NPASS Compound

Structure

NPC270241 OpenBabel07101718282D 36 41 0 0 1 0 0 0 0 0999 V2000 -5.7839 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -5.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 -4.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7839 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 -3.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -3.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7839 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6942 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0519 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0519 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9179 -2.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1859 -0.3090 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 -3.1859 -2.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3198 -3.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 8 2 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 15 2 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 13 27 1 0 0 0 0 14 20 2 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 32 1 0 0 0 0 19 13 1 1 0 0 0 19 22 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 22 29 2 0 0 0 0 22 33 1 0 0 0 0 23 31 1 0 0 0 0 23 34 2 0 0 0 0 24 27 1 6 0 0 0 24 30 1 0 0 0 0 24 32 1 0 0 0 0 25 26 1 0 0 0 0 25 32 1 0 0 0 0 25 35 2 0 0 0 0 26 30 1 0 0 0 0 27 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	485.21
Volume:	485.353
LogP:	2.738
LogD:	2.752
LogS:	-4.327
# Rotatable Bonds:	3
TPSA:	120.06
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	4.202
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.186
MDCK Permeability:	2.8760252462234348e-05
Pgp-inhibitor:	0.223
Pgp-substrate:	0.926
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.588

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	77.0146255493164%
Volume Distribution (VD):	0.843
Pgp-substrate:	4.874345302581787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.281
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.322
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.912
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.685
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	1.756
Half-life (T1/2):	0.43

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.81
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.096
Carcinogencity:	0.69
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.75

Download Data

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

Natural Product: NPC270241

Natural Product ID:	NPC270241
*Common Name:**	Quinadoline A
IUPAC Name:	(4R)-4-[[(3aR,4S)-4-hydroxy-2,2-dimethyl-1-oxo-3,3a-dihydroimidazo[1,2-a]indol-4-yl]methyl]-1-propan-2-ylidene-4H-pyrazino[2,1-b]quinazoline-3,6-dione
Synonyms:
Standard InCHIKey:	LCHQPVCRYDVSTJ-BRBPODBZSA-N
Standard InCHI:	InChI=1S/C27H27N5O4/c1-14(2)20-21-28-17-11-7-5-9-15(17)23(34)31(21)19(22(33)29-20)13-27(36)16-10-6-8-12-18(16)32-24(27)30-26(3,4)25(32)35/h5-12,19,24,30,36H,13H2,1-4H3,(H,29,33)/t19-,24-,27+/m1/s1
SMILES:	CC(=C1N=C(O)[C@H](n2c1nc1ccccc1c2=O)C[C@@]1(O)[C@@H]2NC(C(=O)N2c2c1cccc2)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386533
PubChem CID:	71725623
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*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
NPO33176	cladosporium sp.	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23758051]
NPO40343	Scedosporium apiospermum	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32130008]

☑ 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
EC50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	EC50	=	2340.0	nM	PMID[558233]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	100000.0	nM	PMID[558232]

☑ 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 NPC270241 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	447
0.1-0.2	2910
0.2-0.3	13715
0.3-0.4	17239
0.4-0.5	3577
0.5-0.6	3034
0.6-0.7	1591
0.7-0.8	119
0.8-0.85	23
0.85-0.9	20
0.9-0.95	10
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9946	High Similarity	NPC471155
0.9891	High Similarity	NPC225400
0.9838	High Similarity	NPC472538
0.9838	High Similarity	NPC470786
0.9465	High Similarity	NPC295548
0.9235	High Similarity	NPC248601
0.8947	High Similarity	NPC106118
0.8789	High Similarity	NPC472540
0.8789	High Similarity	NPC472539
0.8789	High Similarity	NPC470787
0.8743	High Similarity	NPC472541
0.8743	High Similarity	NPC472542
0.8663	High Similarity	NPC471198
0.8614	High Similarity	NPC471197
0.8586	High Similarity	NPC285192
0.8454	Intermediate Similarity	NPC471199
0.8341	Intermediate Similarity	NPC15384
0.8341	Intermediate Similarity	NPC244425
0.8333	Intermediate Similarity	NPC471195
0.8333	Intermediate Similarity	NPC471196
0.7884	Intermediate Similarity	NPC355
0.7853	Intermediate Similarity	NPC475607
0.7846	Intermediate Similarity	NPC307396
0.7812	Intermediate Similarity	NPC474081
0.7801	Intermediate Similarity	NPC470548
0.7801	Intermediate Similarity	NPC475594
0.7772	Intermediate Similarity	NPC475761
0.7772	Intermediate Similarity	NPC474041
0.7766	Intermediate Similarity	NPC471130
0.7739	Intermediate Similarity	NPC276430
0.7701	Intermediate Similarity	NPC68650
0.7677	Intermediate Similarity	NPC473815
0.766	Intermediate Similarity	NPC88970
0.763	Intermediate Similarity	NPC471194
0.763	Intermediate Similarity	NPC153980
0.763	Intermediate Similarity	NPC471193
0.763	Intermediate Similarity	NPC6865
0.7619	Intermediate Similarity	NPC189116
0.7596	Intermediate Similarity	NPC471191
0.7583	Intermediate Similarity	NPC72956
0.7553	Intermediate Similarity	NPC154478
0.754	Intermediate Similarity	NPC84317
0.7442	Intermediate Similarity	NPC471192
0.7433	Intermediate Similarity	NPC295021
0.743	Intermediate Similarity	NPC471663
0.7385	Intermediate Similarity	NPC272174
0.7374	Intermediate Similarity	NPC475685
0.7368	Intermediate Similarity	NPC471436
0.736	Intermediate Similarity	NPC14849
0.7318	Intermediate Similarity	NPC31097
0.7304	Intermediate Similarity	NPC92803
0.7282	Intermediate Similarity	NPC472118
0.7273	Intermediate Similarity	NPC474896
0.7259	Intermediate Similarity	NPC328611
0.7236	Intermediate Similarity	NPC182057
0.7236	Intermediate Similarity	NPC147298
0.7236	Intermediate Similarity	NPC131450
0.7206	Intermediate Similarity	NPC18890
0.7192	Intermediate Similarity	NPC150308
0.7188	Intermediate Similarity	NPC471122
0.7172	Intermediate Similarity	NPC248862
0.7165	Intermediate Similarity	NPC113056
0.7165	Intermediate Similarity	NPC138293
0.7162	Intermediate Similarity	NPC220851
0.7156	Intermediate Similarity	NPC471944
0.7128	Intermediate Similarity	NPC300596
0.7128	Intermediate Similarity	NPC237649
0.7128	Intermediate Similarity	NPC471124
0.7105	Intermediate Similarity	NPC117032
0.7065	Intermediate Similarity	NPC475094
0.705	Intermediate Similarity	NPC471743
0.7037	Intermediate Similarity	NPC71238
0.7035	Intermediate Similarity	NPC177261
0.7033	Intermediate Similarity	NPC198401
0.7026	Intermediate Similarity	NPC476231
0.6977	Remote Similarity	NPC254850
0.6977	Remote Similarity	NPC477181
0.6977	Remote Similarity	NPC477178
0.6977	Remote Similarity	NPC477180
0.6973	Remote Similarity	NPC207554
0.6944	Remote Similarity	NPC477174
0.6944	Remote Similarity	NPC477173
0.6944	Remote Similarity	NPC470490
0.6941	Remote Similarity	NPC54981
0.6931	Remote Similarity	NPC324445
0.693	Remote Similarity	NPC477179
0.693	Remote Similarity	NPC471762
0.6912	Remote Similarity	NPC243850
0.6912	Remote Similarity	NPC470488
0.6904	Remote Similarity	NPC14812
0.6895	Remote Similarity	NPC254798
0.6895	Remote Similarity	NPC475359
0.6895	Remote Similarity	NPC191817
0.6886	Remote Similarity	NPC157931
0.6881	Remote Similarity	NPC470491
0.6881	Remote Similarity	NPC475259
0.6881	Remote Similarity	NPC471945
0.6881	Remote Similarity	NPC471950
0.6863	Remote Similarity	NPC39822
0.686	Remote Similarity	NPC473615
0.6856	Remote Similarity	NPC194740
0.6849	Remote Similarity	NPC471951
0.6849	Remote Similarity	NPC471946
0.6848	Remote Similarity	NPC300299
0.6845	Remote Similarity	NPC43477
0.6845	Remote Similarity	NPC2823
0.6845	Remote Similarity	NPC21429
0.6827	Remote Similarity	NPC229484
0.682	Remote Similarity	NPC473376
0.6812	Remote Similarity	NPC259626
0.6802	Remote Similarity	NPC27904
0.6802	Remote Similarity	NPC472102
0.6802	Remote Similarity	NPC309531
0.6794	Remote Similarity	NPC292675
0.6783	Remote Similarity	NPC66777
0.6782	Remote Similarity	NPC285622
0.6782	Remote Similarity	NPC475532
0.678	Remote Similarity	NPC91179
0.6779	Remote Similarity	NPC17273
0.6779	Remote Similarity	NPC141612
0.6779	Remote Similarity	NPC135601
0.6768	Remote Similarity	NPC472117
0.6767	Remote Similarity	NPC89987
0.6763	Remote Similarity	NPC2933
0.6753	Remote Similarity	NPC326363
0.6751	Remote Similarity	NPC276085
0.675	Remote Similarity	NPC472114
0.675	Remote Similarity	NPC279527
0.675	Remote Similarity	NPC472115
0.675	Remote Similarity	NPC214960
0.6749	Remote Similarity	NPC165285
0.6739	Remote Similarity	NPC257851
0.6737	Remote Similarity	NPC136002
0.6718	Remote Similarity	NPC471132
0.6715	Remote Similarity	NPC256288
0.6708	Remote Similarity	NPC314882
0.6702	Remote Similarity	NPC311658
0.6701	Remote Similarity	NPC222029
0.6685	Remote Similarity	NPC207428
0.6684	Remote Similarity	NPC122553
0.6681	Remote Similarity	NPC477714
0.6681	Remote Similarity	NPC229893
0.6667	Remote Similarity	NPC471536
0.6667	Remote Similarity	NPC478006
0.6667	Remote Similarity	NPC17698
0.6667	Remote Similarity	NPC177996
0.6667	Remote Similarity	NPC470489
0.6667	Remote Similarity	NPC322064
0.6667	Remote Similarity	NPC147983
0.6652	Remote Similarity	NPC54744
0.6652	Remote Similarity	NPC475969
0.6652	Remote Similarity	NPC475859
0.6652	Remote Similarity	NPC122886
0.6651	Remote Similarity	NPC316282
0.6649	Remote Similarity	NPC83214
0.6638	Remote Similarity	NPC325976
0.6637	Remote Similarity	NPC477715
0.6635	Remote Similarity	NPC221873
0.6634	Remote Similarity	NPC129486
0.6633	Remote Similarity	NPC469903
0.6626	Remote Similarity	NPC63109
0.6618	Remote Similarity	NPC242269
0.6609	Remote Similarity	NPC476817
0.6609	Remote Similarity	NPC470730
0.6609	Remote Similarity	NPC477175
0.6608	Remote Similarity	NPC303658
0.6606	Remote Similarity	NPC478075
0.6606	Remote Similarity	NPC16249
0.6604	Remote Similarity	NPC128582
0.6603	Remote Similarity	NPC97584
0.66	Remote Similarity	NPC289776
0.66	Remote Similarity	NPC191863
0.66	Remote Similarity	NPC133470
0.6599	Remote Similarity	NPC74619
0.6588	Remote Similarity	NPC17059
0.6584	Remote Similarity	NPC182131
0.6583	Remote Similarity	NPC36495
0.6583	Remote Similarity	NPC473003
0.6581	Remote Similarity	NPC474877
0.6579	Remote Similarity	NPC471164
0.6579	Remote Similarity	NPC471574
0.6574	Remote Similarity	NPC315467
0.6573	Remote Similarity	NPC203628
0.6571	Remote Similarity	NPC133003
0.6564	Remote Similarity	NPC144691
0.6562	Remote Similarity	NPC320968
0.6557	Remote Similarity	NPC213629
0.6555	Remote Similarity	NPC470317
0.6553	Remote Similarity	NPC165743
0.6549	Remote Similarity	NPC478157
0.6545	Remote Similarity	NPC472241
0.6545	Remote Similarity	NPC303374
0.6544	Remote Similarity	NPC100863
0.654	Remote Similarity	NPC477549
0.6538	Remote Similarity	NPC470729
0.6538	Remote Similarity	NPC477176
0.6538	Remote Similarity	NPC69843
0.6533	Remote Similarity	NPC104345
0.6532	Remote Similarity	NPC270918
0.6528	Remote Similarity	NPC472242

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 NPC270241 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	565
0.2-0.3	858
0.3-0.4	1530
0.4-0.5	2455
0.5-0.6	2150
0.6-0.7	1177
0.7-0.8	187
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8103	Intermediate Similarity	NPD5042	Phase 1
0.8031	Intermediate Similarity	NPD6557	Phase 2
0.7739	Intermediate Similarity	NPD8240	Discontinued
0.7685	Intermediate Similarity	NPD5856	Discontinued
0.7525	Intermediate Similarity	NPD5923	Phase 1
0.7513	Intermediate Similarity	NPD3990	Phase 3
0.7462	Intermediate Similarity	NPD3989	Phase 3
0.7398	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4092	Approved
0.731	Intermediate Similarity	NPD4091	Approved
0.7259	Intermediate Similarity	NPD3522	Approved
0.7236	Intermediate Similarity	NPD3998	Approved
0.7236	Intermediate Similarity	NPD3999	Approved
0.7236	Intermediate Similarity	NPD3997	Approved
0.7186	Intermediate Similarity	NPD3991	Approved
0.7186	Intermediate Similarity	NPD3996	Approved
0.7186	Intermediate Similarity	NPD3992	Approved
0.7186	Intermediate Similarity	NPD3994	Approved
0.7186	Intermediate Similarity	NPD3993	Approved
0.7186	Intermediate Similarity	NPD3995	Approved
0.7157	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7817	Phase 1
0.7122	Intermediate Similarity	NPD7855	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD7232	Discontinued
0.7105	Intermediate Similarity	NPD3248	Phase 1
0.7101	Intermediate Similarity	NPD7570	Approved
0.7101	Intermediate Similarity	NPD7569	Approved
0.7091	Intermediate Similarity	NPD2813	Phase 3
0.7091	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6017	Discontinued
0.7054	Intermediate Similarity	NPD6753	Phase 1
0.7054	Intermediate Similarity	NPD6752	Phase 1
0.7	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD951	Approved
0.699	Remote Similarity	NPD4515	Suspended
0.6986	Remote Similarity	NPD3918	Approved
0.6986	Remote Similarity	NPD3917	Approved
0.6986	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6486	Approved
0.6959	Remote Similarity	NPD6487	Approved
0.6947	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3915	Approved
0.6939	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4412	Phase 2
0.6923	Remote Similarity	NPD7617	Discontinued
0.6911	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8114	Approved
0.6898	Remote Similarity	NPD8115	Approved
0.6881	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3780	Phase 2
0.6875	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6301	Phase 2
0.6859	Remote Similarity	NPD979	Approved
0.6857	Remote Similarity	NPD5937	Approved
0.6854	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8311	Discontinued
0.678	Remote Similarity	NPD5445	Approved
0.6771	Remote Similarity	NPD4942	Approved
0.6769	Remote Similarity	NPD7072	Phase 2
0.6757	Remote Similarity	NPD7225	Discontinued
0.6757	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6199	Discontinued
0.6751	Remote Similarity	NPD4393	Approved
0.6751	Remote Similarity	NPD33	Approved
0.6741	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6164	Phase 2
0.6739	Remote Similarity	NPD6165	Phase 2
0.6736	Remote Similarity	NPD5748	Phase 2
0.6728	Remote Similarity	NPD3774	Approved
0.6728	Remote Similarity	NPD3775	Approved
0.6728	Remote Similarity	NPD3773	Approved
0.6724	Remote Similarity	NPD7552	Discontinued
0.6712	Remote Similarity	NPD6260	Discontinued
0.6711	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6142	Phase 3
0.67	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6879	Phase 2
0.6699	Remote Similarity	NPD6878	Phase 2
0.6685	Remote Similarity	NPD1919	Approved
0.6685	Remote Similarity	NPD1920	Approved
0.6684	Remote Similarity	NPD4430	Phase 2
0.6684	Remote Similarity	NPD5024	Approved
0.6683	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5552	Discontinued
0.6682	Remote Similarity	NPD7727	Phase 2
0.6667	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2791	Discontinued
0.6667	Remote Similarity	NPD3353	Approved
0.6667	Remote Similarity	NPD1524	Phase 1
0.6667	Remote Similarity	NPD4948	Discontinued
0.6653	Remote Similarity	NPD4946	Phase 2
0.6651	Remote Similarity	NPD5515	Phase 2
0.6651	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5076	Approved
0.6651	Remote Similarity	NPD5077	Approved
0.6636	Remote Similarity	NPD7568	Phase 1
0.6623	Remote Similarity	NPD8289	Discontinued
0.6623	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3802	Phase 3
0.6618	Remote Similarity	NPD4330	Approved
0.6618	Remote Similarity	NPD4329	Approved
0.6616	Remote Similarity	NPD7011	Discontinued
0.6616	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2369	Discontinued
0.6598	Remote Similarity	NPD4888	Discontinued
0.6598	Remote Similarity	NPD5423	Phase 2
0.6595	Remote Similarity	NPD7694	Discontinued
0.6593	Remote Similarity	NPD8149	Discontinued
0.6592	Remote Similarity	NPD4982	Discontinued
0.6592	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1059	Phase 2
0.6588	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7572	Phase 2
0.6568	Remote Similarity	NPD7551	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7550	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7091	Discontinued
0.6565	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7470	Discontinued
0.6555	Remote Similarity	NPD7677	Discontinued
0.655	Remote Similarity	NPD5989	Phase 1
0.6549	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7970	Approved
0.6548	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD6829	Phase 2
0.6537	Remote Similarity	NPD5997	Discontinued
0.6537	Remote Similarity	NPD6173	Approved
0.6533	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5807	Phase 2
0.6528	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4317	Approved
0.6522	Remote Similarity	NPD3792	Approved
0.652	Remote Similarity	NPD6596	Phase 2
0.6518	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5901	Discontinued
0.6514	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD7308	Discontinued
0.6514	Remote Similarity	NPD6249	Phase 2
0.6514	Remote Similarity	NPD6248	Phase 2
0.6513	Remote Similarity	NPD5941	Approved
0.6513	Remote Similarity	NPD5942	Approved
0.6512	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.651	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1625	Approved
0.6508	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8094	Discontinued
0.6504	Remote Similarity	NPD3243	Approved
0.6502	Remote Similarity	NPD2443	Approved
0.6502	Remote Similarity	NPD2442	Approved
0.65	Remote Similarity	NPD7599	Phase 2
0.65	Remote Similarity	NPD6532	Discontinued
0.6498	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1571	Phase 2
0.6496	Remote Similarity	NPD7767	Approved
0.6495	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6218	Discontinued
0.649	Remote Similarity	NPD3782	Discontinued
0.6488	Remote Similarity	NPD3776	Discontinued
0.6488	Remote Similarity	NPD7921	Approved
0.6488	Remote Similarity	NPD3959	Phase 2
0.6488	Remote Similarity	NPD3962	Phase 2
0.6482	Remote Similarity	NPD7105	Phase 1
0.648	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5821	Approved
0.6473	Remote Similarity	NPD3968	Approved
0.6468	Remote Similarity	NPD5196	Approved
0.6468	Remote Similarity	NPD5194	Approved
0.6468	Remote Similarity	NPD5197	Approved
0.6466	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD2790	Discontinued
0.6465	Remote Similarity	NPD7786	Discontinued
0.6463	Remote Similarity	NPD7878	Phase 2
0.646	Remote Similarity	NPD8097	Phase 3
0.646	Remote Similarity	NPD8096	Phase 3
0.646	Remote Similarity	NPD8093	Discontinued
0.6459	Remote Similarity	NPD3227	Phase 2
0.6453	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.645	Remote Similarity	NPD212	Discontinued
0.6447	Remote Similarity	NPD6733	Discontinued
0.6444	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7065	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5840	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data