NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	350.08
Volume:	334.787
LogP:	1.751
LogD:	1.712
LogS:	-4.204
# Rotatable Bonds:	0
TPSA:	99.52
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	5.1
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:	-5.652
MDCK Permeability:	8.789294042799156e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.409
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	94.15462493896484%
Volume Distribution (VD):	0.816
Pgp-substrate:	3.410384178161621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.204
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.281
CYP2C19-substrate:	0.242
CYP2C9-inhibitor:	0.825
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.805
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.773

ADMET: Excretion

Clearance (CL):	0.93
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.579
Drug-inuced Liver Injury (DILI):	0.608
AMES Toxicity:	0.889
Rat Oral Acute Toxicity:	0.494
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.931
Carcinogencity:	0.623
Eye Corrosion:	0.003
Eye Irritation:	0.803
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC478218

Natural Product ID:	NPC478218
*Common Name:**	Plecmillin A
IUPAC Name:	(1R,3R,9S,10S,12R)-7,8',9-trihydroxyspiro[2,11-dioxatetracyclo[6.4.1.04,13.010,12]trideca-4(13),5,7-triene-3,4'-naphthalene]-1'-one
Synonyms:
Standard InCHIKey:	KLUZLYJDODRQCZ-YHDCXSKOSA-N
Standard InCHI:	InChI=1S/C20H14O6/c21-10-3-1-2-8-13(10)12(23)6-7-20(8)9-4-5-11(22)15-14(9)17(26-20)19-18(25-19)16(15)24/h1-7,16-19,21-22,24H/t16-,17+,18-,19+,20-/m0/s1
SMILES:	C1=CC2=C(C(=O)C=C[C@@]23C4=C5[C@@H](O3)[C@@H]6[C@@H](O6)[C@H](C5=C(C=C4)O)O)C(=C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	132548501
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 NPC478218 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	408
0.1-0.2	1484
0.2-0.3	3169
0.3-0.4	8086
0.4-0.5	10402
0.5-0.6	4423
0.6-0.7	6723
0.7-0.8	7420
0.8-0.85	564
0.85-0.9	15
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC478220
0.9605	High Similarity	NPC478222
0.9459	High Similarity	NPC478219
0.9404	High Similarity	NPC478133
0.929	High Similarity	NPC478229
0.9103	High Similarity	NPC478134
0.9091	High Similarity	NPC478223
0.8671	High Similarity	NPC477833
0.8636	High Similarity	NPC290695
0.8636	High Similarity	NPC106524
0.859	High Similarity	NPC227485
0.8589	High Similarity	NPC473094
0.858	High Similarity	NPC472049
0.8571	High Similarity	NPC472402
0.8571	High Similarity	NPC52161
0.8571	High Similarity	NPC162751
0.8562	High Similarity	NPC470810
0.8544	High Similarity	NPC314257
0.8537	High Similarity	NPC473096
0.8537	High Similarity	NPC473095
0.8506	High Similarity	NPC285122
0.85	High Similarity	NPC193749
0.8481	Intermediate Similarity	NPC474622
0.8481	Intermediate Similarity	NPC474621
0.8476	Intermediate Similarity	NPC225419
0.8476	Intermediate Similarity	NPC150131
0.8466	Intermediate Similarity	NPC478020
0.8466	Intermediate Similarity	NPC478022
0.8466	Intermediate Similarity	NPC108433
0.8457	Intermediate Similarity	NPC473961
0.8447	Intermediate Similarity	NPC471976
0.8428	Intermediate Similarity	NPC68727
0.8421	Intermediate Similarity	NPC130485
0.8418	Intermediate Similarity	NPC268992
0.8418	Intermediate Similarity	NPC113608
0.8418	Intermediate Similarity	NPC470337
0.8418	Intermediate Similarity	NPC470338
0.8418	Intermediate Similarity	NPC51824
0.8418	Intermediate Similarity	NPC180944
0.8418	Intermediate Similarity	NPC470340
0.8415	Intermediate Similarity	NPC178173
0.8415	Intermediate Similarity	NPC235610
0.8415	Intermediate Similarity	NPC170245
0.8405	Intermediate Similarity	NPC124038
0.8395	Intermediate Similarity	NPC316457
0.8395	Intermediate Similarity	NPC3629
0.8387	Intermediate Similarity	NPC470570
0.8385	Intermediate Similarity	NPC183402
0.8385	Intermediate Similarity	NPC470339
0.8377	Intermediate Similarity	NPC48762
0.8377	Intermediate Similarity	NPC218866
0.8377	Intermediate Similarity	NPC300684
0.8377	Intermediate Similarity	NPC103910
0.8377	Intermediate Similarity	NPC48130
0.8377	Intermediate Similarity	NPC193703
0.8377	Intermediate Similarity	NPC244691
0.8377	Intermediate Similarity	NPC84568
0.8377	Intermediate Similarity	NPC21599
0.8375	Intermediate Similarity	NPC208152
0.8375	Intermediate Similarity	NPC78492
0.8366	Intermediate Similarity	NPC469520
0.8364	Intermediate Similarity	NPC477154
0.8364	Intermediate Similarity	NPC117854
0.8364	Intermediate Similarity	NPC6588
0.8354	Intermediate Similarity	NPC474772
0.8354	Intermediate Similarity	NPC477276
0.8354	Intermediate Similarity	NPC205918
0.8354	Intermediate Similarity	NPC11608
0.8354	Intermediate Similarity	NPC472423
0.8354	Intermediate Similarity	NPC297404
0.8354	Intermediate Similarity	NPC474744
0.8354	Intermediate Similarity	NPC326520
0.8353	Intermediate Similarity	NPC208069
0.8333	Intermediate Similarity	NPC328102
0.8333	Intermediate Similarity	NPC472135
0.8333	Intermediate Similarity	NPC472055
0.8333	Intermediate Similarity	NPC119767
0.8333	Intermediate Similarity	NPC53362
0.8333	Intermediate Similarity	NPC166583
0.8333	Intermediate Similarity	NPC284495
0.8323	Intermediate Similarity	NPC34482
0.8323	Intermediate Similarity	NPC83272
0.8323	Intermediate Similarity	NPC121333
0.8323	Intermediate Similarity	NPC170055
0.8323	Intermediate Similarity	NPC294501
0.8323	Intermediate Similarity	NPC473113
0.8313	Intermediate Similarity	NPC152477
0.8313	Intermediate Similarity	NPC288813
0.8312	Intermediate Similarity	NPC476473
0.8312	Intermediate Similarity	NPC21873
0.8303	Intermediate Similarity	NPC119589
0.8303	Intermediate Similarity	NPC173292
0.8303	Intermediate Similarity	NPC128293
0.8303	Intermediate Similarity	NPC53640
0.8302	Intermediate Similarity	NPC474533
0.8302	Intermediate Similarity	NPC473996
0.8302	Intermediate Similarity	NPC476238
0.8302	Intermediate Similarity	NPC474534
0.8302	Intermediate Similarity	NPC285623
0.8302	Intermediate Similarity	NPC31627
0.8302	Intermediate Similarity	NPC327269
0.8301	Intermediate Similarity	NPC91019
0.8301	Intermediate Similarity	NPC106519
0.8293	Intermediate Similarity	NPC186686
0.8293	Intermediate Similarity	NPC475985
0.8291	Intermediate Similarity	NPC147735
0.8291	Intermediate Similarity	NPC177308
0.8291	Intermediate Similarity	NPC225854
0.8291	Intermediate Similarity	NPC472421
0.8291	Intermediate Similarity	NPC290954
0.8291	Intermediate Similarity	NPC255641
0.8291	Intermediate Similarity	NPC280295
0.8291	Intermediate Similarity	NPC56204
0.8291	Intermediate Similarity	NPC124478
0.8284	Intermediate Similarity	NPC475233
0.8282	Intermediate Similarity	NPC30655
0.8282	Intermediate Similarity	NPC74854
0.8282	Intermediate Similarity	NPC269117
0.8282	Intermediate Similarity	NPC117985
0.8282	Intermediate Similarity	NPC45124
0.8282	Intermediate Similarity	NPC311740
0.8282	Intermediate Similarity	NPC96031
0.828	Intermediate Similarity	NPC142846
0.8274	Intermediate Similarity	NPC154986
0.8274	Intermediate Similarity	NPC98776
0.8272	Intermediate Similarity	NPC186113
0.8269	Intermediate Similarity	NPC316769
0.8269	Intermediate Similarity	NPC147250
0.8269	Intermediate Similarity	NPC300540
0.8263	Intermediate Similarity	NPC478021
0.8263	Intermediate Similarity	NPC472276
0.8263	Intermediate Similarity	NPC241874
0.8261	Intermediate Similarity	NPC164427
0.8261	Intermediate Similarity	NPC478027
0.8253	Intermediate Similarity	NPC324522
0.8253	Intermediate Similarity	NPC103633
0.8253	Intermediate Similarity	NPC234497
0.8253	Intermediate Similarity	NPC105414
0.8253	Intermediate Similarity	NPC470341
0.8253	Intermediate Similarity	NPC472058
0.8253	Intermediate Similarity	NPC107009
0.825	Intermediate Similarity	NPC155686
0.825	Intermediate Similarity	NPC474824
0.825	Intermediate Similarity	NPC135522
0.825	Intermediate Similarity	NPC182921
0.825	Intermediate Similarity	NPC7989
0.825	Intermediate Similarity	NPC223701
0.825	Intermediate Similarity	NPC469405
0.825	Intermediate Similarity	NPC472583
0.825	Intermediate Similarity	NPC470408
0.825	Intermediate Similarity	NPC218870
0.8247	Intermediate Similarity	NPC474300
0.8242	Intermediate Similarity	NPC472450
0.8242	Intermediate Similarity	NPC293319
0.8242	Intermediate Similarity	NPC26386
0.8242	Intermediate Similarity	NPC275780
0.8242	Intermediate Similarity	NPC239752
0.8242	Intermediate Similarity	NPC473286
0.8242	Intermediate Similarity	NPC470735
0.8242	Intermediate Similarity	NPC300053
0.8242	Intermediate Similarity	NPC472277
0.8242	Intermediate Similarity	NPC471788
0.8242	Intermediate Similarity	NPC329647
0.8239	Intermediate Similarity	NPC472636
0.8239	Intermediate Similarity	NPC472422
0.8239	Intermediate Similarity	NPC471675
0.8239	Intermediate Similarity	NPC470569
0.8239	Intermediate Similarity	NPC263384
0.8239	Intermediate Similarity	NPC244577
0.8239	Intermediate Similarity	NPC472420
0.8239	Intermediate Similarity	NPC471676
0.8239	Intermediate Similarity	NPC46882
0.8239	Intermediate Similarity	NPC46564
0.8239	Intermediate Similarity	NPC132990
0.8239	Intermediate Similarity	NPC207346
0.8239	Intermediate Similarity	NPC472580
0.8232	Intermediate Similarity	NPC474033
0.8232	Intermediate Similarity	NPC472964
0.8232	Intermediate Similarity	NPC474034
0.8232	Intermediate Similarity	NPC476247
0.8232	Intermediate Similarity	NPC81679
0.8232	Intermediate Similarity	NPC472635
0.8232	Intermediate Similarity	NPC329760
0.8232	Intermediate Similarity	NPC229632
0.8228	Intermediate Similarity	NPC89442
0.8221	Intermediate Similarity	NPC84571
0.8221	Intermediate Similarity	NPC472902
0.8221	Intermediate Similarity	NPC475784
0.8221	Intermediate Similarity	NPC472624
0.8221	Intermediate Similarity	NPC161947
0.8221	Intermediate Similarity	NPC321399
0.8221	Intermediate Similarity	NPC155302
0.8221	Intermediate Similarity	NPC36217
0.8217	Intermediate Similarity	NPC81835
0.8217	Intermediate Similarity	NPC51070
0.8217	Intermediate Similarity	NPC222298
0.8217	Intermediate Similarity	NPC476463
0.8214	Intermediate Similarity	NPC248593
0.8214	Intermediate Similarity	NPC472620
0.8214	Intermediate Similarity	NPC28589

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 NPC478218 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	859
0.2-0.3	1642
0.3-0.4	2744
0.4-0.5	1977
0.5-0.6	1070
0.6-0.7	380
0.7-0.8	129
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
0.8291	Intermediate Similarity	NPD4380	Phase 2
0.8036	Intermediate Similarity	NPD3751	Discontinued
0.8035	Intermediate Similarity	NPD8150	Discontinued
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5494	Approved
0.7963	Intermediate Similarity	NPD1934	Approved
0.7933	Intermediate Similarity	NPD3764	Approved
0.7929	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1470	Approved
0.7818	Intermediate Similarity	NPD3882	Suspended
0.7811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6166	Phase 2
0.7805	Intermediate Similarity	NPD2801	Approved
0.7798	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3749	Approved
0.7765	Intermediate Similarity	NPD7473	Discontinued
0.7758	Intermediate Similarity	NPD5402	Approved
0.7746	Intermediate Similarity	NPD6559	Discontinued
0.7742	Intermediate Similarity	NPD1510	Phase 2
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7722	Intermediate Similarity	NPD3750	Approved
0.7712	Intermediate Similarity	NPD943	Approved
0.7711	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD5408	Approved
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD5405	Approved
0.7692	Intermediate Similarity	NPD5406	Approved
0.7692	Intermediate Similarity	NPD5404	Approved
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7688	Intermediate Similarity	NPD1511	Approved
0.7687	Intermediate Similarity	NPD1201	Approved
0.7673	Intermediate Similarity	NPD6190	Approved
0.7667	Intermediate Similarity	NPD6535	Approved
0.7667	Intermediate Similarity	NPD6534	Approved
0.7665	Intermediate Similarity	NPD7075	Discontinued
0.7657	Intermediate Similarity	NPD8313	Approved
0.7657	Intermediate Similarity	NPD8312	Approved
0.7651	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2534	Approved
0.7593	Intermediate Similarity	NPD1512	Approved
0.759	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7561	Intermediate Similarity	NPD3226	Approved
0.7554	Intermediate Similarity	NPD6776	Approved
0.7554	Intermediate Similarity	NPD6777	Approved
0.7554	Intermediate Similarity	NPD6780	Approved
0.7554	Intermediate Similarity	NPD6779	Approved
0.7554	Intermediate Similarity	NPD6778	Approved
0.7554	Intermediate Similarity	NPD6781	Approved
0.7554	Intermediate Similarity	NPD6782	Approved
0.7541	Intermediate Similarity	NPD7699	Phase 2
0.7541	Intermediate Similarity	NPD7700	Phase 2
0.753	Intermediate Similarity	NPD6801	Discontinued
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7516	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7484	Intermediate Similarity	NPD1240	Approved
0.7473	Intermediate Similarity	NPD6823	Phase 2
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7054	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7411	Suspended
0.7439	Intermediate Similarity	NPD5403	Approved
0.7438	Intermediate Similarity	NPD2800	Approved
0.7433	Intermediate Similarity	NPD7435	Discontinued
0.743	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD7472	Approved
0.7425	Intermediate Similarity	NPD37	Approved
0.7423	Intermediate Similarity	NPD5401	Approved
0.7421	Intermediate Similarity	NPD2346	Discontinued
0.7412	Intermediate Similarity	NPD6234	Discontinued
0.7407	Intermediate Similarity	NPD3300	Phase 2
0.7405	Intermediate Similarity	NPD3748	Approved
0.7396	Intermediate Similarity	NPD4966	Approved
0.7396	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD4967	Phase 2
0.7389	Intermediate Similarity	NPD1607	Approved
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.7386	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1465	Phase 2
0.7375	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2796	Approved
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.734	Intermediate Similarity	NPD7697	Approved
0.734	Intermediate Similarity	NPD7698	Approved
0.734	Intermediate Similarity	NPD7696	Phase 3
0.7337	Intermediate Similarity	NPD3817	Phase 2
0.7326	Intermediate Similarity	NPD1247	Approved
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7322	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6212	Phase 3
0.7322	Intermediate Similarity	NPD6213	Phase 3
0.7314	Intermediate Similarity	NPD7228	Approved
0.7303	Intermediate Similarity	NPD7808	Phase 3
0.7302	Intermediate Similarity	NPD7871	Phase 2
0.7302	Intermediate Similarity	NPD7870	Phase 2
0.7302	Intermediate Similarity	NPD8320	Phase 1
0.7302	Intermediate Similarity	NPD8319	Approved
0.7299	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7701	Phase 2
0.7263	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6799	Approved
0.7244	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2344	Approved
0.7202	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7874	Approved
0.7202	Intermediate Similarity	NPD6599	Discontinued
0.7188	Intermediate Similarity	NPD2799	Discontinued
0.7178	Intermediate Similarity	NPD4628	Phase 3
0.7178	Intermediate Similarity	NPD8166	Discontinued
0.7178	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7801	Approved
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.715	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD1164	Approved
0.7126	Intermediate Similarity	NPD920	Approved
0.711	Intermediate Similarity	NPD919	Approved
0.7108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5711	Approved
0.7086	Intermediate Similarity	NPD5710	Approved
0.7066	Intermediate Similarity	NPD6273	Approved
0.7045	Intermediate Similarity	NPD3926	Phase 2
0.703	Intermediate Similarity	NPD2309	Approved
0.7029	Intermediate Similarity	NPD7199	Phase 2
0.7024	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD447	Suspended
0.6994	Remote Similarity	NPD7266	Discontinued
0.6993	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5760	Phase 2
0.6977	Remote Similarity	NPD8455	Phase 2
0.6977	Remote Similarity	NPD5761	Phase 2
0.6975	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7003	Approved
0.6962	Remote Similarity	NPD3027	Phase 3
0.6962	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7240	Approved
0.6951	Remote Similarity	NPD2424	Discontinued
0.6946	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7458	Discontinued
0.6933	Remote Similarity	NPD9493	Approved
0.6923	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD4954	Approved
0.6923	Remote Similarity	NPD36	Approved
0.6923	Remote Similarity	NPD5028	Approved
0.6923	Remote Similarity	NPD5034	Approved
0.6923	Remote Similarity	NPD5026	Approved
0.6923	Remote Similarity	NPD4955	Approved
0.6919	Remote Similarity	NPD6844	Discontinued
0.6918	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4111	Phase 1
0.6911	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1243	Approved
0.6899	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7229	Phase 3
0.689	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7930	Approved
0.6882	Remote Similarity	NPD4287	Approved
0.6879	Remote Similarity	NPD2798	Approved
0.6868	Remote Similarity	NPD5030	Phase 2
0.6867	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5038	Approved
0.6865	Remote Similarity	NPD5037	Approved
0.6854	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6651	Approved
0.6847	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4288	Approved
0.6836	Remote Similarity	NPD8127	Discontinued
0.6835	Remote Similarity	NPD2861	Phase 2
0.6835	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4060	Phase 1
0.6832	Remote Similarity	NPD4665	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