NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.18
Volume:	248.481
LogP:	4.006
LogD:	4.005
LogS:	-4.196
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	5.584
Fsp3:	0.867
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:	-4.364
MDCK Permeability:	1.7036691133398563e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.611
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.638

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.324
Plasma Protein Binding (PPB):	89.76961517333984%
Volume Distribution (VD):	1.343
Pgp-substrate:	7.059194087982178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.694
CYP1A2-substrate:	0.58
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.173
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	16.747
Half-life (T1/2):	0.599

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.329
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.248
Carcinogencity:	0.057
Eye Corrosion:	0.395
Eye Irritation:	0.163
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC474248

Natural Product ID:	NPC474248
*Common Name:**	Isolemnalol
IUPAC Name:	n.a.
Synonyms:	Isolemnalol
Standard InCHIKey:	LTXWSWWXNHYXCW-UJOWSUJOSA-N
Standard InCHI:	InChI=1S/C15H24O/c1-8(2)10-5-6-15(4)13-9(3)7-11(16)14(15)12(10)13/h7-8,10-14,16H,5-6H2,1-4H3/t10-,11-,12+,13-,14+,15-/m0/s1
SMILES:	CC1=CC(C2C3C1C2(CCC3C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464171
PubChem CID:	44584342
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO33357	lemnalia carvicorni	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	uM	PMID[479006]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	uM	PMID[479006]

☑ 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 NPC474248 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	190
0.1-0.2	1598
0.2-0.3	7624
0.3-0.4	16641
0.4-0.5	7992
0.5-0.6	5607
0.6-0.7	2450
0.7-0.8	508
0.8-0.85	74
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC171225
0.9254	High Similarity	NPC34834
0.9242	High Similarity	NPC96484
0.9231	High Similarity	NPC202017
0.9219	High Similarity	NPC107540
0.8923	High Similarity	NPC96793
0.8923	High Similarity	NPC323424
0.8824	High Similarity	NPC471560
0.8806	High Similarity	NPC114651
0.8676	High Similarity	NPC208999
0.8657	High Similarity	NPC475897
0.8611	High Similarity	NPC244488
0.8611	High Similarity	NPC247325
0.8571	High Similarity	NPC23954
0.8529	High Similarity	NPC69649
0.8529	High Similarity	NPC68703
0.8493	Intermediate Similarity	NPC91594
0.8485	Intermediate Similarity	NPC473759
0.8485	Intermediate Similarity	NPC81615
0.8485	Intermediate Similarity	NPC174956
0.8485	Intermediate Similarity	NPC474155
0.8451	Intermediate Similarity	NPC265485
0.8451	Intermediate Similarity	NPC220939
0.8429	Intermediate Similarity	NPC92801
0.8406	Intermediate Similarity	NPC471238
0.8382	Intermediate Similarity	NPC279434
0.8378	Intermediate Similarity	NPC167891
0.8378	Intermediate Similarity	NPC83351
0.8358	Intermediate Similarity	NPC68656
0.8356	Intermediate Similarity	NPC265588
0.8356	Intermediate Similarity	NPC253190
0.8333	Intermediate Similarity	NPC306727
0.8333	Intermediate Similarity	NPC476366
0.8333	Intermediate Similarity	NPC201048
0.831	Intermediate Similarity	NPC164022
0.831	Intermediate Similarity	NPC477792
0.8286	Intermediate Similarity	NPC473893
0.8267	Intermediate Similarity	NPC30986
0.8267	Intermediate Similarity	NPC143182
0.8267	Intermediate Similarity	NPC84694
0.8267	Intermediate Similarity	NPC28862
0.8267	Intermediate Similarity	NPC209430
0.8267	Intermediate Similarity	NPC109546
0.8267	Intermediate Similarity	NPC81306
0.8267	Intermediate Similarity	NPC47982
0.8261	Intermediate Similarity	NPC197805
0.8243	Intermediate Similarity	NPC470711
0.8243	Intermediate Similarity	NPC74995
0.8243	Intermediate Similarity	NPC470758
0.8219	Intermediate Similarity	NPC133580
0.8219	Intermediate Similarity	NPC32832
0.8194	Intermediate Similarity	NPC182717
0.8194	Intermediate Similarity	NPC130665
0.8194	Intermediate Similarity	NPC474743
0.8194	Intermediate Similarity	NPC471799
0.8194	Intermediate Similarity	NPC474140
0.8182	Intermediate Similarity	NPC66020
0.8169	Intermediate Similarity	NPC145498
0.8158	Intermediate Similarity	NPC295131
0.8158	Intermediate Similarity	NPC234193
0.8143	Intermediate Similarity	NPC216460
0.8133	Intermediate Similarity	NPC474216
0.8133	Intermediate Similarity	NPC476314
0.8125	Intermediate Similarity	NPC48891
0.8116	Intermediate Similarity	NPC222366
0.8116	Intermediate Similarity	NPC476039
0.8116	Intermediate Similarity	NPC473929
0.8116	Intermediate Similarity	NPC286669
0.8108	Intermediate Similarity	NPC470749
0.8088	Intermediate Similarity	NPC290367
0.8088	Intermediate Similarity	NPC225415
0.8082	Intermediate Similarity	NPC471797
0.8082	Intermediate Similarity	NPC469534
0.8082	Intermediate Similarity	NPC100334
0.8082	Intermediate Similarity	NPC469533
0.8082	Intermediate Similarity	NPC469593
0.8056	Intermediate Similarity	NPC110799
0.8056	Intermediate Similarity	NPC242001
0.8056	Intermediate Similarity	NPC471271
0.8056	Intermediate Similarity	NPC471268
0.8056	Intermediate Similarity	NPC167706
0.8056	Intermediate Similarity	NPC471272
0.8052	Intermediate Similarity	NPC264245
0.8052	Intermediate Similarity	NPC23852
0.8052	Intermediate Similarity	NPC209620
0.8052	Intermediate Similarity	NPC476646
0.8026	Intermediate Similarity	NPC242767
0.8026	Intermediate Similarity	NPC308038
0.8026	Intermediate Similarity	NPC152061
0.7973	Intermediate Similarity	NPC162742
0.7973	Intermediate Similarity	NPC471723
0.7973	Intermediate Similarity	NPC134847
0.7973	Intermediate Similarity	NPC230301
0.7973	Intermediate Similarity	NPC304309
0.7973	Intermediate Similarity	NPC136188
0.7973	Intermediate Similarity	NPC22105
0.7973	Intermediate Similarity	NPC28657
0.7973	Intermediate Similarity	NPC285893
0.7973	Intermediate Similarity	NPC257347
0.7973	Intermediate Similarity	NPC288035
0.7973	Intermediate Similarity	NPC141071
0.7971	Intermediate Similarity	NPC163678
0.7971	Intermediate Similarity	NPC258595
0.7969	Intermediate Similarity	NPC148216
0.7969	Intermediate Similarity	NPC148163
0.7969	Intermediate Similarity	NPC130209
0.7949	Intermediate Similarity	NPC202389
0.7949	Intermediate Similarity	NPC49964
0.7949	Intermediate Similarity	NPC189972
0.7949	Intermediate Similarity	NPC50964
0.7949	Intermediate Similarity	NPC101462
0.7949	Intermediate Similarity	NPC87489
0.7945	Intermediate Similarity	NPC259049
0.7922	Intermediate Similarity	NPC206062
0.7922	Intermediate Similarity	NPC96362
0.7922	Intermediate Similarity	NPC241290
0.7922	Intermediate Similarity	NPC209944
0.7922	Intermediate Similarity	NPC164840
0.7922	Intermediate Similarity	NPC148685
0.7922	Intermediate Similarity	NPC157895
0.7922	Intermediate Similarity	NPC104120
0.791	Intermediate Similarity	NPC240506
0.7895	Intermediate Similarity	NPC473943
0.7895	Intermediate Similarity	NPC477514
0.7895	Intermediate Similarity	NPC11908
0.7887	Intermediate Similarity	NPC276616
0.7887	Intermediate Similarity	NPC160209
0.7887	Intermediate Similarity	NPC32055
0.7887	Intermediate Similarity	NPC245795
0.7867	Intermediate Similarity	NPC122418
0.7867	Intermediate Similarity	NPC321016
0.7867	Intermediate Similarity	NPC120098
0.7867	Intermediate Similarity	NPC240604
0.7867	Intermediate Similarity	NPC189883
0.7867	Intermediate Similarity	NPC202642
0.7867	Intermediate Similarity	NPC265328
0.7867	Intermediate Similarity	NPC30590
0.7867	Intermediate Similarity	NPC290598
0.7867	Intermediate Similarity	NPC106364
0.7867	Intermediate Similarity	NPC129165
0.7867	Intermediate Similarity	NPC300324
0.7867	Intermediate Similarity	NPC27765
0.7867	Intermediate Similarity	NPC96319
0.7867	Intermediate Similarity	NPC107059
0.7867	Intermediate Similarity	NPC321381
0.7867	Intermediate Similarity	NPC470362
0.7867	Intermediate Similarity	NPC263582
0.7867	Intermediate Similarity	NPC46160
0.7867	Intermediate Similarity	NPC113733
0.7867	Intermediate Similarity	NPC134330
0.7857	Intermediate Similarity	NPC149680
0.7857	Intermediate Similarity	NPC326310
0.7857	Intermediate Similarity	NPC267027
0.7857	Intermediate Similarity	NPC476406
0.7848	Intermediate Similarity	NPC317458
0.7848	Intermediate Similarity	NPC475789
0.7848	Intermediate Similarity	NPC474634
0.7848	Intermediate Similarity	NPC470384
0.7846	Intermediate Similarity	NPC179024
0.7838	Intermediate Similarity	NPC477138
0.7838	Intermediate Similarity	NPC91858
0.7838	Intermediate Similarity	NPC243342
0.7826	Intermediate Similarity	NPC101128
0.7826	Intermediate Similarity	NPC309300
0.7821	Intermediate Similarity	NPC474683
0.7821	Intermediate Similarity	NPC7505
0.7821	Intermediate Similarity	NPC474759
0.7821	Intermediate Similarity	NPC47761
0.7821	Intermediate Similarity	NPC474731
0.7821	Intermediate Similarity	NPC82986
0.7821	Intermediate Similarity	NPC474752
0.7821	Intermediate Similarity	NPC249423
0.7821	Intermediate Similarity	NPC6663
0.7808	Intermediate Similarity	NPC242992
0.7794	Intermediate Similarity	NPC79576
0.7794	Intermediate Similarity	NPC194208
0.7794	Intermediate Similarity	NPC68679
0.7794	Intermediate Similarity	NPC321867
0.7794	Intermediate Similarity	NPC282694
0.7794	Intermediate Similarity	NPC207007
0.7778	Intermediate Similarity	NPC9942
0.7763	Intermediate Similarity	NPC130136
0.7763	Intermediate Similarity	NPC90979
0.7763	Intermediate Similarity	NPC157996
0.7763	Intermediate Similarity	NPC34019
0.7763	Intermediate Similarity	NPC472805
0.7763	Intermediate Similarity	NPC471798
0.7763	Intermediate Similarity	NPC214570
0.7763	Intermediate Similarity	NPC34177
0.7763	Intermediate Similarity	NPC155986
0.7763	Intermediate Similarity	NPC198968
0.7763	Intermediate Similarity	NPC101475
0.7763	Intermediate Similarity	NPC203403
0.7763	Intermediate Similarity	NPC40394
0.7763	Intermediate Similarity	NPC318495
0.775	Intermediate Similarity	NPC83702
0.775	Intermediate Similarity	NPC238485
0.775	Intermediate Similarity	NPC205845
0.775	Intermediate Similarity	NPC474047
0.775	Intermediate Similarity	NPC231310

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 NPC474248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1835
0.2-0.3	4280
0.3-0.4	2042
0.4-0.5	460
0.5-0.6	233
0.6-0.7	85
0.7-0.8	25
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
0.7973	Intermediate Similarity	NPD7339	Approved
0.7973	Intermediate Similarity	NPD6942	Approved
0.7969	Intermediate Similarity	NPD342	Phase 1
0.7867	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD368	Approved
0.7733	Intermediate Similarity	NPD8264	Approved
0.7564	Intermediate Similarity	NPD7645	Phase 2
0.747	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6924	Approved
0.7368	Intermediate Similarity	NPD6926	Approved
0.7342	Intermediate Similarity	NPD6929	Approved
0.7333	Intermediate Similarity	NPD4243	Approved
0.7297	Intermediate Similarity	NPD6922	Approved
0.7297	Intermediate Similarity	NPD6923	Approved
0.7284	Intermediate Similarity	NPD3667	Approved
0.725	Intermediate Similarity	NPD6931	Approved
0.725	Intermediate Similarity	NPD6930	Phase 2
0.725	Intermediate Similarity	NPD7525	Registered
0.7215	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7144	Approved
0.72	Intermediate Similarity	NPD7143	Approved
0.7179	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD4784	Approved
0.7143	Intermediate Similarity	NPD4785	Approved
0.7108	Intermediate Similarity	NPD4786	Approved
0.7108	Intermediate Similarity	NPD3665	Phase 1
0.7108	Intermediate Similarity	NPD3666	Approved
0.7108	Intermediate Similarity	NPD3133	Approved
0.7105	Intermediate Similarity	NPD7151	Approved
0.7105	Intermediate Similarity	NPD7152	Approved
0.7105	Intermediate Similarity	NPD7150	Approved
0.7089	Intermediate Similarity	NPD5776	Phase 2
0.7089	Intermediate Similarity	NPD6925	Approved
0.7059	Intermediate Similarity	NPD4219	Approved
0.7051	Intermediate Similarity	NPD4190	Phase 3
0.7051	Intermediate Similarity	NPD5275	Approved
0.7037	Intermediate Similarity	NPD7332	Phase 2
0.7037	Intermediate Similarity	NPD7514	Phase 3
0.7	Intermediate Similarity	NPD7145	Approved
0.6988	Remote Similarity	NPD6695	Phase 3
0.6951	Remote Similarity	NPD6902	Approved
0.6941	Remote Similarity	NPD3618	Phase 1
0.6905	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7509	Discontinued
0.6829	Remote Similarity	NPD4748	Discontinued
0.6824	Remote Similarity	NPD6893	Approved
0.6747	Remote Similarity	NPD6898	Phase 1
0.6744	Remote Similarity	NPD5279	Phase 3
0.6744	Remote Similarity	NPD4519	Discontinued
0.6744	Remote Similarity	NPD4623	Approved
0.6707	Remote Similarity	NPD4195	Approved
0.6705	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6556	Remote Similarity	NPD7515	Phase 2
0.6556	Remote Similarity	NPD6079	Approved
0.6517	Remote Similarity	NPD4753	Phase 2
0.6512	Remote Similarity	NPD3668	Phase 3
0.6506	Remote Similarity	NPD6683	Phase 2
0.6484	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6437	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD4695	Discontinued
0.6421	Remote Similarity	NPD7640	Approved
0.6421	Remote Similarity	NPD7639	Approved
0.6375	Remote Similarity	NPD4732	Discontinued
0.6374	Remote Similarity	NPD7087	Discontinued
0.6333	Remote Similarity	NPD6051	Approved
0.6322	Remote Similarity	NPD4197	Approved
0.6316	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD7638	Approved
0.6304	Remote Similarity	NPD6399	Phase 3
0.6289	Remote Similarity	NPD5211	Phase 2
0.6277	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4697	Phase 3
0.6277	Remote Similarity	NPD5221	Approved
0.6277	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5329	Approved
0.6237	Remote Similarity	NPD7748	Approved
0.6212	Remote Similarity	NPD385	Approved
0.6212	Remote Similarity	NPD384	Approved
0.6211	Remote Similarity	NPD5173	Approved
0.6211	Remote Similarity	NPD4755	Approved
0.6196	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD3617	Approved
0.619	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5280	Approved
0.618	Remote Similarity	NPD5690	Phase 2
0.618	Remote Similarity	NPD5330	Approved
0.618	Remote Similarity	NPD7334	Approved
0.618	Remote Similarity	NPD4690	Approved
0.618	Remote Similarity	NPD4693	Phase 3
0.618	Remote Similarity	NPD4688	Approved
0.618	Remote Similarity	NPD7146	Approved
0.618	Remote Similarity	NPD6409	Approved
0.618	Remote Similarity	NPD6684	Approved
0.618	Remote Similarity	NPD4689	Approved
0.618	Remote Similarity	NPD4694	Approved
0.618	Remote Similarity	NPD7521	Approved
0.618	Remote Similarity	NPD4138	Approved
0.618	Remote Similarity	NPD5205	Approved
0.617	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD5210	Approved
0.6164	Remote Similarity	NPD287	Approved
0.6162	Remote Similarity	NPD5141	Approved
0.6146	Remote Similarity	NPD5290	Discontinued
0.6136	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5778	Approved
0.6129	Remote Similarity	NPD5779	Approved
0.6092	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7136	Phase 2
0.6082	Remote Similarity	NPD4696	Approved
0.6082	Remote Similarity	NPD5285	Approved
0.6082	Remote Similarity	NPD5286	Approved
0.6082	Remote Similarity	NPD4700	Approved
0.6067	Remote Similarity	NPD1694	Approved
0.6067	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4723	Approved
0.6044	Remote Similarity	NPD4722	Approved
0.6044	Remote Similarity	NPD6903	Approved
0.6044	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD6083	Phase 2
0.6042	Remote Similarity	NPD6084	Phase 2
0.6042	Remote Similarity	NPD7902	Approved
0.6023	Remote Similarity	NPD4788	Approved
0.6022	Remote Similarity	NPD6411	Approved
0.602	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5695	Phase 3
0.5977	Remote Similarity	NPD4692	Approved
0.5977	Remote Similarity	NPD4139	Approved
0.596	Remote Similarity	NPD5225	Approved
0.596	Remote Similarity	NPD5226	Approved
0.596	Remote Similarity	NPD4633	Approved
0.596	Remote Similarity	NPD5224	Approved
0.5952	Remote Similarity	NPD1346	Approved
0.5921	Remote Similarity	NPD4194	Approved
0.5921	Remote Similarity	NPD4191	Approved
0.5921	Remote Similarity	NPD4193	Approved
0.5921	Remote Similarity	NPD4192	Approved
0.59	Remote Similarity	NPD5174	Approved
0.59	Remote Similarity	NPD4754	Approved
0.59	Remote Similarity	NPD5175	Approved
0.59	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5737	Approved
0.587	Remote Similarity	NPD6672	Approved
0.5862	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4820	Approved
0.5862	Remote Similarity	NPD4821	Approved
0.5862	Remote Similarity	NPD4819	Approved
0.5862	Remote Similarity	NPD4822	Approved
0.5859	Remote Similarity	NPD4159	Approved
0.5851	Remote Similarity	NPD5281	Approved
0.5851	Remote Similarity	NPD5284	Approved
0.5846	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5362	Discontinued
0.5843	Remote Similarity	NPD5331	Approved
0.5843	Remote Similarity	NPD5332	Approved
0.5821	Remote Similarity	NPD4265	Approved
0.5816	Remote Similarity	NPD5696	Approved
0.5814	Remote Similarity	NPD4271	Approved
0.5814	Remote Similarity	NPD4268	Approved
0.5806	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6101	Approved
0.5802	Remote Similarity	NPD791	Approved
0.5802	Remote Similarity	NPD15	Approved
0.5802	Remote Similarity	NPD4137	Phase 3
0.58	Remote Similarity	NPD7632	Discontinued
0.5795	Remote Similarity	NPD4790	Discontinued
0.5784	Remote Similarity	NPD6402	Approved
0.5784	Remote Similarity	NPD6675	Approved
0.5784	Remote Similarity	NPD7128	Approved
0.5784	Remote Similarity	NPD4768	Approved
0.5784	Remote Similarity	NPD4767	Approved
0.5784	Remote Similarity	NPD5739	Approved
0.5758	Remote Similarity	NPD6404	Discontinued
0.5745	Remote Similarity	NPD4096	Approved
0.5732	Remote Similarity	NPD4747	Approved
0.5732	Remote Similarity	NPD4691	Approved
0.573	Remote Similarity	NPD4270	Approved
0.573	Remote Similarity	NPD4269	Approved
0.5729	Remote Similarity	NPD7900	Approved
0.5729	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5697	Approved
0.5728	Remote Similarity	NPD5701	Approved
0.5728	Remote Similarity	NPD6412	Phase 2
0.5696	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD7115	Discovery
0.5682	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7320	Approved
0.5673	Remote Similarity	NPD6881	Approved
0.5673	Remote Similarity	NPD5168	Approved
0.5673	Remote Similarity	NPD6899	Approved
0.5673	Remote Similarity	NPD6011	Approved
0.5673	Remote Similarity	NPD4730	Approved
0.5673	Remote Similarity	NPD4729	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