity	NPD4060	Phase 1
0.6803	Remote Similarity	NPD2933	Approved
0.6803	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6099	Approved
0.6803	Remote Similarity	NPD6100	Approved
0.6803	Remote Similarity	NPD2934	Approved
0.679	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3268	Approved
0.6779	Remote Similarity	NPD2800	Approved
0.6779	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4661	Approved
0.6776	Remote Similarity	NPD4662	Approved
0.6774	Remote Similarity	NPD9495	Approved
0.6772	Remote Similarity	NPD164	Approved
0.6772	Remote Similarity	NPD3882	Suspended
0.6766	Remote Similarity	NPD5035	Approved
0.6765	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD230	Phase 1
0.675	Remote Similarity	NPD5494	Approved
0.6748	Remote Similarity	NPD1809	Phase 2
0.6747	Remote Similarity	NPD6559	Discontinued
0.6746	Remote Similarity	NPD1932	Approved
0.6739	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1019	Discontinued
0.6735	Remote Similarity	NPD4308	Phase 3
0.673	Remote Similarity	NPD7075	Discontinued
0.673	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1751	Approved
0.6715	Remote Similarity	NPD17	Approved
0.6713	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3818	Discontinued
0.6692	Remote Similarity	NPD2182	Approved
0.6692	Remote Similarity	NPD2329	Discontinued
0.6691	Remote Similarity	NPD9269	Phase 2
0.669	Remote Similarity	NPD4140	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