NPASS Compound

Structure

NPC474790 OpenBabel07101719252D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.5254 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0997 4.9449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3943 3.8744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4817 3.0428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4598 3.2507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7688 4.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7470 4.4097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0560 5.3607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4161 3.6665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 29 1 0 0 0 0 5 29 1 0 0 0 0 8 35 1 0 0 0 0 9 11 1 0 0 0 0 9 13 2 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 27 1 0 0 0 0 23 32 2 0 0 0 0 24 29 1 0 0 0 0 24 30 1 1 0 0 0 25 30 1 6 0 0 0 25 31 1 0 0 0 0 26 29 1 0 0 0 0 26 33 2 0 0 0 0 27 31 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 30 6 1 1 0 0 0 31 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.31
Volume:	533.132
LogP:	4.441
LogD:	4.23
LogS:	-5.323
# Rotatable Bonds:	6
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.245
Synthetic Accessibility Score:	4.625
Fsp3:	0.581
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:	-5.075
MDCK Permeability:	2.373004099354148e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	95.5482406616211%
Volume Distribution (VD):	1.233
Pgp-substrate:	5.195535182952881%

ADMET: Metabolism

CYP1A2-inhibitor:	0.311
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.85
CYP2C19-substrate:	0.935
CYP2C9-inhibitor:	0.895
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.94
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	6.435
Half-life (T1/2):	0.34

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.653
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.904
Carcinogencity:	0.733
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC474790

Natural Product ID:	NPC474790
*Common Name:**	Stellettin E Methyl Ester
IUPAC Name:	methyl (2E,4E,6E,8E,10Z)-10-[(3aS,5aR,9aR,9bS)-3a,6,6,9a-tetramethyl-2,7-dioxo-4,5,5a,8,9,9b-hexahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2,6-dimethylundeca-2,4,6,8-tetraenoate
Synonyms:	stellettin E methyl ester
Standard InCHIKey:	UNVNGRLSNXYHBW-LGGDZVJISA-N
Standard InCHI:	InChI=1S/C31H42O4/c1-20(12-10-14-22(3)28(34)35-8)11-9-13-21(2)27-23(32)19-25-30(6)18-16-26(33)29(4,5)24(30)15-17-31(25,27)7/h9-14,24-25H,15-19H2,1-8H3/b12-10+,13-9+,20-11+,22-14+,27-21+/t24-,25-,30-,31-/m0/s1
SMILES:	CC(=CC=CC(=C1C(=O)CC2C1(CCC3C2(CCC(=O)C3(C)C)C)C)C)C=CC=C(C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482799
PubChem CID:	6519633
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620246]
NPO32624	rhabdastrella aff. distincta	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18826276]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4.2	ug.mL-1	PMID[543719]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[543719]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[543719]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[543719]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	5.0	ug.mL-1	PMID[543719]

☑ 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 NPC474790 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	175
0.1-0.2	1217
0.2-0.3	5257
0.3-0.4	15062
0.4-0.5	9089
0.5-0.6	7869
0.6-0.7	3413
0.7-0.8	551
0.8-0.85	41
0.85-0.9	12
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474976
0.9277	High Similarity	NPC474844
0.9268	High Similarity	NPC163016
0.9268	High Similarity	NPC75315
0.9125	High Similarity	NPC469805
0.9125	High Similarity	NPC469804
0.9012	High Similarity	NPC279639
0.9012	High Similarity	NPC3856
0.8889	High Similarity	NPC94200
0.8889	High Similarity	NPC469799
0.8889	High Similarity	NPC469806
0.8875	High Similarity	NPC469797
0.8875	High Similarity	NPC469798
0.8831	High Similarity	NPC20025
0.8831	High Similarity	NPC474796
0.8831	High Similarity	NPC329866
0.8831	High Similarity	NPC474797
0.878	High Similarity	NPC118423
0.875	High Similarity	NPC190211
0.8718	High Similarity	NPC65650
0.869	High Similarity	NPC168248
0.8659	High Similarity	NPC268122
0.8625	High Similarity	NPC105197
0.8621	High Similarity	NPC474018
0.8621	High Similarity	NPC473986
0.8462	Intermediate Similarity	NPC108368
0.8462	Intermediate Similarity	NPC276336
0.8462	Intermediate Similarity	NPC57079
0.8395	Intermediate Similarity	NPC470052
0.8375	Intermediate Similarity	NPC469793
0.8375	Intermediate Similarity	NPC469796
0.8372	Intermediate Similarity	NPC476293
0.8372	Intermediate Similarity	NPC477228
0.8352	Intermediate Similarity	NPC110937
0.8352	Intermediate Similarity	NPC2049
0.8295	Intermediate Similarity	NPC474842
0.8295	Intermediate Similarity	NPC475965
0.828	Intermediate Similarity	NPC168319
0.828	Intermediate Similarity	NPC194028
0.8276	Intermediate Similarity	NPC196407
0.8272	Intermediate Similarity	NPC470557
0.8256	Intermediate Similarity	NPC472863
0.8235	Intermediate Similarity	NPC87552
0.8214	Intermediate Similarity	NPC472239
0.8182	Intermediate Similarity	NPC284561
0.8148	Intermediate Similarity	NPC4509
0.8148	Intermediate Similarity	NPC474463
0.814	Intermediate Similarity	NPC60350
0.814	Intermediate Similarity	NPC189311
0.8132	Intermediate Similarity	NPC33473
0.8132	Intermediate Similarity	NPC171395
0.8111	Intermediate Similarity	NPC469939
0.8101	Intermediate Similarity	NPC54123
0.8068	Intermediate Similarity	NPC472302
0.8043	Intermediate Similarity	NPC301534
0.8043	Intermediate Similarity	NPC250757
0.8025	Intermediate Similarity	NPC469803
0.8025	Intermediate Similarity	NPC476346
0.8025	Intermediate Similarity	NPC473171
0.8023	Intermediate Similarity	NPC16287
0.8023	Intermediate Similarity	NPC178025
0.8023	Intermediate Similarity	NPC181743
0.8	Intermediate Similarity	NPC32577
0.8	Intermediate Similarity	NPC155332
0.8	Intermediate Similarity	NPC200513
0.8	Intermediate Similarity	NPC3511
0.8	Intermediate Similarity	NPC251705
0.8	Intermediate Similarity	NPC303613
0.8	Intermediate Similarity	NPC474228
0.8	Intermediate Similarity	NPC142253
0.8	Intermediate Similarity	NPC472867
0.8	Intermediate Similarity	NPC100297
0.8	Intermediate Similarity	NPC114540
0.7978	Intermediate Similarity	NPC285982
0.7978	Intermediate Similarity	NPC177141
0.7978	Intermediate Similarity	NPC66344
0.7975	Intermediate Similarity	NPC251929
0.7975	Intermediate Similarity	NPC2634
0.7975	Intermediate Similarity	NPC265782
0.7938	Intermediate Similarity	NPC189863
0.7938	Intermediate Similarity	NPC266570
0.7935	Intermediate Similarity	NPC293052
0.7935	Intermediate Similarity	NPC209355
0.7931	Intermediate Similarity	NPC8571
0.7927	Intermediate Similarity	NPC69408
0.7927	Intermediate Similarity	NPC40353
0.7922	Intermediate Similarity	NPC185587
0.7917	Intermediate Similarity	NPC329345
0.7917	Intermediate Similarity	NPC473283
0.7917	Intermediate Similarity	NPC475526
0.7912	Intermediate Similarity	NPC472871
0.7912	Intermediate Similarity	NPC242069
0.7901	Intermediate Similarity	NPC309852
0.7895	Intermediate Similarity	NPC310981
0.7882	Intermediate Similarity	NPC40228
0.7875	Intermediate Similarity	NPC305501
0.7875	Intermediate Similarity	NPC21944
0.7875	Intermediate Similarity	NPC234707
0.7875	Intermediate Similarity	NPC115023
0.7875	Intermediate Similarity	NPC133253
0.7875	Intermediate Similarity	NPC470078
0.7872	Intermediate Similarity	NPC98868
0.7865	Intermediate Similarity	NPC472870
0.7857	Intermediate Similarity	NPC170793
0.7849	Intermediate Similarity	NPC122324
0.7849	Intermediate Similarity	NPC151725
0.7849	Intermediate Similarity	NPC106425
0.7848	Intermediate Similarity	NPC139397
0.7841	Intermediate Similarity	NPC220478
0.7826	Intermediate Similarity	NPC473431
0.7826	Intermediate Similarity	NPC477130
0.7826	Intermediate Similarity	NPC477129
0.7826	Intermediate Similarity	NPC473280
0.7826	Intermediate Similarity	NPC471078
0.7826	Intermediate Similarity	NPC473435
0.7816	Intermediate Similarity	NPC149869
0.7816	Intermediate Similarity	NPC475100
0.7812	Intermediate Similarity	NPC320447
0.7805	Intermediate Similarity	NPC293803
0.7805	Intermediate Similarity	NPC255650
0.7802	Intermediate Similarity	NPC23217
0.7802	Intermediate Similarity	NPC204341
0.7791	Intermediate Similarity	NPC321289
0.7791	Intermediate Similarity	NPC327969
0.7789	Intermediate Similarity	NPC266955
0.7778	Intermediate Similarity	NPC180015
0.7778	Intermediate Similarity	NPC56747
0.7778	Intermediate Similarity	NPC470045
0.7778	Intermediate Similarity	NPC109576
0.7778	Intermediate Similarity	NPC470044
0.7778	Intermediate Similarity	NPC5509
0.7778	Intermediate Similarity	NPC174342
0.7778	Intermediate Similarity	NPC130016
0.7778	Intermediate Similarity	NPC262043
0.7766	Intermediate Similarity	NPC253826
0.7766	Intermediate Similarity	NPC202705
0.7765	Intermediate Similarity	NPC474509
0.7753	Intermediate Similarity	NPC128644
0.7753	Intermediate Similarity	NPC236618
0.7753	Intermediate Similarity	NPC181327
0.775	Intermediate Similarity	NPC35734
0.775	Intermediate Similarity	NPC282593
0.775	Intermediate Similarity	NPC159577
0.775	Intermediate Similarity	NPC307176
0.775	Intermediate Similarity	NPC260040
0.7742	Intermediate Similarity	NPC295347
0.7732	Intermediate Similarity	NPC72151
0.7727	Intermediate Similarity	NPC65661
0.7727	Intermediate Similarity	NPC29447
0.7727	Intermediate Similarity	NPC470048
0.7711	Intermediate Similarity	NPC27205
0.7708	Intermediate Similarity	NPC282524
0.7708	Intermediate Similarity	NPC115899
0.7701	Intermediate Similarity	NPC97913
0.7701	Intermediate Similarity	NPC470047
0.7701	Intermediate Similarity	NPC470046
0.7692	Intermediate Similarity	NPC476437
0.7692	Intermediate Similarity	NPC469595
0.7692	Intermediate Similarity	NPC161638
0.7692	Intermediate Similarity	NPC476369
0.7692	Intermediate Similarity	NPC212679
0.7692	Intermediate Similarity	NPC51486
0.7692	Intermediate Similarity	NPC273199
0.7692	Intermediate Similarity	NPC220454
0.7684	Intermediate Similarity	NPC252295
0.7683	Intermediate Similarity	NPC255021
0.7677	Intermediate Similarity	NPC329048
0.7677	Intermediate Similarity	NPC330011
0.7667	Intermediate Similarity	NPC117122
0.7667	Intermediate Similarity	NPC226863
0.766	Intermediate Similarity	NPC471153
0.7654	Intermediate Similarity	NPC181204
0.7653	Intermediate Similarity	NPC472868
0.764	Intermediate Similarity	NPC195640
0.764	Intermediate Similarity	NPC472869
0.764	Intermediate Similarity	NPC186975
0.7634	Intermediate Similarity	NPC38830
0.7634	Intermediate Similarity	NPC299100
0.7625	Intermediate Similarity	NPC256846
0.7625	Intermediate Similarity	NPC182815
0.7619	Intermediate Similarity	NPC91665
0.7619	Intermediate Similarity	NPC472300
0.7614	Intermediate Similarity	NPC472864
0.7614	Intermediate Similarity	NPC320801
0.7614	Intermediate Similarity	NPC164577
0.7614	Intermediate Similarity	NPC19849
0.7609	Intermediate Similarity	NPC218301
0.7609	Intermediate Similarity	NPC470113
0.7604	Intermediate Similarity	NPC35751
0.76	Intermediate Similarity	NPC475418
0.76	Intermediate Similarity	NPC318363
0.76	Intermediate Similarity	NPC473482
0.76	Intermediate Similarity	NPC220155
0.759	Intermediate Similarity	NPC68624
0.7586	Intermediate Similarity	NPC240302
0.7586	Intermediate Similarity	NPC16321
0.7586	Intermediate Similarity	NPC320514
0.7582	Intermediate Similarity	NPC36668
0.7582	Intermediate Similarity	NPC118011
0.7582	Intermediate Similarity	NPC173042

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 NPC474790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1199
0.2-0.3	4091
0.3-0.4	2591
0.4-0.5	659
0.5-0.6	246
0.6-0.7	169
0.7-0.8	36
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD4058	Approved
0.8	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4691	Approved
0.7901	Intermediate Similarity	NPD4687	Approved
0.7901	Intermediate Similarity	NPD5733	Approved
0.7848	Intermediate Similarity	NPD4137	Phase 3
0.775	Intermediate Similarity	NPD4747	Approved
0.7667	Intermediate Similarity	NPD6672	Approved
0.7667	Intermediate Similarity	NPD5737	Approved
0.7654	Intermediate Similarity	NPD5276	Approved
0.764	Intermediate Similarity	NPD5330	Approved
0.764	Intermediate Similarity	NPD7146	Approved
0.764	Intermediate Similarity	NPD6684	Approved
0.764	Intermediate Similarity	NPD7334	Approved
0.764	Intermediate Similarity	NPD7521	Approved
0.764	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD5693	Phase 1
0.7473	Intermediate Similarity	NPD6903	Approved
0.7473	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5694	Approved
0.7419	Intermediate Similarity	NPD6050	Approved
0.7391	Intermediate Similarity	NPD6904	Approved
0.7391	Intermediate Similarity	NPD6080	Approved
0.7391	Intermediate Similarity	NPD6673	Approved
0.7333	Intermediate Similarity	NPD1694	Approved
0.7312	Intermediate Similarity	NPD5692	Phase 3
0.7312	Intermediate Similarity	NPD5207	Approved
0.7303	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5281	Approved
0.7234	Intermediate Similarity	NPD5284	Approved
0.7191	Intermediate Similarity	NPD5209	Approved
0.7188	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8039	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7128	Intermediate Similarity	NPD5785	Approved
0.7097	Intermediate Similarity	NPD5208	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7065	Intermediate Similarity	NPD6098	Approved
0.7041	Intermediate Similarity	NPD6083	Phase 2
0.7041	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3573	Approved
0.6979	Remote Similarity	NPD6399	Phase 3
0.6932	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD7637	Suspended
0.6875	Remote Similarity	NPD6079	Approved
0.6848	Remote Similarity	NPD3666	Approved
0.6848	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD3665	Phase 1
0.6842	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5695	Phase 3
0.6837	Remote Similarity	NPD5654	Approved
0.6813	Remote Similarity	NPD4221	Approved
0.6813	Remote Similarity	NPD4223	Phase 3
0.68	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD5329	Approved
0.6762	Remote Similarity	NPD6899	Approved
0.6762	Remote Similarity	NPD6881	Approved
0.6735	Remote Similarity	NPD7748	Approved
0.6735	Remote Similarity	NPD7900	Approved
0.6735	Remote Similarity	NPD6001	Approved
0.6735	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6404	Discontinued
0.6702	Remote Similarity	NPD4623	Approved
0.6702	Remote Similarity	NPD5280	Approved
0.6702	Remote Similarity	NPD5279	Phase 3
0.6702	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4694	Approved
0.6702	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD4519	Discontinued
0.6702	Remote Similarity	NPD3618	Phase 1
0.6701	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.663	Remote Similarity	NPD3667	Approved
0.6604	Remote Similarity	NPD6011	Approved
0.6604	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5222	Approved
0.66	Remote Similarity	NPD5221	Approved
0.66	Remote Similarity	NPD7732	Phase 3
0.6596	Remote Similarity	NPD5363	Approved
0.6593	Remote Similarity	NPD4695	Discontinued
0.6574	Remote Similarity	NPD8130	Phase 1
0.6574	Remote Similarity	NPD6847	Approved
0.6574	Remote Similarity	NPD6649	Approved
0.6574	Remote Similarity	NPD6869	Approved
0.6574	Remote Similarity	NPD6617	Approved
0.6574	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6556	Remote Similarity	NPD3617	Approved
0.6543	Remote Similarity	NPD4191	Approved
0.6543	Remote Similarity	NPD4194	Approved
0.6543	Remote Similarity	NPD4193	Approved
0.6543	Remote Similarity	NPD4192	Approved
0.6542	Remote Similarity	NPD6012	Approved
0.6542	Remote Similarity	NPD6013	Approved
0.6542	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6535	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD4693	Phase 3
0.6526	Remote Similarity	NPD4138	Approved
0.6526	Remote Similarity	NPD4689	Approved
0.6526	Remote Similarity	NPD4688	Approved
0.6526	Remote Similarity	NPD4690	Approved
0.6526	Remote Similarity	NPD5205	Approved
0.6522	Remote Similarity	NPD8028	Phase 2
0.6514	Remote Similarity	NPD8297	Approved
0.6514	Remote Similarity	NPD6882	Approved
0.6484	Remote Similarity	NPD4195	Approved
0.6471	Remote Similarity	NPD4225	Approved
0.6455	Remote Similarity	NPD7094	Approved
0.6455	Remote Similarity	NPD6858	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD5211	Phase 2
0.6442	Remote Similarity	NPD7632	Discontinued
0.6415	Remote Similarity	NPD6008	Approved
0.6408	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5285	Approved
0.6408	Remote Similarity	NPD5286	Approved
0.6389	Remote Similarity	NPD6373	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6383	Remote Similarity	NPD4788	Approved
0.6383	Remote Similarity	NPD5362	Discontinued
0.6375	Remote Similarity	NPD287	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6346	Remote Similarity	NPD5223	Approved
0.6339	Remote Similarity	NPD6868	Approved
0.6321	Remote Similarity	NPD5141	Approved
0.6306	Remote Similarity	NPD4632	Approved
0.63	Remote Similarity	NPD4202	Approved
0.6286	Remote Similarity	NPD5225	Approved
0.6286	Remote Similarity	NPD5226	Approved
0.6286	Remote Similarity	NPD4633	Approved
0.6286	Remote Similarity	NPD5224	Approved
0.6277	Remote Similarity	NPD4269	Approved
0.6277	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD4697	Phase 3
0.6275	Remote Similarity	NPD7614	Phase 1
0.6273	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4096	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4252	Approved
0.6228	Remote Similarity	NPD6335	Approved
0.6226	Remote Similarity	NPD5174	Approved
0.6226	Remote Similarity	NPD5175	Approved
0.6224	Remote Similarity	NPD4518	Approved
0.6214	Remote Similarity	NPD4755	Approved
0.6204	Remote Similarity	NPD6412	Phase 2
0.62	Remote Similarity	NPD8034	Phase 2
0.62	Remote Similarity	NPD6411	Approved
0.62	Remote Similarity	NPD8035	Phase 2
0.6186	Remote Similarity	NPD5786	Approved
0.6176	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7100	Approved
0.6174	Remote Similarity	NPD7101	Approved
0.617	Remote Similarity	NPD5369	Approved
0.6148	Remote Similarity	NPD7260	Phase 2
0.6146	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6317	Approved
0.614	Remote Similarity	NPD6009	Approved
0.6139	Remote Similarity	NPD5779	Approved
0.6139	Remote Similarity	NPD5778	Approved
0.6139	Remote Similarity	NPD5133	Approved
0.6136	Remote Similarity	NPD7144	Approved
0.6136	Remote Similarity	NPD7143	Approved
0.6132	Remote Similarity	NPD5091	Approved
0.6105	Remote Similarity	NPD6435	Approved
0.6102	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4700	Approved
0.6087	Remote Similarity	NPD6313	Approved
0.6087	Remote Similarity	NPD4756	Discovery
0.6087	Remote Similarity	NPD6314	Approved
0.6078	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6053	Discontinued
0.6068	Remote Similarity	NPD7503	Approved
0.6067	Remote Similarity	NPD7152	Approved
0.6067	Remote Similarity	NPD5777	Approved
0.6067	Remote Similarity	NPD7150	Approved
0.6067	Remote Similarity	NPD7151	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