NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.17
Volume:	266.061
LogP:	2.714
LogD:	2.597
LogS:	-3.595
# Rotatable Bonds:	1
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	6.146
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.651
MDCK Permeability:	1.9626240828074515e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.441
Plasma Protein Binding (PPB):	56.12699890136719%
Volume Distribution (VD):	1.337
Pgp-substrate:	50.58228302001953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.128
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.085
CYP2C9-substrate:	0.179
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.315
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	6.431
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.519
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.249
Carcinogencity:	0.937
Eye Corrosion:	0.02
Eye Irritation:	0.518
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC133580

Natural Product ID:	NPC133580
*Common Name:**	MEARYUDHAHZZAZ-FDEJFUCISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MEARYUDHAHZZAZ-FDEJFUCISA-N
Standard InCHI:	InChI=1S/C15H24O3/c1-10-6-5-7-14(4)9-12-11(13(2,3)16)8-15(10,14)18-17-12/h8,10,12,16H,5-7,9H2,1-4H3/t10-,12+,14-,15-/m0/s1
SMILES:	C[C@H]1CCC[C@@]2(C)C[C@@H]3C(=C[C@]12OO3)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251442
PubChem CID:	23642708
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
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[17845002]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24370010]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722490]
NPO13916	Nephthea erecta	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	>	10.0	ug ml-1	PMID[568992]
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[568992]

☑ 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 NPC133580 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	187
0.1-0.2	1472
0.2-0.3	5864
0.3-0.4	16126
0.4-0.5	9087
0.5-0.6	6334
0.6-0.7	2955
0.7-0.8	611
0.8-0.85	54
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9155	High Similarity	NPC259049
0.8493	Intermediate Similarity	NPC23954
0.8421	Intermediate Similarity	NPC470711
0.8421	Intermediate Similarity	NPC470758
0.8378	Intermediate Similarity	NPC220939
0.8378	Intermediate Similarity	NPC265485
0.8356	Intermediate Similarity	NPC34834
0.8289	Intermediate Similarity	NPC470749
0.8267	Intermediate Similarity	NPC201048
0.8267	Intermediate Similarity	NPC476366
0.8243	Intermediate Similarity	NPC471272
0.8243	Intermediate Similarity	NPC164022
0.8219	Intermediate Similarity	NPC474248
0.8182	Intermediate Similarity	NPC91594
0.8158	Intermediate Similarity	NPC32832
0.8108	Intermediate Similarity	NPC92801
0.8095	Intermediate Similarity	NPC101886
0.8082	Intermediate Similarity	NPC471238
0.8082	Intermediate Similarity	NPC96484
0.8056	Intermediate Similarity	NPC202017
0.8052	Intermediate Similarity	NPC265588
0.8028	Intermediate Similarity	NPC96793
0.8028	Intermediate Similarity	NPC323424
0.8	Intermediate Similarity	NPC14380
0.8	Intermediate Similarity	NPC476646
0.8	Intermediate Similarity	NPC167706
0.8	Intermediate Similarity	NPC249423
0.8	Intermediate Similarity	NPC477792
0.7976	Intermediate Similarity	NPC212596
0.7976	Intermediate Similarity	NPC4574
0.7973	Intermediate Similarity	NPC471560
0.7945	Intermediate Similarity	NPC68703
0.7945	Intermediate Similarity	NPC69649
0.7945	Intermediate Similarity	NPC171225
0.7927	Intermediate Similarity	NPC83702
0.7927	Intermediate Similarity	NPC205845
0.7917	Intermediate Similarity	NPC258595
0.7901	Intermediate Similarity	NPC155521
0.7901	Intermediate Similarity	NPC87489
0.7901	Intermediate Similarity	NPC49964
0.7901	Intermediate Similarity	NPC101462
0.7901	Intermediate Similarity	NPC296701
0.7901	Intermediate Similarity	NPC218616
0.7887	Intermediate Similarity	NPC81615
0.7887	Intermediate Similarity	NPC174956
0.7875	Intermediate Similarity	NPC295131
0.7875	Intermediate Similarity	NPC96362
0.7867	Intermediate Similarity	NPC283316
0.7857	Intermediate Similarity	NPC304083
0.7848	Intermediate Similarity	NPC167891
0.7848	Intermediate Similarity	NPC83351
0.7848	Intermediate Similarity	NPC11908
0.7838	Intermediate Similarity	NPC276616
0.7821	Intermediate Similarity	NPC253190
0.7821	Intermediate Similarity	NPC247325
0.7821	Intermediate Similarity	NPC244488
0.7808	Intermediate Similarity	NPC279434
0.7792	Intermediate Similarity	NPC306727
0.7792	Intermediate Similarity	NPC471797
0.7792	Intermediate Similarity	NPC91858
0.7791	Intermediate Similarity	NPC470390
0.7791	Intermediate Similarity	NPC270511
0.7791	Intermediate Similarity	NPC245410
0.7791	Intermediate Similarity	NPC192437
0.7778	Intermediate Similarity	NPC264245
0.7778	Intermediate Similarity	NPC47761
0.7778	Intermediate Similarity	NPC101128
0.7765	Intermediate Similarity	NPC475605
0.7763	Intermediate Similarity	NPC471268
0.7763	Intermediate Similarity	NPC471271
0.775	Intermediate Similarity	NPC143182
0.775	Intermediate Similarity	NPC81306
0.775	Intermediate Similarity	NPC30986
0.775	Intermediate Similarity	NPC273410
0.775	Intermediate Similarity	NPC109546
0.775	Intermediate Similarity	NPC80530
0.775	Intermediate Similarity	NPC84694
0.775	Intermediate Similarity	NPC209430
0.775	Intermediate Similarity	NPC47982
0.775	Intermediate Similarity	NPC233295
0.775	Intermediate Similarity	NPC28862
0.7746	Intermediate Similarity	NPC321867
0.7746	Intermediate Similarity	NPC207007
0.7746	Intermediate Similarity	NPC68679
0.7738	Intermediate Similarity	NPC6391
0.7738	Intermediate Similarity	NPC299068
0.7733	Intermediate Similarity	NPC473893
0.7733	Intermediate Similarity	NPC234511
0.7722	Intermediate Similarity	NPC475025
0.7722	Intermediate Similarity	NPC130136
0.7722	Intermediate Similarity	NPC474230
0.7711	Intermediate Similarity	NPC231310
0.7711	Intermediate Similarity	NPC185568
0.7703	Intermediate Similarity	NPC139207
0.7703	Intermediate Similarity	NPC185874
0.7703	Intermediate Similarity	NPC114651
0.7692	Intermediate Similarity	NPC291503
0.7683	Intermediate Similarity	NPC202389
0.7674	Intermediate Similarity	NPC470361
0.7671	Intermediate Similarity	NPC282619
0.7671	Intermediate Similarity	NPC208198
0.7671	Intermediate Similarity	NPC2728
0.7671	Intermediate Similarity	NPC172613
0.7671	Intermediate Similarity	NPC11555
0.7671	Intermediate Similarity	NPC60837
0.7662	Intermediate Similarity	NPC182717
0.7662	Intermediate Similarity	NPC474743
0.7662	Intermediate Similarity	NPC471799
0.7662	Intermediate Similarity	NPC474140
0.7662	Intermediate Similarity	NPC130665
0.7654	Intermediate Similarity	NPC234193
0.7654	Intermediate Similarity	NPC471266
0.7654	Intermediate Similarity	NPC322313
0.7654	Intermediate Similarity	NPC164840
0.7654	Intermediate Similarity	NPC95124
0.7654	Intermediate Similarity	NPC209944
0.7654	Intermediate Similarity	NPC206062
0.7654	Intermediate Similarity	NPC236237
0.7654	Intermediate Similarity	NPC102253
0.7654	Intermediate Similarity	NPC241290
0.7647	Intermediate Similarity	NPC470620
0.7647	Intermediate Similarity	NPC149224
0.7632	Intermediate Similarity	NPC189745
0.7625	Intermediate Similarity	NPC474216
0.7625	Intermediate Similarity	NPC230295
0.7625	Intermediate Similarity	NPC300499
0.7625	Intermediate Similarity	NPC196753
0.7625	Intermediate Similarity	NPC476314
0.7625	Intermediate Similarity	NPC473943
0.7625	Intermediate Similarity	NPC477514
0.7625	Intermediate Similarity	NPC6978
0.7625	Intermediate Similarity	NPC138621
0.7625	Intermediate Similarity	NPC167037
0.7625	Intermediate Similarity	NPC253807
0.7625	Intermediate Similarity	NPC158662
0.7625	Intermediate Similarity	NPC285761
0.7625	Intermediate Similarity	NPC98386
0.7625	Intermediate Similarity	NPC244385
0.7619	Intermediate Similarity	NPC266511
0.7619	Intermediate Similarity	NPC471344
0.7619	Intermediate Similarity	NPC318390
0.7619	Intermediate Similarity	NPC274448
0.7619	Intermediate Similarity	NPC470360
0.7606	Intermediate Similarity	NPC66020
0.7606	Intermediate Similarity	NPC240506
0.76	Intermediate Similarity	NPC94192
0.76	Intermediate Similarity	NPC245795
0.76	Intermediate Similarity	NPC208999
0.76	Intermediate Similarity	NPC266578
0.7595	Intermediate Similarity	NPC106432
0.759	Intermediate Similarity	NPC185605
0.759	Intermediate Similarity	NPC82623
0.759	Intermediate Similarity	NPC470384
0.759	Intermediate Similarity	NPC475789
0.759	Intermediate Similarity	NPC474634
0.759	Intermediate Similarity	NPC134481
0.7586	Intermediate Similarity	NPC80561
0.7586	Intermediate Similarity	NPC291484
0.7586	Intermediate Similarity	NPC204188
0.7586	Intermediate Similarity	NPC11216
0.7586	Intermediate Similarity	NPC329596
0.7586	Intermediate Similarity	NPC3345
0.7568	Intermediate Similarity	NPC476406
0.7564	Intermediate Similarity	NPC243342
0.7564	Intermediate Similarity	NPC477138
0.7564	Intermediate Similarity	NPC100334
0.7561	Intermediate Similarity	NPC23852
0.7561	Intermediate Similarity	NPC209620
0.7561	Intermediate Similarity	NPC471270
0.7558	Intermediate Similarity	NPC133588
0.7558	Intermediate Similarity	NPC67872
0.7558	Intermediate Similarity	NPC471952
0.7534	Intermediate Similarity	NPC107540
0.7534	Intermediate Similarity	NPC225415
0.7534	Intermediate Similarity	NPC68656
0.7534	Intermediate Similarity	NPC300593
0.7532	Intermediate Similarity	NPC242992
0.7532	Intermediate Similarity	NPC242001
0.7532	Intermediate Similarity	NPC110799
0.7531	Intermediate Similarity	NPC31258
0.7531	Intermediate Similarity	NPC291379
0.7531	Intermediate Similarity	NPC53744
0.7529	Intermediate Similarity	NPC261266
0.7529	Intermediate Similarity	NPC476104
0.7529	Intermediate Similarity	NPC255143
0.7529	Intermediate Similarity	NPC262085
0.7529	Intermediate Similarity	NPC470955
0.7529	Intermediate Similarity	NPC293287
0.7529	Intermediate Similarity	NPC152808
0.75	Intermediate Similarity	NPC101475
0.75	Intermediate Similarity	NPC194208
0.75	Intermediate Similarity	NPC472805
0.75	Intermediate Similarity	NPC157996
0.75	Intermediate Similarity	NPC198968
0.75	Intermediate Similarity	NPC79576
0.75	Intermediate Similarity	NPC471798
0.75	Intermediate Similarity	NPC474047
0.75	Intermediate Similarity	NPC74995
0.75	Intermediate Similarity	NPC318495
0.75	Intermediate Similarity	NPC475027

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 NPC133580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1751
0.2-0.3	4128
0.3-0.4	2243
0.4-0.5	506
0.5-0.6	217
0.6-0.7	117
0.7-0.8	21
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
0.7746	Intermediate Similarity	NPD368	Approved
0.7654	Intermediate Similarity	NPD7525	Registered
0.7531	Intermediate Similarity	NPD7645	Phase 2
0.7375	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6942	Approved
0.725	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6930	Phase 2
0.7229	Intermediate Similarity	NPD6931	Approved
0.7125	Intermediate Similarity	NPD6924	Approved
0.7125	Intermediate Similarity	NPD6926	Approved
0.7108	Intermediate Similarity	NPD6929	Approved
0.7093	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4243	Approved
0.7037	Intermediate Similarity	NPD8264	Approved
0.7024	Intermediate Similarity	NPD7514	Phase 3
0.7024	Intermediate Similarity	NPD7332	Phase 2
0.6988	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6695	Phase 3
0.6951	Remote Similarity	NPD6933	Approved
0.6914	Remote Similarity	NPD4784	Approved
0.6914	Remote Similarity	NPD4785	Approved
0.6901	Remote Similarity	NPD342	Phase 1
0.6867	Remote Similarity	NPD5776	Phase 2
0.6867	Remote Similarity	NPD6925	Approved
0.686	Remote Similarity	NPD3667	Approved
0.6829	Remote Similarity	NPD4190	Phase 3
0.6829	Remote Similarity	NPD5275	Approved
0.6824	Remote Similarity	NPD7509	Discontinued
0.6818	Remote Similarity	NPD6893	Approved
0.6786	Remote Similarity	NPD7145	Approved
0.6744	Remote Similarity	NPD6898	Phase 1
0.6744	Remote Similarity	NPD6902	Approved
0.6742	Remote Similarity	NPD4519	Discontinued
0.6742	Remote Similarity	NPD3618	Phase 1
0.6742	Remote Similarity	NPD4623	Approved
0.6706	Remote Similarity	NPD4195	Approved
0.6705	Remote Similarity	NPD4786	Approved
0.6705	Remote Similarity	NPD3666	Approved
0.6705	Remote Similarity	NPD3665	Phase 1
0.6705	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6633	Remote Similarity	NPD5211	Phase 2
0.6628	Remote Similarity	NPD4748	Discontinued
0.6625	Remote Similarity	NPD6923	Approved
0.6625	Remote Similarity	NPD6922	Approved
0.6562	Remote Similarity	NPD4755	Approved
0.6543	Remote Similarity	NPD7144	Approved
0.6543	Remote Similarity	NPD7143	Approved
0.6522	Remote Similarity	NPD5328	Approved
0.6522	Remote Similarity	NPD4753	Phase 2
0.6512	Remote Similarity	NPD6683	Phase 2
0.65	Remote Similarity	NPD5141	Approved
0.6477	Remote Similarity	NPD4223	Phase 3
0.6477	Remote Similarity	NPD4221	Approved
0.6463	Remote Similarity	NPD7151	Approved
0.6463	Remote Similarity	NPD7152	Approved
0.6463	Remote Similarity	NPD7150	Approved
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD7639	Approved
0.6429	Remote Similarity	NPD4700	Approved
0.6429	Remote Similarity	NPD7640	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.6386	Remote Similarity	NPD4732	Discontinued
0.6383	Remote Similarity	NPD7087	Discontinued
0.6383	Remote Similarity	NPD7515	Phase 2
0.6383	Remote Similarity	NPD6079	Approved
0.6374	Remote Similarity	NPD5279	Phase 3
0.6344	Remote Similarity	NPD6051	Approved
0.6333	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD4197	Approved
0.6327	Remote Similarity	NPD7638	Approved
0.6327	Remote Similarity	NPD4225	Approved
0.6316	Remote Similarity	NPD6399	Phase 3
0.63	Remote Similarity	NPD5225	Approved
0.63	Remote Similarity	NPD5226	Approved
0.63	Remote Similarity	NPD5224	Approved
0.63	Remote Similarity	NPD4633	Approved
0.6264	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD4695	Discontinued
0.6238	Remote Similarity	NPD5174	Approved
0.6238	Remote Similarity	NPD5175	Approved
0.6224	Remote Similarity	NPD7902	Approved
0.62	Remote Similarity	NPD5223	Approved
0.6196	Remote Similarity	NPD5690	Phase 2
0.6196	Remote Similarity	NPD4690	Approved
0.6196	Remote Similarity	NPD4689	Approved
0.6196	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5205	Approved
0.6196	Remote Similarity	NPD4694	Approved
0.6196	Remote Similarity	NPD4138	Approved
0.6196	Remote Similarity	NPD4693	Phase 3
0.6196	Remote Similarity	NPD4688	Approved
0.6196	Remote Similarity	NPD5280	Approved
0.6186	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD5210	Approved
0.6186	Remote Similarity	NPD5695	Phase 3
0.6133	Remote Similarity	NPD4219	Approved
0.6122	Remote Similarity	NPD5221	Approved
0.6122	Remote Similarity	NPD4697	Phase 3
0.6122	Remote Similarity	NPD5222	Approved
0.6122	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7128	Approved
0.6117	Remote Similarity	NPD4767	Approved
0.6117	Remote Similarity	NPD6675	Approved
0.6117	Remote Similarity	NPD6402	Approved
0.6117	Remote Similarity	NPD4768	Approved
0.6117	Remote Similarity	NPD5739	Approved
0.6087	Remote Similarity	NPD1696	Phase 3
0.6087	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4754	Approved
0.6067	Remote Similarity	NPD4819	Approved
0.6067	Remote Similarity	NPD4822	Approved
0.6067	Remote Similarity	NPD4821	Approved
0.6067	Remote Similarity	NPD4820	Approved
0.6064	Remote Similarity	NPD4722	Approved
0.6064	Remote Similarity	NPD4723	Approved
0.6061	Remote Similarity	NPD6084	Phase 2
0.6061	Remote Similarity	NPD6083	Phase 2
0.6061	Remote Similarity	NPD5173	Approved
0.6058	Remote Similarity	NPD5697	Approved
0.6058	Remote Similarity	NPD5701	Approved
0.6044	Remote Similarity	NPD4788	Approved
0.6042	Remote Similarity	NPD7637	Suspended
0.6042	Remote Similarity	NPD6411	Approved
0.6042	Remote Similarity	NPD5281	Approved
0.6042	Remote Similarity	NPD5284	Approved
0.604	Remote Similarity	NPD4159	Approved
0.6024	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3617	Approved
0.6022	Remote Similarity	NPD7521	Approved
0.6022	Remote Similarity	NPD5330	Approved
0.6022	Remote Similarity	NPD7334	Approved
0.6022	Remote Similarity	NPD6409	Approved
0.6022	Remote Similarity	NPD6684	Approved
0.6022	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD5696	Approved
0.6	Remote Similarity	NPD5290	Discontinued
0.6	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD4692	Approved
0.6	Remote Similarity	NPD4139	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD6899	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD7320	Approved
0.5978	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1346	Approved
0.5957	Remote Similarity	NPD3573	Approved
0.5946	Remote Similarity	NPD7328	Approved
0.5946	Remote Similarity	NPD7327	Approved
0.5943	Remote Similarity	NPD6012	Approved
0.5943	Remote Similarity	NPD6013	Approved
0.5943	Remote Similarity	NPD6014	Approved
0.5943	Remote Similarity	NPD6373	Approved
0.5943	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD7136	Phase 2
0.5934	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7503	Approved
0.5918	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7900	Approved
0.5914	Remote Similarity	NPD1694	Approved
0.5905	Remote Similarity	NPD6412	Phase 2
0.5895	Remote Similarity	NPD6903	Approved
0.5895	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD7516	Approved
0.5888	Remote Similarity	NPD6883	Approved
0.5888	Remote Similarity	NPD7290	Approved
0.5888	Remote Similarity	NPD5250	Approved
0.5888	Remote Similarity	NPD5249	Phase 3
0.5888	Remote Similarity	NPD4634	Approved
0.5888	Remote Similarity	NPD5248	Approved
0.5888	Remote Similarity	NPD7102	Approved
0.5888	Remote Similarity	NPD5247	Approved
0.5888	Remote Similarity	NPD5251	Approved
0.5882	Remote Similarity	NPD5344	Discontinued
0.5876	Remote Similarity	NPD8034	Phase 2
0.5876	Remote Similarity	NPD8035	Phase 2
0.5849	Remote Similarity	NPD6011	Approved
0.5843	Remote Similarity	NPD4271	Approved
0.5843	Remote Similarity	NPD4268	Approved
0.5843	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD8377	Approved
0.5841	Remote Similarity	NPD8294	Approved
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD791	Approved
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD5217	Approved
0.5833	Remote Similarity	NPD6847	Approved
0.5833	Remote Similarity	NPD6649	Approved
0.5833	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD6869	Approved
0.5833	Remote Similarity	NPD5216	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