NPASS Compound

Structure

CID124636 OpenBabel06191715482D 31 35 0 0 0 0 0 0 0 0999 V2000 -1.2259 2.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1956 1.7668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6994 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6985 -0.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8882 -1.8694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8864 0.0051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2561 -2.8218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6171 0.9586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1396 1.7731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4438 -3.2899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1848 3.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8116 -0.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2818 2.5813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0761 -1.4016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2610 -1.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6233 0.0146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0752 -0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1288 3.4082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8157 -1.3985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4482 -1.4053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4409 -0.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6209 -1.8777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8033 -1.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8074 -0.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6063 2.5938 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6311 -2.8207 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2624 0.0049 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0082 -1.8695 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5955 4.2289 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 -1.8662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 17 2 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 31 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 18 25 2 3 0 0 0 18 29 1 0 0 0 0 19 28 2 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 0 0 0 0 22 26 2 0 0 0 0 23 24 2 0 0 0 0 23 28 1 0 0 0 0 24 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.15
Volume:	431.953
LogP:	4.291
LogD:	3.725
LogS:	-3.782
# Rotatable Bonds:	4
TPSA:	94.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	4.111
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.475
MDCK Permeability:	1.7792168364394456e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.768
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	95.9673080444336%
Volume Distribution (VD):	1.817
Pgp-substrate:	2.306307315826416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.656
CYP2C19-substrate:	0.122
CYP2C9-inhibitor:	0.339
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.872
CYP2D6-substrate:	0.801
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	4.592
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.695
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.9
Rat Oral Acute Toxicity:	0.44
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.715
Carcinogencity:	0.548
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC124636

Natural Product ID:	NPC124636
*Common Name:**	HYPFBWXPSYPBCL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HYPFBWXPSYPBCL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H22N4O2S/c1-13(2)11-18(29)25-9-8-16-21-20-15(14-5-3-4-6-17(14)27-21)7-10-26-22(20)23-24(16)31-12-19(30)28-23/h3-7,10-11,27H,8-9,12H2,1-2H3,(H,25,29)(H,28,30)
SMILES:	CC(=CC(=NCCc1c2SCC(=Nc2c2c3c1[nH]c1ccccc1c3ccn2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL127939
PubChem CID:	10025716
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
NPO14024	Cystodytes violatinctus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23961991]
NPO32634	cystodytes sp. ascidian	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7525959]
NPO13848	Amomum daniellii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14024	Cystodytes violatinctus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO394	Psilostrophe villosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15255	Piptadenia contorta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9122	Pycnanthemum lanceolatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8019	Pentaceras australe	Species	Rutaceae	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	5
Others	3

Activity Type	# Activity
Cell Line	4
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	=	16300.0	nM	PMID[478996]
NPT1083	Cell Line	A-375	Homo sapiens	IC50	>	10000.0	nM	PMID[478997]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	9990.0	nM	PMID[478997]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	19000.0	nM	PMID[478997]
NPT27	Others	Unspecified		IC50	=	8100.0	nM	PMID[478996]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	1.0	n.a.	PMID[478996]
NPT320	Protein Family	DNA topoisomerase II	Homo sapiens	IC90	=	138000.0	nM	PMID[478996]
NPT2	Others	Unspecified		K	>	100.0	uM	PMID[478996]

☑ 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 NPC124636 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	854
0.1-0.2	12508
0.2-0.3	19697
0.3-0.4	4903
0.4-0.5	2278
0.5-0.6	2079
0.6-0.7	368
0.7-0.8	1
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC193370
0.984	High Similarity	NPC66699
0.9681	High Similarity	NPC175916
0.9005	High Similarity	NPC77022
0.896	High Similarity	NPC216221
0.8856	High Similarity	NPC173344
0.8812	High Similarity	NPC149014
0.8465	Intermediate Similarity	NPC147810
0.7236	Intermediate Similarity	NPC297034
0.7101	Intermediate Similarity	NPC255909
0.7073	Intermediate Similarity	NPC467063
0.7019	Intermediate Similarity	NPC103119
0.6983	Remote Similarity	NPC24802
0.6965	Remote Similarity	NPC201634
0.6919	Remote Similarity	NPC272458
0.6915	Remote Similarity	NPC91895
0.6878	Remote Similarity	NPC176199
0.6878	Remote Similarity	NPC215795
0.6864	Remote Similarity	NPC477111
0.6837	Remote Similarity	NPC265576
0.6832	Remote Similarity	NPC194411
0.6829	Remote Similarity	NPC248454
0.6821	Remote Similarity	NPC216713
0.6818	Remote Similarity	NPC474791
0.6809	Remote Similarity	NPC314102
0.6809	Remote Similarity	NPC251722
0.6791	Remote Similarity	NPC272483
0.6784	Remote Similarity	NPC215584
0.6784	Remote Similarity	NPC44773
0.678	Remote Similarity	NPC280852
0.6772	Remote Similarity	NPC169433
0.6769	Remote Similarity	NPC105818
0.6769	Remote Similarity	NPC24678
0.6761	Remote Similarity	NPC216550
0.6748	Remote Similarity	NPC68354
0.6734	Remote Similarity	NPC135141
0.6734	Remote Similarity	NPC92796
0.6732	Remote Similarity	NPC275305
0.6732	Remote Similarity	NPC37423
0.6716	Remote Similarity	NPC317105
0.6701	Remote Similarity	NPC325903
0.6699	Remote Similarity	NPC163055
0.6697	Remote Similarity	NPC477113
0.6697	Remote Similarity	NPC475288
0.6683	Remote Similarity	NPC193740
0.6683	Remote Similarity	NPC164228
0.6667	Remote Similarity	NPC157583
0.6667	Remote Similarity	NPC38736
0.6667	Remote Similarity	NPC471957
0.6667	Remote Similarity	NPC225018
0.6667	Remote Similarity	NPC201380
0.6667	Remote Similarity	NPC179787
0.665	Remote Similarity	NPC206819
0.665	Remote Similarity	NPC56765
0.665	Remote Similarity	NPC318065
0.6649	Remote Similarity	NPC159856
0.6634	Remote Similarity	NPC478184
0.6634	Remote Similarity	NPC478182
0.6633	Remote Similarity	NPC321911
0.6633	Remote Similarity	NPC124005
0.6633	Remote Similarity	NPC184476
0.6623	Remote Similarity	NPC469727
0.6618	Remote Similarity	NPC63751
0.6617	Remote Similarity	NPC122141
0.6615	Remote Similarity	NPC63545
0.66	Remote Similarity	NPC469897
0.6599	Remote Similarity	NPC40070
0.6592	Remote Similarity	NPC166492
0.6592	Remote Similarity	NPC473362
0.6582	Remote Similarity	NPC470111
0.6582	Remote Similarity	NPC469811
0.6567	Remote Similarity	NPC475990
0.6566	Remote Similarity	NPC470823
0.6564	Remote Similarity	NPC471741
0.6564	Remote Similarity	NPC314372
0.6552	Remote Similarity	NPC90723
0.655	Remote Similarity	NPC51054
0.6546	Remote Similarity	NPC190296
0.6544	Remote Similarity	NPC294693
0.653	Remote Similarity	NPC34837
0.6524	Remote Similarity	NPC24864
0.6517	Remote Similarity	NPC236711
0.6517	Remote Similarity	NPC167635
0.6514	Remote Similarity	NPC128244
0.6507	Remote Similarity	NPC59269
0.6507	Remote Similarity	NPC477110
0.6504	Remote Similarity	NPC475422
0.6502	Remote Similarity	NPC470203
0.65	Remote Similarity	NPC476219
0.6495	Remote Similarity	NPC317030
0.649	Remote Similarity	NPC471579
0.6488	Remote Similarity	NPC49954
0.6488	Remote Similarity	NPC474561
0.6485	Remote Similarity	NPC293487
0.6484	Remote Similarity	NPC167710
0.6482	Remote Similarity	NPC470233
0.6479	Remote Similarity	NPC15102
0.6473	Remote Similarity	NPC470498
0.6471	Remote Similarity	NPC194640
0.6471	Remote Similarity	NPC472587
0.6471	Remote Similarity	NPC271734
0.6468	Remote Similarity	NPC133366
0.6465	Remote Similarity	NPC37548
0.6465	Remote Similarity	NPC187951
0.6463	Remote Similarity	NPC250835
0.6462	Remote Similarity	NPC320863
0.6462	Remote Similarity	NPC48938
0.6462	Remote Similarity	NPC20144
0.6453	Remote Similarity	NPC470204
0.6452	Remote Similarity	NPC324149
0.645	Remote Similarity	NPC200214
0.645	Remote Similarity	NPC161108
0.645	Remote Similarity	NPC73952
0.645	Remote Similarity	NPC469786
0.645	Remote Similarity	NPC469763
0.645	Remote Similarity	NPC25008
0.645	Remote Similarity	NPC469765
0.645	Remote Similarity	NPC259644
0.645	Remote Similarity	NPC469760
0.6449	Remote Similarity	NPC474707
0.6447	Remote Similarity	NPC129042
0.6441	Remote Similarity	NPC469308
0.6436	Remote Similarity	NPC286427
0.6435	Remote Similarity	NPC231536
0.6432	Remote Similarity	NPC148592
0.6429	Remote Similarity	NPC88115
0.6429	Remote Similarity	NPC242556
0.6429	Remote Similarity	NPC237188
0.6422	Remote Similarity	NPC282231
0.6422	Remote Similarity	NPC474177
0.6419	Remote Similarity	NPC204565
0.6418	Remote Similarity	NPC212376
0.6418	Remote Similarity	NPC80597
0.6418	Remote Similarity	NPC211572
0.6418	Remote Similarity	NPC70922
0.6418	Remote Similarity	NPC75540
0.6416	Remote Similarity	NPC87755
0.6409	Remote Similarity	NPC229332
0.6408	Remote Similarity	NPC478183
0.6404	Remote Similarity	NPC41257
0.6404	Remote Similarity	NPC474880
0.6404	Remote Similarity	NPC221786
0.6402	Remote Similarity	NPC282398
0.6389	Remote Similarity	NPC173028
0.6389	Remote Similarity	NPC65215
0.6382	Remote Similarity	NPC288445
0.6381	Remote Similarity	NPC150048
0.6381	Remote Similarity	NPC203754
0.6379	Remote Similarity	NPC473310
0.6373	Remote Similarity	NPC473320
0.6373	Remote Similarity	NPC229173
0.6373	Remote Similarity	NPC279918
0.6368	Remote Similarity	NPC256893
0.6359	Remote Similarity	NPC469783
0.6359	Remote Similarity	NPC469761
0.6359	Remote Similarity	NPC469779
0.6359	Remote Similarity	NPC469780
0.6359	Remote Similarity	NPC469784
0.6359	Remote Similarity	NPC95783
0.6359	Remote Similarity	NPC469768
0.6359	Remote Similarity	NPC469767
0.6356	Remote Similarity	NPC475070
0.6356	Remote Similarity	NPC19170
0.6355	Remote Similarity	NPC469762
0.6351	Remote Similarity	NPC326575
0.635	Remote Similarity	NPC53947
0.6346	Remote Similarity	NPC32534
0.6345	Remote Similarity	NPC297862
0.6341	Remote Similarity	NPC478185
0.6339	Remote Similarity	NPC328318
0.6339	Remote Similarity	NPC106757
0.6339	Remote Similarity	NPC328596
0.6339	Remote Similarity	NPC182507
0.6338	Remote Similarity	NPC233936
0.6337	Remote Similarity	NPC470507
0.6336	Remote Similarity	NPC304926
0.6336	Remote Similarity	NPC476041
0.6332	Remote Similarity	NPC21605
0.6329	Remote Similarity	NPC56233
0.6329	Remote Similarity	NPC160105
0.6329	Remote Similarity	NPC49217
0.6327	Remote Similarity	NPC469766
0.6327	Remote Similarity	NPC88121
0.6326	Remote Similarity	NPC308931
0.6326	Remote Similarity	NPC99939
0.6321	Remote Similarity	NPC11126
0.6316	Remote Similarity	NPC6982
0.6316	Remote Similarity	NPC82331
0.6313	Remote Similarity	NPC86288
0.6313	Remote Similarity	NPC285731
0.6311	Remote Similarity	NPC311276
0.6308	Remote Similarity	NPC88097
0.6308	Remote Similarity	NPC73767
0.6308	Remote Similarity	NPC110126
0.6305	Remote Similarity	NPC476464
0.6305	Remote Similarity	NPC469785
0.6304	Remote Similarity	NPC31385
0.6304	Remote Similarity	NPC75726
0.6304	Remote Similarity	NPC110602
0.6303	Remote Similarity	NPC474958

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 NPC124636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	940
0.2-0.3	1005
0.3-0.4	2501
0.4-0.5	2238
0.5-0.6	1779
0.6-0.7	331
0.7-0.8	7
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
0.7961	Intermediate Similarity	NPD2815	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD3348	Phase 2
0.75	Intermediate Similarity	NPD3859	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2720	Phase 1
0.729	Intermediate Similarity	NPD4865	Approved
0.7282	Intermediate Similarity	NPD1235	Phase 3
0.7113	Intermediate Similarity	NPD1648	Phase 1
0.7113	Intermediate Similarity	NPD1647	Phase 1
0.7108	Intermediate Similarity	NPD5106	Approved
0.7108	Intermediate Similarity	NPD5105	Approved
0.7053	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7469	Discontinued
0.705	Intermediate Similarity	NPD3609	Approved
0.705	Intermediate Similarity	NPD3610	Approved
0.7016	Intermediate Similarity	NPD1661	Suspended
0.701	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2771	Approved
0.6919	Remote Similarity	NPD5315	Discontinued
0.6897	Remote Similarity	NPD4128	Approved
0.689	Remote Similarity	NPD7394	Phase 2
0.689	Remote Similarity	NPD3961	Discontinued
0.6887	Remote Similarity	NPD5428	Discontinued
0.6869	Remote Similarity	NPD6224	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD2641	Approved
0.6866	Remote Similarity	NPD2640	Approved
0.6866	Remote Similarity	NPD6132	Phase 1
0.6866	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3401	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD5409	Clinical (unspecified phase)
0.684	Remote Similarity	NPD3404	Approved
0.6839	Remote Similarity	NPD4547	Phase 3
0.6837	Remote Similarity	NPD6285	Phase 2
0.6837	Remote Similarity	NPD976	Approved
0.6837	Remote Similarity	NPD975	Approved
0.6837	Remote Similarity	NPD977	Approved
0.6835	Remote Similarity	NPD4886	Phase 2
0.6829	Remote Similarity	NPD4181	Approved
0.6818	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7867	Phase 1
0.681	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4473	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4509	Discontinued
0.6763	Remote Similarity	NPD4050	Phase 1
0.6749	Remote Similarity	NPD5412	Discontinued
0.6748	Remote Similarity	NPD3506	Approved
0.6748	Remote Similarity	NPD3505	Approved
0.6741	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5046	Discontinued
0.6732	Remote Similarity	NPD5065	Approved
0.6728	Remote Similarity	NPD1315	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD3100	Discontinued
0.6716	Remote Similarity	NPD3323	Discontinued
0.6715	Remote Similarity	NPD4079	Approved
0.6715	Remote Similarity	NPD4076	Approved
0.6714	Remote Similarity	NPD3082	Discontinued
0.6714	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD1683	Approved
0.6701	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.67	Remote Similarity	NPD1403	Approved
0.67	Remote Similarity	NPD1404	Approved
0.67	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6044	Discontinued
0.6696	Remote Similarity	NPD7423	Phase 2
0.6682	Remote Similarity	NPD4615	Phase 2
0.6682	Remote Similarity	NPD3231	Approved
0.6667	Remote Similarity	NPD5864	Phase 2
0.6667	Remote Similarity	NPD1253	Approved
0.6667	Remote Similarity	NPD6968	Phase 2
0.6667	Remote Similarity	NPD6969	Phase 2
0.6667	Remote Similarity	NPD1256	Approved
0.6667	Remote Similarity	NPD1255	Approved
0.6667	Remote Similarity	NPD1254	Approved
0.6667	Remote Similarity	NPD7564	Discontinued
0.6667	Remote Similarity	NPD7027	Phase 3
0.6667	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6178	Phase 3
0.6651	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6239	Discontinued
0.665	Remote Similarity	NPD6492	Phase 2
0.665	Remote Similarity	NPD2639	Approved
0.665	Remote Similarity	NPD2642	Approved
0.6632	Remote Similarity	NPD4510	Discontinued
0.6618	Remote Similarity	NPD4640	Approved
0.6618	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD4075	Phase 2
0.6618	Remote Similarity	NPD4639	Approved
0.6618	Remote Similarity	NPD4638	Approved
0.6618	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD2837	Discontinued
0.6609	Remote Similarity	NPD7540	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4472	Approved
0.6607	Remote Similarity	NPD4471	Approved
0.6604	Remote Similarity	NPD7026	Phase 2
0.6592	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD917	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4024	Phase 3
0.6584	Remote Similarity	NPD2385	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6771	Discontinued
0.6579	Remote Similarity	NPD6957	Approved
0.6579	Remote Similarity	NPD6958	Approved
0.6575	Remote Similarity	NPD5828	Phase 2
0.6566	Remote Similarity	NPD2882	Phase 1
0.6561	Remote Similarity	NPD3015	Discontinued
0.6557	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6156	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4999	Phase 3
0.6544	Remote Similarity	NPD4998	Phase 3
0.6537	Remote Similarity	NPD5021	Discontinued
0.6535	Remote Similarity	NPD7188	Phase 3
0.6532	Remote Similarity	NPD6139	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7052	Phase 1
0.6524	Remote Similarity	NPD947	Approved
0.6522	Remote Similarity	NPD2021	Discontinued
0.652	Remote Similarity	NPD6749	Phase 1
0.652	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD4463	Approved
0.6515	Remote Similarity	NPD4462	Approved
0.6512	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6281	Approved
0.6509	Remote Similarity	NPD4957	Phase 2
0.6507	Remote Similarity	NPD6711	Approved
0.6505	Remote Similarity	NPD5436	Phase 1
0.6494	Remote Similarity	NPD5270	Discontinued
0.649	Remote Similarity	NPD4883	Approved
0.6484	Remote Similarity	NPD3830	Phase 1
0.6484	Remote Similarity	NPD5462	Discontinued
0.6484	Remote Similarity	NPD7021	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3279	Phase 2
0.6471	Remote Similarity	NPD3583	Phase 2
0.6468	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4992	Phase 1
0.6462	Remote Similarity	NPD725	Discontinued
0.6462	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.646	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4044	Discontinued
0.6456	Remote Similarity	NPD5862	Discovery
0.6452	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4902	Discontinued
0.6447	Remote Similarity	NPD3330	Phase 1
0.6441	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3843	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD2172	Phase 1
0.6432	Remote Similarity	NPD4051	Discontinued
0.6429	Remote Similarity	NPD7208	Approved
0.6429	Remote Similarity	NPD7209	Approved
0.6429	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7111	Discontinued
0.6429	Remote Similarity	NPD7207	Approved
0.6429	Remote Similarity	NPD6131	Phase 1
0.6425	Remote Similarity	NPD4650	Approved
0.6422	Remote Similarity	NPD2717	Phase 2
0.6419	Remote Similarity	NPD8431	Approved
0.641	Remote Similarity	NPD1722	Approved
0.6409	Remote Similarity	NPD6664	Approved
0.6404	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD715	Phase 3
0.6398	Remote Similarity	NPD6352	Phase 2
0.6396	Remote Similarity	NPD6149	Phase 2
0.6396	Remote Similarity	NPD6816	Phase 3
0.6396	Remote Similarity	NPD6389	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD3116	Approved
0.6394	Remote Similarity	NPD3117	Approved
0.6394	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7619	Phase 3
0.6393	Remote Similarity	NPD7618	Phase 3
0.6382	Remote Similarity	NPD2430	Phase 2
0.6381	Remote Similarity	NPD2751	Phase 1
0.6378	Remote Similarity	NPD2006	Phase 2
0.6377	Remote Similarity	NPD4320	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2481	Approved
0.6368	Remote Similarity	NPD2479	Phase 3
0.6368	Remote Similarity	NPD7063	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7216	Approved
0.6364	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7217	Approved
0.6359	Remote Similarity	NPD2818	Discontinued
0.6359	Remote Similarity	NPD7135	Phase 2
0.6355	Remote Similarity	NPD2145	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2144	Approved
0.6346	Remote Similarity	NPD1326	Approved
0.6346	Remote Similarity	NPD1325	Approved
0.6341	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2058	Phase 2
0.634	Remote Similarity	NPD2059	Approved
0.634	Remote Similarity	NPD2057	Approved
0.6339	Remote Similarity	NPD8073	Approved
0.6337	Remote Similarity	NPD2165	Phase 1
0.6337	Remote Similarity	NPD1328	Approved
0.633	Remote Similarity	NPD3419	Clinical (unspecified phase)

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