NPASS Compound

Structure

NPC471466 OpenBabel07101719242D 28 29 0 0 1 0 0 0 0 0999 V2000 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -1.3660 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 6.5000 -1.8660 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -0.0000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 1 1 1 0 0 0 11 27 1 0 0 0 0 12 2 1 6 0 0 0 12 15 1 0 0 0 0 12 28 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 23 1 1 0 0 0 16 24 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 25 2 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	375.193
LogP:	3.154
LogD:	2.719
LogS:	-4.235
# Rotatable Bonds:	8
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	4.055
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.608
MDCK Permeability:	3.826219472102821e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.836

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.948
Plasma Protein Binding (PPB):	75.55032348632812%
Volume Distribution (VD):	1.374
Pgp-substrate:	20.662612915039062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.14
CYP3A4-substrate:	0.829

ADMET: Excretion

Clearance (CL):	6.501
Half-life (T1/2):	0.449

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.767
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.156
Rat Oral Acute Toxicity:	0.338
Maximum Recommended Daily Dose:	0.414
Skin Sensitization:	0.442
Carcinogencity:	0.805
Eye Corrosion:	0.039
Eye Irritation:	0.026
Respiratory Toxicity:	0.152

Download Data

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

Natural Product: NPC471466

Natural Product ID:	NPC471466
*Common Name:**	[(2S)-1-[(2R,3S)-3-Hydroxy-2-Methyl-6-Oxo-2,3-Dihydropyran-5-Yl]Propan-2-Yl] 3,3,3-Trifluoro-2-Methoxy-2-Phenylpropanoate
IUPAC Name:	[(2S)-1-[(2R,3S)-3-hydroxy-2-methyl-6-oxo-2,3-dihydropyran-5-yl]propan-2-yl] 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
Synonyms:
Standard InCHIKey:	ZTGBVWKZUBPQIZ-XCDIBOFSSA-N
Standard InCHI:	InChI=1S/C19H21F3O6/c1-11(9-13-10-15(23)12(2)28-16(13)24)27-17(25)18(26-3,19(20,21)22)14-7-5-4-6-8-14/h4-8,10-12,15,23H,9H2,1-3H3/t11-,12+,15-,18?/m0/s1
SMILES:	CC1C(C=C(C(=O)O1)CC(C)OC(=O)C(C2=CC=CC=C2)(C(F)(F)F)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251681
PubChem CID:	44445590
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO4417	Aspergillus ostianus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994702]
NPO4417	Aspergillus ostianus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1807834]
NPO4417	Aspergillus ostianus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078344]
NPO4417	Aspergillus ostianus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	Inhibition	=	25.0	%	PMID[538064]

☑ 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 NPC471466 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	236
0.1-0.2	946
0.2-0.3	2651
0.3-0.4	7174
0.4-0.5	11445
0.5-0.6	13221
0.6-0.7	6293
0.7-0.8	695
0.8-0.85	34
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8291	Intermediate Similarity	NPC472316
0.8291	Intermediate Similarity	NPC136962
0.8291	Intermediate Similarity	NPC474376
0.8291	Intermediate Similarity	NPC472315
0.8291	Intermediate Similarity	NPC475203
0.8264	Intermediate Similarity	NPC474363
0.825	Intermediate Similarity	NPC158282
0.819	Intermediate Similarity	NPC160382
0.8182	Intermediate Similarity	NPC265002
0.8154	Intermediate Similarity	NPC472707
0.8136	Intermediate Similarity	NPC37115
0.812	Intermediate Similarity	NPC171831
0.812	Intermediate Similarity	NPC280616
0.812	Intermediate Similarity	NPC242913
0.8115	Intermediate Similarity	NPC153053
0.8099	Intermediate Similarity	NPC234376
0.8099	Intermediate Similarity	NPC321852
0.8062	Intermediate Similarity	NPC246166
0.8033	Intermediate Similarity	NPC272524
0.8017	Intermediate Similarity	NPC260818
0.8017	Intermediate Similarity	NPC476003
0.8	Intermediate Similarity	NPC472247
0.7967	Intermediate Similarity	NPC307651
0.7955	Intermediate Similarity	NPC301857
0.7951	Intermediate Similarity	NPC474314
0.7939	Intermediate Similarity	NPC169913
0.7934	Intermediate Similarity	NPC174099
0.7926	Intermediate Similarity	NPC136608
0.7926	Intermediate Similarity	NPC477281
0.7926	Intermediate Similarity	NPC477280
0.7926	Intermediate Similarity	NPC38420
0.7926	Intermediate Similarity	NPC19719
0.7923	Intermediate Similarity	NPC57607
0.7917	Intermediate Similarity	NPC277788
0.791	Intermediate Similarity	NPC108553
0.791	Intermediate Similarity	NPC233692
0.7868	Intermediate Similarity	NPC477896
0.7868	Intermediate Similarity	NPC477367
0.7868	Intermediate Similarity	NPC232888
0.7863	Intermediate Similarity	NPC275576
0.7863	Intermediate Similarity	NPC79608
0.7863	Intermediate Similarity	NPC476033
0.7852	Intermediate Similarity	NPC477364
0.7851	Intermediate Similarity	NPC17417
0.7851	Intermediate Similarity	NPC10251
0.7851	Intermediate Similarity	NPC85493
0.7851	Intermediate Similarity	NPC469636
0.7846	Intermediate Similarity	NPC14141
0.7845	Intermediate Similarity	NPC210529
0.7845	Intermediate Similarity	NPC175852
0.7845	Intermediate Similarity	NPC160548
0.7826	Intermediate Similarity	NPC475195
0.7823	Intermediate Similarity	NPC172525
0.7812	Intermediate Similarity	NPC473243
0.7805	Intermediate Similarity	NPC82899
0.7805	Intermediate Similarity	NPC270699
0.7805	Intermediate Similarity	NPC477250
0.7794	Intermediate Similarity	NPC477368
0.7794	Intermediate Similarity	NPC28836
0.7794	Intermediate Similarity	NPC311492
0.7787	Intermediate Similarity	NPC251854
0.7787	Intermediate Similarity	NPC196246
0.7787	Intermediate Similarity	NPC214067
0.7787	Intermediate Similarity	NPC93084
0.7778	Intermediate Similarity	NPC239358
0.7769	Intermediate Similarity	NPC56493
0.7761	Intermediate Similarity	NPC272946
0.776	Intermediate Similarity	NPC474685
0.7754	Intermediate Similarity	NPC71638
0.7754	Intermediate Similarity	NPC64230
0.775	Intermediate Similarity	NPC269457
0.7742	Intermediate Similarity	NPC128368
0.7742	Intermediate Similarity	NPC161611
0.7737	Intermediate Similarity	NPC477893
0.7731	Intermediate Similarity	NPC301943
0.7731	Intermediate Similarity	NPC474365
0.7724	Intermediate Similarity	NPC474157
0.7724	Intermediate Similarity	NPC305912
0.7724	Intermediate Similarity	NPC1082
0.7721	Intermediate Similarity	NPC472248
0.7721	Intermediate Similarity	NPC323379
0.7721	Intermediate Similarity	NPC327204
0.771	Intermediate Similarity	NPC138798
0.7705	Intermediate Similarity	NPC281604
0.7705	Intermediate Similarity	NPC83628
0.7705	Intermediate Similarity	NPC265407
0.7705	Intermediate Similarity	NPC474364
0.7704	Intermediate Similarity	NPC319995
0.7704	Intermediate Similarity	NPC17567
0.7704	Intermediate Similarity	NPC289415
0.7698	Intermediate Similarity	NPC473301
0.7698	Intermediate Similarity	NPC149691
0.7686	Intermediate Similarity	NPC119271
0.7681	Intermediate Similarity	NPC52523
0.7681	Intermediate Similarity	NPC217673
0.768	Intermediate Similarity	NPC308744
0.7667	Intermediate Similarity	NPC85977
0.766	Intermediate Similarity	NPC182869
0.7652	Intermediate Similarity	NPC295664
0.7647	Intermediate Similarity	NPC233860
0.7647	Intermediate Similarity	NPC475569
0.7639	Intermediate Similarity	NPC205389
0.7634	Intermediate Similarity	NPC223351
0.7627	Intermediate Similarity	NPC325497
0.7626	Intermediate Similarity	NPC27721
0.7623	Intermediate Similarity	NPC20485
0.7623	Intermediate Similarity	NPC156648
0.7619	Intermediate Similarity	NPC306740
0.7619	Intermediate Similarity	NPC469509
0.7619	Intermediate Similarity	NPC210092
0.7612	Intermediate Similarity	NPC477370
0.7609	Intermediate Similarity	NPC200154
0.7606	Intermediate Similarity	NPC45307
0.76	Intermediate Similarity	NPC474176
0.7597	Intermediate Similarity	NPC204784
0.7594	Intermediate Similarity	NPC236405
0.7594	Intermediate Similarity	NPC476599
0.7594	Intermediate Similarity	NPC477363
0.7589	Intermediate Similarity	NPC473497
0.7589	Intermediate Similarity	NPC475413
0.7589	Intermediate Similarity	NPC474303
0.7583	Intermediate Similarity	NPC91820
0.7583	Intermediate Similarity	NPC82426
0.7583	Intermediate Similarity	NPC234305
0.7571	Intermediate Similarity	NPC67349
0.7571	Intermediate Similarity	NPC279676
0.7571	Intermediate Similarity	NPC9905
0.7569	Intermediate Similarity	NPC477737
0.7556	Intermediate Similarity	NPC217431
0.7554	Intermediate Similarity	NPC472372
0.7554	Intermediate Similarity	NPC182217
0.7554	Intermediate Similarity	NPC233350
0.7554	Intermediate Similarity	NPC472374
0.7554	Intermediate Similarity	NPC202729
0.7554	Intermediate Similarity	NPC70680
0.7542	Intermediate Similarity	NPC78701
0.7542	Intermediate Similarity	NPC154517
0.7542	Intermediate Similarity	NPC35448
0.7541	Intermediate Similarity	NPC477251
0.754	Intermediate Similarity	NPC237366
0.7537	Intermediate Similarity	NPC472706
0.7537	Intermediate Similarity	NPC114096
0.7537	Intermediate Similarity	NPC477365
0.7536	Intermediate Similarity	NPC477359
0.7535	Intermediate Similarity	NPC192658
0.7535	Intermediate Similarity	NPC472546
0.7534	Intermediate Similarity	NPC477099
0.7534	Intermediate Similarity	NPC232583
0.7534	Intermediate Similarity	NPC477101
0.7534	Intermediate Similarity	NPC25484
0.7534	Intermediate Similarity	NPC477097
0.7521	Intermediate Similarity	NPC249067
0.7521	Intermediate Similarity	NPC31786
0.752	Intermediate Similarity	NPC185840
0.7518	Intermediate Similarity	NPC87934
0.7518	Intermediate Similarity	NPC100913
0.7518	Intermediate Similarity	NPC476643
0.7518	Intermediate Similarity	NPC275592
0.7518	Intermediate Similarity	NPC162613
0.7518	Intermediate Similarity	NPC472547
0.75	Intermediate Similarity	NPC477098
0.75	Intermediate Similarity	NPC27712
0.75	Intermediate Similarity	NPC108532
0.75	Intermediate Similarity	NPC304956
0.75	Intermediate Similarity	NPC134131
0.75	Intermediate Similarity	NPC469927
0.75	Intermediate Similarity	NPC39549
0.75	Intermediate Similarity	NPC25043
0.75	Intermediate Similarity	NPC477100
0.75	Intermediate Similarity	NPC127857
0.75	Intermediate Similarity	NPC42234
0.75	Intermediate Similarity	NPC472703
0.7483	Intermediate Similarity	NPC477894
0.7483	Intermediate Similarity	NPC471103
0.7483	Intermediate Similarity	NPC477277
0.7483	Intermediate Similarity	NPC477278
0.7483	Intermediate Similarity	NPC95449
0.7482	Intermediate Similarity	NPC290833
0.7482	Intermediate Similarity	NPC475262
0.7482	Intermediate Similarity	NPC68517
0.7482	Intermediate Similarity	NPC265459
0.7481	Intermediate Similarity	NPC148026
0.7479	Intermediate Similarity	NPC80115
0.7479	Intermediate Similarity	NPC98911
0.7479	Intermediate Similarity	NPC472318
0.7479	Intermediate Similarity	NPC146351
0.7466	Intermediate Similarity	NPC81698
0.7466	Intermediate Similarity	NPC473215
0.7466	Intermediate Similarity	NPC476975
0.7466	Intermediate Similarity	NPC60509
0.7466	Intermediate Similarity	NPC250046
0.7465	Intermediate Similarity	NPC472576
0.7465	Intermediate Similarity	NPC27377
0.7465	Intermediate Similarity	NPC291599
0.7465	Intermediate Similarity	NPC156709
0.7465	Intermediate Similarity	NPC87448
0.7465	Intermediate Similarity	NPC118080
0.7465	Intermediate Similarity	NPC242355
0.7465	Intermediate Similarity	NPC97947
0.7465	Intermediate Similarity	NPC179505

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 NPC471466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	693
0.2-0.3	1471
0.3-0.4	2703
0.4-0.5	2375
0.5-0.6	1307
0.6-0.7	354
0.7-0.8	41
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8347	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD2067	Discontinued
0.8049	Intermediate Similarity	NPD2629	Approved
0.7869	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD2182	Approved
0.7845	Intermediate Similarity	NPD9495	Approved
0.784	Intermediate Similarity	NPD4198	Discontinued
0.7674	Intermediate Similarity	NPD5306	Approved
0.7674	Intermediate Similarity	NPD5305	Approved
0.763	Intermediate Similarity	NPD7008	Discontinued
0.7615	Intermediate Similarity	NPD4106	Approved
0.7615	Intermediate Similarity	NPD4136	Approved
0.7615	Intermediate Similarity	NPD4135	Approved
0.7591	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4807	Approved
0.7557	Intermediate Similarity	NPD4806	Approved
0.7521	Intermediate Similarity	NPD164	Approved
0.7521	Intermediate Similarity	NPD1237	Approved
0.75	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7236	Approved
0.7462	Intermediate Similarity	NPD4105	Approved
0.7462	Intermediate Similarity	NPD4102	Approved
0.7438	Intermediate Similarity	NPD6647	Phase 2
0.7388	Intermediate Similarity	NPD5667	Approved
0.7377	Intermediate Similarity	NPD5909	Discontinued
0.7353	Intermediate Similarity	NPD5204	Approved
0.7333	Intermediate Similarity	NPD1238	Approved
0.7319	Intermediate Similarity	NPD6798	Discontinued
0.7299	Intermediate Similarity	NPD5203	Approved
0.7299	Intermediate Similarity	NPD4617	Approved
0.7299	Intermediate Similarity	NPD4620	Approved
0.7299	Intermediate Similarity	NPD5201	Approved
0.7286	Intermediate Similarity	NPD6355	Discontinued
0.728	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6233	Phase 2
0.7244	Intermediate Similarity	NPD969	Suspended
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7234	Intermediate Similarity	NPD6653	Approved
0.7226	Intermediate Similarity	NPD3662	Phase 3
0.7226	Intermediate Similarity	NPD3664	Approved
0.7226	Intermediate Similarity	NPD3661	Approved
0.7226	Intermediate Similarity	NPD3663	Approved
0.7206	Intermediate Similarity	NPD2160	Approved
0.7206	Intermediate Similarity	NPD2159	Approved
0.7206	Intermediate Similarity	NPD2628	Approved
0.7206	Intermediate Similarity	NPD2627	Approved
0.7206	Intermediate Similarity	NPD2625	Approved
0.7206	Intermediate Similarity	NPD2626	Approved
0.7192	Intermediate Similarity	NPD6190	Approved
0.719	Intermediate Similarity	NPD2066	Phase 3
0.7174	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4062	Phase 3
0.7133	Intermediate Similarity	NPD4308	Phase 3
0.7109	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5120	Approved
0.7092	Intermediate Similarity	NPD5121	Approved
0.7092	Intermediate Similarity	NPD5119	Approved
0.7071	Intermediate Similarity	NPD4621	Approved
0.7071	Intermediate Similarity	NPD4619	Approved
0.7059	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6085	Phase 2
0.7029	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5647	Approved
0.702	Intermediate Similarity	NPD7239	Suspended
0.7007	Intermediate Similarity	NPD2575	Approved
0.7	Intermediate Similarity	NPD5454	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9545	Approved
0.6972	Remote Similarity	NPD6310	Approved
0.6972	Remote Similarity	NPD6309	Approved
0.6972	Remote Similarity	NPD6311	Approved
0.697	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6362	Approved
0.6957	Remote Similarity	NPD2797	Approved
0.6954	Remote Similarity	NPD5403	Approved
0.695	Remote Similarity	NPD3764	Approved
0.6949	Remote Similarity	NPD9258	Approved
0.6949	Remote Similarity	NPD9256	Approved
0.6947	Remote Similarity	NPD5951	Approved
0.6942	Remote Similarity	NPD1989	Approved
0.6912	Remote Similarity	NPD6287	Discontinued
0.6905	Remote Similarity	NPD5048	Discontinued
0.6897	Remote Similarity	NPD7033	Discontinued
0.688	Remote Similarity	NPD1930	Approved
0.688	Remote Similarity	NPD1929	Approved
0.688	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7095	Approved
0.6875	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2329	Discontinued
0.6871	Remote Similarity	NPD4534	Discontinued
0.687	Remote Similarity	NPD6010	Discontinued
0.6863	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5402	Approved
0.6853	Remote Similarity	NPD4307	Phase 2
0.6849	Remote Similarity	NPD4173	Approved
0.6849	Remote Similarity	NPD4172	Approved
0.6846	Remote Similarity	NPD3887	Approved
0.6846	Remote Similarity	NPD2354	Approved
0.6842	Remote Similarity	NPD9493	Approved
0.6839	Remote Similarity	NPD6801	Discontinued
0.6831	Remote Similarity	NPD2313	Discontinued
0.6831	Remote Similarity	NPD3268	Approved
0.6821	Remote Similarity	NPD5401	Approved
0.6807	Remote Similarity	NPD1090	Approved
0.6807	Remote Similarity	NPD1089	Approved
0.6807	Remote Similarity	NPD1086	Approved
0.6803	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2788	Approved
0.6777	Remote Similarity	NPD1202	Approved
0.6776	Remote Similarity	NPD5049	Phase 3
0.6765	Remote Similarity	NPD5126	Approved
0.6765	Remote Similarity	NPD5125	Phase 3
0.6757	Remote Similarity	NPD5958	Discontinued
0.6755	Remote Similarity	NPD6799	Approved
0.6748	Remote Similarity	NPD1564	Approved
0.6748	Remote Similarity	NPD1565	Approved
0.6748	Remote Similarity	NPD1566	Phase 3
0.6736	Remote Similarity	NPD3373	Approved
0.6736	Remote Similarity	NPD4060	Phase 1
0.6723	Remote Similarity	NPD800	Approved
0.6721	Remote Similarity	NPD1693	Approved
0.6719	Remote Similarity	NPD6685	Approved
0.671	Remote Similarity	NPD6599	Discontinued
0.6709	Remote Similarity	NPD7058	Phase 2
0.6709	Remote Similarity	NPD7057	Phase 3
0.6694	Remote Similarity	NPD1088	Approved
0.669	Remote Similarity	NPD230	Phase 1
0.6689	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3673	Approved
0.6667	Remote Similarity	NPD7961	Discontinued
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD3672	Approved
0.6667	Remote Similarity	NPD1932	Approved
0.6667	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6645	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2199	Approved
0.6643	Remote Similarity	NPD2198	Approved
0.6642	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7798	Approved
0.6638	Remote Similarity	NPD9491	Approved
0.6622	Remote Similarity	NPD2935	Discontinued
0.6619	Remote Similarity	NPD9717	Approved
0.6619	Remote Similarity	NPD6637	Approved
0.6618	Remote Similarity	NPD1894	Discontinued
0.6617	Remote Similarity	NPD2652	Approved
0.6617	Remote Similarity	NPD2650	Approved
0.6617	Remote Similarity	NPD1241	Discontinued
0.6612	Remote Similarity	NPD1239	Approved
0.661	Remote Similarity	NPD9259	Approved
0.661	Remote Similarity	NPD9257	Approved
0.6601	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7097	Phase 1
0.6597	Remote Similarity	NPD411	Approved
0.6587	Remote Similarity	NPD8368	Discontinued
0.6577	Remote Similarity	NPD6002	Phase 3
0.6577	Remote Similarity	NPD2346	Discontinued
0.6577	Remote Similarity	NPD2353	Approved
0.6577	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5763	Approved
0.6577	Remote Similarity	NPD5762	Approved
0.6577	Remote Similarity	NPD6004	Phase 3
0.6577	Remote Similarity	NPD6005	Phase 3
0.6577	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4340	Discontinued
0.6575	Remote Similarity	NPD447	Suspended
0.6573	Remote Similarity	NPD6832	Phase 2
0.6571	Remote Similarity	NPD5157	Phase 1
0.6571	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5159	Phase 2
0.6565	Remote Similarity	NPD5240	Approved
0.6565	Remote Similarity	NPD5236	Approved
0.6565	Remote Similarity	NPD5237	Approved
0.6565	Remote Similarity	NPD5239	Approved
0.6565	Remote Similarity	NPD5235	Approved
0.6561	Remote Similarity	NPD3274	Phase 2
0.6556	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1282	Approved
0.6555	Remote Similarity	NPD1087	Approved
0.6554	Remote Similarity	NPD7305	Phase 1
0.6552	Remote Similarity	NPD7715	Approved
0.6552	Remote Similarity	NPD7714	Approved
0.6549	Remote Similarity	NPD2798	Approved
0.6549	Remote Similarity	NPD4980	Approved
0.6545	Remote Similarity	NPD7799	Discontinued
0.6541	Remote Similarity	NPD5277	Phase 2
0.6538	Remote Similarity	NPD3455	Phase 2
0.6533	Remote Similarity	NPD2424	Discontinued
0.6533	Remote Similarity	NPD2897	Discontinued
0.6532	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2201	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