NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.13
Volume:	243.441
LogP:	3.699
LogD:	3.22
LogS:	-3.75
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	4.446
Fsp3:	0.6
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:	-4.673
MDCK Permeability:	2.2602178432862274e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.048
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	94.77056884765625%
Volume Distribution (VD):	1.095
Pgp-substrate:	4.039018154144287%

ADMET: Metabolism

CYP1A2-inhibitor:	0.847
CYP1A2-substrate:	0.815
CYP2C19-inhibitor:	0.428
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.652
CYP2D6-inhibitor:	0.659
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	18.289
Half-life (T1/2):	0.32

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.398
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.229
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.869
Carcinogencity:	0.754
Eye Corrosion:	0.01
Eye Irritation:	0.577
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC266868

Natural Product ID:	NPC266868
*Common Name:**	Laurentristich-4-Ol
IUPAC Name:	(1'S,2S,5'R)-1',6-dimethylspiro[3H-1-benzofuran-2,2'-bicyclo[3.1.0]hexane]-5-ol
Synonyms:	Laurentristich-4-Ol
Standard InCHIKey:	BHDVYQMSXFNVLY-UGFHNGPFSA-N
Standard InCHI:	InChI=1S/C15H18O2/c1-9-5-13-10(6-12(9)16)7-15(17-13)4-3-11-8-14(11,15)2/h5-6,11,16H,3-4,7-8H2,1-2H3/t11-,14+,15+/m1/s1
SMILES:	Oc1cc2C[C@@]3(Oc2cc1C)CC[C@H]1[C@]3(C)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463530
PubChem CID:	21778174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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[545418]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[545418]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[545418]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[545418]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[545418]

☑ 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 NPC266868 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	475
0.1-0.2	1856
0.2-0.3	3851
0.3-0.4	11921
0.4-0.5	7842
0.5-0.6	10581
0.6-0.7	5666
0.7-0.8	489
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8898	High Similarity	NPC252962
0.8651	High Similarity	NPC96423
0.8492	Intermediate Similarity	NPC471449
0.8433	Intermediate Similarity	NPC51262
0.8295	Intermediate Similarity	NPC48623
0.8295	Intermediate Similarity	NPC168707
0.8244	Intermediate Similarity	NPC248557
0.8217	Intermediate Similarity	NPC475529
0.8217	Intermediate Similarity	NPC45663
0.8203	Intermediate Similarity	NPC51341
0.8148	Intermediate Similarity	NPC196193
0.8148	Intermediate Similarity	NPC325003
0.8145	Intermediate Similarity	NPC275627
0.808	Intermediate Similarity	NPC98372
0.8049	Intermediate Similarity	NPC306295
0.8049	Intermediate Similarity	NPC64586
0.8047	Intermediate Similarity	NPC187993
0.8047	Intermediate Similarity	NPC238176
0.803	Intermediate Similarity	NPC96940
0.8015	Intermediate Similarity	NPC11089
0.8	Intermediate Similarity	NPC47288
0.7984	Intermediate Similarity	NPC139047
0.797	Intermediate Similarity	NPC61685
0.7969	Intermediate Similarity	NPC69539
0.7941	Intermediate Similarity	NPC472797
0.7939	Intermediate Similarity	NPC218753
0.7937	Intermediate Similarity	NPC474920
0.7899	Intermediate Similarity	NPC85595
0.7899	Intermediate Similarity	NPC472798
0.7891	Intermediate Similarity	NPC473718
0.7887	Intermediate Similarity	NPC221134
0.7886	Intermediate Similarity	NPC30416
0.7886	Intermediate Similarity	NPC310456
0.7868	Intermediate Similarity	NPC38604
0.7868	Intermediate Similarity	NPC176590
0.7868	Intermediate Similarity	NPC211179
0.7863	Intermediate Similarity	NPC474131
0.7857	Intermediate Similarity	NPC327382
0.7842	Intermediate Similarity	NPC211352
0.7832	Intermediate Similarity	NPC125861
0.7829	Intermediate Similarity	NPC236070
0.7829	Intermediate Similarity	NPC242580
0.7829	Intermediate Similarity	NPC126759
0.7826	Intermediate Similarity	NPC153019
0.7823	Intermediate Similarity	NPC233320
0.781	Intermediate Similarity	NPC96719
0.781	Intermediate Similarity	NPC472795
0.781	Intermediate Similarity	NPC222108
0.781	Intermediate Similarity	NPC472796
0.7803	Intermediate Similarity	NPC473875
0.7801	Intermediate Similarity	NPC327735
0.7801	Intermediate Similarity	NPC126101
0.7794	Intermediate Similarity	NPC469386
0.7786	Intermediate Similarity	NPC85895
0.7786	Intermediate Similarity	NPC137294
0.7786	Intermediate Similarity	NPC32152
0.7778	Intermediate Similarity	NPC124030
0.7778	Intermediate Similarity	NPC131397
0.7778	Intermediate Similarity	NPC476254
0.777	Intermediate Similarity	NPC27578
0.777	Intermediate Similarity	NPC289624
0.7761	Intermediate Similarity	NPC261992
0.7744	Intermediate Similarity	NPC475839
0.7742	Intermediate Similarity	NPC53740
0.7737	Intermediate Similarity	NPC81261
0.7737	Intermediate Similarity	NPC281499
0.7727	Intermediate Similarity	NPC232295
0.7721	Intermediate Similarity	NPC245060
0.7717	Intermediate Similarity	NPC54373
0.7717	Intermediate Similarity	NPC469912
0.771	Intermediate Similarity	NPC283616
0.7698	Intermediate Similarity	NPC472590
0.7698	Intermediate Similarity	NPC160623
0.7687	Intermediate Similarity	NPC188997
0.7687	Intermediate Similarity	NPC74137
0.7687	Intermediate Similarity	NPC150026
0.7681	Intermediate Similarity	NPC16577
0.7669	Intermediate Similarity	NPC129176
0.7664	Intermediate Similarity	NPC46978
0.7661	Intermediate Similarity	NPC47284
0.766	Intermediate Similarity	NPC71372
0.7647	Intermediate Similarity	NPC81641
0.7647	Intermediate Similarity	NPC470726
0.7643	Intermediate Similarity	NPC469611
0.7626	Intermediate Similarity	NPC196621
0.7612	Intermediate Similarity	NPC212965
0.7591	Intermediate Similarity	NPC470724
0.7589	Intermediate Similarity	NPC469610
0.7589	Intermediate Similarity	NPC105554
0.7586	Intermediate Similarity	NPC472791
0.7586	Intermediate Similarity	NPC472792
0.7574	Intermediate Similarity	NPC474237
0.7571	Intermediate Similarity	NPC8899
0.7568	Intermediate Similarity	NPC211758
0.7568	Intermediate Similarity	NPC87794
0.7557	Intermediate Similarity	NPC290470
0.7557	Intermediate Similarity	NPC154256
0.7557	Intermediate Similarity	NPC141001
0.7556	Intermediate Similarity	NPC473464
0.7556	Intermediate Similarity	NPC120638
0.7556	Intermediate Similarity	NPC46586
0.7556	Intermediate Similarity	NPC302211
0.7556	Intermediate Similarity	NPC476332
0.7556	Intermediate Similarity	NPC204535
0.7554	Intermediate Similarity	NPC206028
0.7552	Intermediate Similarity	NPC474610
0.7552	Intermediate Similarity	NPC472800
0.754	Intermediate Similarity	NPC320439
0.7538	Intermediate Similarity	NPC471534
0.7537	Intermediate Similarity	NPC277798
0.7537	Intermediate Similarity	NPC100108
0.7537	Intermediate Similarity	NPC212559
0.7536	Intermediate Similarity	NPC473134
0.7536	Intermediate Similarity	NPC186889
0.7534	Intermediate Similarity	NPC323126
0.7519	Intermediate Similarity	NPC184302
0.7519	Intermediate Similarity	NPC280760
0.7519	Intermediate Similarity	NPC228452
0.7518	Intermediate Similarity	NPC251549
0.7518	Intermediate Similarity	NPC293801
0.7517	Intermediate Similarity	NPC473049
0.7517	Intermediate Similarity	NPC472794
0.75	Intermediate Similarity	NPC24327
0.75	Intermediate Similarity	NPC98804
0.75	Intermediate Similarity	NPC12870
0.75	Intermediate Similarity	NPC90645
0.75	Intermediate Similarity	NPC474130
0.75	Intermediate Similarity	NPC472457
0.75	Intermediate Similarity	NPC269212
0.75	Intermediate Similarity	NPC168657
0.75	Intermediate Similarity	NPC470727
0.7483	Intermediate Similarity	NPC135767
0.7483	Intermediate Similarity	NPC184607
0.7483	Intermediate Similarity	NPC155392
0.7483	Intermediate Similarity	NPC477616
0.7483	Intermediate Similarity	NPC274721
0.7482	Intermediate Similarity	NPC223912
0.7482	Intermediate Similarity	NPC19694
0.7481	Intermediate Similarity	NPC469719
0.7481	Intermediate Similarity	NPC232165
0.748	Intermediate Similarity	NPC72729
0.7465	Intermediate Similarity	NPC269528
0.7464	Intermediate Similarity	NPC476006
0.7464	Intermediate Similarity	NPC128321
0.7464	Intermediate Similarity	NPC82299
0.7463	Intermediate Similarity	NPC14177
0.746	Intermediate Similarity	NPC469913
0.7448	Intermediate Similarity	NPC19869
0.7448	Intermediate Similarity	NPC292882
0.7448	Intermediate Similarity	NPC183781
0.7447	Intermediate Similarity	NPC78575
0.7447	Intermediate Similarity	NPC82503
0.7445	Intermediate Similarity	NPC276962
0.7445	Intermediate Similarity	NPC147896
0.7445	Intermediate Similarity	NPC270030
0.7445	Intermediate Similarity	NPC190086
0.7444	Intermediate Similarity	NPC190514
0.7442	Intermediate Similarity	NPC266937
0.7442	Intermediate Similarity	NPC77772
0.7442	Intermediate Similarity	NPC470770
0.744	Intermediate Similarity	NPC272029
0.7432	Intermediate Similarity	NPC317237
0.7432	Intermediate Similarity	NPC44530
0.7432	Intermediate Similarity	NPC277951
0.7431	Intermediate Similarity	NPC141717
0.7431	Intermediate Similarity	NPC194847
0.7431	Intermediate Similarity	NPC21797
0.7431	Intermediate Similarity	NPC475628
0.7426	Intermediate Similarity	NPC18128
0.7426	Intermediate Similarity	NPC77789
0.7426	Intermediate Similarity	NPC297057
0.7424	Intermediate Similarity	NPC150624
0.7419	Intermediate Similarity	NPC477685
0.7415	Intermediate Similarity	NPC470937
0.7413	Intermediate Similarity	NPC193026
0.7413	Intermediate Similarity	NPC49603
0.7413	Intermediate Similarity	NPC187616
0.7413	Intermediate Similarity	NPC16485
0.741	Intermediate Similarity	NPC473221
0.7398	Intermediate Similarity	NPC33675
0.7398	Intermediate Similarity	NPC299762
0.7397	Intermediate Similarity	NPC79372
0.7397	Intermediate Similarity	NPC160283
0.7397	Intermediate Similarity	NPC475012
0.7397	Intermediate Similarity	NPC254759
0.7397	Intermediate Similarity	NPC27495
0.7397	Intermediate Similarity	NPC76312
0.7394	Intermediate Similarity	NPC13005
0.7394	Intermediate Similarity	NPC18842
0.7391	Intermediate Similarity	NPC105031
0.7385	Intermediate Similarity	NPC177962
0.7385	Intermediate Similarity	NPC62867
0.7383	Intermediate Similarity	NPC469642
0.7379	Intermediate Similarity	NPC476171
0.7376	Intermediate Similarity	NPC220935
0.7376	Intermediate Similarity	NPC27187
0.7376	Intermediate Similarity	NPC470225
0.7368	Intermediate Similarity	NPC320864
0.7368	Intermediate Similarity	NPC33270
0.7368	Intermediate Similarity	NPC244816

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 NPC266868 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	988
0.2-0.3	1866
0.3-0.4	2924
0.4-0.5	1708
0.5-0.6	1020
0.6-0.7	230
0.7-0.8	32
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8819	High Similarity	NPD6696	Suspended
0.806	Intermediate Similarity	NPD2861	Phase 2
0.8031	Intermediate Similarity	NPD6671	Approved
0.803	Intermediate Similarity	NPD4749	Approved
0.7883	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1398	Phase 1
0.7829	Intermediate Similarity	NPD7340	Approved
0.7681	Intermediate Similarity	NPD4625	Phase 3
0.766	Intermediate Similarity	NPD6353	Approved
0.7622	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD6100	Approved
0.7591	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4624	Approved
0.7589	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD5327	Phase 3
0.748	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1778	Approved
0.7448	Intermediate Similarity	NPD5762	Approved
0.7448	Intermediate Similarity	NPD5763	Approved
0.741	Intermediate Similarity	NPD1712	Approved
0.7394	Intermediate Similarity	NPD4140	Approved
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7297	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2157	Approved
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7273	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3620	Phase 2
0.7236	Intermediate Similarity	NPD288	Approved
0.7226	Intermediate Similarity	NPD1611	Approved
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7206	Intermediate Similarity	NPD4059	Approved
0.7188	Intermediate Similarity	NPD968	Approved
0.7154	Intermediate Similarity	NPD4750	Phase 3
0.7154	Intermediate Similarity	NPD844	Approved
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7635	Approved
0.7113	Intermediate Similarity	NPD4908	Phase 1
0.7111	Intermediate Similarity	NPD7644	Approved
0.708	Intermediate Similarity	NPD4626	Approved
0.7059	Intermediate Similarity	NPD3091	Approved
0.705	Intermediate Similarity	NPD1608	Approved
0.705	Intermediate Similarity	NPD2232	Approved
0.705	Intermediate Similarity	NPD2233	Approved
0.705	Intermediate Similarity	NPD2230	Approved
0.7042	Intermediate Similarity	NPD2237	Approved
0.7042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3092	Approved
0.6963	Remote Similarity	NPD7157	Approved
0.6954	Remote Similarity	NPD3892	Phase 2
0.6939	Remote Similarity	NPD6653	Approved
0.6939	Remote Similarity	NPD4097	Suspended
0.6934	Remote Similarity	NPD1548	Phase 1
0.6918	Remote Similarity	NPD4060	Phase 1
0.6901	Remote Similarity	NPD3094	Phase 2
0.6887	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5691	Approved
0.687	Remote Similarity	NPD290	Approved
0.6857	Remote Similarity	NPD3705	Approved
0.6857	Remote Similarity	NPD422	Phase 1
0.6849	Remote Similarity	NPD8032	Phase 2
0.6839	Remote Similarity	NPD6090	Discontinued
0.6835	Remote Similarity	NPD17	Approved
0.6831	Remote Similarity	NPD8651	Approved
0.6818	Remote Similarity	NPD2684	Approved
0.6806	Remote Similarity	NPD5736	Approved
0.6803	Remote Similarity	NPD2238	Phase 2
0.6803	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1613	Approved
0.68	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD228	Approved
0.6761	Remote Similarity	NPD4359	Approved
0.6746	Remote Similarity	NPD1809	Phase 2
0.6738	Remote Similarity	NPD1091	Approved
0.6735	Remote Similarity	NPD6663	Approved
0.6731	Remote Similarity	NPD6273	Approved
0.672	Remote Similarity	NPD845	Approved
0.6715	Remote Similarity	NPD709	Approved
0.6714	Remote Similarity	NPD3095	Discontinued
0.6714	Remote Similarity	NPD3019	Approved
0.6714	Remote Similarity	NPD2932	Approved
0.6712	Remote Similarity	NPD7095	Approved
0.6691	Remote Similarity	NPD7741	Discontinued
0.669	Remote Similarity	NPD2231	Phase 2
0.669	Remote Similarity	NPD2235	Phase 2
0.6667	Remote Similarity	NPD7985	Registered
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD987	Approved
0.6646	Remote Similarity	NPD5761	Phase 2
0.6646	Remote Similarity	NPD5760	Phase 2
0.6646	Remote Similarity	NPD5929	Approved
0.6644	Remote Similarity	NPD3657	Discovery
0.6643	Remote Similarity	NPD1357	Approved
0.6623	Remote Similarity	NPD7033	Discontinued
0.6621	Remote Similarity	NPD6584	Phase 3
0.6618	Remote Similarity	NPD7843	Approved
0.6618	Remote Similarity	NPD821	Approved
0.6615	Remote Similarity	NPD846	Approved
0.6615	Remote Similarity	NPD940	Approved
0.6601	Remote Similarity	NPD7037	Approved
0.6599	Remote Similarity	NPD3027	Phase 3
0.6597	Remote Similarity	NPD1283	Approved
0.6589	Remote Similarity	NPD3020	Approved
0.6573	Remote Similarity	NPD1840	Phase 2
0.6569	Remote Similarity	NPD5283	Phase 1
0.6561	Remote Similarity	NPD2532	Approved
0.6561	Remote Similarity	NPD2534	Approved
0.6561	Remote Similarity	NPD2533	Approved
0.6558	Remote Similarity	NPD6674	Discontinued
0.6547	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1375	Discontinued
0.6533	Remote Similarity	NPD6355	Discontinued
0.6532	Remote Similarity	NPD9295	Approved
0.6531	Remote Similarity	NPD600	Approved
0.6531	Remote Similarity	NPD596	Approved
0.6525	Remote Similarity	NPD1651	Approved
0.6525	Remote Similarity	NPD3445	Approved
0.6525	Remote Similarity	NPD3444	Approved
0.6525	Remote Similarity	NPD3443	Approved
0.6516	Remote Similarity	NPD4628	Phase 3
0.6516	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4110	Phase 3
0.651	Remote Similarity	NPD4870	Approved
0.6507	Remote Similarity	NPD558	Phase 2
0.6507	Remote Similarity	NPD5647	Approved
0.6506	Remote Similarity	NPD7199	Phase 2
0.6506	Remote Similarity	NPD8127	Discontinued
0.6503	Remote Similarity	NPD1535	Discovery
0.6503	Remote Similarity	NPD2560	Approved
0.6503	Remote Similarity	NPD2563	Approved
0.65	Remote Similarity	NPD3226	Approved
0.6496	Remote Similarity	NPD1138	Approved
0.6494	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2342	Discontinued
0.6479	Remote Similarity	NPD2667	Approved
0.6479	Remote Similarity	NPD2668	Approved
0.6474	Remote Similarity	NPD7312	Approved
0.6474	Remote Similarity	NPD7310	Approved
0.6474	Remote Similarity	NPD4577	Approved
0.6474	Remote Similarity	NPD2677	Approved
0.6474	Remote Similarity	NPD7313	Approved
0.6474	Remote Similarity	NPD7311	Approved
0.6474	Remote Similarity	NPD4578	Approved
0.6471	Remote Similarity	NPD2161	Phase 2
0.6467	Remote Similarity	NPD1558	Phase 1
0.6458	Remote Similarity	NPD1481	Phase 2
0.6454	Remote Similarity	NPD1182	Approved
0.6452	Remote Similarity	NPD2800	Approved
0.6443	Remote Similarity	NPD3268	Approved
0.6438	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7309	Approved
0.6429	Remote Similarity	NPD2970	Approved
0.6429	Remote Similarity	NPD2969	Approved
0.6429	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2346	Discontinued
0.6424	Remote Similarity	NPD7831	Phase 2
0.6424	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7833	Phase 2
0.6423	Remote Similarity	NPD1137	Approved
0.6423	Remote Similarity	NPD1139	Approved
0.6418	Remote Similarity	NPD1445	Approved
0.6418	Remote Similarity	NPD1444	Approved
0.6415	Remote Similarity	NPD2675	Approved
0.6415	Remote Similarity	NPD2676	Approved
0.6414	Remote Similarity	NPD6583	Phase 3
0.6414	Remote Similarity	NPD6582	Phase 2
0.641	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD497	Approved
0.64	Remote Similarity	NPD3163	Approved
0.64	Remote Similarity	NPD840	Approved
0.64	Remote Similarity	NPD839	Approved
0.64	Remote Similarity	NPD3162	Approved
0.6397	Remote Similarity	NPD1792	Phase 2
0.6397	Remote Similarity	NPD3022	Approved
0.6397	Remote Similarity	NPD3021	Approved
0.6395	Remote Similarity	NPD3691	Phase 2
0.6395	Remote Similarity	NPD3690	Phase 2
0.6392	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD2489	Approved
0.6391	Remote Similarity	NPD27	Approved
0.6389	Remote Similarity	NPD1281	Approved
0.6387	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6234	Discontinued
0.6377	Remote Similarity	NPD5535	Approved
0.6375	Remote Similarity	NPD5699	Approved
0.6369	Remote Similarity	NPD3051	Approved
0.6364	Remote Similarity	NPD4967	Phase 2
0.6364	Remote Similarity	NPD4965	Approved
0.6364	Remote Similarity	NPD2935	Discontinued
0.6364	Remote Similarity	NPD4966	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