NPASS Compound

Structure

NPC216550 OpenBabel07101719242D 23 27 0 0 0 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5709 0.6072 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 -3.6285 1.3759 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 0.0000 2.0000 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 -2.8764 0.2728 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 -2.2395 0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 1.4757 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 -1.6026 0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9916 1.8102 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 -2.8017 -0.7244 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7517 -0.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 9 2 0 0 0 0 4 11 2 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 13 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	299.07
Volume:	298.672
LogP:	3.685
LogD:	2.439
LogS:	-5.795
# Rotatable Bonds:	0
TPSA:	75.44
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	3.01
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.012
MDCK Permeability:	1.6500202036695555e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.762

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	97.70572662353516%
Volume Distribution (VD):	0.445
Pgp-substrate:	1.9233837127685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.719
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.658
CYP2D6-substrate:	0.741
CYP3A4-inhibitor:	0.33
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	1.426
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.928
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.933
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.801
Carcinogencity:	0.903
Eye Corrosion:	0.004
Eye Irritation:	0.701
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC216550

Natural Product ID:	NPC216550
*Common Name:**	MCTCVKDGNCPADW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	11-Hydroxyascididemin
Standard InCHIKey:	MCTCVKDGNCPADW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H9N3O2/c22-12-6-8-20-16-14(12)18(23)17-13-10(5-7-19-15(13)16)9-3-1-2-4-11(9)21-17/h1-8H,(H,20,22)
SMILES:	c1ccc2c(c1)c1ccnc3-c4c(c(=O)cc[nH]4)C(=O)c(c13)n2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL122557
PubChem CID:	393838
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	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	12
MIC	3
Others	1

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1535	Cell Line	U-87 MG	Homo sapiens	IC50	=	4000.0	nM	PMID[474712]
NPT933	Cell Line	U373 MG	Homo sapiens	IC50	=	6000.0	nM	PMID[474712]
NPT550	Cell Line	T-24	Homo sapiens	IC50	=	4000.0	nM	PMID[474712]
NPT1505	Cell Line	J82	Homo sapiens	IC50	=	6000.0	nM	PMID[474712]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	4000.0	nM	PMID[474712]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	5000.0	nM	PMID[474712]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2000.0	nM	PMID[474712]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	3000.0	nM	PMID[474712]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5000.0	nM	PMID[474712]
NPT2331	Cell Line	A-427	Homo sapiens	IC50	=	1000.0	nM	PMID[474712]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	5000.0	nM	PMID[474712]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6000.0	nM	PMID[474712]
NPT2	Others	Unspecified		MTD	>	160.0	mg kg-1	PMID[474712]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	2600.0	nM	PMID[474713]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	10500.0	nM	PMID[474713]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	42000.0	nM	PMID[474714]

☑ 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 NPC216550 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	845
0.1-0.2	8935
0.2-0.3	15230
0.3-0.4	12683
0.4-0.5	1514
0.5-0.6	2154
0.6-0.7	1141
0.7-0.8	170
0.8-0.85	22
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9326	High Similarity	NPC167710
0.9249	High Similarity	NPC467063
0.8846	High Similarity	NPC128244
0.8743	High Similarity	NPC157583
0.8636	High Similarity	NPC237188
0.8516	High Similarity	NPC103119
0.8315	Intermediate Similarity	NPC255909
0.8254	Intermediate Similarity	NPC34837
0.8182	Intermediate Similarity	NPC272458
0.8138	Intermediate Similarity	NPC326422
0.8087	Intermediate Similarity	NPC191415
0.8051	Intermediate Similarity	NPC472064
0.801	Intermediate Similarity	NPC469727
0.7959	Intermediate Similarity	NPC472065
0.7923	Intermediate Similarity	NPC284775
0.7903	Intermediate Similarity	NPC477003
0.7897	Intermediate Similarity	NPC106757
0.7889	Intermediate Similarity	NPC70949
0.7857	Intermediate Similarity	NPC317701
0.7853	Intermediate Similarity	NPC304203
0.7849	Intermediate Similarity	NPC102755
0.7842	Intermediate Similarity	NPC476460
0.7835	Intermediate Similarity	NPC284338
0.7829	Intermediate Similarity	NPC251391
0.7817	Intermediate Similarity	NPC88115
0.7806	Intermediate Similarity	NPC472062
0.7806	Intermediate Similarity	NPC472063
0.7806	Intermediate Similarity	NPC472069
0.7806	Intermediate Similarity	NPC328318
0.7806	Intermediate Similarity	NPC328596
0.7771	Intermediate Similarity	NPC70406
0.776	Intermediate Similarity	NPC252572
0.7742	Intermediate Similarity	NPC73994
0.7732	Intermediate Similarity	NPC106824
0.7727	Intermediate Similarity	NPC327592
0.7701	Intermediate Similarity	NPC105811
0.7696	Intermediate Similarity	NPC324091
0.7688	Intermediate Similarity	NPC317373
0.7688	Intermediate Similarity	NPC467188
0.7672	Intermediate Similarity	NPC133003
0.7657	Intermediate Similarity	NPC123906
0.7654	Intermediate Similarity	NPC80681
0.7654	Intermediate Similarity	NPC474492
0.7653	Intermediate Similarity	NPC81535
0.7637	Intermediate Similarity	NPC56233
0.7632	Intermediate Similarity	NPC118084
0.7624	Intermediate Similarity	NPC478184
0.7624	Intermediate Similarity	NPC265100
0.7611	Intermediate Similarity	NPC470680
0.7611	Intermediate Similarity	NPC100104
0.7581	Intermediate Similarity	NPC151635
0.7579	Intermediate Similarity	NPC308931
0.7579	Intermediate Similarity	NPC99939
0.7574	Intermediate Similarity	NPC472070
0.7563	Intermediate Similarity	NPC237414
0.7527	Intermediate Similarity	NPC469529
0.7526	Intermediate Similarity	NPC47190
0.7514	Intermediate Similarity	NPC313889
0.7514	Intermediate Similarity	NPC473878
0.7514	Intermediate Similarity	NPC262338
0.7514	Intermediate Similarity	NPC471655
0.75	Intermediate Similarity	NPC79356
0.75	Intermediate Similarity	NPC102592
0.7486	Intermediate Similarity	NPC209362
0.7486	Intermediate Similarity	NPC42372
0.7472	Intermediate Similarity	NPC217021
0.7472	Intermediate Similarity	NPC470679
0.7463	Intermediate Similarity	NPC318299
0.7459	Intermediate Similarity	NPC293487
0.7447	Intermediate Similarity	NPC83774
0.7438	Intermediate Similarity	NPC116555
0.7435	Intermediate Similarity	NPC21429
0.7433	Intermediate Similarity	NPC293216
0.7432	Intermediate Similarity	NPC271797
0.7432	Intermediate Similarity	NPC478182
0.7432	Intermediate Similarity	NPC21174
0.7427	Intermediate Similarity	NPC317752
0.7403	Intermediate Similarity	NPC213914
0.7401	Intermediate Similarity	NPC100726
0.7391	Intermediate Similarity	NPC237740
0.7391	Intermediate Similarity	NPC115232
0.7389	Intermediate Similarity	NPC229055
0.7387	Intermediate Similarity	NPC477004
0.7377	Intermediate Similarity	NPC242116
0.7368	Intermediate Similarity	NPC61011
0.7368	Intermediate Similarity	NPC477042
0.7358	Intermediate Similarity	NPC17273
0.7358	Intermediate Similarity	NPC135601
0.7358	Intermediate Similarity	NPC141612
0.7351	Intermediate Similarity	NPC478183
0.7348	Intermediate Similarity	NPC74357
0.7321	Intermediate Similarity	NPC267811
0.7316	Intermediate Similarity	NPC11126
0.7295	Intermediate Similarity	NPC471193
0.7295	Intermediate Similarity	NPC471194
0.7292	Intermediate Similarity	NPC470205
0.7286	Intermediate Similarity	NPC227582
0.7283	Intermediate Similarity	NPC478185
0.7277	Intermediate Similarity	NPC229893
0.7277	Intermediate Similarity	NPC79777
0.7273	Intermediate Similarity	NPC471943
0.7273	Intermediate Similarity	NPC202812
0.7273	Intermediate Similarity	NPC32534
0.7264	Intermediate Similarity	NPC121327
0.7258	Intermediate Similarity	NPC114637
0.7254	Intermediate Similarity	NPC228835
0.7254	Intermediate Similarity	NPC46895
0.7249	Intermediate Similarity	NPC297034
0.7243	Intermediate Similarity	NPC274981
0.724	Intermediate Similarity	NPC470677
0.7238	Intermediate Similarity	NPC281094
0.7238	Intermediate Similarity	NPC27041
0.7236	Intermediate Similarity	NPC472116
0.723	Intermediate Similarity	NPC216612
0.7214	Intermediate Similarity	NPC74413
0.7212	Intermediate Similarity	NPC473218
0.7212	Intermediate Similarity	NPC470702
0.7212	Intermediate Similarity	NPC477413
0.7196	Intermediate Similarity	NPC322482
0.7196	Intermediate Similarity	NPC161861
0.7192	Intermediate Similarity	NPC143977
0.7188	Intermediate Similarity	NPC88110
0.7188	Intermediate Similarity	NPC234403
0.7188	Intermediate Similarity	NPC182940
0.7179	Intermediate Similarity	NPC62749
0.7178	Intermediate Similarity	NPC252338
0.7177	Intermediate Similarity	NPC470703
0.7164	Intermediate Similarity	NPC474916
0.7163	Intermediate Similarity	NPC72956
0.7157	Intermediate Similarity	NPC154339
0.7151	Intermediate Similarity	NPC317105
0.7143	Intermediate Similarity	NPC17059
0.7143	Intermediate Similarity	NPC325903
0.7143	Intermediate Similarity	NPC201634
0.7135	Intermediate Similarity	NPC12649
0.7129	Intermediate Similarity	NPC153980
0.7129	Intermediate Similarity	NPC220797
0.7129	Intermediate Similarity	NPC474318
0.7129	Intermediate Similarity	NPC475914
0.7129	Intermediate Similarity	NPC201266
0.7129	Intermediate Similarity	NPC268744
0.7129	Intermediate Similarity	NPC6865
0.7129	Intermediate Similarity	NPC153123
0.7127	Intermediate Similarity	NPC40070
0.7112	Intermediate Similarity	NPC233380
0.7111	Intermediate Similarity	NPC469811
0.7108	Intermediate Similarity	NPC57398
0.7108	Intermediate Similarity	NPC260900
0.7101	Intermediate Similarity	NPC266249
0.71	Intermediate Similarity	NPC157828
0.71	Intermediate Similarity	NPC195239
0.7098	Intermediate Similarity	NPC24864
0.7097	Intermediate Similarity	NPC225018
0.7097	Intermediate Similarity	NPC194881
0.7094	Intermediate Similarity	NPC77241
0.7094	Intermediate Similarity	NPC166209
0.7094	Intermediate Similarity	NPC13456
0.7094	Intermediate Similarity	NPC269203
0.7092	Intermediate Similarity	NPC469359
0.709	Intermediate Similarity	NPC91895
0.7077	Intermediate Similarity	NPC258480
0.7072	Intermediate Similarity	NPC321911
0.7071	Intermediate Similarity	NPC472112
0.7071	Intermediate Similarity	NPC268966
0.7065	Intermediate Similarity	NPC472293
0.7065	Intermediate Similarity	NPC11445
0.7059	Intermediate Similarity	NPC471944
0.7056	Intermediate Similarity	NPC474259
0.7056	Intermediate Similarity	NPC63545
0.7056	Intermediate Similarity	NPC477415
0.7056	Intermediate Similarity	NPC23476
0.705	Intermediate Similarity	NPC267343
0.705	Intermediate Similarity	NPC473821
0.7048	Intermediate Similarity	NPC118940
0.7047	Intermediate Similarity	NPC55772
0.7044	Intermediate Similarity	NPC474767
0.7043	Intermediate Similarity	NPC122141
0.7033	Intermediate Similarity	NPC123839
0.703	Intermediate Similarity	NPC473814
0.703	Intermediate Similarity	NPC74153
0.703	Intermediate Similarity	NPC78767
0.7028	Intermediate Similarity	NPC471192
0.7026	Intermediate Similarity	NPC117027
0.7017	Intermediate Similarity	NPC201380
0.7017	Intermediate Similarity	NPC179787
0.7015	Intermediate Similarity	NPC93390
0.7014	Intermediate Similarity	NPC221100
0.7014	Intermediate Similarity	NPC234078
0.7005	Intermediate Similarity	NPC238457
0.7	Intermediate Similarity	NPC472292
0.7	Intermediate Similarity	NPC86288
0.6995	Remote Similarity	NPC472260
0.6995	Remote Similarity	NPC14113
0.6995	Remote Similarity	NPC84827
0.6995	Remote Similarity	NPC145885
0.699	Remote Similarity	NPC110158
0.6989	Remote Similarity	NPC314102
0.6989	Remote Similarity	NPC251722
0.6985	Remote Similarity	NPC475874
0.6979	Remote Similarity	NPC110500

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 NPC216550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	416
0.1-0.2	813
0.2-0.3	1028
0.3-0.4	2695
0.4-0.5	1934
0.5-0.6	1689
0.6-0.7	524
0.7-0.8	51
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
0.8132	Intermediate Similarity	NPD2479	Phase 3
0.8132	Intermediate Similarity	NPD2481	Approved
0.8	Intermediate Similarity	NPD7564	Discontinued
0.7838	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4051	Discontinued
0.7772	Intermediate Similarity	NPD4848	Phase 1
0.7761	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD5446	Phase 2
0.7632	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1270	Approved
0.7596	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD4988	Discontinued
0.7541	Intermediate Similarity	NPD6446	Discontinued
0.7526	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD2336	Approved
0.7474	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7207	Approved
0.7463	Intermediate Similarity	NPD7209	Approved
0.7463	Intermediate Similarity	NPD7208	Approved
0.7435	Intermediate Similarity	NPD6178	Phase 3
0.7418	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6152	Phase 1
0.7377	Intermediate Similarity	NPD5400	Approved
0.7376	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5473	Discontinued
0.7358	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD2753	Discontinued
0.7351	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4922	Phase 2
0.734	Intermediate Similarity	NPD4883	Approved
0.7337	Intermediate Similarity	NPD3583	Phase 2
0.7333	Intermediate Similarity	NPD7404	Approved
0.733	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2307	Discontinued
0.7323	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1343	Approved
0.7304	Intermediate Similarity	NPD1506	Discontinued
0.7302	Intermediate Similarity	NPD3238	Discontinued
0.7283	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6771	Discontinued
0.7277	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3394	Approved
0.7273	Intermediate Similarity	NPD3389	Approved
0.7273	Intermediate Similarity	NPD3393	Approved
0.7255	Intermediate Similarity	NPD5491	Phase 3
0.7255	Intermediate Similarity	NPD5489	Phase 1
0.7251	Intermediate Similarity	NPD5198	Approved
0.7251	Intermediate Similarity	NPD5199	Approved
0.7251	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3078	Approved
0.7225	Intermediate Similarity	NPD3079	Approved
0.7225	Intermediate Similarity	NPD3076	Approved
0.7225	Intermediate Similarity	NPD3077	Approved
0.7214	Intermediate Similarity	NPD2405	Phase 3
0.7212	Intermediate Similarity	NPD2411	Approved
0.7212	Intermediate Similarity	NPD6954	Phase 2
0.7206	Intermediate Similarity	NPD8114	Approved
0.7206	Intermediate Similarity	NPD8115	Approved
0.7194	Intermediate Similarity	NPD7175	Phase 1
0.7188	Intermediate Similarity	NPD3927	Phase 2
0.7186	Intermediate Similarity	NPD7618	Phase 3
0.7186	Intermediate Similarity	NPD7619	Phase 3
0.7184	Intermediate Similarity	NPD6459	Phase 2
0.7177	Intermediate Similarity	NPD5888	Phase 2
0.7171	Intermediate Similarity	NPD2008	Discontinued
0.7164	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7027	Phase 3
0.7143	Intermediate Similarity	NPD2837	Discontinued
0.7136	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8289	Discontinued
0.7122	Intermediate Similarity	NPD3247	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7187	Phase 2
0.71	Intermediate Similarity	NPD7406	Phase 2
0.7095	Intermediate Similarity	NPD6787	Phase 2
0.7094	Intermediate Similarity	NPD6479	Discontinued
0.7092	Intermediate Similarity	NPD7026	Phase 2
0.7088	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5475	Discontinued
0.7072	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5017	Discontinued
0.7056	Intermediate Similarity	NPD2770	Discontinued
0.7056	Intermediate Similarity	NPD3961	Discontinued
0.7053	Intermediate Similarity	NPD3905	Phase 3
0.7048	Intermediate Similarity	NPD7454	Approved
0.7048	Intermediate Similarity	NPD7455	Approved
0.7041	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4299	Phase 1
0.7039	Intermediate Similarity	NPD5901	Discontinued
0.7031	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3320	Approved
0.7026	Intermediate Similarity	NPD3318	Approved
0.7026	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3319	Phase 1
0.7019	Intermediate Similarity	NPD7665	Phase 2
0.7019	Intermediate Similarity	NPD7666	Phase 3
0.7017	Intermediate Similarity	NPD4547	Phase 3
0.7015	Intermediate Similarity	NPD5853	Phase 3
0.7015	Intermediate Similarity	NPD5855	Phase 3
0.701	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5809	Phase 3
0.7	Intermediate Similarity	NPD5505	Discontinued
0.699	Remote Similarity	NPD4304	Discovery
0.699	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD482	Approved
0.6965	Remote Similarity	NPD460	Discontinued
0.6963	Remote Similarity	NPD6470	Phase 3
0.6961	Remote Similarity	NPD5854	Approved
0.6959	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6664	Approved
0.6943	Remote Similarity	NPD4075	Phase 2
0.6943	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2879	Approved
0.6942	Remote Similarity	NPD6268	Phase 1
0.6942	Remote Similarity	NPD2881	Approved
0.6938	Remote Similarity	NPD2442	Approved
0.6938	Remote Similarity	NPD2509	Approved
0.6938	Remote Similarity	NPD2443	Approved
0.6938	Remote Similarity	NPD2510	Approved
0.6938	Remote Similarity	NPD7191	Phase 2
0.6934	Remote Similarity	NPD3794	Approved
0.6934	Remote Similarity	NPD3795	Approved
0.6931	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2720	Phase 1
0.6927	Remote Similarity	NPD750	Phase 2
0.6927	Remote Similarity	NPD1722	Approved
0.6923	Remote Similarity	NPD7010	Phase 3
0.6919	Remote Similarity	NPD975	Approved
0.6919	Remote Similarity	NPD977	Approved
0.6919	Remote Similarity	NPD976	Approved
0.6912	Remote Similarity	NPD1982	Phase 1
0.6904	Remote Similarity	NPD2091	Phase 2
0.6904	Remote Similarity	NPD2096	Phase 2
0.6901	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5686	Approved
0.69	Remote Similarity	NPD5685	Approved
0.6893	Remote Similarity	NPD7727	Phase 2
0.6893	Remote Similarity	NPD7817	Phase 1
0.6889	Remote Similarity	NPD2006	Phase 2
0.6889	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2430	Phase 2
0.6884	Remote Similarity	NPD4429	Discontinued
0.6881	Remote Similarity	NPD3222	Phase 2
0.6878	Remote Similarity	NPD3323	Discontinued
0.6878	Remote Similarity	NPD7049	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6987	Phase 1
0.6868	Remote Similarity	NPD7469	Discontinued
0.6866	Remote Similarity	NPD1658	Discontinued
0.6865	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6164	Phase 2
0.6864	Remote Similarity	NPD6165	Phase 2
0.686	Remote Similarity	NPD991	Phase 2
0.686	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD3348	Phase 2
0.6856	Remote Similarity	NPD5104	Approved
0.6853	Remote Similarity	NPD2094	Phase 2
0.6853	Remote Similarity	NPD2095	Phase 2
0.6853	Remote Similarity	NPD2092	Phase 2
0.6851	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2915	Discontinued
0.6842	Remote Similarity	NPD7568	Phase 1
0.6842	Remote Similarity	NPD3967	Approved
0.6839	Remote Similarity	NPD715	Phase 3
0.6839	Remote Similarity	NPD4524	Discontinued
0.6837	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4376	Phase 3
0.6828	Remote Similarity	NPD2061	Approved
0.6825	Remote Similarity	NPD1600	Suspended
0.6825	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD9343	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3411	Phase 2
0.681	Remote Similarity	NPD3410	Approved
0.68	Remote Similarity	NPD7394	Phase 2
0.68	Remote Similarity	NPD3246	Discontinued
0.6798	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6999	Discontinued
0.6796	Remote Similarity	NPD7308	Discontinued
0.6794	Remote Similarity	NPD5426	Phase 3
0.6793	Remote Similarity	NPD3100	Discontinued
0.6787	Remote Similarity	NPD4845	Discontinued
0.6786	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5555	Phase 1

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