NPASS Compound

Structure

NPC476322 OpenBabel07101718232D 34 36 0 0 0 0 0 0 0 0999 V2000 1.1042 -3.0915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8125 1.5994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6272 -3.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2638 1.8066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6504 -2.7199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3038 1.2791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1951 -3.5035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6834 1.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2871 -2.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7147 0.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7812 -3.5247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0984 1.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0313 -1.7318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0261 0.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3582 -3.4193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5363 1.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1051 -1.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2234 -0.1887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1104 -2.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9247 0.1394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8990 -3.1925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0231 1.3976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2444 -3.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9635 0.6569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1157 -0.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2973 -0.7705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4959 -0.1530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1104 -1.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3784 -1.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2366 0.5366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3784 -2.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5831 1.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 5.2444 -1.3546 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 5 1 0 0 0 0 2 4 1 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 23 2 0 0 0 0 19 28 1 0 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 34 1 0 0 0 0 27 33 2 0 0 0 0 28 34 2 0 0 0 0 29 31 2 0 0 0 0 29 34 1 0 0 0 0 30 32 2 0 0 0 0 30 33 1 0 0 0 0 M CHG 2 33 1 34 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.38
Volume:	539.897
LogP:	6.615
LogD:	5.278
LogS:	-3.252
# Rotatable Bonds:	0
TPSA:	7.76
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	5.595
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.345
MDCK Permeability:	2.4979073714348488e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.989
Human Intestinal Absorption (HIA):	0.938
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	93.14698028564453%
Volume Distribution (VD):	2.419
Pgp-substrate:	2.724454641342163%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.829
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.686

ADMET: Excretion

Clearance (CL):	4.848
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.828
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.525
Skin Sensitization:	0.975
Carcinogencity:	0.178
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC476322

Natural Product ID:	NPC476322
*Common Name:**	QKEZYVWHBBLGIK-NFLUSIDLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QKEZYVWHBBLGIK-NFLUSIDLSA-N
Standard InCHI:	InChI=1S/C32H48N2/c1-3-7-11-15-21-31-23-19-28-34(29-31)26-18-14-10-6-2-4-8-12-16-22-32-24-20-27-33(30-32)25-17-13-9-5-1/h11-12,15-16,19-20,23-24,27-30H,1-10,13-14,17-18,21-22,25-26H2/q+2/b15-11-,16-12-
SMILES:	C1CCCC[N+]2=CC=CC(=C2)CC=CCCCCCCCC[N+]3=CC=CC(=C3)CC=CCCC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564308
PubChem CID:	25227562
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001764] Pyridinium derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575970]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17848089]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Pacific	n.a.	PMID[19133758]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Culasian Point, Leyte, Philippines (S 1119.00', E 12435.60')	1991-MAR	PMID[22873824]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[24128145]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	>	20.0	ug.mL-1	PMID[466197]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[466197]
NPT3470	Cell Line	WEHI-164	Mus musculus	IC50	>	20.0	ug.mL-1	PMID[466197]

☑ 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 NPC476322 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	971
0.1-0.2	11676
0.2-0.3	18623
0.3-0.4	6209
0.4-0.5	2711
0.5-0.6	1731
0.6-0.7	554
0.7-0.8	176
0.8-0.85	26
0.85-0.9	13
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC476131
0.9512	High Similarity	NPC69914
0.9333	High Similarity	NPC329825
0.9237	High Similarity	NPC240136
0.9237	High Similarity	NPC471402
0.9237	High Similarity	NPC297486
0.8843	High Similarity	NPC91958
0.879	High Similarity	NPC290094
0.8689	High Similarity	NPC143603
0.8651	High Similarity	NPC245244
0.8651	High Similarity	NPC146373
0.8651	High Similarity	NPC166424
0.8644	High Similarity	NPC27802
0.8629	High Similarity	NPC182570
0.8629	High Similarity	NPC265605
0.8629	High Similarity	NPC48564
0.8583	High Similarity	NPC202957
0.8583	High Similarity	NPC169625
0.845	Intermediate Similarity	NPC89490
0.839	Intermediate Similarity	NPC76540
0.8385	Intermediate Similarity	NPC329896
0.8385	Intermediate Similarity	NPC475105
0.8385	Intermediate Similarity	NPC475090
0.8372	Intermediate Similarity	NPC471311
0.8372	Intermediate Similarity	NPC471313
0.8346	Intermediate Similarity	NPC46358
0.8281	Intermediate Similarity	NPC27740
0.8222	Intermediate Similarity	NPC251722
0.8222	Intermediate Similarity	NPC314102
0.8197	Intermediate Similarity	NPC235843
0.8182	Intermediate Similarity	NPC282398
0.812	Intermediate Similarity	NPC101165
0.812	Intermediate Similarity	NPC471322
0.8102	Intermediate Similarity	NPC32002
0.8102	Intermediate Similarity	NPC315348
0.8102	Intermediate Similarity	NPC316811
0.8099	Intermediate Similarity	NPC40070
0.8034	Intermediate Similarity	NPC83987
0.7985	Intermediate Similarity	NPC256893
0.7956	Intermediate Similarity	NPC150259
0.7917	Intermediate Similarity	NPC470233
0.7852	Intermediate Similarity	NPC324611
0.7826	Intermediate Similarity	NPC471312
0.7817	Intermediate Similarity	NPC86288
0.7795	Intermediate Similarity	NPC476566
0.7787	Intermediate Similarity	NPC231655
0.773	Intermediate Similarity	NPC469766
0.7708	Intermediate Similarity	NPC477974
0.7698	Intermediate Similarity	NPC65408
0.7676	Intermediate Similarity	NPC20144
0.766	Intermediate Similarity	NPC469767
0.766	Intermediate Similarity	NPC469783
0.766	Intermediate Similarity	NPC469761
0.766	Intermediate Similarity	NPC469784
0.766	Intermediate Similarity	NPC469779
0.766	Intermediate Similarity	NPC469780
0.766	Intermediate Similarity	NPC469768
0.7643	Intermediate Similarity	NPC169433
0.7612	Intermediate Similarity	NPC135488
0.7597	Intermediate Similarity	NPC81561
0.7589	Intermediate Similarity	NPC73767
0.7586	Intermediate Similarity	NPC470111
0.7519	Intermediate Similarity	NPC148140
0.7517	Intermediate Similarity	NPC63545
0.75	Intermediate Similarity	NPC138842
0.75	Intermediate Similarity	NPC96102
0.75	Intermediate Similarity	NPC471323
0.7467	Intermediate Similarity	NPC129721
0.7466	Intermediate Similarity	NPC201380
0.7466	Intermediate Similarity	NPC469811
0.7466	Intermediate Similarity	NPC179787
0.7465	Intermediate Similarity	NPC110126
0.7465	Intermediate Similarity	NPC104483
0.7464	Intermediate Similarity	NPC82295
0.7447	Intermediate Similarity	NPC105127
0.7447	Intermediate Similarity	NPC84911
0.7434	Intermediate Similarity	NPC124542
0.7434	Intermediate Similarity	NPC59779
0.7434	Intermediate Similarity	NPC471177
0.7431	Intermediate Similarity	NPC477977
0.7426	Intermediate Similarity	NPC212125
0.7415	Intermediate Similarity	NPC321911
0.7405	Intermediate Similarity	NPC54102
0.7405	Intermediate Similarity	NPC162689
0.74	Intermediate Similarity	NPC476464
0.7397	Intermediate Similarity	NPC288838
0.7391	Intermediate Similarity	NPC315320
0.7386	Intermediate Similarity	NPC478182
0.7383	Intermediate Similarity	NPC325903
0.7376	Intermediate Similarity	NPC29886
0.7376	Intermediate Similarity	NPC261195
0.7372	Intermediate Similarity	NPC201634
0.7365	Intermediate Similarity	NPC53947
0.7361	Intermediate Similarity	NPC476454
0.7351	Intermediate Similarity	NPC469897
0.7343	Intermediate Similarity	NPC88097
0.7338	Intermediate Similarity	NPC471178
0.7308	Intermediate Similarity	NPC84268
0.7303	Intermediate Similarity	NPC477591
0.7303	Intermediate Similarity	NPC56765
0.7303	Intermediate Similarity	NPC293487
0.7299	Intermediate Similarity	NPC306397
0.7293	Intermediate Similarity	NPC215519
0.7292	Intermediate Similarity	NPC279081
0.729	Intermediate Similarity	NPC56233
0.7287	Intermediate Similarity	NPC473901
0.7273	Intermediate Similarity	NPC78375
0.7273	Intermediate Similarity	NPC476446
0.7273	Intermediate Similarity	NPC469813
0.7248	Intermediate Similarity	NPC105818
0.7248	Intermediate Similarity	NPC24678
0.7237	Intermediate Similarity	NPC193740
0.7237	Intermediate Similarity	NPC167635
0.7219	Intermediate Similarity	NPC476219
0.7219	Intermediate Similarity	NPC70922
0.7219	Intermediate Similarity	NPC212376
0.7219	Intermediate Similarity	NPC211572
0.7219	Intermediate Similarity	NPC80597
0.7219	Intermediate Similarity	NPC75540
0.7211	Intermediate Similarity	NPC314372
0.7208	Intermediate Similarity	NPC470203
0.7208	Intermediate Similarity	NPC71079
0.7206	Intermediate Similarity	NPC122718
0.7197	Intermediate Similarity	NPC116961
0.7192	Intermediate Similarity	NPC190296
0.7183	Intermediate Similarity	NPC198988
0.7179	Intermediate Similarity	NPC478183
0.7174	Intermediate Similarity	NPC165370
0.7172	Intermediate Similarity	NPC230002
0.7172	Intermediate Similarity	NPC2949
0.7172	Intermediate Similarity	NPC59084
0.7171	Intermediate Similarity	NPC51054
0.7163	Intermediate Similarity	NPC322488
0.7162	Intermediate Similarity	NPC143872
0.7161	Intermediate Similarity	NPC474217
0.7161	Intermediate Similarity	NPC90723
0.7161	Intermediate Similarity	NPC97367
0.7161	Intermediate Similarity	NPC478184
0.7152	Intermediate Similarity	NPC25008
0.7152	Intermediate Similarity	NPC469765
0.7152	Intermediate Similarity	NPC469786
0.7152	Intermediate Similarity	NPC469760
0.7152	Intermediate Similarity	NPC73952
0.7152	Intermediate Similarity	NPC259644
0.7152	Intermediate Similarity	NPC469763
0.7143	Intermediate Similarity	NPC470204
0.7143	Intermediate Similarity	NPC215584
0.7143	Intermediate Similarity	NPC44773
0.7133	Intermediate Similarity	NPC29702
0.7131	Intermediate Similarity	NPC213774
0.7125	Intermediate Similarity	NPC280852
0.7124	Intermediate Similarity	NPC216643
0.7124	Intermediate Similarity	NPC236711
0.7123	Intermediate Similarity	NPC473868
0.7123	Intermediate Similarity	NPC63157
0.7122	Intermediate Similarity	NPC471589
0.7115	Intermediate Similarity	NPC477975
0.7115	Intermediate Similarity	NPC85918
0.7114	Intermediate Similarity	NPC21605
0.7097	Intermediate Similarity	NPC478185
0.7095	Intermediate Similarity	NPC159856
0.7095	Intermediate Similarity	NPC285731
0.7078	Intermediate Similarity	NPC318065
0.7078	Intermediate Similarity	NPC92796
0.7078	Intermediate Similarity	NPC135141
0.7078	Intermediate Similarity	NPC206819
0.707	Intermediate Similarity	NPC278366
0.707	Intermediate Similarity	NPC127730
0.707	Intermediate Similarity	NPC98187
0.7059	Intermediate Similarity	NPC469785
0.7051	Intermediate Similarity	NPC317105
0.7042	Intermediate Similarity	NPC330326
0.7039	Intermediate Similarity	NPC200214
0.7032	Intermediate Similarity	NPC122141
0.7019	Intermediate Similarity	NPC203754
0.7019	Intermediate Similarity	NPC150048
0.7014	Intermediate Similarity	NPC325252
0.7013	Intermediate Similarity	NPC469762
0.7013	Intermediate Similarity	NPC286427
0.7	Intermediate Similarity	NPC471957
0.6993	Remote Similarity	NPC476297
0.6987	Remote Similarity	NPC225018
0.6981	Remote Similarity	NPC32534
0.6981	Remote Similarity	NPC91895
0.698	Remote Similarity	NPC469525
0.698	Remote Similarity	NPC467188
0.6978	Remote Similarity	NPC476140
0.6968	Remote Similarity	NPC41257
0.6963	Remote Similarity	NPC11863
0.6957	Remote Similarity	NPC297034
0.6957	Remote Similarity	NPC471579
0.6937	Remote Similarity	NPC82331
0.6934	Remote Similarity	NPC56856
0.6923	Remote Similarity	NPC255229
0.6923	Remote Similarity	NPC229173
0.6923	Remote Similarity	NPC81229
0.6901	Remote Similarity	NPC22079
0.6899	Remote Similarity	NPC274229
0.6887	Remote Similarity	NPC105811
0.6883	Remote Similarity	NPC34844

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 NPC476322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	866
0.2-0.3	1038
0.3-0.4	2097
0.4-0.5	2539
0.5-0.6	1554
0.6-0.7	480
0.7-0.8	123
0.8-0.85	12
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8814	High Similarity	NPD4823	Approved
0.8814	High Similarity	NPD4824	Approved
0.881	High Similarity	NPD2119	Approved
0.881	High Similarity	NPD2118	Approved
0.8692	High Similarity	NPD3944	Approved
0.8692	High Similarity	NPD3942	Approved
0.8629	High Similarity	NPD271	Approved
0.8629	High Similarity	NPD270	Clinical (unspecified phase)
0.8629	High Similarity	NPD268	Approved
0.8605	High Similarity	NPD3475	Approved
0.8605	High Similarity	NPD3476	Approved
0.8473	Intermediate Similarity	NPD1995	Approved
0.8473	Intermediate Similarity	NPD1993	Approved
0.8473	Intermediate Similarity	NPD1994	Approved
0.8462	Intermediate Similarity	NPD715	Phase 3
0.8409	Intermediate Similarity	NPD4030	Approved
0.8409	Intermediate Similarity	NPD4029	Approved
0.8409	Intermediate Similarity	NPD4028	Approved
0.8372	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD991	Phase 2
0.8372	Intermediate Similarity	NPD1598	Discontinued
0.8293	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD4547	Phase 3
0.8209	Intermediate Similarity	NPD2142	Approved
0.8209	Intermediate Similarity	NPD2141	Approved
0.8209	Intermediate Similarity	NPD2140	Approved
0.8154	Intermediate Similarity	NPD9583	Approved
0.8143	Intermediate Similarity	NPD7469	Discontinued
0.814	Intermediate Similarity	NPD9357	Approved
0.8102	Intermediate Similarity	NPD2072	Approved
0.8102	Intermediate Similarity	NPD2074	Approved
0.8102	Intermediate Similarity	NPD2073	Approved
0.8102	Intermediate Similarity	NPD2070	Approved
0.8102	Intermediate Similarity	NPD2075	Approved
0.8102	Intermediate Similarity	NPD2069	Approved
0.8102	Intermediate Similarity	NPD2068	Approved
0.8102	Intermediate Similarity	NPD2071	Approved
0.8015	Intermediate Similarity	NPD792	Discontinued
0.7984	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2006	Phase 2
0.7899	Intermediate Similarity	NPD2896	Discontinued
0.7862	Intermediate Similarity	NPD2837	Discontinued
0.7847	Intermediate Similarity	NPD2462	Phase 3
0.7847	Intermediate Similarity	NPD2466	Phase 3
0.7847	Intermediate Similarity	NPD2465	Approved
0.7842	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD4510	Discontinued
0.7794	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD9098	Phase 3
0.7746	Intermediate Similarity	NPD3813	Approved
0.7737	Intermediate Similarity	NPD3385	Approved
0.7734	Intermediate Similarity	NPD9396	Approved
0.7734	Intermediate Similarity	NPD9392	Approved
0.773	Intermediate Similarity	NPD1722	Approved
0.7708	Intermediate Similarity	NPD1270	Approved
0.7708	Intermediate Similarity	NPD4702	Approved
0.7708	Intermediate Similarity	NPD4703	Approved
0.7703	Intermediate Similarity	NPD6497	Approved
0.7698	Intermediate Similarity	NPD201	Phase 2
0.7698	Intermediate Similarity	NPD200	Phase 2
0.7671	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1649	Discontinued
0.7655	Intermediate Similarity	NPD2430	Phase 2
0.7643	Intermediate Similarity	NPD1380	Discovery
0.7639	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3339	Approved
0.76	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD803	Phase 1
0.7586	Intermediate Similarity	NPD2110	Approved
0.7574	Intermediate Similarity	NPD3654	Approved
0.7571	Intermediate Similarity	NPD6554	Approved
0.7571	Intermediate Similarity	NPD45	Approved
0.7552	Intermediate Similarity	NPD3717	Discontinued
0.7535	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD5418	Discontinued
0.7533	Intermediate Similarity	NPD5255	Approved
0.75	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1988	Phase 1
0.7483	Intermediate Similarity	NPD1383	Phase 3
0.7483	Intermediate Similarity	NPD1382	Phase 2
0.7466	Intermediate Similarity	NPD1661	Suspended
0.7465	Intermediate Similarity	NPD786	Approved
0.745	Intermediate Similarity	NPD2165	Phase 1
0.7434	Intermediate Similarity	NPD5315	Discontinued
0.7434	Intermediate Similarity	NPD6771	Discontinued
0.7434	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3262	Approved
0.7432	Intermediate Similarity	NPD4641	Discontinued
0.7431	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD9284	Approved
0.7415	Intermediate Similarity	NPD3100	Discontinued
0.74	Intermediate Similarity	NPD3114	Approved
0.74	Intermediate Similarity	NPD3115	Approved
0.74	Intermediate Similarity	NPD3113	Approved
0.74	Intermediate Similarity	NPD3112	Approved
0.7391	Intermediate Similarity	NPD9206	Approved
0.7391	Intermediate Similarity	NPD9207	Approved
0.7383	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD9598	Discontinued
0.7355	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2582	Approved
0.7351	Intermediate Similarity	NPD2581	Approved
0.7351	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4804	Approved
0.7343	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD9726	Discontinued
0.7333	Intermediate Similarity	NPD977	Approved
0.7333	Intermediate Similarity	NPD2809	Approved
0.7333	Intermediate Similarity	NPD975	Approved
0.7333	Intermediate Similarity	NPD976	Approved
0.7325	Intermediate Similarity	NPD7216	Approved
0.7325	Intermediate Similarity	NPD7217	Approved
0.732	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8026	Phase 1
0.731	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD272	Approved
0.7299	Intermediate Similarity	NPD9080	Approved
0.7297	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1183	Approved
0.7296	Intermediate Similarity	NPD7111	Discontinued
0.729	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6446	Discontinued
0.726	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2511	Approved
0.7254	Intermediate Similarity	NPD1256	Approved
0.7254	Intermediate Similarity	NPD1255	Approved
0.7254	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1254	Approved
0.7254	Intermediate Similarity	NPD1253	Approved
0.7244	Intermediate Similarity	NPD5862	Discovery
0.7244	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4805	Approved
0.7237	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2720	Phase 1
0.7219	Intermediate Similarity	NPD1328	Approved
0.7219	Intermediate Similarity	NPD2061	Approved
0.7208	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4973	Approved
0.7185	Intermediate Similarity	NPD5787	Discontinued
0.7176	Intermediate Similarity	NPD60	Approved
0.7171	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2580	Discontinued
0.7164	Intermediate Similarity	NPD4811	Discontinued
0.7161	Intermediate Similarity	NPD3323	Discontinued
0.716	Intermediate Similarity	NPD8408	Discontinued
0.7152	Intermediate Similarity	NPD1917	Discontinued
0.7143	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5671	Approved
0.7134	Intermediate Similarity	NPD2333	Discontinued
0.7133	Intermediate Similarity	NPD2172	Phase 1
0.7125	Intermediate Similarity	NPD6044	Discontinued
0.7125	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5020	Approved
0.7097	Intermediate Similarity	NPD5400	Approved
0.7092	Intermediate Similarity	NPD809	Discontinued
0.7089	Intermediate Similarity	NPD4024	Phase 3
0.7083	Intermediate Similarity	NPD9506	Approved
0.7075	Intermediate Similarity	NPD4047	Discontinued
0.707	Intermediate Similarity	NPD5636	Discontinued
0.7068	Intermediate Similarity	NPD8840	Approved
0.7059	Intermediate Similarity	NPD6026	Approved
0.7059	Intermediate Similarity	NPD1561	Phase 2
0.7055	Intermediate Similarity	NPD2222	Discontinued
0.7051	Intermediate Similarity	NPD8129	Discovery
0.7051	Intermediate Similarity	NPD3583	Phase 2
0.7047	Intermediate Similarity	NPD1683	Approved
0.7044	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD9100	Approved
0.7037	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2640	Approved
0.7025	Intermediate Similarity	NPD2641	Approved
0.7025	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7913	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD490	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD925	Approved
0.7006	Intermediate Similarity	NPD926	Approved
0.7	Intermediate Similarity	NPD5324	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD174	Discontinued
0.6968	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD425	Approved
0.6962	Remote Similarity	NPD5611	Phase 2
0.6962	Remote Similarity	NPD424	Approved
0.6957	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2104	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