NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.21
Volume:	297.783
LogP:	4.036
LogD:	3.731
LogS:	-4.484
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	4.142
Fsp3:	0.824
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:	-4.71
MDCK Permeability:	2.7036476240027696e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.157

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.683
Plasma Protein Binding (PPB):	77.8442611694336%
Volume Distribution (VD):	1.684
Pgp-substrate:	28.461078643798828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.116
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.207
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.181
CYP2C9-substrate:	0.447
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.682
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	3.522
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.647
Drug-inuced Liver Injury (DILI):	0.128
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.547
Carcinogencity:	0.079
Eye Corrosion:	0.815
Eye Irritation:	0.963
Respiratory Toxicity:	0.867

Download Data

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

Natural Product: NPC474768

Natural Product ID:	NPC474768
*Common Name:**	(-)-4Alpha-O-Acetyl-Selin-11-En
IUPAC Name:	[(1R,4aR,8aR)-1,4a-dimethyl-7-prop-1-en-2-yl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-yl] acetate
Synonyms:
Standard InCHIKey:	HMOQLGSFVQRRMO-XMMHPARDSA-N
Standard InCHI:	InChI=1S/C17H28O2/c1-12(2)14-7-10-16(4)8-6-9-17(5,15(16)11-14)19-13(3)18/h14-15H,1,6-11H2,2-5H3/t14?,15-,16-,17-/m1/s1
SMILES:	CC(=C)C1CCC2(CCCC(C2C1)(C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481843
PubChem CID:	44575319
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO24464	Nephthea brassica	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[10579864]
NPO24464	Nephthea brassica	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	4

Activity Type	# Activity
Cell Line	4

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	ug ml-1	PMID[523161]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[523161]
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.44	ug ml-1	PMID[523161]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.12	ug ml-1	PMID[523161]

☑ 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 NPC474768 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	202
0.1-0.2	2235
0.2-0.3	11624
0.3-0.4	13309
0.4-0.5	6706
0.5-0.6	5860
0.6-0.7	2477
0.7-0.8	275
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8286	Intermediate Similarity	NPC71152
0.8194	Intermediate Similarity	NPC84868
0.8108	Intermediate Similarity	NPC206735
0.8095	Intermediate Similarity	NPC240206
0.8095	Intermediate Similarity	NPC474769
0.8095	Intermediate Similarity	NPC189290
0.8056	Intermediate Similarity	NPC92489
0.8	Intermediate Similarity	NPC476101
0.7973	Intermediate Similarity	NPC47808
0.7973	Intermediate Similarity	NPC305835
0.7973	Intermediate Similarity	NPC263951
0.7945	Intermediate Similarity	NPC132542
0.7941	Intermediate Similarity	NPC469868
0.7917	Intermediate Similarity	NPC39362
0.7895	Intermediate Similarity	NPC476458
0.7895	Intermediate Similarity	NPC476935
0.7895	Intermediate Similarity	NPC258153
0.7867	Intermediate Similarity	NPC304194
0.7826	Intermediate Similarity	NPC139785
0.7792	Intermediate Similarity	NPC476927
0.7792	Intermediate Similarity	NPC473592
0.7778	Intermediate Similarity	NPC264779
0.7763	Intermediate Similarity	NPC290495
0.7763	Intermediate Similarity	NPC475951
0.7763	Intermediate Similarity	NPC195334
0.7761	Intermediate Similarity	NPC101128
0.7733	Intermediate Similarity	NPC118987
0.7703	Intermediate Similarity	NPC283619
0.7692	Intermediate Similarity	NPC306951
0.7662	Intermediate Similarity	NPC472504
0.7662	Intermediate Similarity	NPC286786
0.7647	Intermediate Similarity	NPC258595
0.7647	Intermediate Similarity	NPC64123
0.7639	Intermediate Similarity	NPC279241
0.7639	Intermediate Similarity	NPC12680
0.7632	Intermediate Similarity	NPC269791
0.7632	Intermediate Similarity	NPC170038
0.7632	Intermediate Similarity	NPC474978
0.7595	Intermediate Similarity	NPC164424
0.7576	Intermediate Similarity	NPC204173
0.7571	Intermediate Similarity	NPC290445
0.7571	Intermediate Similarity	NPC36616
0.7568	Intermediate Similarity	NPC104806
0.7564	Intermediate Similarity	NPC471037
0.7564	Intermediate Similarity	NPC5280
0.7564	Intermediate Similarity	NPC139206
0.7564	Intermediate Similarity	NPC132386
0.7564	Intermediate Similarity	NPC473742
0.7536	Intermediate Similarity	NPC42630
0.7536	Intermediate Similarity	NPC103734
0.7536	Intermediate Similarity	NPC84562
0.7534	Intermediate Similarity	NPC475517
0.7534	Intermediate Similarity	NPC18819
0.7534	Intermediate Similarity	NPC46610
0.7534	Intermediate Similarity	NPC474524
0.7532	Intermediate Similarity	NPC223330
0.7532	Intermediate Similarity	NPC20096
0.7532	Intermediate Similarity	NPC48673
0.7532	Intermediate Similarity	NPC209318
0.7532	Intermediate Similarity	NPC142163
0.7532	Intermediate Similarity	NPC170303
0.7532	Intermediate Similarity	NPC108476
0.7532	Intermediate Similarity	NPC232625
0.75	Intermediate Similarity	NPC192999
0.75	Intermediate Similarity	NPC100906
0.75	Intermediate Similarity	NPC471475
0.75	Intermediate Similarity	NPC153987
0.75	Intermediate Similarity	NPC476438
0.75	Intermediate Similarity	NPC44083
0.7468	Intermediate Similarity	NPC299963
0.7468	Intermediate Similarity	NPC239362
0.7468	Intermediate Similarity	NPC475509
0.7467	Intermediate Similarity	NPC219809
0.7467	Intermediate Similarity	NPC66105
0.7467	Intermediate Similarity	NPC474433
0.7467	Intermediate Similarity	NPC472300
0.7436	Intermediate Similarity	NPC226988
0.7436	Intermediate Similarity	NPC2524
0.7436	Intermediate Similarity	NPC474979
0.7436	Intermediate Similarity	NPC256112
0.7429	Intermediate Similarity	NPC476928
0.7429	Intermediate Similarity	NPC185874
0.7429	Intermediate Similarity	NPC253303
0.7429	Intermediate Similarity	NPC139207
0.7429	Intermediate Similarity	NPC269077
0.7407	Intermediate Similarity	NPC30421
0.7407	Intermediate Similarity	NPC476932
0.7407	Intermediate Similarity	NPC166857
0.7403	Intermediate Similarity	NPC469802
0.7403	Intermediate Similarity	NPC233332
0.7403	Intermediate Similarity	NPC274522
0.7403	Intermediate Similarity	NPC476265
0.7397	Intermediate Similarity	NPC330659
0.7397	Intermediate Similarity	NPC244708
0.7397	Intermediate Similarity	NPC36310
0.7397	Intermediate Similarity	NPC161187
0.7391	Intermediate Similarity	NPC60837
0.7391	Intermediate Similarity	NPC11555
0.7391	Intermediate Similarity	NPC282619
0.7391	Intermediate Similarity	NPC172613
0.7391	Intermediate Similarity	NPC2728
0.7391	Intermediate Similarity	NPC208198
0.7375	Intermediate Similarity	NPC98270
0.7375	Intermediate Similarity	NPC474013
0.7375	Intermediate Similarity	NPC191965
0.7368	Intermediate Similarity	NPC321690
0.7368	Intermediate Similarity	NPC321514
0.7368	Intermediate Similarity	NPC63020
0.7361	Intermediate Similarity	NPC235586
0.7361	Intermediate Similarity	NPC163020
0.7361	Intermediate Similarity	NPC91369
0.7342	Intermediate Similarity	NPC52108
0.7342	Intermediate Similarity	NPC474789
0.7333	Intermediate Similarity	NPC20466
0.7333	Intermediate Similarity	NPC476601
0.7333	Intermediate Similarity	NPC470766
0.7333	Intermediate Similarity	NPC198473
0.7324	Intermediate Similarity	NPC94192
0.7324	Intermediate Similarity	NPC244790
0.7317	Intermediate Similarity	NPC93411
0.7308	Intermediate Similarity	NPC327002
0.7308	Intermediate Similarity	NPC25554
0.7297	Intermediate Similarity	NPC22134
0.7297	Intermediate Similarity	NPC166797
0.7284	Intermediate Similarity	NPC471042
0.7284	Intermediate Similarity	NPC286153
0.7284	Intermediate Similarity	NPC10005
0.7284	Intermediate Similarity	NPC474970
0.7284	Intermediate Similarity	NPC185638
0.7284	Intermediate Similarity	NPC9892
0.7284	Intermediate Similarity	NPC91525
0.7284	Intermediate Similarity	NPC9231
0.7284	Intermediate Similarity	NPC168231
0.7284	Intermediate Similarity	NPC137306
0.7284	Intermediate Similarity	NPC325594
0.7284	Intermediate Similarity	NPC329943
0.7284	Intermediate Similarity	NPC73038
0.7284	Intermediate Similarity	NPC84121
0.7273	Intermediate Similarity	NPC283789
0.7273	Intermediate Similarity	NPC231431
0.7273	Intermediate Similarity	NPC242767
0.726	Intermediate Similarity	NPC167706
0.726	Intermediate Similarity	NPC72343
0.725	Intermediate Similarity	NPC96055
0.725	Intermediate Similarity	NPC139566
0.725	Intermediate Similarity	NPC97505
0.725	Intermediate Similarity	NPC471367
0.725	Intermediate Similarity	NPC156981
0.7246	Intermediate Similarity	NPC144650
0.7237	Intermediate Similarity	NPC212661
0.7237	Intermediate Similarity	NPC238227
0.7237	Intermediate Similarity	NPC471035
0.7237	Intermediate Similarity	NPC189206
0.7231	Intermediate Similarity	NPC39068
0.7231	Intermediate Similarity	NPC141699
0.7222	Intermediate Similarity	NPC476431
0.7215	Intermediate Similarity	NPC471159
0.7215	Intermediate Similarity	NPC123880
0.7206	Intermediate Similarity	NPC41160
0.72	Intermediate Similarity	NPC279666
0.72	Intermediate Similarity	NPC192540
0.7195	Intermediate Similarity	NPC478104
0.7195	Intermediate Similarity	NPC162107
0.7195	Intermediate Similarity	NPC175293
0.7195	Intermediate Similarity	NPC264546
0.7195	Intermediate Similarity	NPC46912
0.7183	Intermediate Similarity	NPC88454
0.7183	Intermediate Similarity	NPC117607
0.7183	Intermediate Similarity	NPC41542
0.7183	Intermediate Similarity	NPC263161
0.7183	Intermediate Similarity	NPC101307
0.7179	Intermediate Similarity	NPC281880
0.7179	Intermediate Similarity	NPC37038
0.7179	Intermediate Similarity	NPC267517
0.7162	Intermediate Similarity	NPC472813
0.7162	Intermediate Similarity	NPC177826
0.716	Intermediate Similarity	NPC476602
0.7143	Intermediate Similarity	NPC179028
0.7143	Intermediate Similarity	NPC10274
0.7143	Intermediate Similarity	NPC19311
0.7143	Intermediate Similarity	NPC230047
0.7143	Intermediate Similarity	NPC4827
0.7125	Intermediate Similarity	NPC243347
0.7125	Intermediate Similarity	NPC170862
0.7125	Intermediate Similarity	NPC107253
0.7123	Intermediate Similarity	NPC283316
0.7121	Intermediate Similarity	NPC165808
0.7108	Intermediate Similarity	NPC473879
0.7108	Intermediate Similarity	NPC224145
0.7108	Intermediate Similarity	NPC106332
0.7108	Intermediate Similarity	NPC474845
0.7108	Intermediate Similarity	NPC4309
0.7108	Intermediate Similarity	NPC160304
0.7108	Intermediate Similarity	NPC50847
0.7105	Intermediate Similarity	NPC89294
0.7105	Intermediate Similarity	NPC475744
0.7105	Intermediate Similarity	NPC246445
0.7105	Intermediate Similarity	NPC899
0.7105	Intermediate Similarity	NPC474316
0.7105	Intermediate Similarity	NPC69143

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 NPC474768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	2610
0.2-0.3	4215
0.3-0.4	1460
0.4-0.5	341
0.5-0.6	245
0.6-0.7	90
0.7-0.8	2
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
0.7407	Intermediate Similarity	NPD3573	Approved
0.7073	Intermediate Similarity	NPD6098	Approved
0.6951	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5208	Approved
0.6897	Remote Similarity	NPD6001	Approved
0.6867	Remote Similarity	NPD7146	Approved
0.6867	Remote Similarity	NPD5330	Approved
0.6867	Remote Similarity	NPD7521	Approved
0.6867	Remote Similarity	NPD6684	Approved
0.6867	Remote Similarity	NPD6409	Approved
0.6867	Remote Similarity	NPD7334	Approved
0.686	Remote Similarity	NPD8034	Phase 2
0.686	Remote Similarity	NPD8035	Phase 2
0.6824	Remote Similarity	NPD6673	Approved
0.6824	Remote Similarity	NPD6051	Approved
0.6824	Remote Similarity	NPD6904	Approved
0.6824	Remote Similarity	NPD6080	Approved
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6903	Approved
0.6706	Remote Similarity	NPD5737	Approved
0.6706	Remote Similarity	NPD6672	Approved
0.6705	Remote Similarity	NPD7748	Approved
0.6705	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6625	Remote Similarity	NPD4195	Approved
0.6625	Remote Similarity	NPD7645	Phase 2
0.6579	Remote Similarity	NPD4243	Approved
0.6571	Remote Similarity	NPD1145	Discontinued
0.6552	Remote Similarity	NPD5207	Approved
0.6552	Remote Similarity	NPD5692	Phase 3
0.6543	Remote Similarity	NPD7525	Registered
0.6517	Remote Similarity	NPD5707	Approved
0.6484	Remote Similarity	NPD7902	Approved
0.6477	Remote Similarity	NPD5694	Approved
0.6477	Remote Similarity	NPD7515	Phase 2
0.6477	Remote Similarity	NPD6050	Approved
0.6413	Remote Similarity	NPD7638	Approved
0.641	Remote Similarity	NPD4784	Approved
0.641	Remote Similarity	NPD4785	Approved
0.6404	Remote Similarity	NPD6399	Phase 3
0.6386	Remote Similarity	NPD4223	Phase 3
0.6386	Remote Similarity	NPD4221	Approved
0.6364	Remote Similarity	NPD5777	Approved
0.6353	Remote Similarity	NPD1694	Approved
0.6351	Remote Similarity	NPD4224	Phase 2
0.6344	Remote Similarity	NPD7639	Approved
0.6344	Remote Similarity	NPD7640	Approved
0.6329	Remote Similarity	NPD3702	Approved
0.6329	Remote Similarity	NPD5275	Approved
0.6329	Remote Similarity	NPD4190	Phase 3
0.631	Remote Similarity	NPD4788	Approved
0.6304	Remote Similarity	NPD6083	Phase 2
0.6304	Remote Similarity	NPD6084	Phase 2
0.6279	Remote Similarity	NPD3618	Phase 1
0.6279	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5695	Phase 3
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5696	Approved
0.6237	Remote Similarity	NPD4225	Approved
0.6235	Remote Similarity	NPD4197	Approved
0.6203	Remote Similarity	NPD6926	Approved
0.6203	Remote Similarity	NPD6924	Approved
0.619	Remote Similarity	NPD3667	Approved
0.6186	Remote Similarity	NPD6675	Approved
0.6186	Remote Similarity	NPD7128	Approved
0.6186	Remote Similarity	NPD6008	Approved
0.6186	Remote Similarity	NPD5739	Approved
0.6186	Remote Similarity	NPD6402	Approved
0.6163	Remote Similarity	NPD5329	Approved
0.6145	Remote Similarity	NPD4695	Discontinued
0.6125	Remote Similarity	NPD6942	Approved
0.6125	Remote Similarity	NPD7339	Approved
0.6122	Remote Similarity	NPD5697	Approved
0.6122	Remote Similarity	NPD5701	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6104	Remote Similarity	NPD4137	Phase 3
0.6098	Remote Similarity	NPD3617	Approved
0.6092	Remote Similarity	NPD4138	Approved
0.6092	Remote Similarity	NPD4623	Approved
0.6092	Remote Similarity	NPD4690	Approved
0.6092	Remote Similarity	NPD4693	Phase 3
0.6092	Remote Similarity	NPD4519	Discontinued
0.6092	Remote Similarity	NPD4689	Approved
0.6092	Remote Similarity	NPD5205	Approved
0.6092	Remote Similarity	NPD4688	Approved
0.6087	Remote Similarity	NPD5654	Approved
0.6067	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5328	Approved
0.6061	Remote Similarity	NPD7320	Approved
0.6061	Remote Similarity	NPD6011	Approved
0.6061	Remote Similarity	NPD6899	Approved
0.6061	Remote Similarity	NPD6881	Approved
0.6049	Remote Similarity	NPD6933	Approved
0.6049	Remote Similarity	NPD6117	Approved
0.6047	Remote Similarity	NPD3668	Phase 3
0.6047	Remote Similarity	NPD3665	Phase 1
0.6047	Remote Similarity	NPD3133	Approved
0.6047	Remote Similarity	NPD3666	Approved
0.6047	Remote Similarity	NPD4786	Approved
0.6044	Remote Similarity	NPD4202	Approved
0.6026	Remote Similarity	NPD4747	Approved
0.6026	Remote Similarity	NPD4691	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5979	Remote Similarity	NPD6052	Approved
0.5976	Remote Similarity	NPD6116	Phase 1
0.5974	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD5360	Phase 3
0.5974	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5959	Approved
0.5952	Remote Similarity	NPD7509	Discontinued
0.5949	Remote Similarity	NPD6081	Approved
0.5941	Remote Similarity	NPD7290	Approved
0.5941	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD7102	Approved
0.5934	Remote Similarity	NPD6411	Approved
0.5934	Remote Similarity	NPD6079	Approved
0.593	Remote Similarity	NPD6695	Phase 3
0.5926	Remote Similarity	NPD8039	Approved
0.5909	Remote Similarity	NPD4694	Approved
0.5909	Remote Similarity	NPD5280	Approved
0.5909	Remote Similarity	NPD5690	Phase 2
0.5904	Remote Similarity	NPD6697	Approved
0.5904	Remote Similarity	NPD6115	Approved
0.5904	Remote Similarity	NPD6118	Approved
0.5904	Remote Similarity	NPD6114	Approved
0.5889	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD8130	Phase 1
0.5882	Remote Similarity	NPD6847	Approved
0.5882	Remote Similarity	NPD6617	Approved
0.5882	Remote Similarity	NPD6649	Approved
0.5882	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6869	Approved
0.5882	Remote Similarity	NPD4692	Approved
0.5882	Remote Similarity	NPD4139	Approved
0.5882	Remote Similarity	NPD6650	Approved
0.5876	Remote Similarity	NPD7632	Discontinued
0.5873	Remote Similarity	NPD367	Approved
0.5867	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD7732	Phase 3
0.5825	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD8297	Approved
0.5802	Remote Similarity	NPD4058	Approved
0.58	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6614	Approved
0.5789	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4755	Approved
0.5765	Remote Similarity	NPD6930	Phase 2
0.5765	Remote Similarity	NPD4748	Discontinued
0.5765	Remote Similarity	NPD6931	Approved
0.5761	Remote Similarity	NPD7637	Suspended
0.575	Remote Similarity	NPD4758	Discontinued
0.5743	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6101	Approved
0.5696	Remote Similarity	NPD6923	Approved
0.5696	Remote Similarity	NPD6922	Approved
0.5696	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7614	Phase 1
0.5684	Remote Similarity	NPD4697	Phase 3
0.5684	Remote Similarity	NPD5221	Approved
0.5684	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5222	Approved
0.5684	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.567	Remote Similarity	NPD4696	Approved
0.567	Remote Similarity	NPD5285	Approved
0.567	Remote Similarity	NPD4700	Approved
0.567	Remote Similarity	NPD5286	Approved
0.5667	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7524	Approved
0.566	Remote Similarity	NPD6274	Approved
0.5647	Remote Similarity	NPD6929	Approved
0.5631	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7143	Approved
0.5625	Remote Similarity	NPD7144	Approved
0.5625	Remote Similarity	NPD2687	Approved
0.5625	Remote Similarity	NPD5173	Approved
0.5625	Remote Similarity	NPD2686	Approved
0.5625	Remote Similarity	NPD2254	Approved
0.5619	Remote Similarity	NPD4632	Approved
0.5619	Remote Similarity	NPD8133	Approved
0.5612	Remote Similarity	NPD5223	Approved
0.561	Remote Similarity	NPD4687	Approved
0.561	Remote Similarity	NPD5733	Approved
0.5607	Remote Similarity	NPD6317	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