NPASS Compound

Structure

NPC474041 OpenBabel07101718192D 28 32 0 0 1 0 0 0 0 0999 V2000 -6.1565 -0.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4134 -1.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9486 0.2421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0214 -2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0269 -2.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4623 -1.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9976 0.5511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -1.9962 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 0.3799 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5602 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2544 -0.1180 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 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3034 0.1910 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -3.0955 1.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 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 19 2 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 21 25 1 0 0 0 0 21 27 2 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.12
Volume:	380.309
LogP:	2.137
LogD:	2.343
LogS:	-4.389
# Rotatable Bonds:	3
TPSA:	72.19
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	2.734
Fsp3:	0.087
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.927
MDCK Permeability:	1.965507362911012e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725
Plasma Protein Binding (PPB):	94.55690002441406%
Volume Distribution (VD):	0.419
Pgp-substrate:	1.6381261348724365%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.604
CYP2C19-inhibitor:	0.678
CYP2C19-substrate:	0.557
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.311
CYP3A4-substrate:	0.92

ADMET: Excretion

Clearance (CL):	0.72
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.829
AMES Toxicity:	0.635
Rat Oral Acute Toxicity:	0.546
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.088
Carcinogencity:	0.714
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.291

Download Data

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

Natural Product: NPC474041

Natural Product ID:	NPC474041
*Common Name:**	6-Hydroxy-6-Phenacylindolo[2,1-B]Quinazolin-12-One
IUPAC Name:	6-hydroxy-6-phenacylindolo[2,1-b]quinazolin-12-one
Synonyms:
Standard InCHIKey:	HWQHXQCQIRAPKU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H16N2O3/c26-20(15-8-2-1-3-9-15)14-23(28)17-11-5-7-13-19(17)25-21(27)16-10-4-6-12-18(16)24-22(23)25/h1-13,28H,14H2
SMILES:	O=C(c1ccccc1)CC1(O)c2ccccc2n2c1nc1ccccc1c2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459039
PubChem CID:	24970704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines [CHEMONTID:0002087] Indoloquinazolines

*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
NPO4147	Phaius mishmensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18507473]
NPO4147	Phaius mishmensis	Species	Orchidaceae	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	3
MIC	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[528377]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[528377]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[528377]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	16910.0	nM	PMID[528378]

☑ 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 NPC474041 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	563
0.1-0.2	3812
0.2-0.3	13511
0.3-0.4	15593
0.4-0.5	5457
0.5-0.6	2820
0.6-0.7	808
0.7-0.8	93
0.8-0.85	31
0.85-0.9	2
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC475607
0.9689	High Similarity	NPC474081
0.9688	High Similarity	NPC475594
0.963	High Similarity	NPC475761
0.9006	High Similarity	NPC473815
0.8229	Intermediate Similarity	NPC475685
0.8208	Intermediate Similarity	NPC470548
0.8166	Intermediate Similarity	NPC88970
0.8101	Intermediate Similarity	NPC150308
0.807	Intermediate Similarity	NPC471130
0.8066	Intermediate Similarity	NPC471195
0.8066	Intermediate Similarity	NPC471196
0.8043	Intermediate Similarity	NPC472539
0.8043	Intermediate Similarity	NPC472540
0.8043	Intermediate Similarity	NPC470787
0.8	Intermediate Similarity	NPC472541
0.8	Intermediate Similarity	NPC472542
0.7953	Intermediate Similarity	NPC476231
0.795	Intermediate Similarity	NPC207554
0.7937	Intermediate Similarity	NPC295548
0.7906	Intermediate Similarity	NPC470786
0.7853	Intermediate Similarity	NPC225400
0.7812	Intermediate Similarity	NPC471155
0.7812	Intermediate Similarity	NPC472538
0.7811	Intermediate Similarity	NPC295021
0.7772	Intermediate Similarity	NPC270241
0.756	Intermediate Similarity	NPC324445
0.7527	Intermediate Similarity	NPC18890
0.7485	Intermediate Similarity	NPC300299
0.7471	Intermediate Similarity	NPC300596
0.7471	Intermediate Similarity	NPC237649
0.7455	Intermediate Similarity	NPC83214
0.7447	Intermediate Similarity	NPC92803
0.7426	Intermediate Similarity	NPC248601
0.7386	Intermediate Similarity	NPC27904
0.7363	Intermediate Similarity	NPC471743
0.736	Intermediate Similarity	NPC471124
0.7344	Intermediate Similarity	NPC471199
0.7291	Intermediate Similarity	NPC15384
0.7291	Intermediate Similarity	NPC244425
0.7249	Intermediate Similarity	NPC221873
0.7232	Intermediate Similarity	NPC154478
0.7232	Intermediate Similarity	NPC471122
0.7206	Intermediate Similarity	NPC471197
0.7198	Intermediate Similarity	NPC355
0.7195	Intermediate Similarity	NPC207428
0.7179	Intermediate Similarity	NPC106118
0.7171	Intermediate Similarity	NPC471198
0.715	Intermediate Similarity	NPC285192
0.7134	Intermediate Similarity	NPC316746
0.7126	Intermediate Similarity	NPC144691
0.7119	Intermediate Similarity	NPC84317
0.7111	Intermediate Similarity	NPC189116
0.7107	Intermediate Similarity	NPC471944
0.7074	Intermediate Similarity	NPC470317
0.7062	Intermediate Similarity	NPC198401
0.7	Intermediate Similarity	NPC472243
0.6965	Remote Similarity	NPC471191
0.6959	Remote Similarity	NPC2823
0.6952	Remote Similarity	NPC220851
0.694	Remote Similarity	NPC182131
0.6931	Remote Similarity	NPC243850
0.6923	Remote Similarity	NPC113056
0.6923	Remote Similarity	NPC138293
0.6923	Remote Similarity	NPC204867
0.6919	Remote Similarity	NPC318183
0.691	Remote Similarity	NPC471132
0.6901	Remote Similarity	NPC315051
0.6882	Remote Similarity	NPC177261
0.6882	Remote Similarity	NPC122553
0.6878	Remote Similarity	NPC72956
0.6867	Remote Similarity	NPC226662
0.686	Remote Similarity	NPC471574
0.6856	Remote Similarity	NPC313293
0.6845	Remote Similarity	NPC153980
0.6845	Remote Similarity	NPC6865
0.6827	Remote Similarity	NPC471192
0.6821	Remote Similarity	NPC472241
0.6818	Remote Similarity	NPC254798
0.6796	Remote Similarity	NPC104345
0.679	Remote Similarity	NPC257490
0.6789	Remote Similarity	NPC88110
0.6771	Remote Similarity	NPC21429
0.6771	Remote Similarity	NPC203635
0.6765	Remote Similarity	NPC16249
0.6763	Remote Similarity	NPC471194
0.6763	Remote Similarity	NPC43477
0.6763	Remote Similarity	NPC471193
0.6757	Remote Similarity	NPC472115
0.6757	Remote Similarity	NPC472114
0.6743	Remote Similarity	NPC136002
0.6719	Remote Similarity	NPC243058
0.6707	Remote Similarity	NPC150863
0.6706	Remote Similarity	NPC253476
0.6705	Remote Similarity	NPC472242
0.6686	Remote Similarity	NPC308197
0.6685	Remote Similarity	NPC199737
0.6685	Remote Similarity	NPC242000
0.6685	Remote Similarity	NPC472117
0.6684	Remote Similarity	NPC471742
0.6684	Remote Similarity	NPC469915
0.6667	Remote Similarity	NPC314431
0.6667	Remote Similarity	NPC314648
0.6667	Remote Similarity	NPC194562
0.6667	Remote Similarity	NPC291962
0.6667	Remote Similarity	NPC117032
0.6667	Remote Similarity	NPC177684
0.6667	Remote Similarity	NPC471164
0.6649	Remote Similarity	NPC313757
0.6649	Remote Similarity	NPC475094
0.6646	Remote Similarity	NPC39818
0.6626	Remote Similarity	NPC161956
0.6626	Remote Similarity	NPC258531
0.6626	Remote Similarity	NPC112373
0.6617	Remote Similarity	NPC474916
0.6615	Remote Similarity	NPC90415
0.6611	Remote Similarity	NPC154602
0.6609	Remote Similarity	NPC242933
0.6608	Remote Similarity	NPC184437
0.6607	Remote Similarity	NPC209389
0.6606	Remote Similarity	NPC254698
0.6597	Remote Similarity	NPC219848
0.6596	Remote Similarity	NPC472118
0.6593	Remote Similarity	NPC114808
0.6575	Remote Similarity	NPC285381
0.6573	Remote Similarity	NPC478039
0.6568	Remote Similarity	NPC280807
0.6568	Remote Similarity	NPC472245
0.6562	Remote Similarity	NPC256268
0.656	Remote Similarity	NPC471762
0.6554	Remote Similarity	NPC314186
0.6553	Remote Similarity	NPC313345
0.6553	Remote Similarity	NPC314855
0.6553	Remote Similarity	NPC313796
0.6553	Remote Similarity	NPC315638
0.6548	Remote Similarity	NPC477998
0.6545	Remote Similarity	NPC129624
0.6541	Remote Similarity	NPC93653
0.6529	Remote Similarity	NPC314098
0.6528	Remote Similarity	NPC298320
0.6526	Remote Similarity	NPC307640
0.6524	Remote Similarity	NPC279385
0.6524	Remote Similarity	NPC179605
0.6522	Remote Similarity	NPC478075
0.6522	Remote Similarity	NPC315545
0.6522	Remote Similarity	NPC314297
0.6514	Remote Similarity	NPC157931
0.6514	Remote Similarity	NPC257851
0.6513	Remote Similarity	NPC285923
0.651	Remote Similarity	NPC14849
0.6509	Remote Similarity	NPC322064
0.6508	Remote Similarity	NPC471943
0.6507	Remote Similarity	NPC314834
0.6505	Remote Similarity	NPC133470
0.6505	Remote Similarity	NPC191863
0.6505	Remote Similarity	NPC289776
0.6492	Remote Similarity	NPC328611
0.6492	Remote Similarity	NPC248862
0.6489	Remote Similarity	NPC278887
0.6489	Remote Similarity	NPC214960
0.6489	Remote Similarity	NPC279527
0.6486	Remote Similarity	NPC103250
0.6485	Remote Similarity	NPC103292
0.6484	Remote Similarity	NPC66777
0.648	Remote Similarity	NPC259678
0.6477	Remote Similarity	NPC182057
0.6477	Remote Similarity	NPC147298
0.6477	Remote Similarity	NPC131450
0.6474	Remote Similarity	NPC474814
0.6474	Remote Similarity	NPC292265
0.6474	Remote Similarity	NPC112336
0.6463	Remote Similarity	NPC226143
0.6452	Remote Similarity	NPC322644
0.6452	Remote Similarity	NPC143457
0.6446	Remote Similarity	NPC268534
0.6443	Remote Similarity	NPC39822
0.6443	Remote Similarity	NPC85613
0.644	Remote Similarity	NPC96901
0.6436	Remote Similarity	NPC299582
0.6433	Remote Similarity	NPC231382
0.6432	Remote Similarity	NPC113946
0.6429	Remote Similarity	NPC470343
0.6429	Remote Similarity	NPC205946
0.6429	Remote Similarity	NPC472244
0.6424	Remote Similarity	NPC130931
0.6422	Remote Similarity	NPC317727
0.6417	Remote Similarity	NPC293458
0.6414	Remote Similarity	NPC206186
0.6412	Remote Similarity	NPC259098
0.6412	Remote Similarity	NPC197680
0.6407	Remote Similarity	NPC283130
0.6407	Remote Similarity	NPC328683
0.6404	Remote Similarity	NPC141454
0.6398	Remote Similarity	NPC36495
0.6396	Remote Similarity	NPC322621
0.6396	Remote Similarity	NPC476341
0.6396	Remote Similarity	NPC49184
0.6386	Remote Similarity	NPC202812
0.6384	Remote Similarity	NPC316202
0.6378	Remote Similarity	NPC29285

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 NPC474041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	642
0.2-0.3	876
0.3-0.4	2086
0.4-0.5	2433
0.5-0.6	1959
0.6-0.7	732
0.7-0.8	65
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7605	Intermediate Similarity	NPD6017	Discontinued
0.7596	Intermediate Similarity	NPD5923	Phase 1
0.7516	Intermediate Similarity	NPD1919	Approved
0.7516	Intermediate Similarity	NPD1920	Approved
0.7447	Intermediate Similarity	NPD5042	Phase 1
0.7389	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4942	Approved
0.7273	Intermediate Similarity	NPD2791	Discontinued
0.7273	Intermediate Similarity	NPD6557	Phase 2
0.7267	Intermediate Similarity	NPD4888	Discontinued
0.7196	Intermediate Similarity	NPD4515	Suspended
0.7176	Intermediate Similarity	NPD4430	Phase 2
0.7128	Intermediate Similarity	NPD5856	Discontinued
0.7077	Intermediate Similarity	NPD5515	Phase 2
0.7048	Intermediate Similarity	NPD1541	Approved
0.7037	Intermediate Similarity	NPD4412	Phase 2
0.7035	Intermediate Similarity	NPD3802	Phase 3
0.7011	Intermediate Similarity	NPD3776	Discontinued
0.6977	Remote Similarity	NPD2820	Phase 3
0.6977	Remote Similarity	NPD1625	Approved
0.6976	Remote Similarity	NPD3780	Phase 2
0.6954	Remote Similarity	NPD1524	Phase 1
0.6932	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2365	Approved
0.6915	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5937	Approved
0.6862	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1189	Approved
0.6816	Remote Similarity	NPD5086	Approved
0.6798	Remote Similarity	NPD6260	Discontinued
0.6796	Remote Similarity	NPD7011	Discontinued
0.6789	Remote Similarity	NPD5445	Approved
0.6786	Remote Similarity	NPD7570	Approved
0.6786	Remote Similarity	NPD8146	Phase 2
0.6786	Remote Similarity	NPD7569	Approved
0.678	Remote Similarity	NPD5593	Approved
0.678	Remote Similarity	NPD5594	Approved
0.6778	Remote Similarity	NPD7072	Phase 2
0.6772	Remote Similarity	NPD3792	Approved
0.6763	Remote Similarity	NPD7225	Discontinued
0.6758	Remote Similarity	NPD33	Approved
0.6758	Remote Similarity	NPD4393	Approved
0.6755	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4988	Discontinued
0.6753	Remote Similarity	NPD4948	Discontinued
0.6753	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1626	Approved
0.6742	Remote Similarity	NPD5748	Phase 2
0.6721	Remote Similarity	NPD2506	Approved
0.6715	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3277	Phase 3
0.6703	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5430	Discontinued
0.6702	Remote Similarity	NPD4329	Approved
0.6702	Remote Similarity	NPD4330	Approved
0.6687	Remote Similarity	NPD1593	Approved
0.6686	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4161	Discontinued
0.6684	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7795	Phase 2
0.6667	Remote Similarity	NPD6483	Approved
0.6667	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9477	Approved
0.6667	Remote Similarity	NPD6484	Approved
0.6667	Remote Similarity	NPD3248	Phase 1
0.6667	Remote Similarity	NPD3990	Phase 3
0.6651	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5504	Discontinued
0.665	Remote Similarity	NPD5591	Approved
0.6649	Remote Similarity	NPD3782	Discontinued
0.6649	Remote Similarity	NPD6163	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD951	Approved
0.6648	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6395	Phase 2
0.6647	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1527	Phase 2
0.6632	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3229	Phase 2
0.6629	Remote Similarity	NPD6566	Discontinued
0.6627	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3989	Phase 3
0.6615	Remote Similarity	NPD3227	Phase 2
0.6613	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7878	Phase 2
0.6601	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2369	Discontinued
0.6592	Remote Similarity	NPD979	Approved
0.6591	Remote Similarity	NPD6301	Phase 2
0.6576	Remote Similarity	NPD2427	Approved
0.657	Remote Similarity	NPD2331	Discontinued
0.657	Remote Similarity	NPD7232	Discontinued
0.657	Remote Similarity	NPD6486	Approved
0.657	Remote Similarity	NPD6487	Approved
0.6569	Remote Similarity	NPD3773	Approved
0.6569	Remote Similarity	NPD3774	Approved
0.6569	Remote Similarity	NPD3775	Approved
0.6567	Remote Similarity	NPD7572	Phase 2
0.6566	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD2336	Approved
0.6562	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD5918	Discontinued
0.655	Remote Similarity	NPD1595	Approved
0.655	Remote Similarity	NPD1594	Phase 3
0.655	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD7186	Phase 3
0.6543	Remote Similarity	NPD2037	Approved
0.6543	Remote Similarity	NPD2404	Discontinued
0.6541	Remote Similarity	NPD4311	Approved
0.6538	Remote Similarity	NPD2790	Discontinued
0.6536	Remote Similarity	NPD7088	Discontinued
0.6535	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6768	Approved
0.6532	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6199	Discontinued
0.6527	Remote Similarity	NPD6320	Approved
0.6526	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1230	Approved
0.6513	Remote Similarity	NPD721	Approved
0.651	Remote Similarity	NPD4092	Approved
0.651	Remote Similarity	NPD5840	Discontinued
0.6509	Remote Similarity	NPD6733	Discontinued
0.6505	Remote Similarity	NPD5901	Discontinued
0.6505	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5637	Discontinued
0.6492	Remote Similarity	NPD3522	Approved
0.6492	Remote Similarity	NPD3423	Phase 2
0.6492	Remote Similarity	NPD3422	Phase 3
0.6492	Remote Similarity	NPD5466	Approved
0.6492	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4514	Approved
0.648	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2813	Phase 3
0.6477	Remote Similarity	NPD3999	Approved
0.6477	Remote Similarity	NPD3998	Approved
0.6477	Remote Similarity	NPD3997	Approved
0.6477	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2431	Approved
0.6474	Remote Similarity	NPD2432	Approved
0.6473	Remote Similarity	NPD7568	Phase 1
0.6473	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4091	Approved
0.6458	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6457	Approved
0.6452	Remote Similarity	NPD6753	Phase 1
0.6452	Remote Similarity	NPD6752	Phase 1
0.6447	Remote Similarity	NPD3315	Phase 3
0.6444	Remote Similarity	NPD7560	Approved
0.6443	Remote Similarity	NPD6879	Phase 2
0.6443	Remote Similarity	NPD6878	Phase 2
0.6443	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.644	Remote Similarity	NPD3377	Discontinued
0.644	Remote Similarity	NPD5997	Discontinued
0.6438	Remote Similarity	NPD4845	Discontinued
0.6436	Remote Similarity	NPD5411	Discontinued
0.6436	Remote Similarity	NPD2307	Discontinued
0.6432	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD212	Discontinued
0.6429	Remote Similarity	NPD5860	Discontinued
0.6429	Remote Similarity	NPD1574	Approved
0.6425	Remote Similarity	NPD3994	Approved
0.6425	Remote Similarity	NPD3991	Approved
0.6425	Remote Similarity	NPD3993	Approved
0.6425	Remote Similarity	NPD5931	Phase 3
0.6425	Remote Similarity	NPD3995	Approved
0.6425	Remote Similarity	NPD3996	Approved
0.6425	Remote Similarity	NPD5933	Phase 3
0.6425	Remote Similarity	NPD5498	Phase 2
0.6425	Remote Similarity	NPD5932	Phase 3
0.6425	Remote Similarity	NPD7552	Discontinued
0.6425	Remote Similarity	NPD6987	Phase 1
0.6425	Remote Similarity	NPD3992	Approved
0.6425	Remote Similarity	NPD3947	Discontinued
0.6422	Remote Similarity	NPD5609	Approved
0.6422	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5608	Approved
0.6418	Remote Similarity	NPD7429	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4871	Phase 2
0.6413	Remote Similarity	NPD6142	Phase 3
0.6413	Remote Similarity	NPD7463	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD478	Approved
0.6404	Remote Similarity	NPD6161	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