NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	396.12
Volume:	380.806
LogP:	1.617
LogD:	1.764
LogS:	-4.335
# Rotatable Bonds:	2
TPSA:	97.75
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	5.114
Fsp3:	0.409
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:	-5.151
MDCK Permeability:	2.8580570869962685e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.36
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.674

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.841
Plasma Protein Binding (PPB):	74.23118591308594%
Volume Distribution (VD):	0.864
Pgp-substrate:	34.157657623291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.535
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.858
CYP2C9-inhibitor:	0.135
CYP2C9-substrate:	0.326
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.393
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.683

ADMET: Excretion

Clearance (CL):	5.941
Half-life (T1/2):	0.14

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.637
AMES Toxicity:	0.824
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.806
Carcinogencity:	0.511
Eye Corrosion:	0.003
Eye Irritation:	0.139
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC478229

Natural Product ID:	NPC478229
*Common Name:**	Plecmillin E
IUPAC Name:	(1R,3R,3'S,9S,10S,12R)-7,9-dihydroxy-3',8'-dimethoxyspiro[2,11-dioxatetracyclo[6.4.1.04,13.010,12]trideca-4(13),5,7-triene-3,4'-2,3-dihydronaphthalene]-1'-one
Synonyms:
Standard InCHIKey:	VONPXYFGBMWMTH-CPUZAZTQSA-N
Standard InCHI:	InChI=1S/C22H20O7/c1-26-13-5-3-4-9-15(13)12(24)8-14(27-2)22(9)10-6-7-11(23)17-16(10)19(29-22)21-20(28-21)18(17)25/h3-7,14,18-21,23,25H,8H2,1-2H3/t14-,18-,19+,20-,21+,22-/m0/s1
SMILES:	CO[C@H]1CC(=O)C2=C([C@]13C4=C5[C@@H](O3)[C@@H]6[C@@H](O6)[C@H](C5=C(C=C4)O)O)C=CC=C2OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	132548505
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 NPC478229 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	407
0.1-0.2	1539
0.2-0.3	3288
0.3-0.4	8421
0.4-0.5	9867
0.5-0.6	4122
0.6-0.7	5636
0.7-0.8	7178
0.8-0.85	1922
0.85-0.9	314
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC478222
0.9419	High Similarity	NPC478223
0.9304	High Similarity	NPC478134
0.929	High Similarity	NPC478218
0.9226	High Similarity	NPC478220
0.9125	High Similarity	NPC472402
0.9119	High Similarity	NPC470810
0.9032	High Similarity	NPC478219
0.9018	High Similarity	NPC225419
0.9018	High Similarity	NPC473094
0.9012	High Similarity	NPC472049
0.8994	High Similarity	NPC477833
0.8987	High Similarity	NPC68727
0.8987	High Similarity	NPC478133
0.8981	High Similarity	NPC268992
0.8981	High Similarity	NPC51824
0.8981	High Similarity	NPC470338
0.8981	High Similarity	NPC470337
0.8981	High Similarity	NPC113608
0.8963	High Similarity	NPC473096
0.8963	High Similarity	NPC473095
0.8957	High Similarity	NPC170245
0.8938	High Similarity	NPC470339
0.8902	High Similarity	NPC150131
0.8902	High Similarity	NPC477154
0.8902	High Similarity	NPC117854
0.8902	High Similarity	NPC6588
0.8896	High Similarity	NPC108433
0.8896	High Similarity	NPC326520
0.8882	High Similarity	NPC284495
0.8882	High Similarity	NPC472055
0.8882	High Similarity	NPC471976
0.8861	High Similarity	NPC180944
0.8841	High Similarity	NPC235610
0.8834	High Similarity	NPC186686
0.8834	High Similarity	NPC475985
0.8834	High Similarity	NPC124038
0.8827	High Similarity	NPC316457
0.8827	High Similarity	NPC3629
0.8812	High Similarity	NPC78492
0.8812	High Similarity	NPC164427
0.8812	High Similarity	NPC208152
0.8797	High Similarity	NPC472636
0.8797	High Similarity	NPC474744
0.8797	High Similarity	NPC474772
0.8797	High Similarity	NPC471675
0.8797	High Similarity	NPC472423
0.8788	High Similarity	NPC103633
0.878	High Similarity	NPC239752
0.878	High Similarity	NPC472450
0.878	High Similarity	NPC473286
0.878	High Similarity	NPC275780
0.878	High Similarity	NPC293319
0.8773	High Similarity	NPC229632
0.8773	High Similarity	NPC473961
0.8773	High Similarity	NPC472635
0.8765	High Similarity	NPC161947
0.8765	High Similarity	NPC208069
0.8765	High Similarity	NPC475784
0.8765	High Similarity	NPC36217
0.8765	High Similarity	NPC155302
0.8765	High Similarity	NPC472624
0.8765	High Similarity	NPC328102
0.8765	High Similarity	NPC321399
0.8743	High Similarity	NPC121333
0.8742	High Similarity	NPC31627
0.8742	High Similarity	NPC476238
0.8742	High Similarity	NPC474843
0.8742	High Similarity	NPC473996
0.8742	High Similarity	NPC475790
0.8742	High Similarity	NPC470340
0.8742	High Similarity	NPC327269
0.8742	High Similarity	NPC285623
0.8735	High Similarity	NPC288813
0.8735	High Similarity	NPC152477
0.8734	High Similarity	NPC225854
0.8734	High Similarity	NPC472421
0.8734	High Similarity	NPC179178
0.8727	High Similarity	NPC173292
0.8727	High Similarity	NPC128293
0.8727	High Similarity	NPC39091
0.8727	High Similarity	NPC119589
0.8727	High Similarity	NPC53640
0.8727	High Similarity	NPC43319
0.872	High Similarity	NPC189473
0.872	High Similarity	NPC476295
0.872	High Similarity	NPC23298
0.872	High Similarity	NPC273959
0.872	High Similarity	NPC248638
0.872	High Similarity	NPC7483
0.872	High Similarity	NPC152659
0.872	High Similarity	NPC236521
0.8718	High Similarity	NPC316769
0.8713	High Similarity	NPC150977
0.8712	High Similarity	NPC45124
0.8712	High Similarity	NPC74854
0.8712	High Similarity	NPC61010
0.8712	High Similarity	NPC474038
0.8712	High Similarity	NPC30655
0.8712	High Similarity	NPC269117
0.8712	High Similarity	NPC117985
0.8712	High Similarity	NPC87431
0.8712	High Similarity	NPC474186
0.8712	High Similarity	NPC474187
0.8712	High Similarity	NPC472632
0.8712	High Similarity	NPC142252
0.8712	High Similarity	NPC96031
0.8704	High Similarity	NPC473990
0.8704	High Similarity	NPC329091
0.8704	High Similarity	NPC324736
0.8704	High Similarity	NPC210459
0.8698	High Similarity	NPC324220
0.8698	High Similarity	NPC478050
0.8698	High Similarity	NPC475233
0.8698	High Similarity	NPC312630
0.8696	High Similarity	NPC24640
0.869	High Similarity	NPC98776
0.8688	High Similarity	NPC469405
0.8688	High Similarity	NPC178964
0.8688	High Similarity	NPC7989
0.8688	High Similarity	NPC95842
0.8688	High Similarity	NPC280530
0.8688	High Similarity	NPC472583
0.8688	High Similarity	NPC223701
0.8683	High Similarity	NPC102277
0.8683	High Similarity	NPC472276
0.8683	High Similarity	NPC279209
0.8679	High Similarity	NPC470569
0.8679	High Similarity	NPC471676
0.8679	High Similarity	NPC474023
0.8679	High Similarity	NPC263384
0.8679	High Similarity	NPC471677
0.8679	High Similarity	NPC474021
0.8679	High Similarity	NPC472422
0.8679	High Similarity	NPC200773
0.8679	High Similarity	NPC472420
0.8679	High Similarity	NPC244577
0.8679	High Similarity	NPC472580
0.8679	High Similarity	NPC240768
0.8675	High Similarity	NPC105414
0.8675	High Similarity	NPC472058
0.8675	High Similarity	NPC324522
0.8675	High Similarity	NPC470341
0.8675	High Similarity	NPC474024
0.8675	High Similarity	NPC234497
0.8675	High Similarity	NPC218226
0.8671	High Similarity	NPC89442
0.8667	High Similarity	NPC472277
0.8667	High Similarity	NPC297404
0.8667	High Similarity	NPC300053
0.8667	High Similarity	NPC471788
0.8667	High Similarity	NPC62261
0.8667	High Similarity	NPC11608
0.8662	High Similarity	NPC222298
0.8662	High Similarity	NPC51070
0.8659	High Similarity	NPC329760
0.8659	High Similarity	NPC476247
0.8659	High Similarity	NPC474034
0.8659	High Similarity	NPC201800
0.8659	High Similarity	NPC211107
0.8659	High Similarity	NPC25152
0.8659	High Similarity	NPC81679
0.8659	High Similarity	NPC474150
0.8659	High Similarity	NPC474162
0.8659	High Similarity	NPC472964
0.8659	High Similarity	NPC474033
0.8654	High Similarity	NPC478019
0.865	High Similarity	NPC192686
0.865	High Similarity	NPC14353
0.865	High Similarity	NPC471973
0.865	High Similarity	NPC476283
0.865	High Similarity	NPC56085
0.865	High Similarity	NPC119209
0.865	High Similarity	NPC299436
0.865	High Similarity	NPC174953
0.865	High Similarity	NPC472902
0.865	High Similarity	NPC228785
0.865	High Similarity	NPC118256
0.865	High Similarity	NPC474287
0.865	High Similarity	NPC475886
0.8642	High Similarity	NPC196448
0.8642	High Similarity	NPC165977
0.8642	High Similarity	NPC284820
0.8642	High Similarity	NPC217677
0.8642	High Similarity	NPC471209
0.8642	High Similarity	NPC472598
0.8642	High Similarity	NPC474055
0.8642	High Similarity	NPC473272
0.8642	High Similarity	NPC136674
0.8642	High Similarity	NPC27337
0.8634	High Similarity	NPC217706
0.8634	High Similarity	NPC48579
0.8634	High Similarity	NPC476169
0.8634	High Similarity	NPC207809
0.8634	High Similarity	NPC304207
0.8634	High Similarity	NPC477958
0.8634	High Similarity	NPC321779
0.8634	High Similarity	NPC175192
0.8634	High Similarity	NPC470681
0.8634	High Similarity	NPC259710

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 NPC478229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	899
0.2-0.3	1682
0.3-0.4	2646
0.4-0.5	1913
0.5-0.6	1063
0.6-0.7	429
0.7-0.8	149
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8616	High Similarity	NPD4380	Phase 2
0.8571	High Similarity	NPD2393	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD5494	Approved
0.8395	Intermediate Similarity	NPD1934	Approved
0.8373	Intermediate Similarity	NPD6959	Discontinued
0.8352	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8284	Intermediate Similarity	NPD7473	Discontinued
0.8242	Intermediate Similarity	NPD3882	Suspended
0.8235	Intermediate Similarity	NPD3818	Discontinued
0.8214	Intermediate Similarity	NPD3787	Discontinued
0.8187	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD2532	Approved
0.8187	Intermediate Similarity	NPD2534	Approved
0.8187	Intermediate Similarity	NPD5844	Phase 1
0.8187	Intermediate Similarity	NPD2533	Approved
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3751	Discontinued
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8084	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7075	Discontinued
0.8075	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7074	Phase 3
0.8034	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD6777	Approved
0.8033	Intermediate Similarity	NPD6776	Approved
0.8033	Intermediate Similarity	NPD6781	Approved
0.8033	Intermediate Similarity	NPD6778	Approved
0.8033	Intermediate Similarity	NPD6782	Approved
0.8033	Intermediate Similarity	NPD6780	Approved
0.8033	Intermediate Similarity	NPD6779	Approved
0.8024	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD7054	Approved
0.7977	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1510	Phase 2
0.7952	Intermediate Similarity	NPD6801	Discontinued
0.7943	Intermediate Similarity	NPD6559	Discontinued
0.7931	Intermediate Similarity	NPD7472	Approved
0.7925	Intermediate Similarity	NPD1549	Phase 2
0.7921	Intermediate Similarity	NPD8150	Discontinued
0.7914	Intermediate Similarity	NPD1512	Approved
0.7911	Intermediate Similarity	NPD2935	Discontinued
0.7903	Intermediate Similarity	NPD7435	Discontinued
0.7898	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7411	Suspended
0.7886	Intermediate Similarity	NPD6797	Phase 2
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD3817	Phase 2
0.7853	Intermediate Similarity	NPD8312	Approved
0.7853	Intermediate Similarity	NPD8313	Approved
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7821	Intermediate Similarity	NPD1240	Approved
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7768	Phase 2
0.7807	Intermediate Similarity	NPD7696	Phase 3
0.7807	Intermediate Similarity	NPD7697	Approved
0.7807	Intermediate Similarity	NPD7698	Approved
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2796	Approved
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7791	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3226	Approved
0.7766	Intermediate Similarity	NPD7871	Phase 2
0.7766	Intermediate Similarity	NPD7870	Phase 2
0.7764	Intermediate Similarity	NPD2800	Approved
0.776	Intermediate Similarity	NPD6534	Approved
0.776	Intermediate Similarity	NPD6535	Approved
0.7754	Intermediate Similarity	NPD6823	Phase 2
0.7738	Intermediate Similarity	NPD37	Approved
0.7737	Intermediate Similarity	NPD7701	Phase 2
0.7736	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8434	Phase 2
0.7722	Intermediate Similarity	NPD1607	Approved
0.7719	Intermediate Similarity	NPD6234	Discontinued
0.7706	Intermediate Similarity	NPD4967	Phase 2
0.7706	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD6799	Approved
0.7656	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD7874	Approved
0.7654	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7699	Phase 2
0.7634	Intermediate Similarity	NPD7700	Phase 2
0.763	Intermediate Similarity	NPD1247	Approved
0.7619	Intermediate Similarity	NPD6599	Discontinued
0.7617	Intermediate Similarity	NPD7801	Approved
0.7614	Intermediate Similarity	NPD7228	Approved
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7607	Intermediate Similarity	NPD3750	Approved
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7588	Intermediate Similarity	NPD1465	Phase 2
0.7586	Intermediate Similarity	NPD5710	Approved
0.7586	Intermediate Similarity	NPD5711	Approved
0.7561	Intermediate Similarity	NPD6190	Approved
0.7545	Intermediate Similarity	NPD5403	Approved
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD2344	Approved
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD943	Approved
0.747	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD5405	Approved
0.7469	Intermediate Similarity	NPD5406	Approved
0.7469	Intermediate Similarity	NPD5404	Approved
0.7469	Intermediate Similarity	NPD5408	Approved
0.7468	Intermediate Similarity	NPD3764	Approved
0.7456	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7458	Discontinued
0.7443	Intermediate Similarity	NPD3926	Phase 2
0.744	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD920	Approved
0.7436	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7783	Phase 2
0.7425	Intermediate Similarity	NPD5401	Approved
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6213	Phase 3
0.7419	Intermediate Similarity	NPD6212	Phase 3
0.7414	Intermediate Similarity	NPD919	Approved
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7396	Intermediate Similarity	NPD8319	Approved
0.7396	Intermediate Similarity	NPD8320	Phase 1
0.7386	Intermediate Similarity	NPD7229	Phase 3
0.7384	Intermediate Similarity	NPD5761	Phase 2
0.7384	Intermediate Similarity	NPD5760	Phase 2
0.7381	Intermediate Similarity	NPD6273	Approved
0.7372	Intermediate Similarity	NPD1470	Approved
0.7358	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2309	Approved
0.7345	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1201	Approved
0.7323	Intermediate Similarity	NPD7930	Approved
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7033	Discontinued
0.7301	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD3027	Phase 3
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7003	Approved
0.7284	Intermediate Similarity	NPD6651	Approved
0.7283	Intermediate Similarity	NPD8455	Phase 2
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6100	Approved
0.7256	Intermediate Similarity	NPD6099	Approved
0.7253	Intermediate Similarity	NPD7240	Approved
0.725	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD1243	Approved
0.7222	Intermediate Similarity	NPD230	Phase 1
0.7211	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3300	Phase 2
0.7202	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5953	Discontinued
0.7196	Intermediate Similarity	NPD4363	Phase 3
0.7196	Intermediate Similarity	NPD4360	Phase 2
0.7184	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8059	Phase 3
0.7182	Intermediate Similarity	NPD7286	Phase 2
0.716	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD8285	Discontinued
0.7127	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD6844	Discontinued
0.7126	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4908	Phase 1
0.7117	Intermediate Similarity	NPD447	Suspended
0.7108	Intermediate Similarity	NPD1471	Phase 3
0.7107	Intermediate Similarity	NPD2798	Approved
0.7094	Intermediate Similarity	NPD4111	Phase 1
0.7081	Intermediate Similarity	NPD4625	Phase 3
0.7074	Intermediate Similarity	NPD4287	Approved
0.7068	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD4361	Phase 2
0.7063	Intermediate Similarity	NPD9494	Approved
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7062	Intermediate Similarity	NPD2493	Approved
0.7062	Intermediate Similarity	NPD2494	Approved
0.7056	Intermediate Similarity	NPD7584	Approved
0.7041	Intermediate Similarity	NPD4583	Approved
0.7041	Intermediate Similarity	NPD4582	Approved
0.7037	Intermediate Similarity	NPD6798	Discontinued

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