NPASS Compound

Structure

NPC136289 OpenBabel07101718222D 30 33 0 0 1 0 0 0 0 0999 V2000 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1084 -3.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -3.3002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 0.0000 C 0 0 1 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 -2.9793 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -3.8002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8885 -1.7907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6634 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 9 18 2 0 0 0 0 11 17 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 25 2 0 0 0 0 13 29 1 0 0 0 0 14 26 2 0 0 0 0 14 30 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 16 27 1 6 0 0 0 17 20 1 0 0 0 0 17 29 1 1 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 1 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 1 0 0 0 21 24 1 0 0 0 0 21 28 2 0 0 0 0 23 6 1 1 0 0 0 24 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	428.993
LogP:	2.572
LogD:	2.131
LogS:	-3.955
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	6.191
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996
MDCK Permeability:	2.4160251996363513e-05
Pgp-inhibitor:	0.942
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.337
Plasma Protein Binding (PPB):	55.90330123901367%
Volume Distribution (VD):	0.852
Pgp-substrate:	46.00323486328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.822
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.102
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.555

ADMET: Excretion

Clearance (CL):	2.243
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.339
AMES Toxicity:	0.143
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.526
Skin Sensitization:	0.324
Carcinogencity:	0.375
Eye Corrosion:	0.012
Eye Irritation:	0.024
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC136289

Natural Product ID:	NPC136289
*Common Name:**	XFKVVBCVBXGLMH-JNEANYDJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XFKVVBCVBXGLMH-JNEANYDJSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-12-15-10-24(21(12)28)11-17(29-13(2)25)20-22(4,5)8-7-19(30-14(3)26)23(20,6)18(24)9-16(15)27/h9,15-17,19-20,27H,1,7-8,10-11H2,2-6H3/t15-,16-,17+,19+,20-,23-,24+/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@]23C[C@H](C(=C)C2=O)[C@@H](C=C3[C@]2([C@H]1C(C)(C)CC[C@@H]2OC(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496475
PubChem CID:	25019750
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33117	jungermannia atrobrunnea	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18665642]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[477625]

☑ 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 NPC136289 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	188
0.1-0.2	1095
0.2-0.3	3778
0.3-0.4	7907
0.4-0.5	13205
0.5-0.6	6198
0.6-0.7	5880
0.7-0.8	3642
0.8-0.85	714
0.85-0.9	83
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC81530
0.9375	High Similarity	NPC476274
0.9278	High Similarity	NPC476240
0.9278	High Similarity	NPC224720
0.9278	High Similarity	NPC476223
0.9072	High Similarity	NPC478056
0.89	High Similarity	NPC236390
0.8866	High Similarity	NPC328371
0.8812	High Similarity	NPC96268
0.88	High Similarity	NPC195290
0.88	High Similarity	NPC119601
0.88	High Similarity	NPC204450
0.88	High Similarity	NPC308726
0.8788	High Similarity	NPC287833
0.8776	High Similarity	NPC474343
0.8776	High Similarity	NPC226986
0.8776	High Similarity	NPC170131
0.8776	High Similarity	NPC253826
0.8763	High Similarity	NPC317586
0.8763	High Similarity	NPC469599
0.8763	High Similarity	NPC134067
0.8763	High Similarity	NPC173875
0.8763	High Similarity	NPC318282
0.8763	High Similarity	NPC98639
0.8763	High Similarity	NPC469995
0.8763	High Similarity	NPC174948
0.8763	High Similarity	NPC470016
0.875	High Similarity	NPC294263
0.8738	High Similarity	NPC189075
0.8738	High Similarity	NPC295244
0.8738	High Similarity	NPC275539
0.8713	High Similarity	NPC159442
0.8713	High Similarity	NPC476237
0.8713	High Similarity	NPC90177
0.87	High Similarity	NPC302537
0.87	High Similarity	NPC163372
0.8687	High Similarity	NPC197386
0.8687	High Similarity	NPC176845
0.8687	High Similarity	NPC114274
0.8679	High Similarity	NPC962
0.8679	High Similarity	NPC250109
0.8673	High Similarity	NPC200054
0.8673	High Similarity	NPC29410
0.866	High Similarity	NPC166906
0.866	High Similarity	NPC184870
0.8646	High Similarity	NPC297265
0.8641	High Similarity	NPC475294
0.8641	High Similarity	NPC472925
0.8641	High Similarity	NPC230541
0.8641	High Similarity	NPC110496
0.8627	High Similarity	NPC28656
0.8627	High Similarity	NPC118911
0.8614	High Similarity	NPC293753
0.8614	High Similarity	NPC56498
0.8611	High Similarity	NPC471854
0.86	High Similarity	NPC218383
0.86	High Similarity	NPC51370
0.86	High Similarity	NPC477521
0.86	High Similarity	NPC205899
0.86	High Similarity	NPC266955
0.8586	High Similarity	NPC121339
0.8586	High Similarity	NPC18319
0.8586	High Similarity	NPC254496
0.8586	High Similarity	NPC108078
0.8586	High Similarity	NPC320306
0.8586	High Similarity	NPC475894
0.8586	High Similarity	NPC107243
0.8586	High Similarity	NPC23680
0.8585	High Similarity	NPC71348
0.8571	High Similarity	NPC197428
0.8571	High Similarity	NPC53565
0.8558	High Similarity	NPC469844
0.8557	High Similarity	NPC476416
0.8557	High Similarity	NPC470224
0.8557	High Similarity	NPC470376
0.8557	High Similarity	NPC69454
0.8557	High Similarity	NPC38232
0.8557	High Similarity	NPC470254
0.8557	High Similarity	NPC170220
0.8557	High Similarity	NPC107674
0.8557	High Similarity	NPC141497
0.8557	High Similarity	NPC470375
0.8544	High Similarity	NPC323834
0.8544	High Similarity	NPC231530
0.8544	High Similarity	NPC278628
0.8542	High Similarity	NPC48010
0.8542	High Similarity	NPC471896
0.8529	High Similarity	NPC264048
0.8529	High Similarity	NPC478057
0.8529	High Similarity	NPC95899
0.8529	High Similarity	NPC55872
0.8529	High Similarity	NPC140723
0.8519	High Similarity	NPC49492
0.8519	High Similarity	NPC266728
0.8519	High Similarity	NPC270929
0.8515	High Similarity	NPC472924
0.8515	High Similarity	NPC115899
0.8515	High Similarity	NPC115862
0.8515	High Similarity	NPC474327
0.8511	High Similarity	NPC473226
0.8511	High Similarity	NPC322159
0.8505	High Similarity	NPC472929
0.8505	High Similarity	NPC122056
0.8505	High Similarity	NPC202889
0.8505	High Similarity	NPC472926
0.8505	High Similarity	NPC25909
0.85	High Similarity	NPC28864
0.85	High Similarity	NPC20479
0.85	High Similarity	NPC162459
0.85	High Similarity	NPC38296
0.85	High Similarity	NPC471717
0.85	High Similarity	NPC98837
0.85	High Similarity	NPC10364
0.85	High Similarity	NPC471038
0.85	High Similarity	NPC48647
0.85	High Similarity	NPC38471
0.8491	Intermediate Similarity	NPC472928
0.8491	Intermediate Similarity	NPC474315
0.8485	Intermediate Similarity	NPC7124
0.8485	Intermediate Similarity	NPC305483
0.8485	Intermediate Similarity	NPC456
0.8485	Intermediate Similarity	NPC249954
0.8485	Intermediate Similarity	NPC301534
0.8485	Intermediate Similarity	NPC104568
0.8485	Intermediate Similarity	NPC250757
0.8485	Intermediate Similarity	NPC96859
0.8485	Intermediate Similarity	NPC235053
0.8485	Intermediate Similarity	NPC472941
0.8485	Intermediate Similarity	NPC3772
0.8485	Intermediate Similarity	NPC328162
0.8485	Intermediate Similarity	NPC13949
0.8476	Intermediate Similarity	NPC474901
0.8476	Intermediate Similarity	NPC141350
0.8476	Intermediate Similarity	NPC475941
0.8469	Intermediate Similarity	NPC119562
0.8469	Intermediate Similarity	NPC472977
0.8469	Intermediate Similarity	NPC279410
0.8469	Intermediate Similarity	NPC472976
0.8469	Intermediate Similarity	NPC159410
0.8469	Intermediate Similarity	NPC469406
0.8462	Intermediate Similarity	NPC220229
0.8462	Intermediate Similarity	NPC475060
0.8462	Intermediate Similarity	NPC44063
0.8455	Intermediate Similarity	NPC475041
0.8455	Intermediate Similarity	NPC61520
0.8454	Intermediate Similarity	NPC110657
0.8454	Intermediate Similarity	NPC63748
0.8454	Intermediate Similarity	NPC154101
0.8454	Intermediate Similarity	NPC473998
0.8454	Intermediate Similarity	NPC107690
0.8454	Intermediate Similarity	NPC472978
0.8454	Intermediate Similarity	NPC26888
0.8454	Intermediate Similarity	NPC186363
0.8454	Intermediate Similarity	NPC212301
0.8454	Intermediate Similarity	NPC250753
0.8454	Intermediate Similarity	NPC86266
0.8454	Intermediate Similarity	NPC233345
0.8447	Intermediate Similarity	NPC189616
0.8447	Intermediate Similarity	NPC235889
0.844	Intermediate Similarity	NPC472927
0.8438	Intermediate Similarity	NPC309603
0.8438	Intermediate Similarity	NPC475921
0.8438	Intermediate Similarity	NPC473999
0.8438	Intermediate Similarity	NPC474704
0.8438	Intermediate Similarity	NPC262858
0.8438	Intermediate Similarity	NPC472240
0.8438	Intermediate Similarity	NPC146554
0.8438	Intermediate Similarity	NPC472973
0.8431	Intermediate Similarity	NPC234892
0.8431	Intermediate Similarity	NPC477915
0.8431	Intermediate Similarity	NPC473424
0.8426	Intermediate Similarity	NPC67259
0.8426	Intermediate Similarity	NPC147912
0.8421	Intermediate Similarity	NPC474684
0.8421	Intermediate Similarity	NPC142361
0.8416	Intermediate Similarity	NPC117685
0.8416	Intermediate Similarity	NPC154072
0.8416	Intermediate Similarity	NPC293866
0.8416	Intermediate Similarity	NPC327431
0.8416	Intermediate Similarity	NPC307954
0.8416	Intermediate Similarity	NPC471041
0.8416	Intermediate Similarity	NPC316964
0.8416	Intermediate Similarity	NPC476303
0.8416	Intermediate Similarity	NPC201406
0.8411	Intermediate Similarity	NPC12046
0.8411	Intermediate Similarity	NPC264634
0.8411	Intermediate Similarity	NPC475524
0.8411	Intermediate Similarity	NPC100267
0.8411	Intermediate Similarity	NPC194951
0.84	Intermediate Similarity	NPC175351
0.84	Intermediate Similarity	NPC121402
0.84	Intermediate Similarity	NPC141401
0.84	Intermediate Similarity	NPC38530
0.84	Intermediate Similarity	NPC132753
0.84	Intermediate Similarity	NPC106557
0.84	Intermediate Similarity	NPC84335
0.84	Intermediate Similarity	NPC285513
0.84	Intermediate Similarity	NPC189880
0.84	Intermediate Similarity	NPC292133
0.84	Intermediate Similarity	NPC151681

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 NPC136289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1328
0.2-0.3	3558
0.3-0.4	2633
0.4-0.5	926
0.5-0.6	190
0.6-0.7	184
0.7-0.8	124
0.8-0.85	41
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6399	Phase 3
0.8558	High Similarity	NPD6899	Approved
0.8558	High Similarity	NPD6881	Approved
0.8544	High Similarity	NPD6675	Approved
0.8544	High Similarity	NPD6402	Approved
0.8544	High Similarity	NPD5739	Approved
0.8544	High Similarity	NPD7128	Approved
0.8491	Intermediate Similarity	NPD6649	Approved
0.8491	Intermediate Similarity	NPD6650	Approved
0.8476	Intermediate Similarity	NPD6373	Approved
0.8476	Intermediate Similarity	NPD6372	Approved
0.8462	Intermediate Similarity	NPD5697	Approved
0.8454	Intermediate Similarity	NPD6079	Approved
0.8438	Intermediate Similarity	NPD5328	Approved
0.8396	Intermediate Similarity	NPD6883	Approved
0.8396	Intermediate Similarity	NPD7290	Approved
0.8396	Intermediate Similarity	NPD7102	Approved
0.8381	Intermediate Similarity	NPD7320	Approved
0.8381	Intermediate Similarity	NPD6011	Approved
0.8318	Intermediate Similarity	NPD8130	Phase 1
0.8318	Intermediate Similarity	NPD6617	Approved
0.8318	Intermediate Similarity	NPD6847	Approved
0.8318	Intermediate Similarity	NPD6869	Approved
0.8302	Intermediate Similarity	NPD6013	Approved
0.8302	Intermediate Similarity	NPD6012	Approved
0.8302	Intermediate Similarity	NPD6014	Approved
0.8286	Intermediate Similarity	NPD5701	Approved
0.8273	Intermediate Similarity	NPD7115	Discovery
0.8252	Intermediate Similarity	NPD5211	Phase 2
0.8241	Intermediate Similarity	NPD8297	Approved
0.8241	Intermediate Similarity	NPD6882	Approved
0.8218	Intermediate Similarity	NPD7902	Approved
0.8148	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3618	Phase 1
0.8119	Intermediate Similarity	NPD4697	Phase 3
0.8119	Intermediate Similarity	NPD5221	Approved
0.8119	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD5222	Approved
0.8105	Intermediate Similarity	NPD4786	Approved
0.81	Intermediate Similarity	NPD7748	Approved
0.8095	Intermediate Similarity	NPD5141	Approved
0.8081	Intermediate Similarity	NPD7515	Phase 2
0.8058	Intermediate Similarity	NPD7639	Approved
0.8058	Intermediate Similarity	NPD5286	Approved
0.8058	Intermediate Similarity	NPD5285	Approved
0.8058	Intermediate Similarity	NPD7640	Approved
0.8058	Intermediate Similarity	NPD4696	Approved
0.8039	Intermediate Similarity	NPD4755	Approved
0.8039	Intermediate Similarity	NPD5173	Approved
0.8019	Intermediate Similarity	NPD6008	Approved
0.7981	Intermediate Similarity	NPD5223	Approved
0.7961	Intermediate Similarity	NPD7638	Approved
0.7921	Intermediate Similarity	NPD7900	Approved
0.7921	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5225	Approved
0.7905	Intermediate Similarity	NPD5226	Approved
0.7905	Intermediate Similarity	NPD4633	Approved
0.7905	Intermediate Similarity	NPD5224	Approved
0.79	Intermediate Similarity	NPD8035	Phase 2
0.79	Intermediate Similarity	NPD8034	Phase 2
0.7895	Intermediate Similarity	NPD3667	Approved
0.7885	Intermediate Similarity	NPD4700	Approved
0.7876	Intermediate Similarity	NPD6335	Approved
0.7864	Intermediate Similarity	NPD6084	Phase 2
0.7864	Intermediate Similarity	NPD6083	Phase 2
0.7857	Intermediate Similarity	NPD6274	Approved
0.7857	Intermediate Similarity	NPD6868	Approved
0.7838	Intermediate Similarity	NPD4632	Approved
0.783	Intermediate Similarity	NPD5175	Approved
0.783	Intermediate Similarity	NPD5174	Approved
0.7822	Intermediate Similarity	NPD4202	Approved
0.7807	Intermediate Similarity	NPD7100	Approved
0.7807	Intermediate Similarity	NPD7101	Approved
0.7788	Intermediate Similarity	NPD4225	Approved
0.7788	Intermediate Similarity	NPD6317	Approved
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7755	Intermediate Similarity	NPD5330	Approved
0.7755	Intermediate Similarity	NPD7146	Approved
0.7755	Intermediate Similarity	NPD7334	Approved
0.7755	Intermediate Similarity	NPD7521	Approved
0.7755	Intermediate Similarity	NPD6409	Approved
0.7755	Intermediate Similarity	NPD6684	Approved
0.7719	Intermediate Similarity	NPD6314	Approved
0.7719	Intermediate Similarity	NPD6313	Approved
0.7677	Intermediate Similarity	NPD3573	Approved
0.7672	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4754	Approved
0.7653	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6009	Approved
0.7619	Intermediate Similarity	NPD5696	Approved
0.76	Intermediate Similarity	NPD6903	Approved
0.76	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6319	Approved
0.7551	Intermediate Similarity	NPD3666	Approved
0.7551	Intermediate Similarity	NPD3665	Phase 1
0.7551	Intermediate Similarity	NPD3133	Approved
0.7549	Intermediate Similarity	NPD6411	Approved
0.7545	Intermediate Similarity	NPD4729	Approved
0.7545	Intermediate Similarity	NPD5128	Approved
0.7545	Intermediate Similarity	NPD4730	Approved
0.7542	Intermediate Similarity	NPD7604	Phase 2
0.7523	Intermediate Similarity	NPD4767	Approved
0.7523	Intermediate Similarity	NPD4768	Approved
0.7521	Intermediate Similarity	NPD5983	Phase 2
0.7521	Intermediate Similarity	NPD6909	Approved
0.7521	Intermediate Similarity	NPD6908	Approved
0.75	Intermediate Similarity	NPD5695	Phase 3
0.7479	Intermediate Similarity	NPD7492	Approved
0.7476	Intermediate Similarity	NPD5779	Approved
0.7476	Intermediate Similarity	NPD5778	Approved
0.7475	Intermediate Similarity	NPD1694	Approved
0.7436	Intermediate Similarity	NPD6054	Approved
0.7417	Intermediate Similarity	NPD6616	Approved
0.7417	Intermediate Similarity	NPD6336	Discontinued
0.7411	Intermediate Similarity	NPD4634	Approved
0.7411	Intermediate Similarity	NPD5251	Approved
0.7411	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5249	Phase 3
0.7411	Intermediate Similarity	NPD5247	Approved
0.7411	Intermediate Similarity	NPD5169	Approved
0.7411	Intermediate Similarity	NPD5135	Approved
0.7411	Intermediate Similarity	NPD5248	Approved
0.7411	Intermediate Similarity	NPD5250	Approved
0.7407	Intermediate Similarity	NPD7632	Discontinued
0.74	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD5168	Approved
0.7379	Intermediate Similarity	NPD5281	Approved
0.7379	Intermediate Similarity	NPD5284	Approved
0.7374	Intermediate Similarity	NPD3668	Phase 3
0.7355	Intermediate Similarity	NPD7078	Approved
0.7353	Intermediate Similarity	NPD6904	Approved
0.7353	Intermediate Similarity	NPD6080	Approved
0.7353	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6101	Approved
0.7353	Intermediate Similarity	NPD6673	Approved
0.7353	Intermediate Similarity	NPD4753	Phase 2
0.7347	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5127	Approved
0.7345	Intermediate Similarity	NPD5216	Approved
0.7345	Intermediate Similarity	NPD5217	Approved
0.7345	Intermediate Similarity	NPD5215	Approved
0.7333	Intermediate Similarity	NPD5210	Approved
0.7333	Intermediate Similarity	NPD4629	Approved
0.732	Intermediate Similarity	NPD7525	Registered
0.7311	Intermediate Similarity	NPD6370	Approved
0.7295	Intermediate Similarity	NPD7736	Approved
0.7292	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6059	Approved
0.7282	Intermediate Similarity	NPD5785	Approved
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD7507	Approved
0.7238	Intermediate Similarity	NPD6001	Approved
0.7232	Intermediate Similarity	NPD6686	Approved
0.7228	Intermediate Similarity	NPD5786	Approved
0.7228	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD6098	Approved
0.7227	Intermediate Similarity	NPD6016	Approved
0.7227	Intermediate Similarity	NPD6015	Approved
0.7213	Intermediate Similarity	NPD8293	Discontinued
0.7212	Intermediate Similarity	NPD7637	Suspended
0.7212	Intermediate Similarity	NPD5693	Phase 1
0.7188	Intermediate Similarity	NPD6116	Phase 1
0.7172	Intermediate Similarity	NPD4221	Approved
0.7172	Intermediate Similarity	NPD4223	Phase 3
0.717	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5988	Approved
0.7158	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD6942	Approved
0.7155	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7129	Intermediate Similarity	NPD5329	Approved
0.7129	Intermediate Similarity	NPD5363	Approved
0.7107	Intermediate Similarity	NPD8328	Phase 3
0.7105	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5362	Discontinued
0.71	Intermediate Similarity	NPD4788	Approved
0.7097	Intermediate Similarity	NPD7319	Approved
0.7087	Intermediate Similarity	NPD5208	Approved
0.7083	Intermediate Similarity	NPD6117	Approved
0.708	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4623	Approved
0.7059	Intermediate Similarity	NPD4519	Discontinued
0.7048	Intermediate Similarity	NPD6050	Approved
0.703	Intermediate Similarity	NPD4197	Approved
0.7019	Intermediate Similarity	NPD6051	Approved
0.7019	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.7	Intermediate Similarity	NPD6435	Approved
0.6952	Remote Similarity	NPD5207	Approved
0.6952	Remote Similarity	NPD5692	Phase 3
0.6939	Remote Similarity	NPD6114	Approved
0.6939	Remote Similarity	NPD6697	Approved
0.6939	Remote Similarity	NPD6118	Approved
0.6939	Remote Similarity	NPD6115	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