NPASS Compound

Structure

NPC106118 OpenBabel07101718222D 31 37 0 0 1 0 0 0 0 0999 V2000 1.2397 1.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8336 -0.9192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8252 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8336 -0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4761 -0.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0838 -1.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8738 -1.3207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0838 0.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1755 0.1250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6847 -0.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9509 2.5325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3340 -0.9192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5733 -0.3956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3340 -0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2241 0.3272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8423 -1.4590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8394 2.1369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5843 -1.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1655 -0.0535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7864 0.9673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8423 0.4863 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6847 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 1.8097 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5843 0.3794 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 2.7378 1.1696 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1655 -0.9192 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6818 2.6232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6847 -1.9453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5843 -2.3247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 5 2 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 12 2 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 11 17 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 25 1 0 0 0 0 15 27 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 17 29 2 0 0 0 0 18 26 2 0 0 0 0 18 30 1 0 0 0 0 19 28 1 0 0 0 0 19 31 2 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 23 1 1 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 23 1 6 0 0 0 22 26 1 0 0 0 0 23 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	413.15
Volume:	401.459
LogP:	0.963
LogD:	1.182
LogS:	-4.165
# Rotatable Bonds:	0
TPSA:	96.33
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	5.561
Fsp3:	0.304
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:	-5.415
MDCK Permeability:	1.89758648048155e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	68.14784240722656%
Volume Distribution (VD):	0.725
Pgp-substrate:	32.16278076171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.615
CYP2C19-inhibitor:	0.105
CYP2C19-substrate:	0.85
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.565
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	4.35
Half-life (T1/2):	0.426

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.879
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.565
Carcinogencity:	0.694
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC106118

Natural Product ID:	NPC106118
*Common Name:**	Spiroquinazoline
IUPAC Name:	n.a.
Synonyms:	spiroquinazoline
Standard InCHIKey:	SIIMITFGYHVBGG-FGSBKAERSA-N
Standard InCHI:	InChI=1S/C23H19N5O3/c1-22-20-25-14-8-4-2-6-12(14)19(31)28(20)16(18(30)26-22)10-23(22)13-7-3-5-9-15(13)27-17(29)11-24-21(23)27/h2-9,16,21,24H,10-11H2,1H3,(H,26,30)/t16-,21+,22+,23+/m1/s1
SMILES:	C[C@]12c3nc4ccccc4c(=O)n3[C@H](C[C@]31c1ccccc1N1C(=O)CN[C@H]31)C(=N2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515179
PubChem CID:	10409484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001859] Pyridopyrimidines

*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
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22329646]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31674782]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32568536]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7517439]
NPO18099	Aspergillus flavipes	Species	Aspergillaceae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT297	Individual Protein	Neurokinin 1 receptor	Homo sapiens	Ki	=	95000.0	nM	PMID[519464]

☑ 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 NPC106118 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	471
0.1-0.2	3309
0.2-0.3	16443
0.3-0.4	15607
0.4-0.5	2645
0.5-0.6	2847
0.6-0.7	1225
0.7-0.8	99
0.8-0.85	25
0.85-0.9	19
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC471199
0.8947	High Similarity	NPC270241
0.8942	High Similarity	NPC225400
0.8895	High Similarity	NPC472538
0.8895	High Similarity	NPC470786
0.8895	High Similarity	NPC471155
0.8639	High Similarity	NPC295548
0.845	Intermediate Similarity	NPC248601
0.8436	Intermediate Similarity	NPC355
0.8182	Intermediate Similarity	NPC307396
0.8158	Intermediate Similarity	NPC276430
0.8146	Intermediate Similarity	NPC68650
0.8083	Intermediate Similarity	NPC472539
0.8083	Intermediate Similarity	NPC470787
0.8083	Intermediate Similarity	NPC472540
0.8041	Intermediate Similarity	NPC472541
0.8041	Intermediate Similarity	NPC472542
0.8	Intermediate Similarity	NPC471198
0.7951	Intermediate Similarity	NPC471197
0.791	Intermediate Similarity	NPC285192
0.7811	Intermediate Similarity	NPC471191
0.7778	Intermediate Similarity	NPC244425
0.7778	Intermediate Similarity	NPC15384
0.7778	Intermediate Similarity	NPC84317
0.7756	Intermediate Similarity	NPC471194
0.7756	Intermediate Similarity	NPC153980
0.7756	Intermediate Similarity	NPC6865
0.7756	Intermediate Similarity	NPC471193
0.7707	Intermediate Similarity	NPC72956
0.7692	Intermediate Similarity	NPC154478
0.756	Intermediate Similarity	NPC471192
0.7551	Intermediate Similarity	NPC471196
0.7551	Intermediate Similarity	NPC471195
0.7473	Intermediate Similarity	NPC295021
0.7407	Intermediate Similarity	NPC472118
0.7322	Intermediate Similarity	NPC117032
0.7308	Intermediate Similarity	NPC71238
0.7287	Intermediate Similarity	NPC138293
0.7287	Intermediate Similarity	NPC113056
0.7254	Intermediate Similarity	NPC475607
0.7249	Intermediate Similarity	NPC471130
0.7216	Intermediate Similarity	NPC14849
0.7216	Intermediate Similarity	NPC474081
0.7204	Intermediate Similarity	NPC54981
0.7202	Intermediate Similarity	NPC470548
0.7202	Intermediate Similarity	NPC475594
0.7191	Intermediate Similarity	NPC207554
0.7179	Intermediate Similarity	NPC475761
0.7179	Intermediate Similarity	NPC474041
0.7159	Intermediate Similarity	NPC300299
0.7143	Intermediate Similarity	NPC88970
0.7128	Intermediate Similarity	NPC276085
0.7113	Intermediate Similarity	NPC328611
0.71	Intermediate Similarity	NPC473815
0.7092	Intermediate Similarity	NPC131450
0.7092	Intermediate Similarity	NPC147298
0.7092	Intermediate Similarity	NPC182057
0.709	Intermediate Similarity	NPC472102
0.709	Intermediate Similarity	NPC309531
0.7074	Intermediate Similarity	NPC104345
0.7074	Intermediate Similarity	NPC222029
0.7062	Intermediate Similarity	NPC177261
0.7062	Intermediate Similarity	NPC285622
0.7049	Intermediate Similarity	NPC324445
0.7033	Intermediate Similarity	NPC477179
0.7031	Intermediate Similarity	NPC214960
0.7031	Intermediate Similarity	NPC279527
0.7026	Intermediate Similarity	NPC248862
0.7016	Intermediate Similarity	NPC189116
0.7005	Intermediate Similarity	NPC477714
0.7	Intermediate Similarity	NPC477180
0.7	Intermediate Similarity	NPC477181
0.7	Intermediate Similarity	NPC477178
0.7	Intermediate Similarity	NPC254850
0.6989	Remote Similarity	NPC207428
0.6983	Remote Similarity	NPC122553
0.6974	Remote Similarity	NPC242269
0.6967	Remote Similarity	NPC477174
0.6967	Remote Similarity	NPC477173
0.6967	Remote Similarity	NPC470490
0.6963	Remote Similarity	NPC472117
0.6961	Remote Similarity	NPC2823
0.6959	Remote Similarity	NPC477715
0.695	Remote Similarity	NPC21429
0.6944	Remote Similarity	NPC83214
0.6934	Remote Similarity	NPC470488
0.6919	Remote Similarity	NPC475094
0.6916	Remote Similarity	NPC191817
0.6916	Remote Similarity	NPC475359
0.6905	Remote Similarity	NPC471436
0.6901	Remote Similarity	NPC475259
0.6901	Remote Similarity	NPC471950
0.6901	Remote Similarity	NPC471945
0.6898	Remote Similarity	NPC66936
0.6884	Remote Similarity	NPC91179
0.6881	Remote Similarity	NPC141612
0.6881	Remote Similarity	NPC17273
0.6881	Remote Similarity	NPC135601
0.6881	Remote Similarity	NPC473615
0.6869	Remote Similarity	NPC471951
0.6869	Remote Similarity	NPC471946
0.6864	Remote Similarity	NPC272174
0.6863	Remote Similarity	NPC128582
0.6848	Remote Similarity	NPC136002
0.6847	Remote Similarity	NPC229484
0.684	Remote Similarity	NPC473376
0.6832	Remote Similarity	NPC259626
0.6822	Remote Similarity	NPC470491
0.6814	Remote Similarity	NPC292675
0.6804	Remote Similarity	NPC472106
0.6802	Remote Similarity	NPC31097
0.68	Remote Similarity	NPC475685
0.6798	Remote Similarity	NPC150308
0.6788	Remote Similarity	NPC472101
0.6788	Remote Similarity	NPC472120
0.6782	Remote Similarity	NPC2933
0.6776	Remote Similarity	NPC301760
0.6771	Remote Similarity	NPC471122
0.6771	Remote Similarity	NPC36495
0.6757	Remote Similarity	NPC474896
0.6748	Remote Similarity	NPC92803
0.6737	Remote Similarity	NPC469903
0.6733	Remote Similarity	NPC256288
0.6731	Remote Similarity	NPC198401
0.6722	Remote Similarity	NPC162417
0.6722	Remote Similarity	NPC316104
0.6719	Remote Similarity	NPC123241
0.6718	Remote Similarity	NPC471124
0.6702	Remote Similarity	NPC237649
0.6702	Remote Similarity	NPC300596
0.6701	Remote Similarity	NPC293458
0.6685	Remote Similarity	NPC471164
0.6685	Remote Similarity	NPC471574
0.6684	Remote Similarity	NPC473003
0.6683	Remote Similarity	NPC17059
0.6667	Remote Similarity	NPC471663
0.6667	Remote Similarity	NPC133003
0.6652	Remote Similarity	NPC220851
0.665	Remote Similarity	NPC18890
0.665	Remote Similarity	NPC475248
0.665	Remote Similarity	NPC63047
0.6632	Remote Similarity	NPC113946
0.663	Remote Similarity	NPC130251
0.6623	Remote Similarity	NPC470730
0.6623	Remote Similarity	NPC477175
0.662	Remote Similarity	NPC471944
0.6615	Remote Similarity	NPC282339
0.6615	Remote Similarity	NPC99632
0.6614	Remote Similarity	NPC109787
0.6605	Remote Similarity	NPC470489
0.6598	Remote Similarity	NPC469902
0.6597	Remote Similarity	NPC473002
0.6594	Remote Similarity	NPC475859
0.6594	Remote Similarity	NPC475969
0.6591	Remote Similarity	NPC54744
0.6576	Remote Similarity	NPC469560
0.657	Remote Similarity	NPC213629
0.6565	Remote Similarity	NPC165743
0.6564	Remote Similarity	NPC225319
0.6557	Remote Similarity	NPC471123
0.6556	Remote Similarity	NPC316746
0.6552	Remote Similarity	NPC286994
0.6552	Remote Similarity	NPC88110
0.6552	Remote Similarity	NPC39822
0.655	Remote Similarity	NPC470729
0.655	Remote Similarity	NPC477176
0.6549	Remote Similarity	NPC476817
0.6546	Remote Similarity	NPC61013
0.6541	Remote Similarity	NPC315051
0.6537	Remote Similarity	NPC97584
0.6536	Remote Similarity	NPC209389
0.6535	Remote Similarity	NPC157931
0.6531	Remote Similarity	NPC472121
0.6522	Remote Similarity	NPC474877
0.6522	Remote Similarity	NPC477177
0.6513	Remote Similarity	NPC193410
0.651	Remote Similarity	NPC285381
0.6507	Remote Similarity	NPC471762
0.6505	Remote Similarity	NPC52262
0.65	Remote Similarity	NPC320968
0.6488	Remote Similarity	NPC470205
0.6485	Remote Similarity	NPC471743
0.6482	Remote Similarity	NPC469904
0.648	Remote Similarity	NPC248117
0.6479	Remote Similarity	NPC171317
0.6473	Remote Similarity	NPC94752
0.6471	Remote Similarity	NPC16659
0.6468	Remote Similarity	NPC243850
0.6466	Remote Similarity	NPC63279
0.6457	Remote Similarity	NPC470731
0.6456	Remote Similarity	NPC228835
0.6453	Remote Similarity	NPC473001
0.645	Remote Similarity	NPC471943
0.6447	Remote Similarity	NPC115588
0.6447	Remote Similarity	NPC286871
0.6438	Remote Similarity	NPC297642
0.6432	Remote Similarity	NPC14812
0.6422	Remote Similarity	NPC219336
0.6422	Remote Similarity	NPC89987
0.6422	Remote Similarity	NPC265710

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 NPC106118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	567
0.2-0.3	968
0.3-0.4	1957
0.4-0.5	2242
0.5-0.6	2091
0.6-0.7	981
0.7-0.8	110
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
0.8158	Intermediate Similarity	NPD8240	Discontinued
0.7617	Intermediate Similarity	NPD6557	Phase 2
0.7424	Intermediate Similarity	NPD5042	Phase 1
0.7409	Intermediate Similarity	NPD3989	Phase 3
0.7371	Intermediate Similarity	NPD3990	Phase 3
0.7322	Intermediate Similarity	NPD3248	Phase 1
0.7254	Intermediate Similarity	NPD4091	Approved
0.7253	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4092	Approved
0.7165	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3995	Approved
0.7128	Intermediate Similarity	NPD3994	Approved
0.7128	Intermediate Similarity	NPD3992	Approved
0.7128	Intermediate Similarity	NPD3991	Approved
0.7128	Intermediate Similarity	NPD3996	Approved
0.7128	Intermediate Similarity	NPD3993	Approved
0.7121	Intermediate Similarity	NPD5923	Phase 1
0.7113	Intermediate Similarity	NPD3522	Approved
0.7113	Intermediate Similarity	NPD7662	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD951	Approved
0.7092	Intermediate Similarity	NPD3998	Approved
0.7092	Intermediate Similarity	NPD3997	Approved
0.7092	Intermediate Similarity	NPD3999	Approved
0.7065	Intermediate Similarity	NPD979	Approved
0.7039	Intermediate Similarity	NPD5856	Discontinued
0.6989	Remote Similarity	NPD1920	Approved
0.6989	Remote Similarity	NPD1919	Approved
0.6973	Remote Similarity	NPD4942	Approved
0.6968	Remote Similarity	NPD7072	Phase 2
0.6963	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4412	Phase 2
0.6938	Remote Similarity	NPD7817	Phase 1
0.6935	Remote Similarity	NPD5748	Phase 2
0.6902	Remote Similarity	NPD6017	Discontinued
0.6901	Remote Similarity	NPD7232	Discontinued
0.6888	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7308	Discontinued
0.6837	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4882	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5024	Approved
0.6791	Remote Similarity	NPD5423	Phase 2
0.6788	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1524	Phase 1
0.6771	Remote Similarity	NPD33	Approved
0.6771	Remote Similarity	NPD4393	Approved
0.6771	Remote Similarity	NPD7599	Phase 2
0.6768	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8115	Approved
0.6761	Remote Similarity	NPD8114	Approved
0.6744	Remote Similarity	NPD6486	Approved
0.6744	Remote Similarity	NPD6487	Approved
0.6743	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7600	Phase 2
0.6732	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6260	Discontinued
0.6715	Remote Similarity	NPD7786	Discontinued
0.6714	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7795	Phase 2
0.6698	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4515	Suspended
0.6667	Remote Similarity	NPD7572	Phase 2
0.6649	Remote Similarity	NPD2790	Discontinued
0.6634	Remote Similarity	NPD4330	Approved
0.6634	Remote Similarity	NPD4329	Approved
0.6632	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4432	Discontinued
0.6614	Remote Similarity	NPD5941	Approved
0.6614	Remote Similarity	NPD5942	Approved
0.6604	Remote Similarity	NPD8050	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD3625	Discontinued
0.659	Remote Similarity	NPD2443	Approved
0.659	Remote Similarity	NPD2442	Approved
0.6589	Remote Similarity	NPD3773	Approved
0.6589	Remote Similarity	NPD3774	Approved
0.6589	Remote Similarity	NPD3775	Approved
0.6584	Remote Similarity	NPD7771	Discontinued
0.6582	Remote Similarity	NPD3790	Phase 2
0.658	Remote Similarity	NPD7091	Discontinued
0.6577	Remote Similarity	NPD2813	Phase 3
0.6577	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5989	Phase 1
0.6555	Remote Similarity	NPD7569	Approved
0.6555	Remote Similarity	NPD7570	Approved
0.6546	Remote Similarity	NPD8630	Approved
0.6546	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6165	Phase 2
0.6535	Remote Similarity	NPD5840	Discontinued
0.6535	Remote Similarity	NPD3792	Approved
0.6535	Remote Similarity	NPD7065	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6164	Phase 2
0.6533	Remote Similarity	NPD2369	Discontinued
0.6533	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.653	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.653	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2820	Phase 3
0.6524	Remote Similarity	NPD6301	Phase 2
0.6522	Remote Similarity	NPD4988	Discontinued
0.6508	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD3782	Discontinued
0.6502	Remote Similarity	NPD7428	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4863	Approved
0.6498	Remote Similarity	NPD7568	Phase 1
0.6486	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3968	Approved
0.6477	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6753	Phase 1
0.6476	Remote Similarity	NPD5937	Approved
0.6476	Remote Similarity	NPD6752	Phase 1
0.6471	Remote Similarity	NPD3227	Phase 2
0.6471	Remote Similarity	NPD7225	Discontinued
0.6471	Remote Similarity	NPD2365	Approved
0.6467	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7552	Discontinued
0.6448	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3246	Discontinued
0.6441	Remote Similarity	NPD3780	Phase 2
0.6436	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3805	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3915	Approved
0.6425	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7619	Phase 3
0.6415	Remote Similarity	NPD7618	Phase 3
0.6414	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3908	Approved
0.6413	Remote Similarity	NPD7970	Approved
0.6413	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD7175	Phase 1
0.6409	Remote Similarity	NPD2408	Discontinued
0.6406	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7995	Phase 2
0.64	Remote Similarity	NPD2037	Approved
0.6396	Remote Similarity	NPD3917	Approved
0.6396	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7657	Approved
0.6396	Remote Similarity	NPD3918	Approved
0.6396	Remote Similarity	NPD7656	Approved
0.6394	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD3411	Phase 2
0.6393	Remote Similarity	NPD3410	Approved
0.6393	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD2950	Approved
0.6393	Remote Similarity	NPD2949	Approved
0.639	Remote Similarity	NPD6879	Phase 2
0.639	Remote Similarity	NPD6878	Phase 2
0.6389	Remote Similarity	NPD7727	Phase 2
0.6389	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7088	Discontinued
0.6384	Remote Similarity	NPD3353	Approved
0.6384	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6768	Approved
0.6382	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7617	Discontinued
0.638	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3425	Discontinued
0.6368	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7210	Clinical (unspecified phase)
0.636	Remote Similarity	NPD8311	Discontinued
0.6359	Remote Similarity	NPD6532	Discontinued
0.6359	Remote Similarity	NPD3470	Approved
0.6359	Remote Similarity	NPD3471	Approved
0.6355	Remote Similarity	NPD2461	Phase 1
0.6354	Remote Similarity	NPD1781	Discontinued
0.6351	Remote Similarity	NPD5504	Discontinued
0.6349	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5526	Phase 2
0.6348	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD3967	Approved
0.6343	Remote Similarity	NPD6805	Discontinued
0.6339	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD2431	Approved
0.6337	Remote Similarity	NPD2432	Approved
0.6336	Remote Similarity	NPD6199	Discontinued
0.6335	Remote Similarity	NPD5510	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