NPASS Compound

Structure

NPC157583 OpenBabel07101719122D 24 27 0 0 0 0 0 0 0 0999 V2000 0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6285 1.6241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5709 2.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 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 2.2971 1.5243 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 2.2395 2.2930 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 5.5000 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 1.6026 2.7272 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 1 11 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 13 2 0 0 0 0 5 15 2 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 20 2 3 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 17 2 0 0 0 0 15 22 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 22 2 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.12
Volume:	327.16
LogP:	2.324
LogD:	2.601
LogS:	-4.746
# Rotatable Bonds:	3
TPSA:	75.11
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	2.963
Fsp3:	0.105
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:	-5.011
MDCK Permeability:	1.1294832802377641e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.085
Human Intestinal Absorption (HIA):	0.631
20% Bioavailability (F20%):	0.415
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.444
Plasma Protein Binding (PPB):	94.7525863647461%
Volume Distribution (VD):	1.169
Pgp-substrate:	2.9148874282836914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.791
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.653
CYP2D6-inhibitor:	0.313
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.576
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	1.703
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.438
Human Hepatotoxicity (H-HT):	0.738
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.903
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.935
Carcinogencity:	0.738
Eye Corrosion:	0.003
Eye Irritation:	0.048
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC157583

Natural Product ID:	NPC157583
*Common Name:**	KMNRTBJOBIPNKQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMNRTBJOBIPNKQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15N3O2/c1-11(23)20-8-6-12-10-16(24)19-17-14(7-9-21-19)13-4-2-3-5-15(13)22-18(12)17/h2-5,7,9-10H,6,8H2,1H3,(H,20,23)
SMILES:	CC(=NCCC1=CC(=O)c2c3c(ccn2)c2ccccc2nc13)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL339820
PubChem CID:	10403519
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:0001810] Pyridoacridones [CHEMONTID:0002826] Pyrido[2,3,4-kl]acridones

*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
NPO32634	cystodytes sp. ascidian	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7525959]

☑ 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	2
Others	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Others	2
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1600.0	nM	PMID[549892]
NPT27	Others	Unspecified		IC50	=	135600.0	nM	PMID[549892]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	1.0	n.a.	PMID[549892]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC90	=	8400.0	nM	PMID[549892]
NPT2	Others	Unspecified		K	=	54.0	uM	PMID[549892]

☑ 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 NPC157583 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	356
0.1-0.2	3521
0.2-0.3	14736
0.3-0.4	17087
0.4-0.5	2972
0.5-0.6	1998
0.6-0.7	1625
0.7-0.8	379
0.8-0.85	13
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9461	High Similarity	NPC255909
0.9152	High Similarity	NPC237188
0.9118	High Similarity	NPC103119
0.8827	High Similarity	NPC328318
0.8827	High Similarity	NPC328596
0.8743	High Similarity	NPC216550
0.8729	High Similarity	NPC327592
0.8681	High Similarity	NPC317373
0.8404	Intermediate Similarity	NPC318299
0.8398	Intermediate Similarity	NPC34837
0.8389	Intermediate Similarity	NPC128244
0.836	Intermediate Similarity	NPC317752
0.8343	Intermediate Similarity	NPC467063
0.8343	Intermediate Similarity	NPC167710
0.8235	Intermediate Similarity	NPC70949
0.8146	Intermediate Similarity	NPC118084
0.8125	Intermediate Similarity	NPC191415
0.8125	Intermediate Similarity	NPC237740
0.8095	Intermediate Similarity	NPC80681
0.7953	Intermediate Similarity	NPC265100
0.7926	Intermediate Similarity	NPC106757
0.7904	Intermediate Similarity	NPC217021
0.7904	Intermediate Similarity	NPC70406
0.7904	Intermediate Similarity	NPC470679
0.7895	Intermediate Similarity	NPC472064
0.788	Intermediate Similarity	NPC326422
0.7861	Intermediate Similarity	NPC56233
0.7853	Intermediate Similarity	NPC284775
0.7844	Intermediate Similarity	NPC473878
0.7842	Intermediate Similarity	NPC88115
0.7801	Intermediate Similarity	NPC472065
0.7791	Intermediate Similarity	NPC242116
0.7778	Intermediate Similarity	NPC102755
0.7765	Intermediate Similarity	NPC73994
0.7754	Intermediate Similarity	NPC106824
0.7751	Intermediate Similarity	NPC251391
0.774	Intermediate Similarity	NPC139763
0.7735	Intermediate Similarity	NPC477003
0.773	Intermediate Similarity	NPC272458
0.773	Intermediate Similarity	NPC47190
0.7716	Intermediate Similarity	NPC251722
0.7716	Intermediate Similarity	NPC314102
0.7688	Intermediate Similarity	NPC304203
0.7676	Intermediate Similarity	NPC476460
0.7672	Intermediate Similarity	NPC284338
0.7672	Intermediate Similarity	NPC81535
0.7662	Intermediate Similarity	NPC216612
0.7657	Intermediate Similarity	NPC114637
0.7644	Intermediate Similarity	NPC472063
0.7644	Intermediate Similarity	NPC472069
0.7644	Intermediate Similarity	NPC472062
0.7633	Intermediate Similarity	NPC313889
0.763	Intermediate Similarity	NPC100104
0.763	Intermediate Similarity	NPC470680
0.7624	Intermediate Similarity	NPC322482
0.7619	Intermediate Similarity	NPC105811
0.7605	Intermediate Similarity	NPC467188
0.7604	Intermediate Similarity	NPC317701
0.7602	Intermediate Similarity	NPC209362
0.76	Intermediate Similarity	NPC115232
0.7579	Intermediate Similarity	NPC237414
0.7574	Intermediate Similarity	NPC123906
0.7572	Intermediate Similarity	NPC474492
0.7566	Intermediate Similarity	NPC227582
0.7543	Intermediate Similarity	NPC478182
0.7529	Intermediate Similarity	NPC40070
0.75	Intermediate Similarity	NPC86288
0.7486	Intermediate Similarity	NPC252572
0.7471	Intermediate Similarity	NPC293487
0.7461	Intermediate Similarity	NPC57398
0.7459	Intermediate Similarity	NPC83774
0.7455	Intermediate Similarity	NPC169433
0.7448	Intermediate Similarity	NPC252338
0.7443	Intermediate Similarity	NPC21174
0.7443	Intermediate Similarity	NPC271797
0.7443	Intermediate Similarity	NPC478184
0.7435	Intermediate Similarity	NPC474916
0.7433	Intermediate Similarity	NPC324091
0.743	Intermediate Similarity	NPC262338
0.7421	Intermediate Similarity	NPC472116
0.7414	Intermediate Similarity	NPC213914
0.7413	Intermediate Similarity	NPC469727
0.7412	Intermediate Similarity	NPC100726
0.7411	Intermediate Similarity	NPC472070
0.7405	Intermediate Similarity	NPC133003
0.7403	Intermediate Similarity	NPC151635
0.7401	Intermediate Similarity	NPC42372
0.7391	Intermediate Similarity	NPC159125
0.7386	Intermediate Similarity	NPC194881
0.7377	Intermediate Similarity	NPC61011
0.7377	Intermediate Similarity	NPC471997
0.7377	Intermediate Similarity	NPC477042
0.7368	Intermediate Similarity	NPC195239
0.7368	Intermediate Similarity	NPC157828
0.736	Intermediate Similarity	NPC41717
0.736	Intermediate Similarity	NPC478183
0.7348	Intermediate Similarity	NPC469529
0.7348	Intermediate Similarity	NPC293216
0.7342	Intermediate Similarity	NPC46358
0.7341	Intermediate Similarity	NPC281094
0.7341	Intermediate Similarity	NPC138842
0.733	Intermediate Similarity	NPC11445
0.7322	Intermediate Similarity	NPC248462
0.731	Intermediate Similarity	NPC470111
0.7306	Intermediate Similarity	NPC474767
0.7306	Intermediate Similarity	NPC74413
0.7302	Intermediate Similarity	NPC117244
0.7302	Intermediate Similarity	NPC473763
0.7299	Intermediate Similarity	NPC229055
0.7293	Intermediate Similarity	NPC477976
0.7288	Intermediate Similarity	NPC478185
0.7283	Intermediate Similarity	NPC24864
0.7283	Intermediate Similarity	NPC15840
0.7278	Intermediate Similarity	NPC91895
0.7278	Intermediate Similarity	NPC190296
0.7278	Intermediate Similarity	NPC32534
0.7273	Intermediate Similarity	NPC141612
0.7273	Intermediate Similarity	NPC135601
0.7273	Intermediate Similarity	NPC17273
0.7273	Intermediate Similarity	NPC62749
0.7268	Intermediate Similarity	NPC121327
0.7258	Intermediate Similarity	NPC46895
0.7258	Intermediate Similarity	NPC207851
0.7257	Intermediate Similarity	NPC74357
0.7249	Intermediate Similarity	NPC154339
0.7241	Intermediate Similarity	NPC27041
0.724	Intermediate Similarity	NPC102592
0.724	Intermediate Similarity	NPC79356
0.7238	Intermediate Similarity	NPC201634
0.7228	Intermediate Similarity	NPC55772
0.7228	Intermediate Similarity	NPC11126
0.7228	Intermediate Similarity	NPC248041
0.7228	Intermediate Similarity	NPC126709
0.7228	Intermediate Similarity	NPC12649
0.7228	Intermediate Similarity	NPC213468
0.7225	Intermediate Similarity	NPC471655
0.7225	Intermediate Similarity	NPC267343
0.7219	Intermediate Similarity	NPC99939
0.7219	Intermediate Similarity	NPC308931
0.7216	Intermediate Similarity	NPC477004
0.7213	Intermediate Similarity	NPC267885
0.7208	Intermediate Similarity	NPC472259
0.7206	Intermediate Similarity	NPC473310
0.7198	Intermediate Similarity	NPC161861
0.7195	Intermediate Similarity	NPC256893
0.7194	Intermediate Similarity	NPC143977
0.7194	Intermediate Similarity	NPC260900
0.7193	Intermediate Similarity	NPC314372
0.7189	Intermediate Similarity	NPC79777
0.7189	Intermediate Similarity	NPC182940
0.7186	Intermediate Similarity	NPC65408
0.7186	Intermediate Similarity	NPC116555
0.7184	Intermediate Similarity	NPC470233
0.7184	Intermediate Similarity	NPC472260
0.7174	Intermediate Similarity	NPC64436
0.7166	Intermediate Similarity	NPC228835
0.7166	Intermediate Similarity	NPC258480
0.7158	Intermediate Similarity	NPC110500
0.7158	Intermediate Similarity	NPC469938
0.7158	Intermediate Similarity	NPC475874
0.7158	Intermediate Similarity	NPC149155
0.7158	Intermediate Similarity	NPC203468
0.7151	Intermediate Similarity	NPC274981
0.7151	Intermediate Similarity	NPC470677
0.7143	Intermediate Similarity	NPC6982
0.7135	Intermediate Similarity	NPC283219
0.7135	Intermediate Similarity	NPC322644
0.7135	Intermediate Similarity	NPC215584
0.7135	Intermediate Similarity	NPC44773
0.7128	Intermediate Similarity	NPC282103
0.7127	Intermediate Similarity	NPC78020
0.7126	Intermediate Similarity	NPC24678
0.7126	Intermediate Similarity	NPC105818
0.712	Intermediate Similarity	NPC150048
0.712	Intermediate Similarity	NPC203754
0.7119	Intermediate Similarity	NPC129721
0.7117	Intermediate Similarity	NPC313823
0.7115	Intermediate Similarity	NPC229893
0.7114	Intermediate Similarity	NPC470020
0.7112	Intermediate Similarity	NPC143533
0.7112	Intermediate Similarity	NPC470205
0.711	Intermediate Similarity	NPC201380
0.711	Intermediate Similarity	NPC179787
0.7105	Intermediate Similarity	NPC321708
0.71	Intermediate Similarity	NPC266249
0.7097	Intermediate Similarity	NPC234403
0.7093	Intermediate Similarity	NPC159856
0.709	Intermediate Similarity	NPC235684
0.709	Intermediate Similarity	NPC478077
0.709	Intermediate Similarity	NPC66210
0.709	Intermediate Similarity	NPC94752
0.7088	Intermediate Similarity	NPC471943
0.7085	Intermediate Similarity	NPC175602
0.7085	Intermediate Similarity	NPC238457
0.7083	Intermediate Similarity	NPC150259
0.7081	Intermediate Similarity	NPC145885
0.7081	Intermediate Similarity	NPC84827
0.7081	Intermediate Similarity	NPC111275
0.7081	Intermediate Similarity	NPC14113
0.7081	Intermediate Similarity	NPC122718

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 NPC157583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	672
0.2-0.3	915
0.3-0.4	1924
0.4-0.5	2301
0.5-0.6	1944
0.6-0.7	995
0.7-0.8	180
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8136	Intermediate Similarity	NPD7564	Discontinued
0.7941	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1270	Approved
0.7901	Intermediate Similarity	NPD4988	Discontinued
0.7861	Intermediate Similarity	NPD6446	Discontinued
0.7831	Intermediate Similarity	NPD4547	Phase 3
0.7816	Intermediate Similarity	NPD1343	Approved
0.7803	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD2720	Phase 1
0.7799	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD2753	Discontinued
0.7742	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3238	Discontinued
0.7692	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5473	Discontinued
0.7657	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD5809	Phase 3
0.7641	Intermediate Similarity	NPD4051	Discontinued
0.7637	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5400	Approved
0.7569	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2479	Phase 3
0.7569	Intermediate Similarity	NPD2481	Approved
0.7554	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6178	Phase 3
0.754	Intermediate Similarity	NPD5505	Discontinued
0.7539	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2336	Approved
0.7485	Intermediate Similarity	NPD2006	Phase 2
0.7471	Intermediate Similarity	NPD2430	Phase 2
0.7459	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7469	Discontinued
0.7449	Intermediate Similarity	NPD7666	Phase 3
0.7449	Intermediate Similarity	NPD7665	Phase 2
0.7442	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4848	Phase 1
0.7414	Intermediate Similarity	NPD4326	Phase 2
0.7405	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3905	Phase 3
0.7396	Intermediate Similarity	NPD6999	Discontinued
0.7396	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6987	Phase 1
0.7385	Intermediate Similarity	NPD7207	Approved
0.7385	Intermediate Similarity	NPD7209	Approved
0.7385	Intermediate Similarity	NPD7208	Approved
0.7374	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6787	Phase 2
0.7349	Intermediate Similarity	NPD2896	Discontinued
0.7345	Intermediate Similarity	NPD3583	Phase 2
0.7341	Intermediate Similarity	NPD2837	Discontinued
0.7337	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2307	Discontinued
0.733	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3942	Approved
0.7317	Intermediate Similarity	NPD3944	Approved
0.7312	Intermediate Similarity	NPD5555	Phase 1
0.7308	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7195	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6954	Phase 2
0.7297	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD750	Phase 2
0.7292	Intermediate Similarity	NPD5446	Phase 2
0.7288	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6771	Discontinued
0.7282	Intermediate Similarity	NPD2879	Approved
0.7282	Intermediate Similarity	NPD2881	Approved
0.7277	Intermediate Similarity	NPD7618	Phase 3
0.7277	Intermediate Similarity	NPD7619	Phase 3
0.7273	Intermediate Similarity	NPD7026	Phase 2
0.7273	Intermediate Similarity	NPD6459	Phase 2
0.7267	Intermediate Similarity	NPD2118	Approved
0.7267	Intermediate Similarity	NPD2119	Approved
0.7264	Intermediate Similarity	NPD5888	Phase 2
0.7253	Intermediate Similarity	NPD4883	Approved
0.725	Intermediate Similarity	NPD6152	Phase 1
0.7241	Intermediate Similarity	NPD180	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD715	Phase 3
0.7236	Intermediate Similarity	NPD2295	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7394	Phase 2
0.7231	Intermediate Similarity	NPD5017	Discontinued
0.7228	Intermediate Similarity	NPD3078	Approved
0.7228	Intermediate Similarity	NPD3079	Approved
0.7228	Intermediate Similarity	NPD3076	Approved
0.7228	Intermediate Similarity	NPD3077	Approved
0.7228	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5862	Discovery
0.7213	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3385	Approved
0.7209	Intermediate Similarity	NPD1661	Suspended
0.7208	Intermediate Similarity	NPD8114	Approved
0.7208	Intermediate Similarity	NPD8115	Approved
0.7208	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6664	Approved
0.7196	Intermediate Similarity	NPD7233	Approved
0.7196	Intermediate Similarity	NPD7234	Approved
0.7194	Intermediate Similarity	NPD7187	Phase 2
0.7192	Intermediate Similarity	NPD3389	Approved
0.7192	Intermediate Similarity	NPD3393	Approved
0.7192	Intermediate Similarity	NPD3394	Approved
0.7186	Intermediate Similarity	NPD200	Phase 2
0.7186	Intermediate Similarity	NPD201	Phase 2
0.7181	Intermediate Similarity	NPD3315	Phase 3
0.7178	Intermediate Similarity	NPD3795	Approved
0.7178	Intermediate Similarity	NPD3794	Approved
0.7173	Intermediate Similarity	NPD4922	Phase 2
0.7172	Intermediate Similarity	NPD7568	Phase 1
0.7166	Intermediate Similarity	NPD4957	Phase 2
0.7158	Intermediate Similarity	NPD482	Approved
0.7157	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7027	Phase 3
0.715	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6481	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3961	Discontinued
0.7136	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2511	Approved
0.7129	Intermediate Similarity	NPD8289	Discontinued
0.7128	Intermediate Similarity	NPD2405	Phase 3
0.7127	Intermediate Similarity	NPD4639	Approved
0.7127	Intermediate Similarity	NPD4638	Approved
0.7127	Intermediate Similarity	NPD4640	Approved
0.7126	Intermediate Similarity	NPD1254	Approved
0.7126	Intermediate Similarity	NPD1256	Approved
0.7126	Intermediate Similarity	NPD1253	Approved
0.7126	Intermediate Similarity	NPD1255	Approved
0.7121	Intermediate Similarity	NPD5901	Discontinued
0.712	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD4524	Discontinued
0.7102	Intermediate Similarity	NPD2809	Approved
0.7102	Intermediate Similarity	NPD6285	Phase 2
0.7102	Intermediate Similarity	NPD2061	Approved
0.7098	Intermediate Similarity	NPD7944	Discontinued
0.7097	Intermediate Similarity	NPD3927	Phase 2
0.7085	Intermediate Similarity	NPD5491	Phase 3
0.7085	Intermediate Similarity	NPD5489	Phase 1
0.7083	Intermediate Similarity	NPD7098	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4615	Phase 2
0.7079	Intermediate Similarity	NPD5255	Approved
0.7074	Intermediate Similarity	NPD2091	Phase 2
0.7074	Intermediate Similarity	NPD2096	Phase 2
0.7068	Intermediate Similarity	NPD1905	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5088	Discontinued
0.7056	Intermediate Similarity	NPD1631	Approved
0.7056	Intermediate Similarity	NPD3323	Discontinued
0.7055	Intermediate Similarity	NPD991	Phase 2
0.7055	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2770	Discontinued
0.705	Intermediate Similarity	NPD1506	Discontinued
0.7049	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD460	Discontinued
0.7044	Intermediate Similarity	NPD4852	Phase 2
0.7044	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3247	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5426	Phase 3
0.7031	Intermediate Similarity	NPD1658	Discontinued
0.703	Intermediate Similarity	NPD3475	Approved
0.703	Intermediate Similarity	NPD3476	Approved
0.7027	Intermediate Similarity	NPD2771	Approved
0.7027	Intermediate Similarity	NPD4075	Phase 2
0.7027	Intermediate Similarity	NPD2751	Phase 1
0.7024	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2094	Phase 2
0.7021	Intermediate Similarity	NPD2092	Phase 2
0.7021	Intermediate Similarity	NPD2095	Phase 2
0.702	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1722	Approved
0.7011	Intermediate Similarity	NPD4702	Approved
0.7011	Intermediate Similarity	NPD4703	Approved
0.701	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4029	Approved
0.7006	Intermediate Similarity	NPD4030	Approved
0.7006	Intermediate Similarity	NPD4028	Approved
0.7005	Intermediate Similarity	NPD6479	Discontinued
0.7	Intermediate Similarity	NPD7001	Phase 3
0.7	Intermediate Similarity	NPD7010	Phase 3
0.6995	Remote Similarity	NPD1575	Approved
0.6995	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD1573	Approved
0.6989	Remote Similarity	NPD7111	Discontinued
0.6985	Remote Similarity	NPD4912	Phase 3
0.6984	Remote Similarity	NPD7483	Phase 2
0.6984	Remote Similarity	NPD7482	Phase 2
0.6983	Remote Similarity	NPD1630	Approved
0.6979	Remote Similarity	NPD6281	Approved
0.6974	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD5065	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