NPASS Compound

Structure

NPC237240 OpenBabel07101718192D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.4392 -3.4392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1980 -0.6072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7617 0.7315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0926 -0.0116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4527 1.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1144 0.1963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4745 1.8905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8272 1.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -2.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8054 1.1474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1581 0.6121 0.0000 C 0 0 1 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 1.3660 -0.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2321 -1.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2431 -0.1969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1636 0.7167 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6072 1.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1980 -2.1248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2213 -0.4048 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 4 19 2 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 9 1 0 0 0 0 8 12 2 0 0 0 0 9 16 1 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 16 1 1 6 0 0 0 16 25 1 0 0 0 0 17 2 1 1 0 0 0 17 25 1 0 0 0 0 18 3 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 15 1 1 0 0 0 22 24 1 0 0 0 0 22 29 1 0 0 0 0 23 30 2 0 0 0 0 23 34 1 0 0 0 0 24 28 1 6 0 0 0 25 31 1 1 0 0 0 26 32 1 1 0 0 0 27 29 2 0 0 0 0 27 33 1 0 0 0 0 28 27 1 6 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	465.25
Volume:	492.474
LogP:	3.166
LogD:	3.197
LogS:	-4.788
# Rotatable Bonds:	2
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	5.773
Fsp3:	0.5
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:	-5.235
MDCK Permeability:	9.490585944149643e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.273
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	95.4656753540039%
Volume Distribution (VD):	1.262
Pgp-substrate:	5.478801727294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.065
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.104
CYP2C19-substrate:	0.476
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	7.794
Half-life (T1/2):	0.019

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.157
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.203
Carcinogencity:	0.689
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC237240

Natural Product ID:	NPC237240
*Common Name:**	OZDYYVVFUQMENY-TZMRIDSPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OZDYYVVFUQMENY-TZMRIDSPSA-N
Standard InCHI:	InChI=1S/C28H35NO5/c1-16-9-8-12-21-26(32)19(4)18(3)24-22(15-20-10-6-5-7-11-20)29-27(33)28(21,24)34-23(30)14-13-17(2)25(16)31/h5-8,10-14,16-18,21-22,24-26,31-32H,4,9,15H2,1-3H3,(H,29,33)/b12-8+,14-13+/t16-,17-,18+,21-,22-,24-,25+,26+,28+/m0/s1
SMILES:	O=C1/C=C/[C@H](C)[C@H](O)[C@@H](C)C/C=C/[C@@H]2[C@]3(O1)C(=N[C@H]([C@@H]3[C@@H](C(=C)[C@H]2O)C)Cc1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497529
PubChem CID:	11705387
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[16792402]
NPO33507	spicaria elegans	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18507474]
NPO41081	Aspergillus sp. CPCC 400735	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29016131]

☑ 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	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	75000.0	nM	PMID[555876]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8800.0	nM	PMID[555876]
NPT2157	Cell Line	SUP-T1	Homo sapiens	CC50	=	95100.0	nM	PMID[555877]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	25800.0	nM	PMID[555877]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	99.99	%	PMID[555877]

☑ 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 NPC237240 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	168
0.1-0.2	745
0.2-0.3	1817
0.3-0.4	5405
0.4-0.5	13925
0.5-0.6	18205
0.6-0.7	2289
0.7-0.8	111
0.8-0.85	10
0.85-0.9	12
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31171
0.9783	High Similarity	NPC201692
0.9638	High Similarity	NPC173934
0.9559	High Similarity	NPC261709
0.9559	High Similarity	NPC111586
0.9559	High Similarity	NPC108852
0.9184	High Similarity	NPC156348
0.8978	High Similarity	NPC90693
0.8978	High Similarity	NPC64897
0.8889	High Similarity	NPC295478
0.8714	High Similarity	NPC175870
0.8681	High Similarity	NPC262216
0.8662	High Similarity	NPC239770
0.8627	High Similarity	NPC15506
0.8603	High Similarity	NPC278097
0.8581	High Similarity	NPC4108
0.844	Intermediate Similarity	NPC228511
0.8425	Intermediate Similarity	NPC49565
0.838	Intermediate Similarity	NPC279045
0.838	Intermediate Similarity	NPC113325
0.8169	Intermediate Similarity	NPC42423
0.8025	Intermediate Similarity	NPC477115
0.7872	Intermediate Similarity	NPC472414
0.7832	Intermediate Similarity	NPC71271
0.7817	Intermediate Similarity	NPC470158
0.7817	Intermediate Similarity	NPC475933
0.7762	Intermediate Similarity	NPC476972
0.7762	Intermediate Similarity	NPC476971
0.7708	Intermediate Similarity	NPC58061
0.7703	Intermediate Similarity	NPC208725
0.7692	Intermediate Similarity	NPC476970
0.7692	Intermediate Similarity	NPC45821
0.7655	Intermediate Similarity	NPC93632
0.7622	Intermediate Similarity	NPC471758
0.7619	Intermediate Similarity	NPC475345
0.7606	Intermediate Similarity	NPC473870
0.7606	Intermediate Similarity	NPC473871
0.7574	Intermediate Similarity	NPC475649
0.7562	Intermediate Similarity	NPC235460
0.7552	Intermediate Similarity	NPC472373
0.7547	Intermediate Similarity	NPC217801
0.7535	Intermediate Similarity	NPC475328
0.7535	Intermediate Similarity	NPC473889
0.753	Intermediate Similarity	NPC278272
0.753	Intermediate Similarity	NPC120667
0.75	Intermediate Similarity	NPC476976
0.75	Intermediate Similarity	NPC476113
0.75	Intermediate Similarity	NPC284022
0.7483	Intermediate Similarity	NPC472415
0.7483	Intermediate Similarity	NPC12016
0.7482	Intermediate Similarity	NPC470820
0.7465	Intermediate Similarity	NPC37641
0.7465	Intermediate Similarity	NPC311175
0.7436	Intermediate Similarity	NPC94602
0.7432	Intermediate Similarity	NPC476977
0.7429	Intermediate Similarity	NPC84129
0.7413	Intermediate Similarity	NPC70973
0.7396	Intermediate Similarity	NPC203005
0.7386	Intermediate Similarity	NPC472547
0.7383	Intermediate Similarity	NPC80599
0.7368	Intermediate Similarity	NPC39549
0.7365	Intermediate Similarity	NPC183722
0.7358	Intermediate Similarity	NPC275839
0.7356	Intermediate Similarity	NPC327699
0.7353	Intermediate Similarity	NPC113012
0.7353	Intermediate Similarity	NPC122926
0.7347	Intermediate Similarity	NPC230331
0.7347	Intermediate Similarity	NPC116057
0.7347	Intermediate Similarity	NPC472413
0.7343	Intermediate Similarity	NPC473439
0.7343	Intermediate Similarity	NPC300827
0.731	Intermediate Similarity	NPC470815
0.7308	Intermediate Similarity	NPC260194
0.7303	Intermediate Similarity	NPC472545
0.7303	Intermediate Similarity	NPC472551
0.7273	Intermediate Similarity	NPC471754
0.7273	Intermediate Similarity	NPC100913
0.7273	Intermediate Similarity	NPC453583
0.7273	Intermediate Similarity	NPC473300
0.7273	Intermediate Similarity	NPC275592
0.7273	Intermediate Similarity	NPC475336
0.7273	Intermediate Similarity	NPC317882
0.7261	Intermediate Similarity	NPC313414
0.7261	Intermediate Similarity	NPC472556
0.726	Intermediate Similarity	NPC473083
0.726	Intermediate Similarity	NPC114927
0.7254	Intermediate Similarity	NPC473860
0.7244	Intermediate Similarity	NPC91703
0.7233	Intermediate Similarity	NPC470274
0.7232	Intermediate Similarity	NPC67246
0.7232	Intermediate Similarity	NPC33372
0.7226	Intermediate Similarity	NPC41481
0.7226	Intermediate Similarity	NPC118080
0.7226	Intermediate Similarity	NPC291599
0.7226	Intermediate Similarity	NPC87448
0.7226	Intermediate Similarity	NPC27377
0.7226	Intermediate Similarity	NPC97947
0.7226	Intermediate Similarity	NPC472576
0.7214	Intermediate Similarity	NPC473869
0.7211	Intermediate Similarity	NPC473111
0.7211	Intermediate Similarity	NPC473082
0.7211	Intermediate Similarity	NPC473110
0.7179	Intermediate Similarity	NPC140021
0.7179	Intermediate Similarity	NPC192658
0.7175	Intermediate Similarity	NPC206211
0.7175	Intermediate Similarity	NPC306001
0.7175	Intermediate Similarity	NPC473400
0.7175	Intermediate Similarity	NPC275170
0.7175	Intermediate Similarity	NPC324251
0.7175	Intermediate Similarity	NPC471629
0.7172	Intermediate Similarity	NPC160493
0.7161	Intermediate Similarity	NPC97667
0.7161	Intermediate Similarity	NPC171207
0.7161	Intermediate Similarity	NPC90614
0.7152	Intermediate Similarity	NPC473541
0.7133	Intermediate Similarity	NPC89324
0.7133	Intermediate Similarity	NPC472388
0.7133	Intermediate Similarity	NPC473443
0.7126	Intermediate Similarity	NPC474607
0.7123	Intermediate Similarity	NPC108286
0.7115	Intermediate Similarity	NPC475128
0.7115	Intermediate Similarity	NPC16912
0.7115	Intermediate Similarity	NPC224491
0.7111	Intermediate Similarity	NPC215892
0.7111	Intermediate Similarity	NPC242662
0.7111	Intermediate Similarity	NPC191193
0.7111	Intermediate Similarity	NPC321072
0.7107	Intermediate Similarity	NPC312393
0.7097	Intermediate Similarity	NPC9905
0.7089	Intermediate Similarity	NPC471139
0.7089	Intermediate Similarity	NPC241951
0.7089	Intermediate Similarity	NPC475122
0.7089	Intermediate Similarity	NPC38696
0.7089	Intermediate Similarity	NPC34943
0.7089	Intermediate Similarity	NPC328824
0.7089	Intermediate Similarity	NPC470152
0.7089	Intermediate Similarity	NPC475759
0.7086	Intermediate Similarity	NPC474650
0.7078	Intermediate Similarity	NPC477557
0.7072	Intermediate Similarity	NPC181964
0.7072	Intermediate Similarity	NPC471606
0.7072	Intermediate Similarity	NPC208553
0.707	Intermediate Similarity	NPC34012
0.707	Intermediate Similarity	NPC472546
0.7067	Intermediate Similarity	NPC225103
0.7055	Intermediate Similarity	NPC473749
0.7051	Intermediate Similarity	NPC162613
0.7051	Intermediate Similarity	NPC87934
0.705	Intermediate Similarity	NPC323007
0.7044	Intermediate Similarity	NPC174982
0.7044	Intermediate Similarity	NPC472571
0.7044	Intermediate Similarity	NPC473088
0.7044	Intermediate Similarity	NPC301946
0.7044	Intermediate Similarity	NPC472568
0.7044	Intermediate Similarity	NPC476973
0.7044	Intermediate Similarity	NPC472572
0.7044	Intermediate Similarity	NPC184817
0.7044	Intermediate Similarity	NPC311825
0.7044	Intermediate Similarity	NPC200471
0.7044	Intermediate Similarity	NPC96903
0.7044	Intermediate Similarity	NPC177940
0.7044	Intermediate Similarity	NPC158663
0.7044	Intermediate Similarity	NPC470157
0.7044	Intermediate Similarity	NPC92867
0.7044	Intermediate Similarity	NPC171525
0.7044	Intermediate Similarity	NPC277053
0.7044	Intermediate Similarity	NPC472575
0.7044	Intermediate Similarity	NPC469349
0.7044	Intermediate Similarity	NPC70403
0.7044	Intermediate Similarity	NPC470159
0.7044	Intermediate Similarity	NPC471104
0.7044	Intermediate Similarity	NPC29704
0.7042	Intermediate Similarity	NPC476476
0.7039	Intermediate Similarity	NPC209851
0.7034	Intermediate Similarity	NPC190663
0.7033	Intermediate Similarity	NPC473558
0.7025	Intermediate Similarity	NPC163087
0.7025	Intermediate Similarity	NPC477894
0.7022	Intermediate Similarity	NPC471623
0.7	Intermediate Similarity	NPC124690
0.7	Intermediate Similarity	NPC195224
0.7	Intermediate Similarity	NPC172769
0.7	Intermediate Similarity	NPC473602
0.7	Intermediate Similarity	NPC166521
0.7	Intermediate Similarity	NPC205
0.7	Intermediate Similarity	NPC478263
0.7	Intermediate Similarity	NPC20255
0.7	Intermediate Similarity	NPC240115
0.7	Intermediate Similarity	NPC281470
0.7	Intermediate Similarity	NPC476757
0.7	Intermediate Similarity	NPC184195
0.6986	Remote Similarity	NPC476184
0.6986	Remote Similarity	NPC476281
0.6981	Remote Similarity	NPC125106
0.6981	Remote Similarity	NPC472569
0.6981	Remote Similarity	NPC476974
0.6981	Remote Similarity	NPC472573
0.6981	Remote Similarity	NPC472570
0.6981	Remote Similarity	NPC80895
0.6981	Remote Similarity	NPC11685

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 NPC237240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	443
0.2-0.3	866
0.3-0.4	2235
0.4-0.5	3297
0.5-0.6	1902
0.6-0.7	286
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7274	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8361	Approved
0.7119	Intermediate Similarity	NPD8360	Approved
0.7086	Intermediate Similarity	NPD8407	Phase 2
0.7072	Intermediate Similarity	NPD8485	Approved
0.7022	Intermediate Similarity	NPD8435	Approved
0.7011	Intermediate Similarity	NPD8368	Discontinued
0.7006	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5981	Approved
0.6805	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4738	Phase 2
0.6781	Remote Similarity	NPD2218	Phase 2
0.6781	Remote Similarity	NPD2217	Approved
0.6774	Remote Similarity	NPD2238	Phase 2
0.6708	Remote Similarity	NPD2575	Approved
0.6708	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7315	Approved
0.6646	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6666	Approved
0.6626	Remote Similarity	NPD6667	Approved
0.6625	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2613	Approved
0.6607	Remote Similarity	NPD6072	Discontinued
0.6596	Remote Similarity	NPD6406	Approved
0.6587	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5126	Approved
0.6577	Remote Similarity	NPD5125	Phase 3
0.6573	Remote Similarity	NPD3644	Approved
0.6573	Remote Similarity	NPD3642	Approved
0.6573	Remote Similarity	NPD3643	Approved
0.6561	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7741	Discontinued
0.6543	Remote Similarity	NPD7565	Approved
0.6532	Remote Similarity	NPD4666	Phase 3
0.6532	Remote Similarity	NPD6746	Phase 2
0.6529	Remote Similarity	NPD5772	Approved
0.6529	Remote Similarity	NPD5773	Approved
0.6515	Remote Similarity	NPD8404	Phase 2
0.6506	Remote Similarity	NPD7526	Approved
0.6506	Remote Similarity	NPD52	Approved
0.6506	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3400	Discontinued
0.6497	Remote Similarity	NPD3090	Approved
0.6497	Remote Similarity	NPD2573	Approved
0.6497	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2566	Approved
0.6497	Remote Similarity	NPD2570	Approved
0.6497	Remote Similarity	NPD3614	Approved
0.6497	Remote Similarity	NPD3087	Approved
0.6497	Remote Similarity	NPD3088	Approved
0.6497	Remote Similarity	NPD3616	Approved
0.6497	Remote Similarity	NPD4746	Phase 3
0.6497	Remote Similarity	NPD4745	Approved
0.6497	Remote Similarity	NPD3615	Approved
0.6497	Remote Similarity	NPD2571	Approved
0.6497	Remote Similarity	NPD2574	Discontinued
0.6497	Remote Similarity	NPD3089	Approved
0.6492	Remote Similarity	NPD7497	Discontinued
0.649	Remote Similarity	NPD5618	Discontinued
0.6488	Remote Similarity	NPD4005	Discontinued
0.6486	Remote Similarity	NPD7522	Discontinued
0.6478	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5709	Phase 3
0.6471	Remote Similarity	NPD6325	Discontinued
0.646	Remote Similarity	NPD2161	Phase 2
0.6443	Remote Similarity	NPD4479	Discontinued
0.6433	Remote Similarity	NPD4621	Approved
0.6433	Remote Similarity	NPD4619	Approved
0.6429	Remote Similarity	NPD6647	Phase 2
0.6429	Remote Similarity	NPD2627	Approved
0.6429	Remote Similarity	NPD2626	Approved
0.6429	Remote Similarity	NPD2160	Approved
0.6429	Remote Similarity	NPD2159	Approved
0.6429	Remote Similarity	NPD2625	Approved
0.6429	Remote Similarity	NPD2628	Approved
0.6425	Remote Similarity	NPD5557	Phase 1
0.642	Remote Similarity	NPD2970	Approved
0.642	Remote Similarity	NPD2969	Approved
0.642	Remote Similarity	NPD1375	Discontinued
0.6415	Remote Similarity	NPD4686	Approved
0.6415	Remote Similarity	NPD4685	Phase 3
0.6415	Remote Similarity	NPD4684	Phase 3
0.6413	Remote Similarity	NPD6841	Approved
0.6413	Remote Similarity	NPD6843	Phase 3
0.6413	Remote Similarity	NPD6842	Approved
0.6408	Remote Similarity	NPD5705	Approved
0.6408	Remote Similarity	NPD5704	Approved
0.6408	Remote Similarity	NPD5706	Approved
0.6404	Remote Similarity	NPD3909	Discontinued
0.6396	Remote Similarity	NPD8462	Phase 1
0.6391	Remote Similarity	NPD3455	Phase 2
0.6389	Remote Similarity	NPD5236	Approved
0.6389	Remote Similarity	NPD5237	Approved
0.6389	Remote Similarity	NPD7007	Discovery
0.6389	Remote Similarity	NPD5235	Approved
0.6389	Remote Similarity	NPD5239	Approved
0.6389	Remote Similarity	NPD5240	Approved
0.6384	Remote Similarity	NPD4481	Phase 3
0.6382	Remote Similarity	NPD2608	Approved
0.6382	Remote Similarity	NPD2610	Approved
0.6382	Remote Similarity	NPD4216	Approved
0.6382	Remote Similarity	NPD3132	Approved
0.6382	Remote Similarity	NPD4217	Approved
0.6382	Remote Similarity	NPD3529	Phase 2
0.6382	Remote Similarity	NPD3131	Approved
0.6382	Remote Similarity	NPD4218	Approved
0.6382	Remote Similarity	NPD2609	Approved
0.6382	Remote Similarity	NPD2611	Approved
0.6382	Remote Similarity	NPD4807	Approved
0.6382	Remote Similarity	NPD4806	Approved
0.6382	Remote Similarity	NPD4215	Approved
0.6382	Remote Similarity	NPD2612	Approved
0.6374	Remote Similarity	NPD5035	Approved
0.6374	Remote Similarity	NPD7312	Approved
0.6374	Remote Similarity	NPD7310	Approved
0.6374	Remote Similarity	NPD7311	Approved
0.6374	Remote Similarity	NPD7313	Approved
0.6368	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3051	Approved
0.6359	Remote Similarity	NPD4663	Approved
0.6358	Remote Similarity	NPD5305	Approved
0.6358	Remote Similarity	NPD5306	Approved
0.6352	Remote Similarity	NPD6310	Approved
0.6352	Remote Similarity	NPD6311	Approved
0.6352	Remote Similarity	NPD6309	Approved
0.6351	Remote Similarity	NPD4198	Discontinued
0.6346	Remote Similarity	NPD5204	Approved
0.634	Remote Similarity	NPD6637	Approved
0.634	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7309	Approved
0.6335	Remote Similarity	NPD2567	Approved
0.6335	Remote Similarity	NPD2569	Approved
0.6335	Remote Similarity	NPD6852	Discontinued
0.6325	Remote Similarity	NPD7236	Approved
0.6324	Remote Similarity	NPD7906	Approved
0.6319	Remote Similarity	NPD5762	Approved
0.6319	Remote Similarity	NPD5763	Approved
0.6319	Remote Similarity	NPD7266	Discontinued
0.6319	Remote Similarity	NPD7549	Discontinued
0.6316	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5090	Approved
0.6316	Remote Similarity	NPD5089	Approved
0.6306	Remote Similarity	NPD5201	Approved
0.6306	Remote Similarity	NPD5203	Approved
0.6306	Remote Similarity	NPD4617	Approved
0.6306	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4620	Approved
0.6304	Remote Similarity	NPD5036	Approved
0.6303	Remote Similarity	NPD6331	Phase 2
0.6298	Remote Similarity	NPD3823	Discontinued
0.6294	Remote Similarity	NPD6685	Approved
0.6294	Remote Similarity	NPD7874	Approved
0.6294	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD27	Approved
0.6292	Remote Similarity	NPD2489	Approved
0.6289	Remote Similarity	NPD7714	Approved
0.6289	Remote Similarity	NPD8320	Phase 1
0.6289	Remote Similarity	NPD8319	Approved
0.6289	Remote Similarity	NPD7715	Approved
0.6287	Remote Similarity	NPD4357	Discontinued
0.6286	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD2629	Approved
0.6284	Remote Similarity	NPD4577	Approved
0.6284	Remote Similarity	NPD4578	Approved
0.6282	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4433	Discontinued
0.6275	Remote Similarity	NPD4480	Approved
0.627	Remote Similarity	NPD5038	Approved
0.627	Remote Similarity	NPD8150	Discontinued
0.627	Remote Similarity	NPD5037	Approved
0.6269	Remote Similarity	NPD6823	Phase 2
0.6266	Remote Similarity	NPD3136	Phase 2
0.6263	Remote Similarity	NPD7801	Approved
0.6258	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD8417	Discontinued
0.625	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5120	Approved
0.625	Remote Similarity	NPD5121	Approved
0.625	Remote Similarity	NPD5119	Approved
0.625	Remote Similarity	NPD3536	Discontinued
0.6243	Remote Similarity	NPD7972	Discontinued
0.6242	Remote Similarity	NPD3663	Approved
0.6242	Remote Similarity	NPD3661	Approved
0.6242	Remote Similarity	NPD3664	Approved
0.6242	Remote Similarity	NPD3662	Phase 3
0.6235	Remote Similarity	NPD7239	Suspended
0.6234	Remote Similarity	NPD2233	Approved
0.6234	Remote Similarity	NPD2230	Approved
0.6234	Remote Similarity	NPD2232	Approved
0.6233	Remote Similarity	NPD2201	Approved
0.6225	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD6385	Approved
0.6221	Remote Similarity	NPD6386	Approved
0.6221	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.622	Remote Similarity	NPD2029	Clinical (unspecified phase)

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