NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	310.06
Volume:	271.282
LogP:	4.449
LogD:	3.48
LogS:	-5.254
# Rotatable Bonds:	1
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.859
Synthetic Accessibility Score:	4.169
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.537
MDCK Permeability:	2.06789918593131e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.4
Plasma Protein Binding (PPB):	97.11514282226562%
Volume Distribution (VD):	2.216
Pgp-substrate:	3.5826053619384766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.628
CYP2C19-inhibitor:	0.532
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.267
CYP2D6-inhibitor:	0.441
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.713
CYP3A4-substrate:	0.664

ADMET: Excretion

Clearance (CL):	9.446
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.429
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.396
Maximum Recommended Daily Dose:	0.577
Skin Sensitization:	0.158
Carcinogencity:	0.846
Eye Corrosion:	0.01
Eye Irritation:	0.152
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC125861

Natural Product ID:	NPC125861
*Common Name:**	Aplysinol
IUPAC Name:	[(3S,3aS,8bS)-7-bromo-3,6,8b-trimethyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-3a-yl]methanol
Synonyms:	Aplysinol
Standard InCHIKey:	QKBMCQNYERBGHD-LKTVYLICSA-N
Standard InCHI:	InChI=1S/C15H19BrO2/c1-9-6-13-11(7-12(9)16)14(3)5-4-10(2)15(14,8-17)18-13/h6-7,10,17H,4-5,8H2,1-3H3/t10-,14-,15-/m0/s1
SMILES:	OC[C@]12Oc3c([C@]2(C)CC[C@@H]1C)cc(c(c3)C)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465589
PubChem CID:	6455632
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974618]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27536968]
NPO6250	Laurencia tristicha	Species	Rhodomelaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[455774]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[455774]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[455774]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[455774]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[455774]

☑ 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 NPC125861 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	465
0.1-0.2	1656
0.2-0.3	4410
0.3-0.4	13695
0.4-0.5	6654
0.5-0.6	12721
0.6-0.7	3045
0.7-0.8	48
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9098	High Similarity	NPC281499
0.8529	High Similarity	NPC475361
0.7832	Intermediate Similarity	NPC266868
0.7571	Intermediate Similarity	NPC96423
0.7569	Intermediate Similarity	NPC469386
0.7447	Intermediate Similarity	NPC475529
0.7432	Intermediate Similarity	NPC51262
0.7431	Intermediate Similarity	NPC252962
0.7415	Intermediate Similarity	NPC11089
0.7415	Intermediate Similarity	NPC196193
0.7386	Intermediate Similarity	NPC474850
0.7386	Intermediate Similarity	NPC474851
0.7351	Intermediate Similarity	NPC327735
0.7324	Intermediate Similarity	NPC473875
0.7255	Intermediate Similarity	NPC183781
0.7237	Intermediate Similarity	NPC126101
0.7234	Intermediate Similarity	NPC329980
0.7226	Intermediate Similarity	NPC470937
0.7222	Intermediate Similarity	NPC188997
0.7219	Intermediate Similarity	NPC16485
0.72	Intermediate Similarity	NPC18842
0.7192	Intermediate Similarity	NPC470726
0.7183	Intermediate Similarity	NPC471449
0.7179	Intermediate Similarity	NPC184607
0.7172	Intermediate Similarity	NPC261992
0.7162	Intermediate Similarity	NPC38604
0.7162	Intermediate Similarity	NPC211179
0.7143	Intermediate Similarity	NPC470724
0.7134	Intermediate Similarity	NPC474777
0.7125	Intermediate Similarity	NPC152947
0.7114	Intermediate Similarity	NPC472795
0.7114	Intermediate Similarity	NPC472797
0.7114	Intermediate Similarity	NPC472796
0.7095	Intermediate Similarity	NPC186889
0.7092	Intermediate Similarity	NPC290470
0.7092	Intermediate Similarity	NPC154256
0.7086	Intermediate Similarity	NPC230219
0.7075	Intermediate Similarity	NPC476254
0.7075	Intermediate Similarity	NPC131397
0.7067	Intermediate Similarity	NPC226493
0.7067	Intermediate Similarity	NPC325003
0.7067	Intermediate Similarity	NPC160081
0.7059	Intermediate Similarity	NPC194034
0.7055	Intermediate Similarity	NPC96940
0.7055	Intermediate Similarity	NPC474130
0.7039	Intermediate Similarity	NPC26394
0.7034	Intermediate Similarity	NPC212965
0.7018	Intermediate Similarity	NPC475976
0.7015	Intermediate Similarity	NPC12870
0.7015	Intermediate Similarity	NPC24327
0.7014	Intermediate Similarity	NPC474131
0.7013	Intermediate Similarity	NPC54743
0.7013	Intermediate Similarity	NPC263367
0.7013	Intermediate Similarity	NPC477939
0.7013	Intermediate Similarity	NPC177160
0.7013	Intermediate Similarity	NPC156502
0.7013	Intermediate Similarity	NPC10737
0.7013	Intermediate Similarity	NPC472800
0.7013	Intermediate Similarity	NPC209985
0.7013	Intermediate Similarity	NPC29799
0.7007	Intermediate Similarity	NPC306295
0.7	Intermediate Similarity	NPC85049
0.6993	Remote Similarity	NPC49603
0.6993	Remote Similarity	NPC193026
0.6993	Remote Similarity	NPC187616
0.6993	Remote Similarity	NPC283616
0.6993	Remote Similarity	NPC211164
0.6987	Remote Similarity	NPC221134
0.6986	Remote Similarity	NPC152946
0.6986	Remote Similarity	NPC150026
0.6986	Remote Similarity	NPC204535
0.6986	Remote Similarity	NPC120638
0.6986	Remote Similarity	NPC46586
0.6985	Remote Similarity	NPC30416
0.6978	Remote Similarity	NPC275627
0.6974	Remote Similarity	NPC2190
0.6974	Remote Similarity	NPC85595
0.6974	Remote Similarity	NPC321502
0.6966	Remote Similarity	NPC218753
0.6962	Remote Similarity	NPC477616
0.6959	Remote Similarity	NPC81641
0.6959	Remote Similarity	NPC124030
0.6954	Remote Similarity	NPC249425
0.6954	Remote Similarity	NPC470727
0.6944	Remote Similarity	NPC32152
0.6944	Remote Similarity	NPC51341
0.6943	Remote Similarity	NPC89341
0.6939	Remote Similarity	NPC474169
0.6939	Remote Similarity	NPC473572
0.6937	Remote Similarity	NPC87794
0.6937	Remote Similarity	NPC211758
0.6933	Remote Similarity	NPC223912
0.6933	Remote Similarity	NPC470084
0.6929	Remote Similarity	NPC228452
0.6929	Remote Similarity	NPC98372
0.6929	Remote Similarity	NPC280760
0.6928	Remote Similarity	NPC227719
0.6928	Remote Similarity	NPC211352
0.6923	Remote Similarity	NPC160932
0.6918	Remote Similarity	NPC48623
0.6918	Remote Similarity	NPC109346
0.6918	Remote Similarity	NPC168707
0.6913	Remote Similarity	NPC206882
0.6913	Remote Similarity	NPC245060
0.6908	Remote Similarity	NPC472590
0.6908	Remote Similarity	NPC153019
0.6908	Remote Similarity	NPC277804
0.6897	Remote Similarity	NPC232295
0.6894	Remote Similarity	NPC20360
0.6892	Remote Similarity	NPC248557
0.6892	Remote Similarity	NPC137117
0.6887	Remote Similarity	NPC475875
0.6883	Remote Similarity	NPC478085
0.6883	Remote Similarity	NPC264956
0.6871	Remote Similarity	NPC71090
0.6871	Remote Similarity	NPC229213
0.6867	Remote Similarity	NPC473708
0.6867	Remote Similarity	NPC474147
0.6867	Remote Similarity	NPC164152
0.6867	Remote Similarity	NPC98745
0.6867	Remote Similarity	NPC471077
0.6863	Remote Similarity	NPC181049
0.6863	Remote Similarity	NPC207400
0.6863	Remote Similarity	NPC472798
0.6863	Remote Similarity	NPC289624
0.6863	Remote Similarity	NPC27578
0.6861	Remote Similarity	NPC310456
0.6859	Remote Similarity	NPC474687
0.6859	Remote Similarity	NPC477938
0.6855	Remote Similarity	NPC274721
0.6855	Remote Similarity	NPC155392
0.6855	Remote Similarity	NPC135767
0.6855	Remote Similarity	NPC474104
0.6852	Remote Similarity	NPC95990
0.6849	Remote Similarity	NPC45663
0.6848	Remote Similarity	NPC469699
0.6846	Remote Similarity	NPC170749
0.6846	Remote Similarity	NPC76119
0.6846	Remote Similarity	NPC4286
0.6842	Remote Similarity	NPC242807
0.6842	Remote Similarity	NPC241522
0.6842	Remote Similarity	NPC257582
0.6842	Remote Similarity	NPC64201
0.6842	Remote Similarity	NPC145305
0.6842	Remote Similarity	NPC187998
0.6842	Remote Similarity	NPC92164
0.6842	Remote Similarity	NPC153739
0.6842	Remote Similarity	NPC42300
0.6842	Remote Similarity	NPC174495
0.6842	Remote Similarity	NPC77040
0.6842	Remote Similarity	NPC90245
0.6839	Remote Similarity	NPC174191
0.6839	Remote Similarity	NPC327382
0.6839	Remote Similarity	NPC93783
0.6838	Remote Similarity	NPC38079
0.6838	Remote Similarity	NPC108875
0.6835	Remote Similarity	NPC263261
0.6835	Remote Similarity	NPC476334
0.6835	Remote Similarity	NPC471414
0.6835	Remote Similarity	NPC473372
0.6835	Remote Similarity	NPC87725
0.6835	Remote Similarity	NPC311530
0.6832	Remote Similarity	NPC113862
0.6831	Remote Similarity	NPC161696
0.6828	Remote Similarity	NPC85895
0.6828	Remote Similarity	NPC137294
0.6828	Remote Similarity	NPC163036
0.6826	Remote Similarity	NPC189730
0.6824	Remote Similarity	NPC317769
0.6824	Remote Similarity	NPC31344
0.6821	Remote Similarity	NPC128208
0.6821	Remote Similarity	NPC282703
0.6821	Remote Similarity	NPC21867
0.6821	Remote Similarity	NPC184733
0.6821	Remote Similarity	NPC11258
0.6821	Remote Similarity	NPC19694
0.6821	Remote Similarity	NPC129570
0.6821	Remote Similarity	NPC45774
0.6818	Remote Similarity	NPC105554
0.6815	Remote Similarity	NPC475836
0.6815	Remote Similarity	NPC292882
0.6815	Remote Similarity	NPC154905
0.6815	Remote Similarity	NPC60373
0.6813	Remote Similarity	NPC277951
0.6813	Remote Similarity	NPC317237
0.6813	Remote Similarity	NPC44530
0.6806	Remote Similarity	NPC320864
0.6806	Remote Similarity	NPC238176
0.6806	Remote Similarity	NPC187993
0.6803	Remote Similarity	NPC475839
0.6803	Remote Similarity	NPC476343
0.68	Remote Similarity	NPC43706
0.6797	Remote Similarity	NPC158078
0.6797	Remote Similarity	NPC27843
0.6797	Remote Similarity	NPC115207
0.6797	Remote Similarity	NPC228346
0.6797	Remote Similarity	NPC78575
0.6797	Remote Similarity	NPC162801
0.6797	Remote Similarity	NPC158079
0.6797	Remote Similarity	NPC7171

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 NPC125861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	990
0.2-0.3	2153
0.3-0.4	2963
0.4-0.5	1595
0.5-0.6	900
0.6-0.7	164
0.7-0.8	6
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
0.7383	Intermediate Similarity	NPD5735	Approved
0.7368	Intermediate Similarity	NPD5762	Approved
0.7368	Intermediate Similarity	NPD5763	Approved
0.7297	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6696	Suspended
0.7143	Intermediate Similarity	NPD7157	Approved
0.7105	Intermediate Similarity	NPD6353	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7027	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1778	Approved
0.7007	Intermediate Similarity	NPD2684	Approved
0.698	Remote Similarity	NPD2861	Phase 2
0.6974	Remote Similarity	NPD4140	Approved
0.6974	Remote Similarity	NPD3620	Phase 2
0.6974	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5327	Phase 3
0.6913	Remote Similarity	NPD4624	Approved
0.6892	Remote Similarity	NPD8651	Approved
0.6883	Remote Similarity	NPD2157	Approved
0.6809	Remote Similarity	NPD7843	Approved
0.6783	Remote Similarity	NPD6671	Approved
0.6774	Remote Similarity	NPD6653	Approved
0.6755	Remote Similarity	NPD1712	Approved
0.6709	Remote Similarity	NPD6002	Phase 3
0.6709	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6004	Phase 3
0.6709	Remote Similarity	NPD6005	Phase 3
0.6709	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4625	Phase 3
0.6646	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD6099	Approved
0.6645	Remote Similarity	NPD4060	Phase 1
0.6626	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6355	Discontinued
0.6599	Remote Similarity	NPD1357	Approved
0.6584	Remote Similarity	NPD3892	Phase 2
0.6581	Remote Similarity	NPD3162	Approved
0.6581	Remote Similarity	NPD3163	Approved
0.6577	Remote Similarity	NPD3092	Approved
0.6577	Remote Similarity	NPD1091	Approved
0.6577	Remote Similarity	NPD1610	Phase 2
0.6558	Remote Similarity	NPD7095	Approved
0.6538	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1613	Approved
0.6528	Remote Similarity	NPD1398	Phase 1
0.651	Remote Similarity	NPD3496	Discontinued
0.6507	Remote Similarity	NPD7340	Approved
0.6503	Remote Similarity	NPD228	Approved
0.6494	Remote Similarity	NPD4908	Phase 1
0.6486	Remote Similarity	NPD5691	Approved
0.6481	Remote Similarity	NPD4110	Phase 3
0.6481	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4628	Phase 3
0.6481	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7199	Phase 2
0.6471	Remote Similarity	NPD5647	Approved
0.6467	Remote Similarity	NPD3705	Approved
0.6443	Remote Similarity	NPD4626	Approved
0.6438	Remote Similarity	NPD2161	Phase 2
0.6429	Remote Similarity	NPD2237	Approved
0.6429	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1608	Approved
0.642	Remote Similarity	NPD6674	Discontinued
0.6419	Remote Similarity	NPD3091	Approved
0.6414	Remote Similarity	NPD5283	Phase 1
0.641	Remote Similarity	NPD7985	Registered
0.641	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3094	Phase 2
0.6397	Remote Similarity	NPD288	Approved
0.6392	Remote Similarity	NPD3657	Discovery
0.6387	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6273	Approved
0.6379	Remote Similarity	NPD8127	Discontinued
0.6376	Remote Similarity	NPD5585	Approved
0.6364	Remote Similarity	NPD4750	Phase 3
0.6354	Remote Similarity	NPD3337	Discontinued
0.6352	Remote Similarity	NPD4097	Suspended
0.6346	Remote Similarity	NPD3027	Phase 3
0.6345	Remote Similarity	NPD821	Approved
0.6343	Remote Similarity	NPD3051	Approved
0.6341	Remote Similarity	NPD2677	Approved
0.6333	Remote Similarity	NPD5846	Approved
0.6333	Remote Similarity	NPD6516	Phase 2
0.6333	Remote Similarity	NPD3095	Discontinued
0.6331	Remote Similarity	NPD7028	Phase 2
0.6329	Remote Similarity	NPD2238	Phase 2
0.6324	Remote Similarity	NPD844	Approved
0.6316	Remote Similarity	NPD2231	Phase 2
0.6316	Remote Similarity	NPD2232	Approved
0.6316	Remote Similarity	NPD2230	Approved
0.6316	Remote Similarity	NPD2235	Phase 2
0.6316	Remote Similarity	NPD2233	Approved
0.6309	Remote Similarity	NPD1548	Phase 1
0.6307	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD2970	Approved
0.6307	Remote Similarity	NPD6687	Approved
0.6307	Remote Similarity	NPD6688	Approved
0.6307	Remote Similarity	NPD2969	Approved
0.6306	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD987	Approved
0.6299	Remote Similarity	NPD1794	Approved
0.6299	Remote Similarity	NPD6362	Approved
0.6296	Remote Similarity	NPD1375	Discontinued
0.6287	Remote Similarity	NPD2183	Approved
0.6287	Remote Similarity	NPD2184	Approved
0.6279	Remote Similarity	NPD2560	Approved
0.6279	Remote Similarity	NPD2563	Approved
0.6275	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7033	Discontinued
0.6273	Remote Similarity	NPD2155	Approved
0.6273	Remote Similarity	NPD2156	Approved
0.6273	Remote Similarity	NPD2154	Approved
0.6273	Remote Similarity	NPD5588	Approved
0.6271	Remote Similarity	NPD27	Approved
0.6271	Remote Similarity	NPD2489	Approved
0.6269	Remote Similarity	NPD9365	Approved
0.6268	Remote Similarity	NPD968	Approved
0.6266	Remote Similarity	NPD8032	Phase 2
0.6266	Remote Similarity	NPD4870	Approved
0.6259	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD558	Phase 2
0.6258	Remote Similarity	NPD2424	Discontinued
0.6258	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD3691	Phase 2
0.6258	Remote Similarity	NPD3690	Phase 2
0.625	Remote Similarity	NPD776	Approved
0.625	Remote Similarity	NPD1611	Approved
0.6226	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD4059	Approved
0.6225	Remote Similarity	NPD17	Approved
0.6211	Remote Similarity	NPD4536	Approved
0.6211	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4538	Approved
0.6205	Remote Similarity	NPD5058	Phase 3
0.6203	Remote Similarity	NPD6798	Discontinued
0.62	Remote Similarity	NPD7741	Discontinued
0.619	Remote Similarity	NPD2676	Approved
0.619	Remote Similarity	NPD2675	Approved
0.6185	Remote Similarity	NPD2296	Approved
0.6185	Remote Similarity	NPD4288	Approved
0.6182	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6331	Phase 2
0.6169	Remote Similarity	NPD4359	Approved
0.6169	Remote Similarity	NPD3685	Discontinued
0.6164	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3444	Approved
0.6159	Remote Similarity	NPD3443	Approved
0.6159	Remote Similarity	NPD3445	Approved
0.6158	Remote Similarity	NPD4010	Discontinued
0.6154	Remote Similarity	NPD6584	Phase 3
0.6138	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD6032	Approved
0.6133	Remote Similarity	NPD7644	Approved
0.6131	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD1283	Approved
0.6127	Remote Similarity	NPD9244	Approved
0.6125	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD1138	Approved
0.6118	Remote Similarity	NPD2668	Approved
0.6118	Remote Similarity	NPD2667	Approved
0.6118	Remote Similarity	NPD4210	Discontinued
0.6115	Remote Similarity	NPD5736	Approved
0.6114	Remote Similarity	NPD7833	Phase 2
0.6114	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD7831	Phase 2
0.6111	Remote Similarity	NPD6620	Discovery
0.6108	Remote Similarity	NPD3122	Phase 3
0.6107	Remote Similarity	NPD2557	Approved
0.6107	Remote Similarity	NPD709	Approved
0.6105	Remote Similarity	NPD6072	Discontinued
0.6104	Remote Similarity	NPD1840	Phase 2
0.6101	Remote Similarity	NPD1336	Approved
0.6099	Remote Similarity	NPD291	Approved
0.6095	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD1182	Approved
0.609	Remote Similarity	NPD1820	Approved
0.609	Remote Similarity	NPD1817	Approved
0.609	Remote Similarity	NPD1819	Approved
0.609	Remote Similarity	NPD1818	Approved
0.609	Remote Similarity	NPD2797	Approved
0.6087	Remote Similarity	NPD1341	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD5960	Phase 3
0.6071	Remote Similarity	NPD1774	Approved
0.6067	Remote Similarity	NPD6071	Discontinued
0.6067	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6663	Approved
0.6061	Remote Similarity	NPD4534	Discontinued
0.6061	Remote Similarity	NPD7037	Approved
0.6061	Remote Similarity	NPD5958	Discontinued
0.6059	Remote Similarity	NPD5699	Approved
0.6059	Remote Similarity	NPD5976	Discontinued
0.6057	Remote Similarity	NPD4965	Approved
0.6057	Remote Similarity	NPD4966	Approved
0.6057	Remote Similarity	NPD4967	Phase 2
0.6054	Remote Similarity	NPD1137	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