NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	249.361
LogP:	3.789
LogD:	3.425
LogS:	-3.466
# Rotatable Bonds:	0
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	4.609
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.723
MDCK Permeability:	3.161989661748521e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.028
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	98.3829574584961%
Volume Distribution (VD):	1.523
Pgp-substrate:	3.5744898319244385%

ADMET: Metabolism

CYP1A2-inhibitor:	0.316
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.726
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.388
CYP2D6-inhibitor:	0.47
CYP2D6-substrate:	0.731
CYP3A4-inhibitor:	0.118
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	5.032
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.639
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.726
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.919
Carcinogencity:	0.413
Eye Corrosion:	0.015
Eye Irritation:	0.275
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC268827

Natural Product ID:	NPC268827
*Common Name:**	Tubipolide B
IUPAC Name:	(4aS,8aR,9aS)-3,5,8a-trimethyl-4,4a,9,9a-tetrahydrobenzo[f][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	MUUFCNJBWLIDFJ-YDHLFZDLSA-N
Standard InCHI:	InChI=1S/C15H18O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h4-6,12-13H,7-8H2,1-3H3/t12-,13-,15-/m0/s1
SMILES:	CC1=C2C[C@H]3C(=CC=C[C@]3(C[C@@H]2OC1=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489544
PubChem CID:	11776031
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO6309	Tubipora musica	Species	Tubiporidae	Eukaryota	n.a.	Formosan stolonifer	n.a.	PMID[11720526]
NPO6309	Tubipora musica	Species	Tubiporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.69	ug ml-1	PMID[497179]

☑ 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 NPC268827 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	173
0.1-0.2	985
0.2-0.3	4716
0.3-0.4	13439
0.4-0.5	11710
0.5-0.6	7743
0.6-0.7	3286
0.7-0.8	600
0.8-0.85	39
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC189206
0.8961	High Similarity	NPC184737
0.8831	High Similarity	NPC54996
0.8588	High Similarity	NPC280149
0.8588	High Similarity	NPC221111
0.8588	High Similarity	NPC182136
0.8588	High Similarity	NPC310479
0.8519	High Similarity	NPC471218
0.8391	Intermediate Similarity	NPC162615
0.8391	Intermediate Similarity	NPC152778
0.8391	Intermediate Similarity	NPC205034
0.8354	Intermediate Similarity	NPC473825
0.8313	Intermediate Similarity	NPC30486
0.8313	Intermediate Similarity	NPC96055
0.8228	Intermediate Similarity	NPC4509
0.8214	Intermediate Similarity	NPC474013
0.8193	Intermediate Similarity	NPC474193
0.8193	Intermediate Similarity	NPC12283
0.8118	Intermediate Similarity	NPC131813
0.8111	Intermediate Similarity	NPC16967
0.8111	Intermediate Similarity	NPC473153
0.809	Intermediate Similarity	NPC477129
0.809	Intermediate Similarity	NPC38830
0.809	Intermediate Similarity	NPC477130
0.809	Intermediate Similarity	NPC470255
0.809	Intermediate Similarity	NPC191521
0.8072	Intermediate Similarity	NPC268122
0.8049	Intermediate Similarity	NPC10636
0.8046	Intermediate Similarity	NPC73995
0.8023	Intermediate Similarity	NPC473891
0.8	Intermediate Similarity	NPC474909
0.8	Intermediate Similarity	NPC177932
0.8	Intermediate Similarity	NPC189311
0.7976	Intermediate Similarity	NPC30502
0.7976	Intermediate Similarity	NPC193198
0.7976	Intermediate Similarity	NPC118423
0.7976	Intermediate Similarity	NPC311070
0.7955	Intermediate Similarity	NPC212679
0.7955	Intermediate Similarity	NPC469595
0.7955	Intermediate Similarity	NPC220454
0.7935	Intermediate Similarity	NPC474440
0.7931	Intermediate Similarity	NPC93411
0.7931	Intermediate Similarity	NPC473879
0.7931	Intermediate Similarity	NPC226863
0.7931	Intermediate Similarity	NPC472302
0.7931	Intermediate Similarity	NPC215831
0.7912	Intermediate Similarity	NPC260796
0.7907	Intermediate Similarity	NPC471219
0.7901	Intermediate Similarity	NPC316500
0.7882	Intermediate Similarity	NPC32223
0.7867	Intermediate Similarity	NPC182794
0.7857	Intermediate Similarity	NPC94200
0.7857	Intermediate Similarity	NPC200513
0.7857	Intermediate Similarity	NPC256112
0.7857	Intermediate Similarity	NPC178676
0.7857	Intermediate Similarity	NPC16321
0.7848	Intermediate Similarity	NPC16349
0.7848	Intermediate Similarity	NPC222244
0.7841	Intermediate Similarity	NPC177141
0.7841	Intermediate Similarity	NPC50488
0.7841	Intermediate Similarity	NPC474396
0.7841	Intermediate Similarity	NPC284561
0.7831	Intermediate Similarity	NPC469802
0.7826	Intermediate Similarity	NPC205143
0.7826	Intermediate Similarity	NPC110937
0.7816	Intermediate Similarity	NPC125925
0.7816	Intermediate Similarity	NPC476600
0.7805	Intermediate Similarity	NPC471220
0.7802	Intermediate Similarity	NPC295347
0.7791	Intermediate Similarity	NPC109528
0.7791	Intermediate Similarity	NPC472442
0.7791	Intermediate Similarity	NPC471795
0.7789	Intermediate Similarity	NPC23584
0.7778	Intermediate Similarity	NPC139692
0.7765	Intermediate Similarity	NPC472440
0.7765	Intermediate Similarity	NPC22611
0.7765	Intermediate Similarity	NPC477124
0.7765	Intermediate Similarity	NPC472377
0.7763	Intermediate Similarity	NPC116013
0.7753	Intermediate Similarity	NPC469372
0.7753	Intermediate Similarity	NPC152467
0.7753	Intermediate Similarity	NPC273199
0.7753	Intermediate Similarity	NPC8062
0.7753	Intermediate Similarity	NPC78973
0.7742	Intermediate Similarity	NPC92275
0.7738	Intermediate Similarity	NPC475665
0.7738	Intermediate Similarity	NPC282293
0.7738	Intermediate Similarity	NPC170303
0.7738	Intermediate Similarity	NPC25554
0.7727	Intermediate Similarity	NPC471956
0.7727	Intermediate Similarity	NPC477128
0.7722	Intermediate Similarity	NPC257618
0.7722	Intermediate Similarity	NPC181587
0.7717	Intermediate Similarity	NPC190713
0.7717	Intermediate Similarity	NPC165632
0.7711	Intermediate Similarity	NPC150646
0.7711	Intermediate Similarity	NPC242767
0.7701	Intermediate Similarity	NPC329692
0.7701	Intermediate Similarity	NPC168248
0.7692	Intermediate Similarity	NPC120351
0.7692	Intermediate Similarity	NPC471994
0.7692	Intermediate Similarity	NPC166143
0.7684	Intermediate Similarity	NPC11956
0.7674	Intermediate Similarity	NPC474693
0.7674	Intermediate Similarity	NPC139566
0.7667	Intermediate Similarity	NPC473944
0.7667	Intermediate Similarity	NPC472811
0.7667	Intermediate Similarity	NPC72845
0.7667	Intermediate Similarity	NPC329842
0.7662	Intermediate Similarity	NPC472266
0.764	Intermediate Similarity	NPC470734
0.764	Intermediate Similarity	NPC173042
0.764	Intermediate Similarity	NPC5509
0.7634	Intermediate Similarity	NPC208094
0.7634	Intermediate Similarity	NPC2049
0.7634	Intermediate Similarity	NPC84335
0.7634	Intermediate Similarity	NPC38530
0.7629	Intermediate Similarity	NPC82251
0.7619	Intermediate Similarity	NPC233332
0.7619	Intermediate Similarity	NPC195424
0.7619	Intermediate Similarity	NPC269791
0.7614	Intermediate Similarity	NPC471796
0.7614	Intermediate Similarity	NPC475678
0.7614	Intermediate Similarity	NPC312561
0.7614	Intermediate Similarity	NPC181327
0.7609	Intermediate Similarity	NPC183012
0.7609	Intermediate Similarity	NPC209355
0.759	Intermediate Similarity	NPC474005
0.759	Intermediate Similarity	NPC35574
0.7586	Intermediate Similarity	NPC65661
0.7586	Intermediate Similarity	NPC106416
0.7586	Intermediate Similarity	NPC475860
0.7586	Intermediate Similarity	NPC86316
0.7586	Intermediate Similarity	NPC476678
0.7586	Intermediate Similarity	NPC110405
0.7586	Intermediate Similarity	NPC473659
0.7586	Intermediate Similarity	NPC473251
0.7586	Intermediate Similarity	NPC42586
0.7586	Intermediate Similarity	NPC30984
0.7586	Intermediate Similarity	NPC474694
0.7582	Intermediate Similarity	NPC472954
0.7582	Intermediate Similarity	NPC472812
0.7582	Intermediate Similarity	NPC53555
0.7582	Intermediate Similarity	NPC475657
0.7582	Intermediate Similarity	NPC7349
0.7582	Intermediate Similarity	NPC115021
0.7579	Intermediate Similarity	NPC168319
0.7579	Intermediate Similarity	NPC194028
0.7564	Intermediate Similarity	NPC276290
0.7561	Intermediate Similarity	NPC27205
0.7558	Intermediate Similarity	NPC42476
0.7558	Intermediate Similarity	NPC57370
0.7558	Intermediate Similarity	NPC474809
0.7558	Intermediate Similarity	NPC321385
0.7558	Intermediate Similarity	NPC222358
0.7556	Intermediate Similarity	NPC474842
0.7556	Intermediate Similarity	NPC302280
0.7556	Intermediate Similarity	NPC475965
0.7553	Intermediate Similarity	NPC278673
0.7553	Intermediate Similarity	NPC57079
0.7553	Intermediate Similarity	NPC108368
0.7529	Intermediate Similarity	NPC42470
0.7528	Intermediate Similarity	NPC24816
0.7528	Intermediate Similarity	NPC196407
0.7528	Intermediate Similarity	NPC472809
0.7528	Intermediate Similarity	NPC106332
0.7528	Intermediate Similarity	NPC472810
0.7527	Intermediate Similarity	NPC134072
0.7527	Intermediate Similarity	NPC112654
0.7527	Intermediate Similarity	NPC234993
0.7527	Intermediate Similarity	NPC242848
0.7527	Intermediate Similarity	NPC209297
0.7527	Intermediate Similarity	NPC475380
0.75	Intermediate Similarity	NPC161998
0.75	Intermediate Similarity	NPC84893
0.75	Intermediate Similarity	NPC114540
0.75	Intermediate Similarity	NPC140277
0.75	Intermediate Similarity	NPC105490
0.75	Intermediate Similarity	NPC220478
0.75	Intermediate Similarity	NPC32577
0.75	Intermediate Similarity	NPC155332
0.75	Intermediate Similarity	NPC471299
0.75	Intermediate Similarity	NPC88507
0.75	Intermediate Similarity	NPC57117
0.75	Intermediate Similarity	NPC470697
0.75	Intermediate Similarity	NPC31058
0.75	Intermediate Similarity	NPC226066
0.75	Intermediate Similarity	NPC469606
0.75	Intermediate Similarity	NPC273005
0.7474	Intermediate Similarity	NPC474012
0.7474	Intermediate Similarity	NPC472644
0.7474	Intermediate Similarity	NPC473204
0.7474	Intermediate Similarity	NPC476299
0.7473	Intermediate Similarity	NPC212948
0.7473	Intermediate Similarity	NPC186363
0.7473	Intermediate Similarity	NPC49420
0.7473	Intermediate Similarity	NPC233345
0.7473	Intermediate Similarity	NPC2882
0.7473	Intermediate Similarity	NPC177037
0.7473	Intermediate Similarity	NPC472814

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 NPC268827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1169
0.2-0.3	3934
0.3-0.4	2616
0.4-0.5	874
0.5-0.6	294
0.6-0.7	101
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD1694	Approved
0.7857	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5209	Approved
0.7439	Intermediate Similarity	NPD8039	Approved
0.7188	Intermediate Similarity	NPD7638	Approved
0.7188	Intermediate Similarity	NPD4225	Approved
0.7179	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7639	Approved
0.7113	Intermediate Similarity	NPD7640	Approved
0.7111	Intermediate Similarity	NPD7146	Approved
0.7111	Intermediate Similarity	NPD6684	Approved
0.7111	Intermediate Similarity	NPD5330	Approved
0.7111	Intermediate Similarity	NPD6409	Approved
0.7111	Intermediate Similarity	NPD7521	Approved
0.7111	Intermediate Similarity	NPD7334	Approved
0.7079	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6051	Approved
0.6957	Remote Similarity	NPD6903	Approved
0.6957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7637	Suspended
0.6848	Remote Similarity	NPD3573	Approved
0.6824	Remote Similarity	NPD8264	Approved
0.6809	Remote Similarity	NPD5207	Approved
0.6795	Remote Similarity	NPD4192	Approved
0.6795	Remote Similarity	NPD4191	Approved
0.6795	Remote Similarity	NPD4194	Approved
0.6795	Remote Similarity	NPD4193	Approved
0.6774	Remote Similarity	NPD6672	Approved
0.6774	Remote Similarity	NPD5737	Approved
0.6771	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7900	Approved
0.6771	Remote Similarity	NPD7748	Approved
0.6768	Remote Similarity	NPD6648	Approved
0.6737	Remote Similarity	NPD5694	Approved
0.6737	Remote Similarity	NPD5693	Phase 1
0.6737	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6632	Remote Similarity	NPD5692	Phase 3
0.6566	Remote Similarity	NPD7902	Approved
0.6562	Remote Similarity	NPD6050	Approved
0.6562	Remote Similarity	NPD7515	Phase 2
0.6559	Remote Similarity	NPD5279	Phase 3
0.6559	Remote Similarity	NPD3618	Phase 1
0.6538	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6101	Approved
0.6495	Remote Similarity	NPD6399	Phase 3
0.6476	Remote Similarity	NPD6686	Approved
0.6471	Remote Similarity	NPD7151	Approved
0.6471	Remote Similarity	NPD7632	Discontinued
0.6471	Remote Similarity	NPD7152	Approved
0.6471	Remote Similarity	NPD7150	Approved
0.6458	Remote Similarity	NPD7838	Discovery
0.6455	Remote Similarity	NPD7115	Discovery
0.6444	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5208	Approved
0.6415	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5284	Approved
0.6392	Remote Similarity	NPD5281	Approved
0.6392	Remote Similarity	NPD6079	Approved
0.6381	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5695	Phase 3
0.6355	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6673	Approved
0.6354	Remote Similarity	NPD6904	Approved
0.6354	Remote Similarity	NPD6080	Approved
0.6354	Remote Similarity	NPD5328	Approved
0.6353	Remote Similarity	NPD7144	Approved
0.6353	Remote Similarity	NPD7143	Approved
0.6344	Remote Similarity	NPD3133	Approved
0.6344	Remote Similarity	NPD3666	Approved
0.6344	Remote Similarity	NPD3665	Phase 1
0.6322	Remote Similarity	NPD4687	Approved
0.6322	Remote Similarity	NPD6924	Approved
0.6322	Remote Similarity	NPD4058	Approved
0.6322	Remote Similarity	NPD6926	Approved
0.6321	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD6899	Approved
0.6321	Remote Similarity	NPD6011	Approved
0.6304	Remote Similarity	NPD3667	Approved
0.6289	Remote Similarity	NPD5785	Approved
0.6286	Remote Similarity	NPD5739	Approved
0.6286	Remote Similarity	NPD6008	Approved
0.6286	Remote Similarity	NPD7128	Approved
0.6286	Remote Similarity	NPD6675	Approved
0.6286	Remote Similarity	NPD6402	Approved
0.6279	Remote Similarity	NPD5276	Approved
0.6277	Remote Similarity	NPD1696	Phase 3
0.6264	Remote Similarity	NPD7332	Phase 2
0.6264	Remote Similarity	NPD7514	Phase 3
0.6263	Remote Similarity	NPD6001	Approved
0.6262	Remote Similarity	NPD6013	Approved
0.6262	Remote Similarity	NPD6014	Approved
0.6262	Remote Similarity	NPD6012	Approved
0.6238	Remote Similarity	NPD6084	Phase 2
0.6238	Remote Similarity	NPD6083	Phase 2
0.6237	Remote Similarity	NPD6695	Phase 3
0.6235	Remote Similarity	NPD6923	Approved
0.6235	Remote Similarity	NPD6922	Approved
0.6228	Remote Similarity	NPD7503	Approved
0.6226	Remote Similarity	NPD5701	Approved
0.6222	Remote Similarity	NPD7145	Approved
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4623	Approved
0.6211	Remote Similarity	NPD6098	Approved
0.6211	Remote Similarity	NPD4519	Discontinued
0.6204	Remote Similarity	NPD6883	Approved
0.6204	Remote Similarity	NPD7290	Approved
0.6204	Remote Similarity	NPD7102	Approved
0.62	Remote Similarity	NPD5654	Approved
0.6196	Remote Similarity	NPD6902	Approved
0.618	Remote Similarity	NPD6933	Approved
0.618	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5696	Approved
0.617	Remote Similarity	NPD4786	Approved
0.617	Remote Similarity	NPD3668	Phase 3
0.617	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7320	Approved
0.6162	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD4195	Approved
0.6154	Remote Similarity	NPD7645	Phase 2
0.6154	Remote Similarity	NPD6929	Approved
0.6147	Remote Similarity	NPD6650	Approved
0.6147	Remote Similarity	NPD8130	Phase 1
0.6147	Remote Similarity	NPD6617	Approved
0.6147	Remote Similarity	NPD6649	Approved
0.6147	Remote Similarity	NPD6847	Approved
0.6147	Remote Similarity	NPD6869	Approved
0.6139	Remote Similarity	NPD5222	Approved
0.6139	Remote Similarity	NPD5221	Approved
0.6139	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5733	Approved
0.6111	Remote Similarity	NPD6372	Approved
0.6111	Remote Similarity	NPD6932	Approved
0.6111	Remote Similarity	NPD5776	Phase 2
0.6111	Remote Similarity	NPD6373	Approved
0.6111	Remote Similarity	NPD6925	Approved
0.6106	Remote Similarity	NPD7327	Approved
0.6106	Remote Similarity	NPD7328	Approved
0.6105	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6882	Approved
0.6091	Remote Similarity	NPD8297	Approved
0.6087	Remote Similarity	NPD6931	Approved
0.6087	Remote Similarity	NPD7509	Discontinued
0.6087	Remote Similarity	NPD6930	Phase 2
0.6078	Remote Similarity	NPD5959	Approved
0.6078	Remote Similarity	NPD5173	Approved
0.6067	Remote Similarity	NPD7339	Approved
0.6067	Remote Similarity	NPD6942	Approved
0.6053	Remote Similarity	NPD7516	Approved
0.6047	Remote Similarity	NPD4137	Phase 3
0.6042	Remote Similarity	NPD5280	Approved
0.6042	Remote Similarity	NPD4694	Approved
0.6036	Remote Similarity	NPD6858	Approved
0.6036	Remote Similarity	NPD7094	Approved
0.602	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.602	Remote Similarity	NPD1695	Approved
0.6019	Remote Similarity	NPD5926	Approved
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8377	Approved
0.598	Remote Similarity	NPD4697	Phase 3
0.5979	Remote Similarity	NPD7750	Discontinued
0.5979	Remote Similarity	NPD7524	Approved
0.5977	Remote Similarity	NPD4691	Approved
0.5977	Remote Similarity	NPD4747	Approved
0.5962	Remote Similarity	NPD4696	Approved
0.5962	Remote Similarity	NPD6404	Discontinued
0.5962	Remote Similarity	NPD5285	Approved
0.5962	Remote Similarity	NPD5286	Approved
0.596	Remote Similarity	NPD46	Approved
0.596	Remote Similarity	NPD6698	Approved
0.5957	Remote Similarity	NPD4223	Phase 3
0.5957	Remote Similarity	NPD4221	Approved
0.5949	Remote Similarity	NPD4219	Approved
0.5948	Remote Similarity	NPD8033	Approved
0.5948	Remote Similarity	NPD8296	Approved
0.5948	Remote Similarity	NPD8335	Approved
0.5948	Remote Similarity	NPD8380	Approved
0.5948	Remote Similarity	NPD8379	Approved
0.5948	Remote Similarity	NPD8378	Approved
0.5938	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6868	Approved
0.5922	Remote Similarity	NPD4755	Approved
0.5918	Remote Similarity	NPD4518	Approved
0.5914	Remote Similarity	NPD7525	Registered
0.5914	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD4695	Discontinued
0.5905	Remote Similarity	NPD5223	Approved
0.59	Remote Similarity	NPD8034	Phase 2
0.59	Remote Similarity	NPD8035	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