NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	290.22
Volume:	335.658
LogP:	6.878
LogD:	4.603
LogS:	-5.34
# Rotatable Bonds:	11
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	2.04
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.737
MDCK Permeability:	1.2637750842259265e-05
Pgp-inhibitor:	0.66
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	99.1687240600586%
Volume Distribution (VD):	2.101
Pgp-substrate:	1.2134191989898682%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.219
CYP2C19-inhibitor:	0.775
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.348
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.747
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	3.437
Half-life (T1/2):	0.187

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.462
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.931
Carcinogencity:	0.088
Eye Corrosion:	0.807
Eye Irritation:	0.992
Respiratory Toxicity:	0.861

Download Data

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

Natural Product: NPC477453

Natural Product ID:	NPC477453
*Common Name:**	Lobophorol B
IUPAC Name:	1-(2-hydroxy-6-undecylphenyl)ethanone
Synonyms:
Standard InCHIKey:	WADCNVWANPTEDF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H30O2/c1-3-4-5-6-7-8-9-10-11-13-17-14-12-15-18(21)19(17)16(2)20/h12,14-15,21H,3-11,13H2,1-2H3
SMILES:	CCCCCCCCCCCC1=C(C(=CC=C1)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122181665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	at depths of 630 m at El Mdano (Tenerife, Canary Islands)	n.a.	PMID[26126835]
NPO11898	Lobophora variegata	Species	Dictyotaceae	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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	Inhibition	=	-1	%	PMID[26126835]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-3.3	%	PMID[26126835]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	65	%	PMID[26126835]

☑ 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 NPC477453 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	254
0.1-0.2	1488
0.2-0.3	3746
0.3-0.4	10971
0.4-0.5	8309
0.5-0.6	6884
0.6-0.7	8011
0.7-0.8	2596
0.8-0.85	310
0.85-0.9	88
0.9-0.95	39
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9386	High Similarity	NPC244994
0.9386	High Similarity	NPC179092
0.9386	High Similarity	NPC159760
0.9386	High Similarity	NPC272454
0.9386	High Similarity	NPC222876
0.9386	High Similarity	NPC301987
0.9386	High Similarity	NPC178395
0.9386	High Similarity	NPC35856
0.9386	High Similarity	NPC26433
0.9386	High Similarity	NPC292665
0.9386	High Similarity	NPC115188
0.9381	High Similarity	NPC233165
0.9381	High Similarity	NPC184579
0.9204	High Similarity	NPC125252
0.9204	High Similarity	NPC269414
0.9196	High Similarity	NPC161304
0.913	High Similarity	NPC206778
0.913	High Similarity	NPC285829
0.9115	High Similarity	NPC108288
0.9083	High Similarity	NPC224584
0.9076	High Similarity	NPC306765
0.906	High Similarity	NPC307174
0.906	High Similarity	NPC244351
0.9027	High Similarity	NPC240163
0.8992	High Similarity	NPC477454
0.8992	High Similarity	NPC167055
0.8992	High Similarity	NPC240744
0.8966	High Similarity	NPC473662
0.8966	High Similarity	NPC216297
0.8966	High Similarity	NPC7151
0.8957	High Similarity	NPC41567
0.8926	High Similarity	NPC48248
0.8917	High Similarity	NPC136342
0.8917	High Similarity	NPC295202
0.8917	High Similarity	NPC49647
0.8917	High Similarity	NPC473691
0.8917	High Similarity	NPC227741
0.8908	High Similarity	NPC173978
0.8908	High Similarity	NPC234890
0.8908	High Similarity	NPC74507
0.8898	High Similarity	NPC300274
0.887	High Similarity	NPC121259
0.8852	High Similarity	NPC92624
0.8843	High Similarity	NPC471530
0.8833	High Similarity	NPC131799
0.8824	High Similarity	NPC477153
0.8824	High Similarity	NPC375356
0.8818	High Similarity	NPC34715
0.878	High Similarity	NPC259942
0.8761	High Similarity	NPC231717
0.876	High Similarity	NPC160499
0.876	High Similarity	NPC231774
0.876	High Similarity	NPC3224
0.875	High Similarity	NPC142956
0.875	High Similarity	NPC68756
0.875	High Similarity	NPC310540
0.875	High Similarity	NPC152525
0.8739	High Similarity	NPC283514
0.8729	High Similarity	NPC190971
0.8718	High Similarity	NPC232178
0.8699	High Similarity	NPC146647
0.8699	High Similarity	NPC34414
0.8699	High Similarity	NPC474546
0.8678	High Similarity	NPC103540
0.8655	High Similarity	NPC198336
0.864	High Similarity	NPC242358
0.864	High Similarity	NPC246693
0.864	High Similarity	NPC110609
0.8629	High Similarity	NPC17840
0.8629	High Similarity	NPC247477
0.8618	High Similarity	NPC282923
0.8609	High Similarity	NPC276111
0.8609	High Similarity	NPC118288
0.8607	High Similarity	NPC96915
0.8607	High Similarity	NPC51037
0.8595	High Similarity	NPC265910
0.8595	High Similarity	NPC91475
0.8595	High Similarity	NPC199273
0.8583	High Similarity	NPC282577
0.8571	High Similarity	NPC115458
0.856	High Similarity	NPC474517
0.856	High Similarity	NPC244699
0.856	High Similarity	NPC7012
0.856	High Similarity	NPC72669
0.856	High Similarity	NPC85342
0.8559	High Similarity	NPC188814
0.8559	High Similarity	NPC195262
0.8548	High Similarity	NPC99731
0.8547	High Similarity	NPC160199
0.8522	High Similarity	NPC242136
0.8512	High Similarity	NPC275145
0.8504	High Similarity	NPC161964
0.8504	High Similarity	NPC282780
0.8504	High Similarity	NPC166480
0.8504	High Similarity	NPC472262
0.8504	High Similarity	NPC287604
0.8496	Intermediate Similarity	NPC95172
0.8492	Intermediate Similarity	NPC58685
0.8482	Intermediate Similarity	NPC141523
0.848	Intermediate Similarity	NPC475741
0.848	Intermediate Similarity	NPC55949
0.8468	Intermediate Similarity	NPC237225
0.8468	Intermediate Similarity	NPC96024
0.8468	Intermediate Similarity	NPC95537
0.8468	Intermediate Similarity	NPC165257
0.8455	Intermediate Similarity	NPC254492
0.8455	Intermediate Similarity	NPC1991
0.8443	Intermediate Similarity	NPC236189
0.8438	Intermediate Similarity	NPC283088
0.8438	Intermediate Similarity	NPC22222
0.8438	Intermediate Similarity	NPC281513
0.843	Intermediate Similarity	NPC217756
0.8425	Intermediate Similarity	NPC53896
0.8425	Intermediate Similarity	NPC43627
0.8425	Intermediate Similarity	NPC225051
0.8417	Intermediate Similarity	NPC165197
0.8417	Intermediate Similarity	NPC149246
0.8413	Intermediate Similarity	NPC205992
0.8407	Intermediate Similarity	NPC279887
0.8407	Intermediate Similarity	NPC68260
0.84	Intermediate Similarity	NPC276238
0.84	Intermediate Similarity	NPC109123
0.84	Intermediate Similarity	NPC278928
0.8387	Intermediate Similarity	NPC84672
0.8387	Intermediate Similarity	NPC181715
0.8387	Intermediate Similarity	NPC69424
0.8387	Intermediate Similarity	NPC72667
0.8387	Intermediate Similarity	NPC176130
0.8387	Intermediate Similarity	NPC78364
0.8387	Intermediate Similarity	NPC470841
0.8376	Intermediate Similarity	NPC322197
0.8374	Intermediate Similarity	NPC123506
0.8374	Intermediate Similarity	NPC287473
0.8374	Intermediate Similarity	NPC262671
0.8374	Intermediate Similarity	NPC201728
0.8372	Intermediate Similarity	NPC272268
0.8362	Intermediate Similarity	NPC211421
0.8359	Intermediate Similarity	NPC474097
0.8359	Intermediate Similarity	NPC50924
0.8359	Intermediate Similarity	NPC12070
0.8347	Intermediate Similarity	NPC196976
0.8347	Intermediate Similarity	NPC25168
0.8347	Intermediate Similarity	NPC154696
0.8346	Intermediate Similarity	NPC477406
0.8346	Intermediate Similarity	NPC470160
0.8333	Intermediate Similarity	NPC198305
0.8333	Intermediate Similarity	NPC26013
0.8333	Intermediate Similarity	NPC136588
0.8333	Intermediate Similarity	NPC199253
0.8333	Intermediate Similarity	NPC117609
0.8333	Intermediate Similarity	NPC282855
0.832	Intermediate Similarity	NPC767
0.832	Intermediate Similarity	NPC41263
0.832	Intermediate Similarity	NPC247250
0.8319	Intermediate Similarity	NPC303264
0.8319	Intermediate Similarity	NPC228737
0.8319	Intermediate Similarity	NPC226699
0.8308	Intermediate Similarity	NPC245923
0.8308	Intermediate Similarity	NPC290030
0.8306	Intermediate Similarity	NPC71610
0.8306	Intermediate Similarity	NPC473751
0.8295	Intermediate Similarity	NPC27407
0.8295	Intermediate Similarity	NPC249272
0.8295	Intermediate Similarity	NPC80035
0.8293	Intermediate Similarity	NPC470162
0.8293	Intermediate Similarity	NPC470163
0.8291	Intermediate Similarity	NPC163154
0.8281	Intermediate Similarity	NPC180261
0.8281	Intermediate Similarity	NPC37299
0.8281	Intermediate Similarity	NPC114183
0.8281	Intermediate Similarity	NPC477536
0.8281	Intermediate Similarity	NPC171968
0.8279	Intermediate Similarity	NPC297193
0.8279	Intermediate Similarity	NPC309765
0.8279	Intermediate Similarity	NPC91105
0.8279	Intermediate Similarity	NPC46634
0.8279	Intermediate Similarity	NPC176208
0.8268	Intermediate Similarity	NPC41847
0.8268	Intermediate Similarity	NPC17083
0.8264	Intermediate Similarity	NPC259703
0.8264	Intermediate Similarity	NPC146642
0.8264	Intermediate Similarity	NPC32322
0.8261	Intermediate Similarity	NPC208229
0.8254	Intermediate Similarity	NPC171460
0.8254	Intermediate Similarity	NPC25736
0.825	Intermediate Similarity	NPC161617
0.825	Intermediate Similarity	NPC473767
0.8246	Intermediate Similarity	NPC317305
0.8246	Intermediate Similarity	NPC100551
0.824	Intermediate Similarity	NPC209959
0.8231	Intermediate Similarity	NPC191976
0.8231	Intermediate Similarity	NPC474813
0.8231	Intermediate Similarity	NPC193358
0.8231	Intermediate Similarity	NPC472308
0.8231	Intermediate Similarity	NPC155211
0.8231	Intermediate Similarity	NPC118919
0.823	Intermediate Similarity	NPC6984
0.8226	Intermediate Similarity	NPC475733
0.8217	Intermediate Similarity	NPC270899
0.8211	Intermediate Similarity	NPC273683

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 NPC477453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	969
0.2-0.3	1290
0.3-0.4	2633
0.4-0.5	2180
0.5-0.6	1242
0.6-0.7	458
0.7-0.8	88
0.8-0.85	7
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9115	High Similarity	NPD405	Clinical (unspecified phase)
0.8974	High Similarity	NPD1201	Approved
0.8678	High Similarity	NPD1470	Approved
0.8246	Intermediate Similarity	NPD74	Approved
0.8246	Intermediate Similarity	NPD9266	Approved
0.8158	Intermediate Similarity	NPD9263	Approved
0.8158	Intermediate Similarity	NPD9264	Approved
0.8158	Intermediate Similarity	NPD9267	Approved
0.8151	Intermediate Similarity	NPD9493	Approved
0.8099	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD2932	Approved
0.8033	Intermediate Similarity	NPD3019	Approved
0.8016	Intermediate Similarity	NPD2798	Approved
0.7955	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1164	Approved
0.7909	Intermediate Similarity	NPD844	Approved
0.7895	Intermediate Similarity	NPD5405	Approved
0.7895	Intermediate Similarity	NPD5404	Approved
0.7895	Intermediate Similarity	NPD5408	Approved
0.7895	Intermediate Similarity	NPD5406	Approved
0.7838	Intermediate Similarity	NPD288	Approved
0.782	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD3300	Phase 2
0.7807	Intermediate Similarity	NPD9261	Approved
0.7788	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD943	Approved
0.7761	Intermediate Similarity	NPD2935	Discontinued
0.7754	Intermediate Similarity	NPD7390	Discontinued
0.7704	Intermediate Similarity	NPD2346	Discontinued
0.7686	Intermediate Similarity	NPD9281	Approved
0.7574	Intermediate Similarity	NPD2344	Approved
0.7568	Intermediate Similarity	NPD845	Approved
0.7559	Intermediate Similarity	NPD9717	Approved
0.7556	Intermediate Similarity	NPD2799	Discontinued
0.7544	Intermediate Similarity	NPD3020	Approved
0.7542	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7635	Approved
0.7519	Intermediate Similarity	NPD1240	Approved
0.7518	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1755	Approved
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4626	Approved
0.7447	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2859	Approved
0.7434	Intermediate Similarity	NPD2860	Approved
0.7426	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4750	Phase 3
0.7407	Intermediate Similarity	NPD1607	Approved
0.7402	Intermediate Similarity	NPD3026	Approved
0.7402	Intermediate Similarity	NPD3023	Approved
0.7398	Intermediate Similarity	NPD5951	Approved
0.7395	Intermediate Similarity	NPD2342	Discontinued
0.7385	Intermediate Similarity	NPD1203	Approved
0.7381	Intermediate Similarity	NPD3024	Approved
0.7381	Intermediate Similarity	NPD3025	Approved
0.7368	Intermediate Similarity	NPD2313	Discontinued
0.7368	Intermediate Similarity	NPD411	Approved
0.7368	Intermediate Similarity	NPD3764	Approved
0.7361	Intermediate Similarity	NPD3226	Approved
0.7357	Intermediate Similarity	NPD2309	Approved
0.7345	Intermediate Similarity	NPD2934	Approved
0.7345	Intermediate Similarity	NPD2933	Approved
0.7344	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD447	Suspended
0.7308	Intermediate Similarity	NPD1876	Approved
0.7302	Intermediate Similarity	NPD9545	Approved
0.7299	Intermediate Similarity	NPD1510	Phase 2
0.7288	Intermediate Similarity	NPD1237	Approved
0.7281	Intermediate Similarity	NPD1809	Phase 2
0.7273	Intermediate Similarity	NPD3021	Approved
0.7273	Intermediate Similarity	NPD3022	Approved
0.7265	Intermediate Similarity	NPD846	Approved
0.7265	Intermediate Similarity	NPD940	Approved
0.7252	Intermediate Similarity	NPD2797	Approved
0.7244	Intermediate Similarity	NPD1651	Approved
0.7203	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2532	Approved
0.7203	Intermediate Similarity	NPD1929	Approved
0.7203	Intermediate Similarity	NPD2533	Approved
0.7203	Intermediate Similarity	NPD2534	Approved
0.7203	Intermediate Similarity	NPD1930	Approved
0.7185	Intermediate Similarity	NPD6663	Approved
0.7176	Intermediate Similarity	NPD1283	Approved
0.7167	Intermediate Similarity	NPD1445	Approved
0.7167	Intermediate Similarity	NPD1444	Approved
0.7163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3750	Approved
0.7163	Intermediate Similarity	NPD7003	Approved
0.7162	Intermediate Similarity	NPD7819	Suspended
0.7154	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD9258	Approved
0.7143	Intermediate Similarity	NPD5736	Approved
0.7143	Intermediate Similarity	NPD9256	Approved
0.7131	Intermediate Similarity	NPD1792	Phase 2
0.7111	Intermediate Similarity	NPD3268	Approved
0.7109	Intermediate Similarity	NPD5691	Approved
0.7094	Intermediate Similarity	NPD2066	Phase 3
0.709	Intermediate Similarity	NPD6832	Phase 2
0.7073	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6671	Approved
0.7063	Intermediate Similarity	NPD255	Approved
0.7063	Intermediate Similarity	NPD256	Approved
0.7059	Intermediate Similarity	NPD520	Approved
0.7054	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3091	Approved
0.7031	Intermediate Similarity	NPD1759	Phase 1
0.7023	Intermediate Similarity	NPD4878	Approved
0.7023	Intermediate Similarity	NPD1608	Approved
0.7021	Intermediate Similarity	NPD1549	Phase 2
0.7016	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9494	Approved
0.7014	Intermediate Similarity	NPD1511	Approved
0.7	Intermediate Similarity	NPD6099	Approved
0.7	Intermediate Similarity	NPD111	Approved
0.7	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD6100	Approved
0.698	Remote Similarity	NPD1934	Approved
0.697	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD1758	Phase 1
0.695	Remote Similarity	NPD1471	Phase 3
0.6948	Remote Similarity	NPD6232	Discontinued
0.6947	Remote Similarity	NPD1281	Approved
0.6935	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2801	Approved
0.6929	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD4059	Approved
0.6923	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD7473	Discontinued
0.6918	Remote Similarity	NPD1512	Approved
0.6911	Remote Similarity	NPD2182	Approved
0.6905	Remote Similarity	NPD1241	Discontinued
0.6897	Remote Similarity	NPD1693	Approved
0.6894	Remote Similarity	NPD9269	Phase 2
0.6892	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD6959	Discontinued
0.6879	Remote Similarity	NPD1551	Phase 2
0.687	Remote Similarity	NPD3496	Discontinued
0.686	Remote Similarity	NPD164	Approved
0.6853	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2800	Approved
0.6846	Remote Similarity	NPD9268	Approved
0.6846	Remote Similarity	NPD4093	Discontinued
0.6846	Remote Similarity	NPD4380	Phase 2
0.6842	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1090	Approved
0.6842	Remote Similarity	NPD1086	Approved
0.6842	Remote Similarity	NPD3882	Suspended
0.6842	Remote Similarity	NPD1089	Approved
0.6833	Remote Similarity	NPD1932	Approved
0.6831	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3092	Approved
0.6815	Remote Similarity	NPD258	Approved
0.6815	Remote Similarity	NPD257	Approved
0.6815	Remote Similarity	NPD1019	Discontinued
0.6809	Remote Similarity	NPD3748	Approved
0.6806	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6273	Approved
0.6797	Remote Similarity	NPD3749	Approved
0.6794	Remote Similarity	NPD1778	Approved
0.6794	Remote Similarity	NPD17	Approved
0.6794	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9259	Approved
0.6786	Remote Similarity	NPD6651	Approved
0.6786	Remote Similarity	NPD9257	Approved
0.6783	Remote Similarity	NPD7609	Phase 3
0.6779	Remote Similarity	NPD2649	Approved
0.6779	Remote Similarity	NPD2651	Approved
0.6776	Remote Similarity	NPD2296	Approved
0.6772	Remote Similarity	NPD2234	Approved
0.6772	Remote Similarity	NPD2229	Approved
0.6772	Remote Similarity	NPD2228	Approved
0.6763	Remote Similarity	NPD4060	Phase 1
0.6761	Remote Similarity	NPD4476	Approved
0.6761	Remote Similarity	NPD4477	Approved
0.6755	Remote Similarity	NPD6844	Discontinued
0.6754	Remote Similarity	NPD800	Approved
0.6752	Remote Similarity	NPD688	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1242	Phase 1
0.6746	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD9568	Approved
0.6741	Remote Similarity	NPD3266	Approved
0.6741	Remote Similarity	NPD3267	Approved
0.6735	Remote Similarity	NPD4662	Approved
0.6735	Remote Similarity	NPD4661	Approved
0.6732	Remote Similarity	NPD7768	Phase 2
0.6724	Remote Similarity	NPD7631	Approved
0.6724	Remote Similarity	NPD1088	Approved
0.6723	Remote Similarity	NPD9495	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