NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	368.09
Volume:	352.134
LogP:	1.22
LogD:	1.244
LogS:	-3.974
# Rotatable Bonds:	0
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	4.994
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.091
MDCK Permeability:	6.460278655140428e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.275
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.091
Plasma Protein Binding (PPB):	93.47030639648438%
Volume Distribution (VD):	0.827
Pgp-substrate:	3.830096960067749%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.277
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.527
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.304
CYP3A4-substrate:	0.644

ADMET: Excretion

Clearance (CL):	1.794
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.181
Drug-inuced Liver Injury (DILI):	0.269
AMES Toxicity:	0.837
Rat Oral Acute Toxicity:	0.409
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.933
Carcinogencity:	0.708
Eye Corrosion:	0.003
Eye Irritation:	0.479
Respiratory Toxicity:	0.555

Download Data

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

Natural Product: NPC478220

Natural Product ID:	NPC478220
*Common Name:**	(1R,9S,10S,11S)-7,8',9,10,11-pentahydroxyspiro[2-oxatricyclo[6.3.1.04,12]dodeca-4(12),5,7-triene-3,4'-naphthalene]-1'-one
IUPAC Name:	(1R,9S,10S,11S)-7,8',9,10,11-pentahydroxyspiro[2-oxatricyclo[6.3.1.04,12]dodeca-4(12),5,7-triene-3,4'-naphthalene]-1'-one
Synonyms:
Standard InCHIKey:	HIOGFAQRTOLYLP-BKNJSMIZSA-N
Standard InCHI:	InChI=1S/C20H16O7/c21-10-3-1-2-8-13(10)12(23)6-7-20(8)9-4-5-11(22)15-14(9)19(27-20)18(26)17(25)16(15)24/h1-7,16-19,21-22,24-26H/t16-,17-,18-,19+,20?/m0/s1
SMILES:	C1=CC2=C(C(=O)C=CC23C4=C5[C@@H](O3)[C@H]([C@H]([C@H](C5=C(C=C4)O)O)O)O)C(=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	162818715
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
NPO33695	Plectania sp.	Species	Sarcosomataceae	Eukaryota	fruiting body	Tibet Plateau Region	n.a.	DOI[10.1002/ejoc.201600562]

☑ 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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478220 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	392
0.1-0.2	1375
0.2-0.3	2931
0.3-0.4	7299
0.4-0.5	10936
0.5-0.6	4312
0.6-0.7	5711
0.7-0.8	7971
0.8-0.85	1662
0.85-0.9	103
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC478218
0.9539	High Similarity	NPC478222
0.9524	High Similarity	NPC478219
0.9276	High Similarity	NPC478223
0.9226	High Similarity	NPC478229
0.9211	High Similarity	NPC478133
0.8917	High Similarity	NPC478134
0.8816	High Similarity	NPC106524
0.8816	High Similarity	NPC290695
0.8766	High Similarity	NPC227485
0.8758	High Similarity	NPC473094
0.875	High Similarity	NPC52161
0.875	High Similarity	NPC162751
0.8742	High Similarity	NPC472402
0.8734	High Similarity	NPC470810
0.8704	High Similarity	NPC473095
0.8704	High Similarity	NPC473096
0.8684	High Similarity	NPC285122
0.8654	High Similarity	NPC474622
0.8654	High Similarity	NPC474621
0.8642	High Similarity	NPC150131
0.8634	High Similarity	NPC478020
0.8634	High Similarity	NPC478022
0.8625	High Similarity	NPC473961
0.8616	High Similarity	NPC471976
0.86	High Similarity	NPC130485
0.8599	High Similarity	NPC68727
0.859	High Similarity	NPC470338
0.859	High Similarity	NPC180944
0.859	High Similarity	NPC470340
0.859	High Similarity	NPC268992
0.859	High Similarity	NPC51824
0.859	High Similarity	NPC113608
0.859	High Similarity	NPC470337
0.858	High Similarity	NPC178173
0.858	High Similarity	NPC170245
0.8571	High Similarity	NPC124038
0.8562	High Similarity	NPC470570
0.8562	High Similarity	NPC3629
0.8553	High Similarity	NPC48130
0.8553	High Similarity	NPC470339
0.8553	High Similarity	NPC84568
0.8553	High Similarity	NPC300684
0.8553	High Similarity	NPC103910
0.8553	High Similarity	NPC218866
0.8544	High Similarity	NPC78492
0.8544	High Similarity	NPC208152
0.8528	High Similarity	NPC6588
0.8528	High Similarity	NPC477154
0.8528	High Similarity	NPC117854
0.8526	High Similarity	NPC472423
0.8526	High Similarity	NPC477276
0.8526	High Similarity	NPC474744
0.8526	High Similarity	NPC474772
0.8519	High Similarity	NPC472049
0.8519	High Similarity	NPC326520
0.85	High Similarity	NPC472055
0.85	High Similarity	NPC284495
0.85	High Similarity	NPC328102
0.8497	Intermediate Similarity	NPC34482
0.8497	Intermediate Similarity	NPC170055
0.8491	Intermediate Similarity	NPC477833
0.8487	Intermediate Similarity	NPC21873
0.8487	Intermediate Similarity	NPC476473
0.8485	Intermediate Similarity	NPC121333
0.8485	Intermediate Similarity	NPC294501
0.8485	Intermediate Similarity	NPC473113
0.8481	Intermediate Similarity	NPC314257
0.8477	Intermediate Similarity	NPC106519
0.8477	Intermediate Similarity	NPC91019
0.8476	Intermediate Similarity	NPC288813
0.8476	Intermediate Similarity	NPC152477
0.8471	Intermediate Similarity	NPC474533
0.8471	Intermediate Similarity	NPC285623
0.8471	Intermediate Similarity	NPC474534
0.8471	Intermediate Similarity	NPC473996
0.8471	Intermediate Similarity	NPC327269
0.8471	Intermediate Similarity	NPC476238
0.8471	Intermediate Similarity	NPC31627
0.8466	Intermediate Similarity	NPC173292
0.8466	Intermediate Similarity	NPC119589
0.8466	Intermediate Similarity	NPC53640
0.8466	Intermediate Similarity	NPC128293
0.8462	Intermediate Similarity	NPC225854
0.8462	Intermediate Similarity	NPC472421
0.8462	Intermediate Similarity	NPC177308
0.8462	Intermediate Similarity	NPC124478
0.8457	Intermediate Similarity	NPC475985
0.8457	Intermediate Similarity	NPC186686
0.8447	Intermediate Similarity	NPC45124
0.8447	Intermediate Similarity	NPC269117
0.8447	Intermediate Similarity	NPC30655
0.8447	Intermediate Similarity	NPC96031
0.8447	Intermediate Similarity	NPC74854
0.8447	Intermediate Similarity	NPC117985
0.8443	Intermediate Similarity	NPC475233
0.8442	Intermediate Similarity	NPC147250
0.8442	Intermediate Similarity	NPC316769
0.8438	Intermediate Similarity	NPC186113
0.8434	Intermediate Similarity	NPC154986
0.8434	Intermediate Similarity	NPC98776
0.8431	Intermediate Similarity	NPC244691
0.8431	Intermediate Similarity	NPC48762
0.8431	Intermediate Similarity	NPC193703
0.8431	Intermediate Similarity	NPC21599
0.8428	Intermediate Similarity	NPC164427
0.8428	Intermediate Similarity	NPC478027
0.8424	Intermediate Similarity	NPC241874
0.8424	Intermediate Similarity	NPC472276
0.8424	Intermediate Similarity	NPC478021
0.8421	Intermediate Similarity	NPC474300
0.8421	Intermediate Similarity	NPC469520
0.8418	Intermediate Similarity	NPC182921
0.8418	Intermediate Similarity	NPC472583
0.8418	Intermediate Similarity	NPC469405
0.8418	Intermediate Similarity	NPC135522
0.8418	Intermediate Similarity	NPC474824
0.8418	Intermediate Similarity	NPC218870
0.8418	Intermediate Similarity	NPC223701
0.8418	Intermediate Similarity	NPC155686
0.8418	Intermediate Similarity	NPC7989
0.8418	Intermediate Similarity	NPC470408
0.8415	Intermediate Similarity	NPC107009
0.8415	Intermediate Similarity	NPC234497
0.8415	Intermediate Similarity	NPC470341
0.8415	Intermediate Similarity	NPC472058
0.8415	Intermediate Similarity	NPC105414
0.8415	Intermediate Similarity	NPC225419
0.8415	Intermediate Similarity	NPC324522
0.8408	Intermediate Similarity	NPC46882
0.8408	Intermediate Similarity	NPC471675
0.8408	Intermediate Similarity	NPC132990
0.8408	Intermediate Similarity	NPC207346
0.8408	Intermediate Similarity	NPC244577
0.8408	Intermediate Similarity	NPC263384
0.8408	Intermediate Similarity	NPC472580
0.8408	Intermediate Similarity	NPC472636
0.8408	Intermediate Similarity	NPC472422
0.8408	Intermediate Similarity	NPC471676
0.8408	Intermediate Similarity	NPC472420
0.8408	Intermediate Similarity	NPC470569
0.8408	Intermediate Similarity	NPC46564
0.8405	Intermediate Similarity	NPC26386
0.8405	Intermediate Similarity	NPC470735
0.8405	Intermediate Similarity	NPC472277
0.8405	Intermediate Similarity	NPC329647
0.8405	Intermediate Similarity	NPC239752
0.8405	Intermediate Similarity	NPC300053
0.8405	Intermediate Similarity	NPC473286
0.8405	Intermediate Similarity	NPC108433
0.8405	Intermediate Similarity	NPC293319
0.8405	Intermediate Similarity	NPC472450
0.8405	Intermediate Similarity	NPC275780
0.8405	Intermediate Similarity	NPC471788
0.8397	Intermediate Similarity	NPC89442
0.8395	Intermediate Similarity	NPC472635
0.8395	Intermediate Similarity	NPC476247
0.8395	Intermediate Similarity	NPC474034
0.8395	Intermediate Similarity	NPC472964
0.8395	Intermediate Similarity	NPC329760
0.8395	Intermediate Similarity	NPC81679
0.8395	Intermediate Similarity	NPC474033
0.8395	Intermediate Similarity	NPC229632
0.8387	Intermediate Similarity	NPC222298
0.8387	Intermediate Similarity	NPC166583
0.8387	Intermediate Similarity	NPC51070
0.8387	Intermediate Similarity	NPC81835
0.8387	Intermediate Similarity	NPC119767
0.8387	Intermediate Similarity	NPC53362
0.8385	Intermediate Similarity	NPC472624
0.8385	Intermediate Similarity	NPC36217
0.8385	Intermediate Similarity	NPC155302
0.8385	Intermediate Similarity	NPC161947
0.8385	Intermediate Similarity	NPC475784
0.8385	Intermediate Similarity	NPC472902
0.8385	Intermediate Similarity	NPC321399
0.8377	Intermediate Similarity	NPC478019
0.8375	Intermediate Similarity	NPC472889
0.8375	Intermediate Similarity	NPC206641
0.8375	Intermediate Similarity	NPC196448
0.8375	Intermediate Similarity	NPC208651
0.8373	Intermediate Similarity	NPC472620
0.8365	Intermediate Similarity	NPC203757
0.8365	Intermediate Similarity	NPC470681
0.8365	Intermediate Similarity	NPC477958
0.8365	Intermediate Similarity	NPC471456
0.8364	Intermediate Similarity	NPC242395
0.8364	Intermediate Similarity	NPC222455
0.8355	Intermediate Similarity	NPC257003
0.8354	Intermediate Similarity	NPC324233
0.8354	Intermediate Similarity	NPC474843
0.8354	Intermediate Similarity	NPC115249
0.8354	Intermediate Similarity	NPC235610
0.8354	Intermediate Similarity	NPC43319
0.8354	Intermediate Similarity	NPC475790
0.8354	Intermediate Similarity	NPC477957
0.8354	Intermediate Similarity	NPC39091
0.8354	Intermediate Similarity	NPC323626
0.8344	Intermediate Similarity	NPC86744
0.8344	Intermediate Similarity	NPC477914

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 NPC478220 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	846
0.2-0.3	1554
0.3-0.4	2671
0.4-0.5	2006
0.5-0.6	1111
0.6-0.7	459
0.7-0.8	152
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8187	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD8150	Discontinued
0.816	Intermediate Similarity	NPD5494	Approved
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3764	Approved
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2801	Approved
0.7952	Intermediate Similarity	NPD6232	Discontinued
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7473	Discontinued
0.7914	Intermediate Similarity	NPD5402	Approved
0.7908	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6559	Discontinued
0.7892	Intermediate Similarity	NPD6959	Discontinued
0.7891	Intermediate Similarity	NPD1470	Approved
0.7886	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3751	Discontinued
0.7866	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5404	Approved
0.7857	Intermediate Similarity	NPD5408	Approved
0.7857	Intermediate Similarity	NPD5405	Approved
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7857	Intermediate Similarity	NPD5406	Approved
0.7853	Intermediate Similarity	NPD7819	Suspended
0.7834	Intermediate Similarity	NPD6190	Approved
0.7818	Intermediate Similarity	NPD3749	Approved
0.7818	Intermediate Similarity	NPD7075	Discontinued
0.7809	Intermediate Similarity	NPD6535	Approved
0.7809	Intermediate Similarity	NPD6534	Approved
0.7805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7799	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2532	Approved
0.7792	Intermediate Similarity	NPD1510	Phase 2
0.7771	Intermediate Similarity	NPD3750	Approved
0.7763	Intermediate Similarity	NPD943	Approved
0.7756	Intermediate Similarity	NPD1549	Phase 2
0.7744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1201	Approved
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7736	Intermediate Similarity	NPD1511	Approved
0.7692	Intermediate Similarity	NPD6779	Approved
0.7692	Intermediate Similarity	NPD6782	Approved
0.7692	Intermediate Similarity	NPD6778	Approved
0.7692	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6776	Approved
0.7692	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6777	Approved
0.7692	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD6781	Approved
0.7683	Intermediate Similarity	NPD6801	Discontinued
0.768	Intermediate Similarity	NPD7700	Phase 2
0.768	Intermediate Similarity	NPD7699	Phase 2
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.7651	Intermediate Similarity	NPD7768	Phase 2
0.7644	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1512	Approved
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7054	Approved
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6823	Phase 2
0.7607	Intermediate Similarity	NPD3226	Approved
0.7593	Intermediate Similarity	NPD5403	Approved
0.7576	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD7472	Approved
0.7571	Intermediate Similarity	NPD8434	Phase 2
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.7564	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3300	Phase 2
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7545	Intermediate Similarity	NPD4966	Approved
0.7545	Intermediate Similarity	NPD4967	Phase 2
0.7545	Intermediate Similarity	NPD4965	Approved
0.7532	Intermediate Similarity	NPD1240	Approved
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7484	Intermediate Similarity	NPD2800	Approved
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7469	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7459	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6212	Phase 3
0.7459	Intermediate Similarity	NPD6213	Phase 3
0.7457	Intermediate Similarity	NPD7228	Approved
0.7452	Intermediate Similarity	NPD3748	Approved
0.7443	Intermediate Similarity	NPD7808	Phase 3
0.7442	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1607	Approved
0.7433	Intermediate Similarity	NPD8319	Approved
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7433	Intermediate Similarity	NPD8320	Phase 1
0.7425	Intermediate Similarity	NPD1465	Phase 2
0.7421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6799	Approved
0.7407	Intermediate Similarity	NPD7701	Phase 2
0.7375	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD1247	Approved
0.7349	Intermediate Similarity	NPD6599	Discontinued
0.7342	Intermediate Similarity	NPD2799	Discontinued
0.733	Intermediate Similarity	NPD7874	Approved
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD8166	Discontinued
0.7329	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7292	Intermediate Similarity	NPD7801	Approved
0.729	Intermediate Similarity	NPD2313	Discontinued
0.7277	Intermediate Similarity	NPD8151	Discontinued
0.725	Intermediate Similarity	NPD2344	Approved
0.7225	Intermediate Similarity	NPD5711	Approved
0.7225	Intermediate Similarity	NPD5710	Approved
0.7222	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6273	Approved
0.7211	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1164	Approved
0.7188	Intermediate Similarity	NPD1551	Phase 2
0.7184	Intermediate Similarity	NPD3926	Phase 2
0.7169	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD920	Approved
0.7168	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7125	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5761	Phase 2
0.7118	Intermediate Similarity	NPD5760	Phase 2
0.7118	Intermediate Similarity	NPD8455	Phase 2
0.7117	Intermediate Similarity	NPD7003	Approved
0.7115	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3027	Phase 3
0.7113	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7783	Phase 2
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7095	Intermediate Similarity	NPD7240	Approved
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7091	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7458	Discontinued
0.7073	Intermediate Similarity	NPD2309	Approved
0.707	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7056	Intermediate Similarity	NPD5034	Approved
0.7056	Intermediate Similarity	NPD5026	Approved
0.7056	Intermediate Similarity	NPD4954	Approved
0.7056	Intermediate Similarity	NPD36	Approved
0.7056	Intermediate Similarity	NPD5028	Approved
0.7056	Intermediate Similarity	NPD4955	Approved
0.7044	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2798	Approved
0.703	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7229	Phase 3
0.7012	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5030	Phase 2
0.7	Intermediate Similarity	NPD6651	Approved
0.6995	Remote Similarity	NPD5038	Approved
0.6995	Remote Similarity	NPD5037	Approved
0.6989	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2861	Phase 2
0.6981	Remote Similarity	NPD4060	Phase 1
0.698	Remote Similarity	NPD9493	Approved
0.6971	Remote Similarity	NPD8127	Discontinued
0.6968	Remote Similarity	NPD1203	Approved
0.6968	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1243	Approved
0.695	Remote Similarity	NPD4665	Approved
0.695	Remote Similarity	NPD4111	Phase 1
0.6944	Remote Similarity	NPD5953	Discontinued
0.6943	Remote Similarity	NPD4908	Phase 1
0.6943	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5036	Approved
0.6933	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7236	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