NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.04
Volume:	274.854
LogP:	5.255
LogD:	3.296
LogS:	-4.177
# Rotatable Bonds:	0
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	3.018
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.128
MDCK Permeability:	6.8533540797943715e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.57
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	97.97388458251953%
Volume Distribution (VD):	0.576
Pgp-substrate:	2.4141557216644287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.778
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.732
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.685
CYP2D6-substrate:	0.519
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	4.274
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.782
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.958
Carcinogencity:	0.93
Eye Corrosion:	0.719
Eye Irritation:	0.985
Respiratory Toxicity:	0.306

Download Data

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

Natural Product: NPC85059

Natural Product ID:	NPC85059
*Common Name:**	Bryoanthrathiophene
IUPAC Name:	n.a.
Synonyms:	Bryoanthrathiophene
Standard InCHIKey:	CAQPQQTZGOIYJT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O3S/c1-7-12-8-3-2-4-9(17)13(8)16(19)14-10(18)5-6-11(20-7)15(12)14/h2-6,17-18H,1H3
SMILES:	Cc1c2-c3cccc(c3C(=O)c3c(ccc(c23)s1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451954
PubChem CID:	10265778
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO9668	Watersipora subtorquata	Species	Watersiporidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350162]

☑ 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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5.0	nM	PMID[512959]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	220.0	nM	PMID[512959]

☑ 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 NPC85059 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	436
0.1-0.2	2082
0.2-0.3	5380
0.3-0.4	14001
0.4-0.5	5990
0.5-0.6	9702
0.6-0.7	4852
0.7-0.8	249
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9404	High Similarity	NPC145990
0.7986	Intermediate Similarity	NPC173978
0.7973	Intermediate Similarity	NPC474517
0.7973	Intermediate Similarity	NPC72669
0.7808	Intermediate Similarity	NPC103540
0.777	Intermediate Similarity	NPC282923
0.777	Intermediate Similarity	NPC48248
0.7724	Intermediate Similarity	NPC300274
0.7718	Intermediate Similarity	NPC99731
0.7712	Intermediate Similarity	NPC474813
0.7697	Intermediate Similarity	NPC287604
0.7697	Intermediate Similarity	NPC472262
0.7697	Intermediate Similarity	NPC161964
0.7671	Intermediate Similarity	NPC375356
0.7662	Intermediate Similarity	NPC245923
0.7647	Intermediate Similarity	NPC283088
0.7635	Intermediate Similarity	NPC3224
0.7632	Intermediate Similarity	NPC225051
0.7632	Intermediate Similarity	NPC115458
0.7619	Intermediate Similarity	NPC142956
0.7616	Intermediate Similarity	NPC205992
0.7517	Intermediate Similarity	NPC96915
0.7517	Intermediate Similarity	NPC160499
0.7516	Intermediate Similarity	NPC314048
0.7516	Intermediate Similarity	NPC96421
0.75	Intermediate Similarity	NPC244699
0.7484	Intermediate Similarity	NPC155211
0.7484	Intermediate Similarity	NPC272268
0.7483	Intermediate Similarity	NPC34414
0.7483	Intermediate Similarity	NPC477453
0.7483	Intermediate Similarity	NPC146647
0.7468	Intermediate Similarity	NPC12070
0.7451	Intermediate Similarity	NPC58685
0.7451	Intermediate Similarity	NPC70622
0.7434	Intermediate Similarity	NPC55949
0.7434	Intermediate Similarity	NPC475741
0.7421	Intermediate Similarity	NPC19631
0.7421	Intermediate Similarity	NPC239136
0.7419	Intermediate Similarity	NPC249272
0.7403	Intermediate Similarity	NPC267205
0.7403	Intermediate Similarity	NPC114183
0.74	Intermediate Similarity	NPC231774
0.7397	Intermediate Similarity	NPC206778
0.7397	Intermediate Similarity	NPC285829
0.7389	Intermediate Similarity	NPC13715
0.7383	Intermediate Similarity	NPC74507
0.7383	Intermediate Similarity	NPC234890
0.7375	Intermediate Similarity	NPC296752
0.7372	Intermediate Similarity	NPC193358
0.7372	Intermediate Similarity	NPC141934
0.7372	Intermediate Similarity	NPC191976
0.7368	Intermediate Similarity	NPC92624
0.7368	Intermediate Similarity	NPC276238
0.7365	Intermediate Similarity	NPC307174
0.7358	Intermediate Similarity	NPC246638
0.7355	Intermediate Similarity	NPC288089
0.7355	Intermediate Similarity	NPC270899
0.7355	Intermediate Similarity	NPC50924
0.7355	Intermediate Similarity	NPC44437
0.7351	Intermediate Similarity	NPC471530
0.7342	Intermediate Similarity	NPC26924
0.7342	Intermediate Similarity	NPC138099
0.7342	Intermediate Similarity	NPC1268
0.7342	Intermediate Similarity	NPC242994
0.7329	Intermediate Similarity	NPC10764
0.7325	Intermediate Similarity	NPC53206
0.7325	Intermediate Similarity	NPC53001
0.7325	Intermediate Similarity	NPC53414
0.7325	Intermediate Similarity	NPC305060
0.7325	Intermediate Similarity	NPC62272
0.7325	Intermediate Similarity	NPC471905
0.732	Intermediate Similarity	NPC259942
0.732	Intermediate Similarity	NPC199253
0.732	Intermediate Similarity	NPC136588
0.7308	Intermediate Similarity	NPC80035
0.7303	Intermediate Similarity	NPC96024
0.7296	Intermediate Similarity	NPC169452
0.7296	Intermediate Similarity	NPC225243
0.7296	Intermediate Similarity	NPC315578
0.7296	Intermediate Similarity	NPC181560
0.729	Intermediate Similarity	NPC53896
0.7285	Intermediate Similarity	NPC306765
0.7278	Intermediate Similarity	NPC61398
0.7278	Intermediate Similarity	NPC416
0.7278	Intermediate Similarity	NPC87723
0.7273	Intermediate Similarity	NPC41847
0.7267	Intermediate Similarity	NPC68756
0.7267	Intermediate Similarity	NPC451542
0.7267	Intermediate Similarity	NPC295712
0.7267	Intermediate Similarity	NPC474203
0.7267	Intermediate Similarity	NPC313047
0.7267	Intermediate Similarity	NPC236189
0.7267	Intermediate Similarity	NPC152525
0.7267	Intermediate Similarity	NPC471682
0.7261	Intermediate Similarity	NPC254847
0.725	Intermediate Similarity	NPC124365
0.725	Intermediate Similarity	NPC106519
0.725	Intermediate Similarity	NPC91019
0.725	Intermediate Similarity	NPC477275
0.7248	Intermediate Similarity	NPC176208
0.7248	Intermediate Similarity	NPC244351
0.7244	Intermediate Similarity	NPC166480
0.7244	Intermediate Similarity	NPC282780
0.7226	Intermediate Similarity	NPC175738
0.7226	Intermediate Similarity	NPC246693
0.7226	Intermediate Similarity	NPC242358
0.7226	Intermediate Similarity	NPC110609
0.7222	Intermediate Similarity	NPC227841
0.7208	Intermediate Similarity	NPC31799
0.7205	Intermediate Similarity	NPC69755
0.7205	Intermediate Similarity	NPC193555
0.7205	Intermediate Similarity	NPC257644
0.7197	Intermediate Similarity	NPC161632
0.7181	Intermediate Similarity	NPC120545
0.7179	Intermediate Similarity	NPC294226
0.7179	Intermediate Similarity	NPC52407
0.7178	Intermediate Similarity	NPC12402
0.7178	Intermediate Similarity	NPC471683
0.7172	Intermediate Similarity	NPC161304
0.7171	Intermediate Similarity	NPC1991
0.717	Intermediate Similarity	NPC4214
0.7162	Intermediate Similarity	NPC216297
0.7162	Intermediate Similarity	NPC473662
0.7162	Intermediate Similarity	NPC7151
0.7161	Intermediate Similarity	NPC85342
0.716	Intermediate Similarity	NPC293545
0.716	Intermediate Similarity	NPC174905
0.7152	Intermediate Similarity	NPC199273
0.7152	Intermediate Similarity	NPC310540
0.7152	Intermediate Similarity	NPC118919
0.7152	Intermediate Similarity	NPC164014
0.7143	Intermediate Similarity	NPC305845
0.7143	Intermediate Similarity	NPC278928
0.7143	Intermediate Similarity	NPC204045
0.7143	Intermediate Similarity	NPC109123
0.7133	Intermediate Similarity	NPC283514
0.7133	Intermediate Similarity	NPC91478
0.7125	Intermediate Similarity	NPC143438
0.7124	Intermediate Similarity	NPC84672
0.7124	Intermediate Similarity	NPC69424
0.7124	Intermediate Similarity	NPC78364
0.7124	Intermediate Similarity	NPC176130
0.7123	Intermediate Similarity	NPC108288
0.7117	Intermediate Similarity	NPC21599
0.7117	Intermediate Similarity	NPC193703
0.7117	Intermediate Similarity	NPC477913
0.7114	Intermediate Similarity	NPC159760
0.7114	Intermediate Similarity	NPC244994
0.7114	Intermediate Similarity	NPC35856
0.7114	Intermediate Similarity	NPC115188
0.7114	Intermediate Similarity	NPC179092
0.7114	Intermediate Similarity	NPC26433
0.7114	Intermediate Similarity	NPC292665
0.7114	Intermediate Similarity	NPC222876
0.7114	Intermediate Similarity	NPC178395
0.7114	Intermediate Similarity	NPC272454
0.7114	Intermediate Similarity	NPC301987
0.7107	Intermediate Similarity	NPC147418
0.7105	Intermediate Similarity	NPC477454
0.7099	Intermediate Similarity	NPC474961
0.7099	Intermediate Similarity	NPC135524
0.7099	Intermediate Similarity	NPC85310
0.7099	Intermediate Similarity	NPC474300
0.7099	Intermediate Similarity	NPC469520
0.7097	Intermediate Similarity	NPC31539
0.7095	Intermediate Similarity	NPC195262
0.7095	Intermediate Similarity	NPC233165
0.7095	Intermediate Similarity	NPC184579
0.7095	Intermediate Similarity	NPC188814
0.7091	Intermediate Similarity	NPC37709
0.7091	Intermediate Similarity	NPC52161
0.7091	Intermediate Similarity	NPC150215
0.7091	Intermediate Similarity	NPC290194
0.7091	Intermediate Similarity	NPC162751
0.7089	Intermediate Similarity	NPC258502
0.7081	Intermediate Similarity	NPC203063
0.7075	Intermediate Similarity	NPC125252
0.7073	Intermediate Similarity	NPC170055
0.7067	Intermediate Similarity	NPC198336
0.7066	Intermediate Similarity	NPC205766
0.7063	Intermediate Similarity	NPC61590
0.7059	Intermediate Similarity	NPC295202
0.7059	Intermediate Similarity	NPC136342
0.7059	Intermediate Similarity	NPC49647
0.7059	Intermediate Similarity	NPC473691
0.7059	Intermediate Similarity	NPC227741
0.7059	Intermediate Similarity	NPC254492
0.7055	Intermediate Similarity	NPC476473
0.7055	Intermediate Similarity	NPC21873
0.7051	Intermediate Similarity	NPC17083
0.7048	Intermediate Similarity	NPC290695
0.7048	Intermediate Similarity	NPC106524
0.7044	Intermediate Similarity	NPC472308
0.7037	Intermediate Similarity	NPC187843
0.7037	Intermediate Similarity	NPC110810
0.703	Intermediate Similarity	NPC300540
0.703	Intermediate Similarity	NPC285122
0.703	Intermediate Similarity	NPC147250
0.7027	Intermediate Similarity	NPC41567
0.7025	Intermediate Similarity	NPC1249

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 NPC85059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	409
0.1-0.2	997
0.2-0.3	1300
0.3-0.4	3403
0.4-0.5	2095
0.5-0.6	788
0.6-0.7	152
0.7-0.8	5
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8028	Intermediate Similarity	NPD1201	Approved
0.7808	Intermediate Similarity	NPD1470	Approved
0.7325	Intermediate Similarity	NPD5406	Approved
0.7325	Intermediate Similarity	NPD5408	Approved
0.7325	Intermediate Similarity	NPD5405	Approved
0.7325	Intermediate Similarity	NPD5404	Approved
0.7261	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7390	Discontinued
0.7123	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6332	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3019	Approved
0.6923	Remote Similarity	NPD6966	Discovery
0.6879	Remote Similarity	NPD3764	Approved
0.6871	Remote Similarity	NPD1246	Approved
0.6867	Remote Similarity	NPD1245	Approved
0.6852	Remote Similarity	NPD2344	Approved
0.6821	Remote Similarity	NPD2932	Approved
0.6813	Remote Similarity	NPD6734	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3226	Approved
0.68	Remote Similarity	NPD7330	Discontinued
0.6776	Remote Similarity	NPD6989	Approved
0.6776	Remote Similarity	NPD6990	Approved
0.6774	Remote Similarity	NPD1164	Approved
0.6748	Remote Similarity	NPD2346	Discontinued
0.6747	Remote Similarity	NPD3300	Phase 2
0.6736	Remote Similarity	NPD2342	Discontinued
0.6711	Remote Similarity	NPD2345	Approved
0.6687	Remote Similarity	NPD2309	Approved
0.6687	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3599	Approved
0.6629	Remote Similarity	NPD3749	Approved
0.6624	Remote Similarity	NPD2798	Approved
0.6581	Remote Similarity	NPD1877	Discontinued
0.6577	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7286	Phase 2
0.6573	Remote Similarity	NPD6232	Discontinued
0.6558	Remote Similarity	NPD3023	Approved
0.6558	Remote Similarity	NPD3026	Approved
0.6556	Remote Similarity	NPD7636	Approved
0.6556	Remote Similarity	NPD7473	Discontinued
0.6536	Remote Similarity	NPD3025	Approved
0.6536	Remote Similarity	NPD3024	Approved
0.6527	Remote Similarity	NPD7003	Approved
0.6517	Remote Similarity	NPD6959	Discontinued
0.651	Remote Similarity	NPD5277	Phase 2
0.6503	Remote Similarity	NPD1607	Approved
0.6503	Remote Similarity	NPD5953	Discontinued
0.6485	Remote Similarity	NPD2935	Discontinued
0.6485	Remote Similarity	NPD7137	Phase 2
0.6481	Remote Similarity	NPD1240	Approved
0.6463	Remote Similarity	NPD5886	Approved
0.6463	Remote Similarity	NPD41	Approved
0.645	Remote Similarity	NPD7440	Discontinued
0.6424	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1510	Phase 2
0.6424	Remote Similarity	NPD5951	Approved
0.6424	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7635	Approved
0.6395	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7819	Suspended
0.6358	Remote Similarity	NPD2313	Discontinued
0.6354	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD74	Approved
0.6351	Remote Similarity	NPD9266	Approved
0.6347	Remote Similarity	NPD1471	Phase 3
0.6347	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7680	Approved
0.634	Remote Similarity	NPD9493	Approved
0.6337	Remote Similarity	NPD5049	Phase 3
0.6331	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD3750	Approved
0.6328	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD2799	Discontinued
0.6323	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4404	Approved
0.6319	Remote Similarity	NPD6663	Approved
0.631	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7229	Phase 3
0.6292	Remote Similarity	NPD7768	Phase 2
0.6291	Remote Similarity	NPD1279	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6559	Discontinued
0.6289	Remote Similarity	NPD1283	Approved
0.6287	Remote Similarity	NPD2862	Discontinued
0.6284	Remote Similarity	NPD9264	Approved
0.6284	Remote Similarity	NPD9263	Approved
0.6284	Remote Similarity	NPD9267	Approved
0.6282	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2534	Approved
0.6279	Remote Similarity	NPD2532	Approved
0.6279	Remote Similarity	NPD2533	Approved
0.6273	Remote Similarity	NPD5736	Approved
0.6272	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD2296	Approved
0.6236	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7305	Phase 1
0.6221	Remote Similarity	NPD1511	Approved
0.622	Remote Similarity	NPD4248	Discontinued
0.6218	Remote Similarity	NPD1651	Approved
0.6215	Remote Similarity	NPD1934	Approved
0.6213	Remote Similarity	NPD1549	Phase 2
0.6205	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5278	Discontinued
0.6188	Remote Similarity	NPD1876	Approved
0.6178	Remote Similarity	NPD2286	Discontinued
0.6176	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD7411	Suspended
0.6154	Remote Similarity	NPD3091	Approved
0.6149	Remote Similarity	NPD1203	Approved
0.6149	Remote Similarity	NPD6273	Approved
0.6149	Remote Similarity	NPD1512	Approved
0.6146	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD8313	Approved
0.6138	Remote Similarity	NPD8312	Approved
0.6131	Remote Similarity	NPD7743	Approved
0.6131	Remote Similarity	NPD7742	Approved
0.6129	Remote Similarity	NPD6020	Phase 2
0.6114	Remote Similarity	NPD2900	Approved
0.6114	Remote Similarity	NPD2901	Approved
0.6111	Remote Similarity	NPD288	Approved
0.6111	Remote Similarity	NPD3882	Suspended
0.6102	Remote Similarity	NPD4380	Phase 2
0.6101	Remote Similarity	NPD3092	Approved
0.6101	Remote Similarity	NPD1281	Approved
0.6098	Remote Similarity	NPD7008	Discontinued
0.6098	Remote Similarity	NPD4625	Phase 3
0.6098	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD1551	Phase 2
0.6095	Remote Similarity	NPD2796	Approved
0.6095	Remote Similarity	NPD6099	Approved
0.6095	Remote Similarity	NPD6100	Approved
0.6095	Remote Similarity	NPD2531	Phase 2
0.6093	Remote Similarity	NPD4750	Phase 3
0.6092	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD2801	Approved
0.6082	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD1243	Approved
0.6082	Remote Similarity	NPD2800	Approved
0.6076	Remote Similarity	NPD4059	Approved
0.6075	Remote Similarity	NPD7177	Discontinued
0.6067	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD4878	Approved
0.6062	Remote Similarity	NPD1608	Approved
0.6054	Remote Similarity	NPD6166	Phase 2
0.6054	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD7015	Phase 2
0.6054	Remote Similarity	NPD7016	Phase 3
0.6054	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD2797	Approved
0.6047	Remote Similarity	NPD8166	Discontinued
0.6047	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD5844	Phase 1
0.6042	Remote Similarity	NPD844	Approved
0.6042	Remote Similarity	NPD8150	Discontinued
0.6038	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD3748	Approved
0.6036	Remote Similarity	NPD4308	Phase 3
0.6034	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5027	Approved
0.6032	Remote Similarity	NPD5031	Approved
0.6032	Remote Similarity	NPD5029	Approved
0.6027	Remote Similarity	NPD3020	Approved
0.6023	Remote Similarity	NPD7974	Phase 3
0.6014	Remote Similarity	NPD9261	Approved
0.6014	Remote Similarity	NPD1929	Approved
0.6014	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD1930	Approved
0.6011	Remote Similarity	NPD1642	Discontinued
0.6	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9281	Approved
0.5989	Remote Similarity	NPD7075	Discontinued
0.5986	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6836	Approved
0.5975	Remote Similarity	NPD4626	Approved
0.5975	Remote Similarity	NPD3095	Discontinued
0.5973	Remote Similarity	NPD1237	Approved
0.5967	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD411	Approved
0.5964	Remote Similarity	NPD3268	Approved
0.5963	Remote Similarity	NPD3972	Approved
0.5963	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD3355	Approved
0.5963	Remote Similarity	NPD3356	Approved
0.5963	Remote Similarity	NPD9717	Approved
0.5955	Remote Similarity	NPD7458	Discontinued
0.5954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD3094	Phase 2

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