NPASS Compound

Structure

NPC472069 OpenBabel07101719152D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 4.0000 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 0.8660 -3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 2.4265 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0376 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2557 -1.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.5860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 10 1 0 0 0 0 3 22 1 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 18 2 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 20 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	297.15
Volume:	309.034
LogP:	3.724
LogD:	2.946
LogS:	-4.695
# Rotatable Bonds:	4
TPSA:	67.07
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.939
Synthetic Accessibility Score:	3.871
Fsp3:	0.353
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781
MDCK Permeability:	2.6433368475409225e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.45
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.518
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.64
Plasma Protein Binding (PPB):	96.28560638427734%
Volume Distribution (VD):	0.842
Pgp-substrate:	3.855682849884033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.662
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.721
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	0.538
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.753
AMES Toxicity:	0.521
Rat Oral Acute Toxicity:	0.431
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.75
Carcinogencity:	0.839
Eye Corrosion:	0.208
Eye Irritation:	0.144
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC472069

Natural Product ID:	NPC472069
*Common Name:**	PMJBMJOXTUFZIA-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PMJBMJOXTUFZIA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H19N3O2/c1-4-10(2)8-19-12-9-20-16-14-11(5-6-18-15(12)14)7-13(22-3)17(16)21/h5-7,9-10,19H,4,8H2,1-3H3
SMILES:	CCC(CNc1cnc2c3c1nccc3C=C(C2=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3335270
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0001857] Naphthyridines

*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
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO27743	Aaptos aaptos	Species	Suberitidae	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
IC50	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[541996]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[541996]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[541996]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[541996]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[541996]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[541996]

☑ 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 NPC472069 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	388
0.1-0.2	3333
0.2-0.3	14156
0.3-0.4	17343
0.4-0.5	3352
0.5-0.6	2135
0.6-0.7	1812
0.7-0.8	169
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472063
1.0	High Similarity	NPC472062
0.9832	High Similarity	NPC284338
0.9727	High Similarity	NPC472064
0.9721	High Similarity	NPC106824
0.957	High Similarity	NPC472070
0.9514	High Similarity	NPC472065
0.9218	High Similarity	NPC118084
0.8	Intermediate Similarity	NPC327592
0.799	Intermediate Similarity	NPC328318
0.799	Intermediate Similarity	NPC328596
0.796	Intermediate Similarity	NPC317373
0.7929	Intermediate Similarity	NPC74413
0.7929	Intermediate Similarity	NPC81535
0.79	Intermediate Similarity	NPC260900
0.7812	Intermediate Similarity	NPC46895
0.7806	Intermediate Similarity	NPC216550
0.7749	Intermediate Similarity	NPC61011
0.7729	Intermediate Similarity	NPC318299
0.7692	Intermediate Similarity	NPC317752
0.7656	Intermediate Similarity	NPC73994
0.765	Intermediate Similarity	NPC227582
0.7644	Intermediate Similarity	NPC83774
0.7644	Intermediate Similarity	NPC157583
0.7635	Intermediate Similarity	NPC143977
0.7624	Intermediate Similarity	NPC121327
0.7614	Intermediate Similarity	NPC472112
0.7563	Intermediate Similarity	NPC103119
0.756	Intermediate Similarity	NPC118940
0.7541	Intermediate Similarity	NPC251391
0.7538	Intermediate Similarity	NPC258480
0.7537	Intermediate Similarity	NPC252338
0.7524	Intermediate Similarity	NPC221100
0.7524	Intermediate Similarity	NPC234078
0.7523	Intermediate Similarity	NPC101350
0.7488	Intermediate Similarity	NPC123395
0.7477	Intermediate Similarity	NPC235685
0.7475	Intermediate Similarity	NPC167710
0.7454	Intermediate Similarity	NPC122436
0.7454	Intermediate Similarity	NPC229893
0.7454	Intermediate Similarity	NPC322482
0.745	Intermediate Similarity	NPC472113
0.744	Intermediate Similarity	NPC238457
0.7438	Intermediate Similarity	NPC34837
0.7426	Intermediate Similarity	NPC128244
0.7413	Intermediate Similarity	NPC267343
0.7406	Intermediate Similarity	NPC474412
0.7402	Intermediate Similarity	NPC103361
0.7399	Intermediate Similarity	NPC472061
0.7387	Intermediate Similarity	NPC255909
0.7379	Intermediate Similarity	NPC57398
0.7377	Intermediate Similarity	NPC123906
0.7374	Intermediate Similarity	NPC66210
0.7371	Intermediate Similarity	NPC237188
0.736	Intermediate Similarity	NPC467063
0.736	Intermediate Similarity	NPC284559
0.7358	Intermediate Similarity	NPC139763
0.735	Intermediate Similarity	NPC154339
0.7347	Intermediate Similarity	NPC191415
0.7343	Intermediate Similarity	NPC317701
0.734	Intermediate Similarity	NPC245916
0.734	Intermediate Similarity	NPC472116
0.7327	Intermediate Similarity	NPC472210
0.7327	Intermediate Similarity	NPC247735
0.7327	Intermediate Similarity	NPC472295
0.7327	Intermediate Similarity	NPC269886
0.7327	Intermediate Similarity	NPC81802
0.7327	Intermediate Similarity	NPC326422
0.7324	Intermediate Similarity	NPC237740
0.7322	Intermediate Similarity	NPC105811
0.7317	Intermediate Similarity	NPC474767
0.7308	Intermediate Similarity	NPC467188
0.73	Intermediate Similarity	NPC196251
0.73	Intermediate Similarity	NPC102338
0.73	Intermediate Similarity	NPC63199
0.73	Intermediate Similarity	NPC111602
0.7297	Intermediate Similarity	NPC70406
0.7286	Intermediate Similarity	NPC266249
0.7243	Intermediate Similarity	NPC313889
0.7219	Intermediate Similarity	NPC209362
0.7217	Intermediate Similarity	NPC123839
0.7208	Intermediate Similarity	NPC15840
0.7206	Intermediate Similarity	NPC135950
0.72	Intermediate Similarity	NPC62749
0.7186	Intermediate Similarity	NPC477003
0.7178	Intermediate Similarity	NPC324091
0.7178	Intermediate Similarity	NPC469489
0.7175	Intermediate Similarity	NPC260434
0.7174	Intermediate Similarity	NPC178858
0.7169	Intermediate Similarity	NPC216612
0.7163	Intermediate Similarity	NPC477979
0.7157	Intermediate Similarity	NPC55772
0.7143	Intermediate Similarity	NPC132539
0.7143	Intermediate Similarity	NPC477043
0.7143	Intermediate Similarity	NPC88115
0.7143	Intermediate Similarity	NPC207686
0.7143	Intermediate Similarity	NPC213914
0.7136	Intermediate Similarity	NPC78767
0.7136	Intermediate Similarity	NPC102755
0.7136	Intermediate Similarity	NPC473814
0.713	Intermediate Similarity	NPC36405
0.7122	Intermediate Similarity	NPC93390
0.7121	Intermediate Similarity	NPC469896
0.7121	Intermediate Similarity	NPC471997
0.7115	Intermediate Similarity	NPC128265
0.7115	Intermediate Similarity	NPC254240
0.7115	Intermediate Similarity	NPC294909
0.7115	Intermediate Similarity	NPC312870
0.7115	Intermediate Similarity	NPC199851
0.7113	Intermediate Similarity	NPC152620
0.7108	Intermediate Similarity	NPC47190
0.7108	Intermediate Similarity	NPC472292
0.7101	Intermediate Similarity	NPC168911
0.71	Intermediate Similarity	NPC207851
0.71	Intermediate Similarity	NPC472119
0.7097	Intermediate Similarity	NPC27041
0.7097	Intermediate Similarity	NPC469727
0.7095	Intermediate Similarity	NPC165599
0.7087	Intermediate Similarity	NPC79356
0.7087	Intermediate Similarity	NPC102592
0.7087	Intermediate Similarity	NPC472293
0.7077	Intermediate Similarity	NPC249614
0.7076	Intermediate Similarity	NPC53534
0.7073	Intermediate Similarity	NPC304203
0.7065	Intermediate Similarity	NPC79062
0.7065	Intermediate Similarity	NPC472107
0.7059	Intermediate Similarity	NPC473878
0.7059	Intermediate Similarity	NPC476460
0.7059	Intermediate Similarity	NPC114974
0.7053	Intermediate Similarity	NPC141454
0.7053	Intermediate Similarity	NPC74153
0.705	Intermediate Similarity	NPC143533
0.7048	Intermediate Similarity	NPC477549
0.7048	Intermediate Similarity	NPC106757
0.7045	Intermediate Similarity	NPC60621
0.7041	Intermediate Similarity	NPC252572
0.7039	Intermediate Similarity	NPC63971
0.7039	Intermediate Similarity	NPC91868
0.7037	Intermediate Similarity	NPC229055
0.7035	Intermediate Similarity	NPC70155
0.7024	Intermediate Similarity	NPC272458
0.702	Intermediate Similarity	NPC14113
0.702	Intermediate Similarity	NPC111275
0.702	Intermediate Similarity	NPC234987
0.702	Intermediate Similarity	NPC84827
0.702	Intermediate Similarity	NPC145885
0.7019	Intermediate Similarity	NPC212213
0.7019	Intermediate Similarity	NPC67288
0.7018	Intermediate Similarity	NPC472285
0.7016	Intermediate Similarity	NPC80681
0.7016	Intermediate Similarity	NPC474492
0.7	Intermediate Similarity	NPC472099
0.7	Intermediate Similarity	NPC323969
0.7	Intermediate Similarity	NPC74357
0.6995	Remote Similarity	NPC472323
0.6995	Remote Similarity	NPC21174
0.6995	Remote Similarity	NPC271797
0.699	Remote Similarity	NPC473821
0.6986	Remote Similarity	NPC472296
0.6986	Remote Similarity	NPC237414
0.6986	Remote Similarity	NPC472297
0.6985	Remote Similarity	NPC12649
0.698	Remote Similarity	NPC133003
0.6979	Remote Similarity	NPC100104
0.6979	Remote Similarity	NPC470680
0.6977	Remote Similarity	NPC309845
0.6977	Remote Similarity	NPC470020
0.6976	Remote Similarity	NPC138370
0.6974	Remote Similarity	NPC70949
0.697	Remote Similarity	NPC151635
0.6968	Remote Similarity	NPC471655
0.6965	Remote Similarity	NPC159125
0.6964	Remote Similarity	NPC478078
0.6961	Remote Similarity	NPC175474
0.6959	Remote Similarity	NPC236668
0.6957	Remote Similarity	NPC220151
0.6957	Remote Similarity	NPC19692
0.6957	Remote Similarity	NPC202812
0.6952	Remote Similarity	NPC100726
0.6951	Remote Similarity	NPC476818
0.695	Remote Similarity	NPC477042
0.6946	Remote Similarity	NPC315555
0.6946	Remote Similarity	NPC235684
0.6944	Remote Similarity	NPC82370
0.6941	Remote Similarity	NPC312645
0.6938	Remote Similarity	NPC470499
0.6938	Remote Similarity	NPC477041
0.6938	Remote Similarity	NPC474916
0.6938	Remote Similarity	NPC131887
0.6938	Remote Similarity	NPC239954
0.6938	Remote Similarity	NPC477044
0.6935	Remote Similarity	NPC284775
0.6927	Remote Similarity	NPC314333
0.6927	Remote Similarity	NPC329858
0.6927	Remote Similarity	NPC146976
0.6923	Remote Similarity	NPC41717
0.6923	Remote Similarity	NPC11445
0.6923	Remote Similarity	NPC56233
0.692	Remote Similarity	NPC470018
0.6916	Remote Similarity	NPC244741

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 NPC472069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	619
0.2-0.3	912
0.3-0.4	1919
0.4-0.5	2509
0.5-0.6	2051
0.6-0.7	869
0.7-0.8	40
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
0.7436	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3393	Approved
0.7371	Intermediate Similarity	NPD3389	Approved
0.7371	Intermediate Similarity	NPD3394	Approved
0.733	Intermediate Similarity	NPD5017	Discontinued
0.7273	Intermediate Similarity	NPD6178	Phase 3
0.7273	Intermediate Similarity	NPD1096	Discontinued
0.7257	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2787	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD8289	Discontinued
0.7225	Intermediate Similarity	NPD3247	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4558	Phase 2
0.715	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3947	Discontinued
0.7143	Intermediate Similarity	NPD8115	Approved
0.7143	Intermediate Similarity	NPD4429	Discontinued
0.7143	Intermediate Similarity	NPD8114	Approved
0.713	Intermediate Similarity	NPD1659	Phase 1
0.713	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4501	Approved
0.7115	Intermediate Similarity	NPD4500	Approved
0.7108	Intermediate Similarity	NPD4376	Phase 3
0.71	Intermediate Similarity	NPD7564	Discontinued
0.7098	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5088	Discontinued
0.7082	Intermediate Similarity	NPD5482	Discontinued
0.7064	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5426	Phase 3
0.7062	Intermediate Similarity	NPD5901	Discontinued
0.7053	Intermediate Similarity	NPD5446	Phase 2
0.7048	Intermediate Similarity	NPD7187	Phase 2
0.7043	Intermediate Similarity	NPD1270	Approved
0.7042	Intermediate Similarity	NPD2510	Approved
0.7042	Intermediate Similarity	NPD2509	Approved
0.7042	Intermediate Similarity	NPD7666	Phase 3
0.7042	Intermediate Similarity	NPD7665	Phase 2
0.7035	Intermediate Similarity	NPD2479	Phase 3
0.7035	Intermediate Similarity	NPD2481	Approved
0.7028	Intermediate Similarity	NPD7568	Phase 1
0.7028	Intermediate Similarity	NPD7010	Phase 3
0.7014	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6242	Discontinued
0.7	Intermediate Similarity	NPD1996	Discontinued
0.6995	Remote Similarity	NPD3583	Phase 2
0.6986	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6999	Discontinued
0.6982	Remote Similarity	NPD6173	Approved
0.6981	Remote Similarity	NPD6987	Phase 1
0.6964	Remote Similarity	NPD6164	Phase 2
0.6964	Remote Similarity	NPD6165	Phase 2
0.6955	Remote Similarity	NPD7404	Approved
0.6952	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4499	Approved
0.692	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7727	Phase 2
0.6919	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7817	Phase 1
0.6901	Remote Similarity	NPD4795	Phase 2
0.6898	Remote Similarity	NPD4051	Discontinued
0.6895	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2336	Approved
0.6888	Remote Similarity	NPD1343	Approved
0.6886	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7191	Phase 2
0.6881	Remote Similarity	NPD3794	Approved
0.6881	Remote Similarity	NPD3795	Approved
0.6881	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1740	Approved
0.6872	Remote Similarity	NPD1739	Approved
0.6869	Remote Similarity	NPD3967	Approved
0.6869	Remote Similarity	NPD750	Phase 2
0.6866	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5475	Discontinued
0.6866	Remote Similarity	NPD3927	Phase 2
0.6863	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6790	Phase 1
0.6847	Remote Similarity	NPD2096	Phase 2
0.6847	Remote Similarity	NPD2091	Phase 2
0.6845	Remote Similarity	NPD5686	Approved
0.6845	Remote Similarity	NPD5685	Approved
0.6842	Remote Similarity	NPD6226	Phase 3
0.6837	Remote Similarity	NPD424	Approved
0.6837	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1506	Discontinued
0.6837	Remote Similarity	NPD425	Approved
0.6835	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4883	Approved
0.6834	Remote Similarity	NPD482	Approved
0.6832	Remote Similarity	NPD3178	Discontinued
0.6828	Remote Similarity	NPD5022	Discontinued
0.6825	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2405	Phase 3
0.6814	Remote Similarity	NPD7730	Approved
0.6814	Remote Similarity	NPD7731	Approved
0.6804	Remote Similarity	NPD5888	Phase 2
0.6802	Remote Similarity	NPD5199	Approved
0.6802	Remote Similarity	NPD5198	Approved
0.68	Remote Similarity	NPD7271	Approved
0.6798	Remote Similarity	NPD2092	Phase 2
0.6798	Remote Similarity	NPD2094	Phase 2
0.6798	Remote Similarity	NPD2095	Phase 2
0.6796	Remote Similarity	NPD6068	Discontinued
0.6794	Remote Similarity	NPD4602	Approved
0.6794	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4600	Approved
0.6792	Remote Similarity	NPD4601	Approved
0.6791	Remote Similarity	NPD7001	Phase 3
0.6786	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3315	Phase 3
0.6779	Remote Similarity	NPD5505	Discontinued
0.6774	Remote Similarity	NPD3968	Approved
0.6774	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD5293	Phase 2
0.6766	Remote Similarity	NPD2753	Discontinued
0.6762	Remote Similarity	NPD4848	Phase 1
0.6762	Remote Similarity	NPD2307	Discontinued
0.6759	Remote Similarity	NPD3411	Phase 2
0.6759	Remote Similarity	NPD3410	Approved
0.6756	Remote Similarity	NPD6752	Phase 1
0.6756	Remote Similarity	NPD6753	Phase 1
0.6754	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7824	Approved
0.6753	Remote Similarity	NPD1630	Approved
0.6749	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7208	Approved
0.6744	Remote Similarity	NPD7209	Approved
0.6744	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7207	Approved
0.6743	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7790	Approved
0.6739	Remote Similarity	NPD7789	Approved
0.6739	Remote Similarity	NPD7953	Approved
0.6739	Remote Similarity	NPD7952	Approved
0.6739	Remote Similarity	NPD7951	Approved
0.6739	Remote Similarity	NPD7791	Approved
0.6739	Remote Similarity	NPD7950	Approved
0.6735	Remote Similarity	NPD5450	Discontinued
0.6733	Remote Similarity	NPD3079	Approved
0.6733	Remote Similarity	NPD3078	Approved
0.6733	Remote Similarity	NPD3076	Approved
0.6733	Remote Similarity	NPD3077	Approved
0.6732	Remote Similarity	NPD5555	Phase 1
0.6732	Remote Similarity	NPD3082	Discontinued
0.6729	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6459	Phase 2
0.6718	Remote Similarity	NPD2511	Approved
0.6716	Remote Similarity	NPD3238	Discontinued
0.6714	Remote Similarity	NPD6479	Discontinued
0.6714	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD2008	Discontinued
0.6713	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6152	Phase 1
0.6712	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1618	Phase 2
0.6699	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4886	Phase 2
0.6696	Remote Similarity	NPD3280	Approved
0.6696	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6771	Discontinued
0.6684	Remote Similarity	NPD4703	Approved
0.6684	Remote Similarity	NPD4702	Approved
0.6684	Remote Similarity	NPD2061	Approved
0.6683	Remote Similarity	NPD1575	Approved
0.6683	Remote Similarity	NPD1573	Approved
0.6683	Remote Similarity	NPD3321	Discontinued
0.6682	Remote Similarity	NPD2411	Approved
0.6682	Remote Similarity	NPD6954	Phase 2
0.6667	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD460	Discontinued
0.6667	Remote Similarity	NPD4988	Discontinued
0.6667	Remote Similarity	NPD5854	Approved
0.6667	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1631	Approved
0.6649	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD7888	Approved
0.6638	Remote Similarity	NPD7887	Approved
0.6636	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5491	Phase 3
0.6636	Remote Similarity	NPD5489	Phase 1
0.6634	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5862	Discovery
0.6622	Remote Similarity	NPD2547	Discontinued
0.6619	Remote Similarity	NPD6665	Discontinued
0.6619	Remote Similarity	NPD3404	Approved
0.6618	Remote Similarity	NPD5473	Discontinued

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