NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.08
Volume:	197.524
LogP:	2.799
LogD:	1.986
LogS:	-3.194
# 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:	0.617
Synthetic Accessibility Score:	2.941
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:	-4.622
MDCK Permeability:	1.738074752211105e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.348

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.47
Plasma Protein Binding (PPB):	84.6788330078125%
Volume Distribution (VD):	0.803
Pgp-substrate:	15.697259902954102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.904
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.26
CYP2C19-substrate:	0.127
CYP2C9-inhibitor:	0.44
CYP2C9-substrate:	0.836
CYP2D6-inhibitor:	0.705
CYP2D6-substrate:	0.657
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	17.263
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.507
AMES Toxicity:	0.443
Rat Oral Acute Toxicity:	0.734
Maximum Recommended Daily Dose:	0.387
Skin Sensitization:	0.913
Carcinogencity:	0.835
Eye Corrosion:	0.1
Eye Irritation:	0.959
Respiratory Toxicity:	0.803

Download Data

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

Natural Product: NPC68756

Natural Product ID:	NPC68756
*Common Name:**	4S-Shinanolone
IUPAC Name:	(4S)-4,8-dihydroxy-6-methyl-3,4-dihydro-2H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	JOCZVRFSKAUXRP-QMMMGPOBSA-N
Standard InCHI:	InChI=1S/C11H12O3/c1-6-4-7-8(12)2-3-9(13)11(7)10(14)5-6/h4-5,8,12,14H,2-3H2,1H3/t8-/m0/s1
SMILES:	Cc1cc2[C@H](CCC(=O)c2c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459915
PubChem CID:	11412869
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
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	bark	Indonesia	n.a.	PMID[15270571]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22313254]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16657	Diospyros maritima	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16657	Diospyros maritima	Species	Ebenaceae	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
ED50	4
IC50	8
Others	8

Activity Type	# Activity
Cell Line	4
Organism	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[529680]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[529680]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[529680]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[529680]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT20	Organism	Candida albicans	Candida albicans	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT21	Organism	Aspergillus niger	Aspergillus niger	Activity	>	1000.0	ug ml-1	PMID[529680]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT1513	Organism	Mycobacterium avium	Mycobacterium avium	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	>	1000.0	ug.mL-1	PMID[529680]
NPT21	Organism	Aspergillus niger	Aspergillus niger	IC50	>	1000.0	ug.mL-1	PMID[529680]

☑ 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 NPC68756 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	278
0.1-0.2	1412
0.2-0.3	3218
0.3-0.4	9311
0.4-0.5	10497
0.5-0.6	6240
0.6-0.7	8530
0.7-0.8	2760
0.8-0.85	342
0.85-0.9	85
0.9-0.95	20
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC152525
0.9664	High Similarity	NPC74507
0.9664	High Similarity	NPC234890
0.9407	High Similarity	NPC216297
0.9407	High Similarity	NPC7151
0.9407	High Similarity	NPC473662
0.9286	High Similarity	NPC314048
0.92	High Similarity	NPC199253
0.92	High Similarity	NPC136588
0.9174	High Similarity	NPC307174
0.9106	High Similarity	NPC131799
0.9076	High Similarity	NPC41567
0.9055	High Similarity	NPC70622
0.9032	High Similarity	NPC227741
0.9032	High Similarity	NPC49647
0.9032	High Similarity	NPC136342
0.9032	High Similarity	NPC295202
0.9024	High Similarity	NPC173978
0.9024	High Similarity	NPC142956
0.9	High Similarity	NPC305060
0.8984	High Similarity	NPC52407
0.8926	High Similarity	NPC285829
0.8926	High Similarity	NPC206778
0.8906	High Similarity	NPC110609
0.8906	High Similarity	NPC246693
0.8906	High Similarity	NPC242358
0.8898	High Similarity	NPC198305
0.8898	High Similarity	NPC31799
0.8889	High Similarity	NPC48248
0.8889	High Similarity	NPC282923
0.888	High Similarity	NPC472047
0.888	High Similarity	NPC160499
0.8862	High Similarity	NPC300274
0.8828	High Similarity	NPC205992
0.8828	High Similarity	NPC85342
0.8824	High Similarity	NPC161304
0.8819	High Similarity	NPC278928
0.8819	High Similarity	NPC146647
0.8819	High Similarity	NPC34414
0.881	High Similarity	NPC470841
0.879	High Similarity	NPC375356
0.879	High Similarity	NPC275145
0.8779	High Similarity	NPC315275
0.875	High Similarity	NPC477453
0.875	High Similarity	NPC55949
0.874	High Similarity	NPC767
0.874	High Similarity	NPC247250
0.873	High Similarity	NPC3224
0.873	High Similarity	NPC306765
0.873	High Similarity	NPC96915
0.872	High Similarity	NPC310540
0.8699	High Similarity	NPC472046
0.8682	High Similarity	NPC471851
0.8682	High Similarity	NPC41847
0.8672	High Similarity	NPC99731
0.8667	High Similarity	NPC474961
0.8661	High Similarity	NPC471530
0.8651	High Similarity	NPC103540
0.8626	High Similarity	NPC202225
0.8615	High Similarity	NPC309430
0.8615	High Similarity	NPC477406
0.8605	High Similarity	NPC147757
0.8605	High Similarity	NPC475741
0.8605	High Similarity	NPC31539
0.8595	High Similarity	NPC108288
0.8594	High Similarity	NPC237225
0.8593	High Similarity	NPC305845
0.8593	High Similarity	NPC204045
0.8583	High Similarity	NPC231774
0.8582	High Similarity	NPC190457
0.8571	High Similarity	NPC199273
0.8571	High Similarity	NPC236189
0.8571	High Similarity	NPC181334
0.8561	High Similarity	NPC161632
0.856	High Similarity	NPC217756
0.856	High Similarity	NPC282577
0.855	High Similarity	NPC78307
0.855	High Similarity	NPC115458
0.855	High Similarity	NPC53896
0.855	High Similarity	NPC225051
0.854	High Similarity	NPC471906
0.854	High Similarity	NPC244691
0.8538	High Similarity	NPC72669
0.8538	High Similarity	NPC244699
0.8538	High Similarity	NPC93015
0.8538	High Similarity	NPC474517
0.8529	High Similarity	NPC135524
0.8527	High Similarity	NPC474546
0.8512	High Similarity	NPC240163
0.8507	High Similarity	NPC206207
0.8507	High Similarity	NPC173980
0.8507	High Similarity	NPC141368
0.8504	High Similarity	NPC240744
0.8504	High Similarity	NPC167055
0.8496	Intermediate Similarity	NPC472308
0.8496	Intermediate Similarity	NPC86524
0.8496	Intermediate Similarity	NPC155211
0.8496	Intermediate Similarity	NPC272268
0.8496	Intermediate Similarity	NPC474813
0.8492	Intermediate Similarity	NPC471187
0.8485	Intermediate Similarity	NPC50924
0.8485	Intermediate Similarity	NPC474394
0.8485	Intermediate Similarity	NPC288089
0.8473	Intermediate Similarity	NPC478190
0.8473	Intermediate Similarity	NPC58685
0.8473	Intermediate Similarity	NPC17843
0.8462	Intermediate Similarity	NPC62219
0.8462	Intermediate Similarity	NPC108129
0.8456	Intermediate Similarity	NPC187843
0.845	Intermediate Similarity	NPC3009
0.8444	Intermediate Similarity	NPC114620
0.8444	Intermediate Similarity	NPC103337
0.8438	Intermediate Similarity	NPC254492
0.8438	Intermediate Similarity	NPC51037
0.8438	Intermediate Similarity	NPC1991
0.8438	Intermediate Similarity	NPC71610
0.8433	Intermediate Similarity	NPC475957
0.8433	Intermediate Similarity	NPC245923
0.8421	Intermediate Similarity	NPC283088
0.8421	Intermediate Similarity	NPC80035
0.8417	Intermediate Similarity	NPC285122
0.8409	Intermediate Similarity	NPC59459
0.8409	Intermediate Similarity	NPC254603
0.8409	Intermediate Similarity	NPC267205
0.8406	Intermediate Similarity	NPC79627
0.8406	Intermediate Similarity	NPC29932
0.84	Intermediate Similarity	NPC190971
0.8394	Intermediate Similarity	NPC329493
0.8387	Intermediate Similarity	NPC473767
0.8387	Intermediate Similarity	NPC232178
0.8382	Intermediate Similarity	NPC183345
0.8374	Intermediate Similarity	NPC269414
0.8374	Intermediate Similarity	NPC125252
0.8372	Intermediate Similarity	NPC72667
0.8372	Intermediate Similarity	NPC69424
0.8372	Intermediate Similarity	NPC176130
0.8372	Intermediate Similarity	NPC78364
0.8372	Intermediate Similarity	NPC84672
0.8359	Intermediate Similarity	NPC472592
0.8359	Intermediate Similarity	NPC287473
0.8359	Intermediate Similarity	NPC123506
0.8358	Intermediate Similarity	NPC254847
0.8346	Intermediate Similarity	NPC287604
0.8346	Intermediate Similarity	NPC161964
0.8346	Intermediate Similarity	NPC198014
0.8346	Intermediate Similarity	NPC273683
0.8346	Intermediate Similarity	NPC474519
0.8346	Intermediate Similarity	NPC12070
0.8346	Intermediate Similarity	NPC472262
0.8345	Intermediate Similarity	NPC170055
0.8333	Intermediate Similarity	NPC154696
0.8321	Intermediate Similarity	NPC124365
0.8309	Intermediate Similarity	NPC477408
0.8309	Intermediate Similarity	NPC143438
0.8309	Intermediate Similarity	NPC476477
0.8309	Intermediate Similarity	NPC256463
0.8309	Intermediate Similarity	NPC306835
0.8309	Intermediate Similarity	NPC26924
0.8309	Intermediate Similarity	NPC299405
0.8309	Intermediate Similarity	NPC471602
0.8309	Intermediate Similarity	NPC216312
0.8309	Intermediate Similarity	NPC29771
0.8309	Intermediate Similarity	NPC1268
0.8309	Intermediate Similarity	NPC111422
0.8308	Intermediate Similarity	NPC96024
0.8306	Intermediate Similarity	NPC184527
0.8296	Intermediate Similarity	NPC53414
0.8296	Intermediate Similarity	NPC471905
0.8296	Intermediate Similarity	NPC53206
0.8286	Intermediate Similarity	NPC143685
0.8286	Intermediate Similarity	NPC300540
0.8286	Intermediate Similarity	NPC136878
0.8284	Intermediate Similarity	NPC258502
0.8284	Intermediate Similarity	NPC281513
0.8284	Intermediate Similarity	NPC249272
0.8284	Intermediate Similarity	NPC22222
0.8281	Intermediate Similarity	NPC117794
0.8273	Intermediate Similarity	NPC48762
0.8273	Intermediate Similarity	NPC300684
0.8273	Intermediate Similarity	NPC218866
0.8273	Intermediate Similarity	NPC48130
0.8273	Intermediate Similarity	NPC84568
0.8271	Intermediate Similarity	NPC477139
0.8271	Intermediate Similarity	NPC114183
0.8271	Intermediate Similarity	NPC171968
0.8268	Intermediate Similarity	NPC244351
0.8268	Intermediate Similarity	NPC283514
0.8261	Intermediate Similarity	NPC85310
0.8261	Intermediate Similarity	NPC474300
0.8261	Intermediate Similarity	NPC469520
0.8258	Intermediate Similarity	NPC7012
0.8258	Intermediate Similarity	NPC17083
0.8254	Intermediate Similarity	NPC35856
0.8254	Intermediate Similarity	NPC301987
0.8254	Intermediate Similarity	NPC292665
0.8254	Intermediate Similarity	NPC115188
0.8254	Intermediate Similarity	NPC159760
0.8254	Intermediate Similarity	NPC26433
0.8254	Intermediate Similarity	NPC244994
0.8254	Intermediate Similarity	NPC222876

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 NPC68756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	951
0.2-0.3	1440
0.3-0.4	2698
0.4-0.5	2127
0.5-0.6	1154
0.6-0.7	437
0.7-0.8	62
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
0.878	High Similarity	NPD1201	Approved
0.8651	High Similarity	NPD1470	Approved
0.8595	High Similarity	NPD405	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD2346	Discontinued
0.7958	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD7390	Discontinued
0.7803	Intermediate Similarity	NPD1164	Approved
0.777	Intermediate Similarity	NPD5404	Approved
0.777	Intermediate Similarity	NPD5406	Approved
0.777	Intermediate Similarity	NPD5405	Approved
0.777	Intermediate Similarity	NPD5408	Approved
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD3226	Approved
0.7615	Intermediate Similarity	NPD3019	Approved
0.7615	Intermediate Similarity	NPD2932	Approved
0.7578	Intermediate Similarity	NPD9493	Approved
0.7569	Intermediate Similarity	NPD3300	Phase 2
0.754	Intermediate Similarity	NPD7635	Approved
0.7538	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD74	Approved
0.7466	Intermediate Similarity	NPD2532	Approved
0.7466	Intermediate Similarity	NPD2533	Approved
0.7466	Intermediate Similarity	NPD2534	Approved
0.7463	Intermediate Similarity	NPD1283	Approved
0.7459	Intermediate Similarity	NPD1237	Approved
0.7447	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1607	Approved
0.7419	Intermediate Similarity	NPD2342	Discontinued
0.7419	Intermediate Similarity	NPD9263	Approved
0.7419	Intermediate Similarity	NPD9264	Approved
0.7419	Intermediate Similarity	NPD9267	Approved
0.7405	Intermediate Similarity	NPD1651	Approved
0.7395	Intermediate Similarity	NPD288	Approved
0.7391	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6959	Discontinued
0.7353	Intermediate Similarity	NPD2798	Approved
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7311	Intermediate Similarity	NPD844	Approved
0.7292	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD5951	Approved
0.7286	Intermediate Similarity	NPD1240	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD2344	Approved
0.7218	Intermediate Similarity	NPD4626	Approved
0.7214	Intermediate Similarity	NPD6663	Approved
0.7213	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1510	Phase 2
0.7203	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6232	Discontinued
0.7197	Intermediate Similarity	NPD3091	Approved
0.7192	Intermediate Similarity	NPD7003	Approved
0.719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5736	Approved
0.717	Intermediate Similarity	NPD7473	Discontinued
0.7114	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4380	Phase 2
0.7103	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD9261	Approved
0.709	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7819	Suspended
0.7075	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8313	Approved
0.7073	Intermediate Similarity	NPD8312	Approved
0.7055	Intermediate Similarity	NPD1549	Phase 2
0.7048	Intermediate Similarity	NPD8150	Discontinued
0.7037	Intermediate Similarity	NPD3026	Approved
0.7037	Intermediate Similarity	NPD3023	Approved
0.7034	Intermediate Similarity	NPD1551	Phase 2
0.7031	Intermediate Similarity	NPD4750	Phase 3
0.7029	Intermediate Similarity	NPD1203	Approved
0.7027	Intermediate Similarity	NPD2309	Approved
0.7023	Intermediate Similarity	NPD497	Approved
0.7023	Intermediate Similarity	NPD9281	Approved
0.7021	Intermediate Similarity	NPD411	Approved
0.7021	Intermediate Similarity	NPD3764	Approved
0.7015	Intermediate Similarity	NPD5691	Approved
0.7015	Intermediate Similarity	NPD3024	Approved
0.7015	Intermediate Similarity	NPD3025	Approved
0.7013	Intermediate Similarity	NPD1934	Approved
0.7012	Intermediate Similarity	NPD4955	Approved
0.7012	Intermediate Similarity	NPD4954	Approved
0.7012	Intermediate Similarity	NPD5034	Approved
0.7012	Intermediate Similarity	NPD5028	Approved
0.7012	Intermediate Similarity	NPD36	Approved
0.7012	Intermediate Similarity	NPD5026	Approved
0.7	Intermediate Similarity	NPD845	Approved
0.6993	Remote Similarity	NPD447	Suspended
0.6986	Remote Similarity	NPD1471	Phase 3
0.6985	Remote Similarity	NPD3092	Approved
0.697	Remote Similarity	NPD3317	Approved
0.6963	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1930	Approved
0.696	Remote Similarity	NPD1929	Approved
0.6957	Remote Similarity	NPD1876	Approved
0.6954	Remote Similarity	NPD6273	Approved
0.6951	Remote Similarity	NPD5030	Phase 2
0.695	Remote Similarity	NPD7008	Discontinued
0.6947	Remote Similarity	NPD495	Approved
0.6947	Remote Similarity	NPD496	Approved
0.6947	Remote Similarity	NPD498	Approved
0.694	Remote Similarity	NPD9545	Approved
0.6934	Remote Similarity	NPD9717	Approved
0.6934	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD2979	Phase 3
0.6923	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3094	Phase 2
0.6903	Remote Similarity	NPD6844	Discontinued
0.6901	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2800	Approved
0.6885	Remote Similarity	NPD1809	Phase 2
0.6884	Remote Similarity	NPD1755	Approved
0.6882	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5710	Approved
0.6875	Remote Similarity	NPD5711	Approved
0.6875	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3020	Approved
0.6853	Remote Similarity	NPD520	Approved
0.6848	Remote Similarity	NPD6559	Discontinued
0.6846	Remote Similarity	NPD4628	Phase 3
0.6846	Remote Similarity	NPD8166	Discontinued
0.6846	Remote Similarity	NPD3400	Discontinued
0.6845	Remote Similarity	NPD5038	Approved
0.6845	Remote Similarity	NPD5037	Approved
0.6838	Remote Similarity	NPD3095	Discontinued
0.6831	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1511	Approved
0.6818	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD2651	Approved
0.6818	Remote Similarity	NPD2649	Approved
0.6809	Remote Similarity	NPD9494	Approved
0.6803	Remote Similarity	NPD6099	Approved
0.6803	Remote Similarity	NPD2796	Approved
0.6803	Remote Similarity	NPD6100	Approved
0.68	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5036	Approved
0.6779	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5844	Phase 1
0.6767	Remote Similarity	NPD2629	Approved
0.6763	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6832	Phase 2
0.6759	Remote Similarity	NPD230	Phase 1
0.6752	Remote Similarity	NPD2801	Approved
0.6748	Remote Similarity	NPD2860	Approved
0.6748	Remote Similarity	NPD2859	Approved
0.6746	Remote Similarity	NPD1932	Approved
0.6744	Remote Similarity	NPD6212	Phase 3
0.6744	Remote Similarity	NPD6213	Phase 3
0.6744	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1611	Approved
0.6738	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4308	Phase 3
0.6733	Remote Similarity	NPD3750	Approved
0.6732	Remote Similarity	NPD1512	Approved
0.673	Remote Similarity	NPD7075	Discontinued
0.672	Remote Similarity	NPD2066	Phase 3
0.6718	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD2286	Discontinued
0.6709	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD6534	Approved
0.6705	Remote Similarity	NPD6535	Approved
0.6692	Remote Similarity	NPD1241	Discontinued
0.6692	Remote Similarity	NPD1398	Phase 1
0.6691	Remote Similarity	NPD4878	Approved
0.6691	Remote Similarity	NPD9269	Phase 2
0.6691	Remote Similarity	NPD1608	Approved
0.669	Remote Similarity	NPD4060	Phase 1
0.669	Remote Similarity	NPD4208	Discontinued
0.6689	Remote Similarity	NPD2438	Suspended
0.6689	Remote Similarity	NPD4477	Approved
0.6689	Remote Similarity	NPD4476	Approved
0.6687	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6166	Phase 2
0.6687	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4661	Approved
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4662	Approved
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD2934	Approved
0.6647	Remote Similarity	NPD5027	Approved
0.6647	Remote Similarity	NPD5029	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