NPASS Compound

Structure

NPC472124 OpenBabel07101719522D 34 36 0 0 1 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -3.4641 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 2.0000 0.0000 C 0 0 1 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 6 7 1 0 0 0 0 7 28 1 0 0 0 0 8 15 2 0 0 0 0 8 30 1 0 0 0 0 9 29 1 0 0 0 0 10 23 2 0 0 0 0 10 29 1 0 0 0 0 11 24 2 0 0 0 0 11 31 1 0 0 0 0 12 25 2 0 0 0 0 12 32 1 0 0 0 0 13 5 1 6 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 6 1 6 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 9 1 1 0 0 0 16 17 1 0 0 0 0 16 33 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 19 1 0 0 0 0 18 31 1 1 0 0 0 19 22 1 0 0 0 0 19 32 1 6 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 30 1 0 0 0 0 21 34 1 1 0 0 0 22 33 1 0 0 0 0 22 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.16
Volume:	453.063
LogP:	1.211
LogD:	1.045
LogS:	-2.832
# Rotatable Bonds:	10
TPSA:	153.12
# H-Bond Aceptor:	12
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.297
Synthetic Accessibility Score:	4.764
Fsp3:	0.636
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:	-5.315
MDCK Permeability:	0.00013233712525106966
Pgp-inhibitor:	0.011
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	24.85297966003418%
Volume Distribution (VD):	1.094
Pgp-substrate:	54.59517288208008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.399
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	1.77
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.256
Human Hepatotoxicity (H-HT):	0.812
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.549
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.381
Skin Sensitization:	0.353
Carcinogencity:	0.688
Eye Corrosion:	0.004
Eye Irritation:	0.044
Respiratory Toxicity:	0.698

Download Data

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

Natural Product: NPC472124

Natural Product ID:	NPC472124
*Common Name:**	PDOGRHLUXBLKAT-FGFQXQBLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PDOGRHLUXBLKAT-FGFQXQBLSA-N
Standard InCHI:	InChI=1S/C22H28O12/c1-5-13-14-6-7-28-20(27)15(14)8-30-21(13)34-22-19(32-12(4)25)18(31-11(3)24)17(26)16(33-22)9-29-10(2)23/h5,8,13-14,16-19,21-22,26H,1,6-7,9H2,2-4H3/t13-,14+,16-,17-,18+,19-,21+,22+/m1/s1
SMILES:	CC(=O)OCC1C(C(C(C(O1)OC2C(C3CCOC(=O)C3=CO2)C=C)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3338636
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24806310]
NPO32460	Gentianella azurea	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25442320]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	200000.0	nM	PMID[534138]

☑ 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 NPC472124 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	204
0.1-0.2	1561
0.2-0.3	5217
0.3-0.4	11609
0.4-0.5	12533
0.5-0.6	8540
0.6-0.7	2695
0.7-0.8	281
0.8-0.85	23
0.85-0.9	13
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472126
1.0	High Similarity	NPC472125
0.9882	High Similarity	NPC307699
0.9651	High Similarity	NPC117596
0.9438	High Similarity	NPC101051
0.9432	High Similarity	NPC61201
0.9425	High Similarity	NPC120021
0.9425	High Similarity	NPC470573
0.9425	High Similarity	NPC216826
0.9425	High Similarity	NPC270908
0.9425	High Similarity	NPC231710
0.9425	High Similarity	NPC65665
0.8842	High Similarity	NPC222062
0.8804	High Similarity	NPC469543
0.8804	High Similarity	NPC170204
0.8778	High Similarity	NPC303451
0.8778	High Similarity	NPC6414
0.875	High Similarity	NPC284929
0.875	High Similarity	NPC118761
0.875	High Similarity	NPC267869
0.875	High Similarity	NPC197541
0.875	High Similarity	NPC234304
0.8646	High Similarity	NPC195510
0.8646	High Similarity	NPC13171
0.8632	High Similarity	NPC22149
0.8632	High Similarity	NPC255677
0.8632	High Similarity	NPC306344
0.8542	High Similarity	NPC298255
0.8542	High Similarity	NPC28304
0.8454	Intermediate Similarity	NPC310804
0.8454	Intermediate Similarity	NPC261117
0.8316	Intermediate Similarity	NPC241911
0.8283	Intermediate Similarity	NPC86095
0.8265	Intermediate Similarity	NPC250545
0.8182	Intermediate Similarity	NPC475928
0.8161	Intermediate Similarity	NPC323472
0.8125	Intermediate Similarity	NPC161293
0.8119	Intermediate Similarity	NPC474285
0.8119	Intermediate Similarity	NPC254538
0.8081	Intermediate Similarity	NPC177013
0.8081	Intermediate Similarity	NPC106668
0.8081	Intermediate Similarity	NPC4899
0.8081	Intermediate Similarity	NPC35185
0.8081	Intermediate Similarity	NPC474730
0.802	Intermediate Similarity	NPC41681
0.802	Intermediate Similarity	NPC170432
0.8	Intermediate Similarity	NPC37240
0.8	Intermediate Similarity	NPC320552
0.8	Intermediate Similarity	NPC27687
0.7979	Intermediate Similarity	NPC327253
0.7941	Intermediate Similarity	NPC148270
0.7941	Intermediate Similarity	NPC197813
0.7941	Intermediate Similarity	NPC80338
0.7917	Intermediate Similarity	NPC294293
0.7912	Intermediate Similarity	NPC266718
0.7826	Intermediate Similarity	NPC470124
0.7822	Intermediate Similarity	NPC197736
0.78	Intermediate Similarity	NPC3488
0.78	Intermediate Similarity	NPC287539
0.7778	Intermediate Similarity	NPC40182
0.7778	Intermediate Similarity	NPC198422
0.7755	Intermediate Similarity	NPC306041
0.7732	Intermediate Similarity	NPC63897
0.7717	Intermediate Similarity	NPC475035
0.7714	Intermediate Similarity	NPC193741
0.7708	Intermediate Similarity	NPC477749
0.7708	Intermediate Similarity	NPC9447
0.7692	Intermediate Similarity	NPC110701
0.7684	Intermediate Similarity	NPC50464
0.767	Intermediate Similarity	NPC127235
0.766	Intermediate Similarity	NPC475037
0.7629	Intermediate Similarity	NPC280390
0.7629	Intermediate Similarity	NPC238090
0.7629	Intermediate Similarity	NPC472195
0.7629	Intermediate Similarity	NPC472196
0.7579	Intermediate Similarity	NPC137368
0.757	Intermediate Similarity	NPC475851
0.757	Intermediate Similarity	NPC475924
0.7551	Intermediate Similarity	NPC2003
0.7551	Intermediate Similarity	NPC25701
0.7551	Intermediate Similarity	NPC71589
0.7551	Intermediate Similarity	NPC159698
0.7549	Intermediate Similarity	NPC201191
0.7549	Intermediate Similarity	NPC471599
0.7526	Intermediate Similarity	NPC294643
0.7526	Intermediate Similarity	NPC274274
0.7526	Intermediate Similarity	NPC473150
0.7525	Intermediate Similarity	NPC244878
0.7524	Intermediate Similarity	NPC473807
0.75	Intermediate Similarity	NPC285588
0.75	Intermediate Similarity	NPC477748
0.75	Intermediate Similarity	NPC93190
0.75	Intermediate Similarity	NPC472290
0.7475	Intermediate Similarity	NPC93869
0.7475	Intermediate Similarity	NPC6765
0.7474	Intermediate Similarity	NPC118077
0.7474	Intermediate Similarity	NPC475186
0.7473	Intermediate Similarity	NPC163362
0.7473	Intermediate Similarity	NPC127295
0.7451	Intermediate Similarity	NPC471637
0.7451	Intermediate Similarity	NPC475157
0.7451	Intermediate Similarity	NPC57586
0.7451	Intermediate Similarity	NPC219038
0.7451	Intermediate Similarity	NPC2313
0.7451	Intermediate Similarity	NPC154132
0.7451	Intermediate Similarity	NPC475655
0.7451	Intermediate Similarity	NPC20673
0.7449	Intermediate Similarity	NPC474835
0.7447	Intermediate Similarity	NPC475034
0.7447	Intermediate Similarity	NPC477746
0.7447	Intermediate Similarity	NPC477747
0.7426	Intermediate Similarity	NPC249171
0.7426	Intermediate Similarity	NPC472015
0.7426	Intermediate Similarity	NPC151093
0.7426	Intermediate Similarity	NPC49833
0.7423	Intermediate Similarity	NPC202886
0.74	Intermediate Similarity	NPC54731
0.7396	Intermediate Similarity	NPC473151
0.7379	Intermediate Similarity	NPC304163
0.7379	Intermediate Similarity	NPC80144
0.7374	Intermediate Similarity	NPC256368
0.7374	Intermediate Similarity	NPC274588
0.7374	Intermediate Similarity	NPC477348
0.7374	Intermediate Similarity	NPC477345
0.7374	Intermediate Similarity	NPC238264
0.7358	Intermediate Similarity	NPC177524
0.7358	Intermediate Similarity	NPC392
0.7358	Intermediate Similarity	NPC219900
0.7347	Intermediate Similarity	NPC472197
0.7347	Intermediate Similarity	NPC110072
0.7347	Intermediate Similarity	NPC470373
0.7347	Intermediate Similarity	NPC472199
0.7347	Intermediate Similarity	NPC470379
0.734	Intermediate Similarity	NPC136699
0.734	Intermediate Similarity	NPC220167
0.7333	Intermediate Similarity	NPC476740
0.7333	Intermediate Similarity	NPC476738
0.7327	Intermediate Similarity	NPC236580
0.7327	Intermediate Similarity	NPC278506
0.7327	Intermediate Similarity	NPC304445
0.7312	Intermediate Similarity	NPC251026
0.7308	Intermediate Similarity	NPC473148
0.7308	Intermediate Similarity	NPC309398
0.7292	Intermediate Similarity	NPC142583
0.7292	Intermediate Similarity	NPC74139
0.729	Intermediate Similarity	NPC133625
0.7282	Intermediate Similarity	NPC67296
0.7282	Intermediate Similarity	NPC476611
0.7282	Intermediate Similarity	NPC4637
0.7282	Intermediate Similarity	NPC98859
0.7282	Intermediate Similarity	NPC198992
0.7273	Intermediate Similarity	NPC320089
0.7255	Intermediate Similarity	NPC307517
0.7255	Intermediate Similarity	NPC37866
0.7255	Intermediate Similarity	NPC81483
0.7255	Intermediate Similarity	NPC61630
0.7255	Intermediate Similarity	NPC169468
0.7253	Intermediate Similarity	NPC133377
0.7245	Intermediate Similarity	NPC473311
0.7241	Intermediate Similarity	NPC474078
0.7238	Intermediate Similarity	NPC469869
0.7234	Intermediate Similarity	NPC473315
0.7234	Intermediate Similarity	NPC142111
0.7228	Intermediate Similarity	NPC143446
0.7228	Intermediate Similarity	NPC475241
0.7228	Intermediate Similarity	NPC473765
0.7228	Intermediate Similarity	NPC475525
0.7228	Intermediate Similarity	NPC476066
0.7228	Intermediate Similarity	NPC473605
0.7228	Intermediate Similarity	NPC256230
0.7228	Intermediate Similarity	NPC475375
0.7228	Intermediate Similarity	NPC475593
0.7228	Intermediate Similarity	NPC170527
0.7228	Intermediate Similarity	NPC475540
0.7228	Intermediate Similarity	NPC475164
0.7222	Intermediate Similarity	NPC472508
0.7222	Intermediate Similarity	NPC83005
0.7216	Intermediate Similarity	NPC470137
0.7216	Intermediate Similarity	NPC248312
0.7204	Intermediate Similarity	NPC469469
0.72	Intermediate Similarity	NPC472198
0.7196	Intermediate Similarity	NPC472507
0.7196	Intermediate Similarity	NPC193765
0.7174	Intermediate Similarity	NPC321728
0.7172	Intermediate Similarity	NPC477349
0.717	Intermediate Similarity	NPC82251
0.717	Intermediate Similarity	NPC315070
0.7158	Intermediate Similarity	NPC98276
0.7158	Intermediate Similarity	NPC259296
0.7158	Intermediate Similarity	NPC473308
0.7157	Intermediate Similarity	NPC155319
0.7157	Intermediate Similarity	NPC96597
0.7157	Intermediate Similarity	NPC475332
0.7157	Intermediate Similarity	NPC474194
0.7157	Intermediate Similarity	NPC125551
0.7157	Intermediate Similarity	NPC476613
0.7157	Intermediate Similarity	NPC91197
0.7157	Intermediate Similarity	NPC239547
0.7157	Intermediate Similarity	NPC476612
0.7157	Intermediate Similarity	NPC309503

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 NPC472124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1879
0.2-0.3	4057
0.3-0.4	2029
0.4-0.5	691
0.5-0.6	262
0.6-0.7	45
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
0.7358	Intermediate Similarity	NPD6686	Approved
0.7255	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6698	Approved
0.7071	Intermediate Similarity	NPD46	Approved
0.7043	Intermediate Similarity	NPD8513	Phase 3
0.7	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8516	Approved
0.6897	Remote Similarity	NPD8515	Approved
0.6897	Remote Similarity	NPD8517	Approved
0.6752	Remote Similarity	NPD7503	Approved
0.6733	Remote Similarity	NPD7838	Discovery
0.6726	Remote Similarity	NPD8133	Approved
0.6639	Remote Similarity	NPD7829	Approved
0.6639	Remote Similarity	NPD7830	Approved
0.6505	Remote Similarity	NPD7983	Approved
0.6393	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD6110	Phase 1
0.6356	Remote Similarity	NPD7641	Discontinued
0.6341	Remote Similarity	NPD8074	Phase 3
0.6339	Remote Similarity	NPD6412	Phase 2
0.6337	Remote Similarity	NPD4249	Approved
0.6333	Remote Similarity	NPD8033	Approved
0.6275	Remote Similarity	NPD4250	Approved
0.6275	Remote Similarity	NPD4251	Approved
0.626	Remote Similarity	NPD8451	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.624	Remote Similarity	NPD7319	Approved
0.623	Remote Similarity	NPD7642	Approved
0.623	Remote Similarity	NPD8328	Phase 3
0.6218	Remote Similarity	NPD7328	Approved
0.6218	Remote Similarity	NPD7327	Approved
0.621	Remote Similarity	NPD8448	Approved
0.6207	Remote Similarity	NPD6053	Discontinued
0.6198	Remote Similarity	NPD8378	Approved
0.6198	Remote Similarity	NPD8444	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8379	Approved
0.619	Remote Similarity	NPD8392	Approved
0.619	Remote Similarity	NPD8391	Approved
0.619	Remote Similarity	NPD8390	Approved
0.6182	Remote Similarity	NPD5344	Discontinued
0.6167	Remote Similarity	NPD7516	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7329	Approved
0.6111	Remote Similarity	NPD7839	Suspended
0.6087	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8341	Approved
0.6048	Remote Similarity	NPD8340	Approved
0.6048	Remote Similarity	NPD8342	Approved
0.6048	Remote Similarity	NPD8299	Approved
0.6016	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6101	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5981	Remote Similarity	NPD5779	Approved
0.5981	Remote Similarity	NPD5778	Approved
0.5978	Remote Similarity	NPD897	Approved
0.5978	Remote Similarity	NPD898	Approved
0.5978	Remote Similarity	NPD896	Approved
0.5935	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6371	Approved
0.5888	Remote Similarity	NPD6411	Approved
0.5882	Remote Similarity	NPD7154	Phase 3
0.5882	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD3669	Approved
0.5872	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7638	Approved
0.5833	Remote Similarity	NPD3181	Approved
0.5806	Remote Similarity	NPD8266	Approved
0.5806	Remote Similarity	NPD8267	Approved
0.5806	Remote Similarity	NPD8268	Approved
0.5806	Remote Similarity	NPD8269	Approved
0.5804	Remote Similarity	NPD7640	Approved
0.5804	Remote Similarity	NPD6648	Approved
0.5804	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1407	Approved
0.5781	Remote Similarity	NPD7736	Approved
0.578	Remote Similarity	NPD5282	Discontinued
0.5765	Remote Similarity	NPD890	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD892	Phase 3
0.5765	Remote Similarity	NPD888	Phase 3
0.5765	Remote Similarity	NPD893	Approved
0.5765	Remote Similarity	NPD891	Phase 3
0.576	Remote Similarity	NPD6370	Approved
0.5741	Remote Similarity	NPD7637	Suspended
0.5738	Remote Similarity	NPD7115	Discovery
0.5738	Remote Similarity	NPD6009	Approved
0.5726	Remote Similarity	NPD6319	Approved
0.57	Remote Similarity	NPD4271	Approved
0.57	Remote Similarity	NPD4268	Approved
0.568	Remote Similarity	NPD6921	Approved
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7492	Approved
0.5667	Remote Similarity	NPD6882	Approved
0.5667	Remote Similarity	NPD6123	Approved
0.5649	Remote Similarity	NPD7260	Phase 2
0.5631	Remote Similarity	NPD6435	Approved
0.5625	Remote Similarity	NPD6616	Approved
0.562	Remote Similarity	NPD4632	Approved
0.56	Remote Similarity	NPD6054	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