NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.09
Volume:	261.239
LogP:	1.782
LogD:	1.787
LogS:	-3.166
# Rotatable Bonds:	1
TPSA:	69.56
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	3.252
Fsp3:	0.133
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:	-5.01
MDCK Permeability:	2.0665303964051418e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.92
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	78.16356658935547%
Volume Distribution (VD):	1.81
Pgp-substrate:	26.240110397338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.077
CYP2C9-substrate:	0.155
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	2.298
Half-life (T1/2):	0.617

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.932
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.83
Carcinogencity:	0.025
Eye Corrosion:	0.003
Eye Irritation:	0.123
Respiratory Toxicity:	0.693

Download Data

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

Natural Product: NPC197680

Natural Product ID:	NPC197680
*Common Name:**	Aflaquinolone G
IUPAC Name:	(3R,4S)-3,4-dihydroxy-4-phenyl-1,3-dihydroquinolin-2-one
Synonyms:	Aflaquinolone G
Standard InCHIKey:	ICAOEYXCZNNQNW-ZFWWWQNUSA-N
Standard InCHI:	InChI=1S/C15H13NO3/c17-13-14(18)16-12-9-5-4-8-11(12)15(13,19)10-6-2-1-3-7-10/h1-9,13,17,19H,(H,16,18)/t13-,15-/m0/s1
SMILES:	OC1=Nc2ccccc2[C@@]([C@H]1O)(O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2024584
PubChem CID:	57381072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines

*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
NPO32934	aspergillus spp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22295903]

☑ 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

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	80000.0	nM	PMID[559032]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	80000.0	nM	PMID[559032]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	80000.0	nM	PMID[559032]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	80000.0	nM	PMID[559032]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	80000.0	nM	PMID[559032]

☑ 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 NPC197680 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	262
0.1-0.2	1333
0.2-0.3	7890
0.3-0.4	11578
0.4-0.5	15732
0.5-0.6	5355
0.6-0.7	507
0.7-0.8	31
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259098
0.838	Intermediate Similarity	NPC184161
0.8372	Intermediate Similarity	NPC325013
0.8333	Intermediate Similarity	NPC10730
0.8333	Intermediate Similarity	NPC10875
0.8095	Intermediate Similarity	NPC291359
0.808	Intermediate Similarity	NPC205652
0.7843	Intermediate Similarity	NPC257354
0.7829	Intermediate Similarity	NPC19555
0.7674	Intermediate Similarity	NPC147957
0.7656	Intermediate Similarity	NPC470550
0.7532	Intermediate Similarity	NPC168153
0.748	Intermediate Similarity	NPC178681
0.7464	Intermediate Similarity	NPC226662
0.7438	Intermediate Similarity	NPC126515
0.7438	Intermediate Similarity	NPC274002
0.7438	Intermediate Similarity	NPC472331
0.7381	Intermediate Similarity	NPC37584
0.7376	Intermediate Similarity	NPC184437
0.7343	Intermediate Similarity	NPC166667
0.7308	Intermediate Similarity	NPC1986
0.7308	Intermediate Similarity	NPC474544
0.7285	Intermediate Similarity	NPC219383
0.7153	Intermediate Similarity	NPC159589
0.7143	Intermediate Similarity	NPC101372
0.7101	Intermediate Similarity	NPC317758
0.6954	Remote Similarity	NPC472100
0.6953	Remote Similarity	NPC211551
0.6933	Remote Similarity	NPC472103
0.6879	Remote Similarity	NPC278097
0.6875	Remote Similarity	NPC476689
0.6875	Remote Similarity	NPC476685
0.6875	Remote Similarity	NPC476687
0.6871	Remote Similarity	NPC126637
0.686	Remote Similarity	NPC78154
0.6855	Remote Similarity	NPC476231
0.6826	Remote Similarity	NPC314394
0.6818	Remote Similarity	NPC9336
0.6809	Remote Similarity	NPC205946
0.6806	Remote Similarity	NPC316746
0.6805	Remote Similarity	NPC133591
0.68	Remote Similarity	NPC477155
0.6786	Remote Similarity	NPC283130
0.6786	Remote Similarity	NPC328683
0.6783	Remote Similarity	NPC295478
0.6765	Remote Similarity	NPC38823
0.6765	Remote Similarity	NPC291759
0.6765	Remote Similarity	NPC207033
0.6759	Remote Similarity	NPC313466
0.675	Remote Similarity	NPC85651
0.6742	Remote Similarity	NPC292758
0.6742	Remote Similarity	NPC65855
0.6733	Remote Similarity	NPC314113
0.6728	Remote Similarity	NPC278887
0.6718	Remote Similarity	NPC76327
0.6709	Remote Similarity	NPC141353
0.6709	Remote Similarity	NPC477156
0.6709	Remote Similarity	NPC477157
0.6709	Remote Similarity	NPC477889
0.6707	Remote Similarity	NPC472443
0.6694	Remote Similarity	NPC476483
0.669	Remote Similarity	NPC474926
0.6688	Remote Similarity	NPC254798
0.6667	Remote Similarity	NPC243162
0.6648	Remote Similarity	NPC472330
0.6648	Remote Similarity	NPC472329
0.6642	Remote Similarity	NPC82963
0.6628	Remote Similarity	NPC473815
0.6607	Remote Similarity	NPC316161
0.6594	Remote Similarity	NPC38458
0.6594	Remote Similarity	NPC311737
0.6588	Remote Similarity	NPC472444
0.6584	Remote Similarity	NPC235628
0.6581	Remote Similarity	NPC161292
0.6573	Remote Similarity	NPC474479
0.6558	Remote Similarity	NPC470824
0.6554	Remote Similarity	NPC228511
0.6543	Remote Similarity	NPC72291
0.6543	Remote Similarity	NPC57105
0.6536	Remote Similarity	NPC60553
0.6535	Remote Similarity	NPC33168
0.6535	Remote Similarity	NPC311242
0.6529	Remote Similarity	NPC475962
0.6528	Remote Similarity	NPC250476
0.6527	Remote Similarity	NPC475594
0.6519	Remote Similarity	NPC153769
0.651	Remote Similarity	NPC113325
0.651	Remote Similarity	NPC279045
0.6509	Remote Similarity	NPC270009
0.6506	Remote Similarity	NPC158129
0.6503	Remote Similarity	NPC313757
0.6497	Remote Similarity	NPC288445
0.6494	Remote Similarity	NPC477890
0.6493	Remote Similarity	NPC255721
0.6488	Remote Similarity	NPC288943
0.6488	Remote Similarity	NPC129624
0.6488	Remote Similarity	NPC475607
0.6485	Remote Similarity	NPC469462
0.648	Remote Similarity	NPC265521
0.6478	Remote Similarity	NPC471132
0.6471	Remote Similarity	NPC478032
0.6471	Remote Similarity	NPC470090
0.6467	Remote Similarity	NPC64205
0.6467	Remote Similarity	NPC175870
0.6463	Remote Similarity	NPC231382
0.6457	Remote Similarity	NPC471195
0.6457	Remote Similarity	NPC471196
0.6452	Remote Similarity	NPC116519
0.645	Remote Similarity	NPC474081
0.6449	Remote Similarity	NPC222982
0.6446	Remote Similarity	NPC477888
0.6434	Remote Similarity	NPC471315
0.6434	Remote Similarity	NPC471314
0.6429	Remote Similarity	NPC472586
0.6418	Remote Similarity	NPC153690
0.6412	Remote Similarity	NPC475761
0.6412	Remote Similarity	NPC474041
0.6402	Remote Similarity	NPC102423
0.64	Remote Similarity	NPC226438
0.6395	Remote Similarity	NPC311936
0.6391	Remote Similarity	NPC203754
0.6391	Remote Similarity	NPC150048
0.6389	Remote Similarity	NPC315632
0.6385	Remote Similarity	NPC228400
0.6385	Remote Similarity	NPC214200
0.638	Remote Similarity	NPC231862
0.638	Remote Similarity	NPC320064
0.6378	Remote Similarity	NPC20142
0.6378	Remote Similarity	NPC215351
0.6378	Remote Similarity	NPC58674
0.6377	Remote Similarity	NPC118202
0.6374	Remote Similarity	NPC265383
0.6374	Remote Similarity	NPC475685
0.6369	Remote Similarity	NPC474409
0.6369	Remote Similarity	NPC34508
0.6358	Remote Similarity	NPC245741
0.6358	Remote Similarity	NPC119579
0.6358	Remote Similarity	NPC153694
0.6358	Remote Similarity	NPC211525
0.6357	Remote Similarity	NPC290515
0.6357	Remote Similarity	NPC303611
0.6357	Remote Similarity	NPC164514
0.6357	Remote Similarity	NPC108606
0.6357	Remote Similarity	NPC226096
0.6353	Remote Similarity	NPC326575
0.6353	Remote Similarity	NPC283152
0.6348	Remote Similarity	NPC79293
0.6348	Remote Similarity	NPC279401
0.6347	Remote Similarity	NPC126481
0.6346	Remote Similarity	NPC471598
0.6345	Remote Similarity	NPC472414
0.6343	Remote Similarity	NPC66083
0.6341	Remote Similarity	NPC472121
0.6341	Remote Similarity	NPC289776
0.6341	Remote Similarity	NPC88970
0.6341	Remote Similarity	NPC191863
0.6341	Remote Similarity	NPC133470
0.6338	Remote Similarity	NPC130931
0.6337	Remote Similarity	NPC260118
0.6329	Remote Similarity	NPC300596
0.6329	Remote Similarity	NPC237649
0.6327	Remote Similarity	NPC71271
0.6322	Remote Similarity	NPC62510
0.6322	Remote Similarity	NPC28425
0.6322	Remote Similarity	NPC276060
0.632	Remote Similarity	NPC172128
0.6311	Remote Similarity	NPC99482
0.631	Remote Similarity	NPC310894
0.6309	Remote Similarity	NPC42423
0.6309	Remote Similarity	NPC473724
0.6307	Remote Similarity	NPC22928
0.6306	Remote Similarity	NPC259678
0.6306	Remote Similarity	NPC470579
0.6304	Remote Similarity	NPC264782
0.6301	Remote Similarity	NPC192939
0.6301	Remote Similarity	NPC215747
0.6299	Remote Similarity	NPC261709
0.6299	Remote Similarity	NPC111586
0.6299	Remote Similarity	NPC108852
0.6296	Remote Similarity	NPC24101
0.6296	Remote Similarity	NPC172937
0.6296	Remote Similarity	NPC96224
0.6296	Remote Similarity	NPC94167
0.629	Remote Similarity	NPC262393
0.6289	Remote Similarity	NPC144691
0.6287	Remote Similarity	NPC44161
0.6281	Remote Similarity	NPC15839
0.628	Remote Similarity	NPC477158
0.628	Remote Similarity	NPC27904
0.6279	Remote Similarity	NPC39822
0.6275	Remote Similarity	NPC181527
0.6272	Remote Similarity	NPC210415
0.6272	Remote Similarity	NPC225381
0.6272	Remote Similarity	NPC21752
0.6272	Remote Similarity	NPC293255
0.6272	Remote Similarity	NPC181138
0.6272	Remote Similarity	NPC298851
0.6272	Remote Similarity	NPC276993
0.6268	Remote Similarity	NPC268572
0.6267	Remote Similarity	NPC208757

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 NPC197680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	654
0.2-0.3	898
0.3-0.4	1176
0.4-0.5	3710
0.5-0.6	2240
0.6-0.7	276
0.7-0.8	10
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
0.7554	Intermediate Similarity	NPD1595	Approved
0.7554	Intermediate Similarity	NPD1594	Phase 3
0.7518	Intermediate Similarity	NPD995	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2322	Discovery
0.7465	Intermediate Similarity	NPD3864	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1908	Phase 2
0.7299	Intermediate Similarity	NPD6320	Approved
0.72	Intermediate Similarity	NPD5881	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD471	Approved
0.7021	Intermediate Similarity	NPD4895	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2579	Approved
0.6923	Remote Similarity	NPD4275	Approved
0.6923	Remote Similarity	NPD3720	Discontinued
0.6923	Remote Similarity	NPD4274	Approved
0.6923	Remote Similarity	NPD3778	Approved
0.6867	Remote Similarity	NPD6301	Phase 2
0.6866	Remote Similarity	NPD5631	Phase 3
0.6861	Remote Similarity	NPD2210	Approved
0.6861	Remote Similarity	NPD2212	Approved
0.6849	Remote Similarity	NPD2791	Discontinued
0.6824	Remote Similarity	NPD4951	Discontinued
0.6821	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD9587	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD478	Approved
0.6786	Remote Similarity	NPD964	Approved
0.6776	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD864	Approved
0.6759	Remote Similarity	NPD865	Approved
0.6755	Remote Similarity	NPD4430	Phase 2
0.6752	Remote Similarity	NPD3296	Phase 1
0.6752	Remote Similarity	NPD5617	Suspended
0.6744	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6789	Approved
0.6733	Remote Similarity	NPD1477	Approved
0.6718	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD9507	Approved
0.6716	Remote Similarity	NPD181	Approved
0.6713	Remote Similarity	NPD1516	Approved
0.6711	Remote Similarity	NPD2387	Approved
0.6709	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2789	Approved
0.6707	Remote Similarity	NPD2215	Approved
0.6707	Remote Similarity	NPD2216	Approved
0.6694	Remote Similarity	NPD1394	Approved
0.669	Remote Similarity	NPD1036	Approved
0.6688	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1542	Approved
0.6667	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1593	Approved
0.6624	Remote Similarity	NPD6158	Phase 2
0.6624	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD9477	Approved
0.6604	Remote Similarity	NPD3236	Phase 3
0.6604	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3525	Discontinued
0.66	Remote Similarity	NPD1169	Approved
0.6594	Remote Similarity	NPD9247	Phase 3
0.6589	Remote Similarity	NPD1540	Approved
0.6584	Remote Similarity	NPD5599	Discontinued
0.6582	Remote Similarity	NPD5811	Approved
0.6575	Remote Similarity	NPD1500	Approved
0.6575	Remote Similarity	NPD1001	Discontinued
0.6567	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD9701	Discontinued
0.6543	Remote Similarity	NPD4871	Phase 2
0.6538	Remote Similarity	NPD4656	Approved
0.6538	Remote Similarity	NPD4658	Approved
0.6535	Remote Similarity	NPD1875	Phase 1
0.6522	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD1633	Approved
0.6519	Remote Similarity	NPD2882	Phase 1
0.6519	Remote Similarity	NPD4003	Phase 3
0.6516	Remote Similarity	NPD5414	Phase 2
0.6508	Remote Similarity	NPD665	Phase 2
0.6506	Remote Similarity	NPD3824	Phase 1
0.6478	Remote Similarity	NPD1634	Approved
0.6475	Remote Similarity	NPD457	Approved
0.6474	Remote Similarity	NPD3359	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1762	Approved
0.6471	Remote Similarity	NPD1764	Approved
0.6452	Remote Similarity	NPD1835	Phase 1
0.6446	Remote Similarity	NPD7474	Suspended
0.6425	Remote Similarity	NPD4605	Approved
0.6425	Remote Similarity	NPD4604	Approved
0.6424	Remote Similarity	NPD1850	Phase 3
0.6423	Remote Similarity	NPD2659	Approved
0.6423	Remote Similarity	NPD3147	Approved
0.6423	Remote Similarity	NPD3149	Approved
0.6423	Remote Similarity	NPD3148	Approved
0.6423	Remote Similarity	NPD3150	Approved
0.6423	Remote Similarity	NPD2658	Approved
0.642	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2188	Approved
0.6412	Remote Similarity	NPD4231	Approved
0.6412	Remote Similarity	NPD4229	Approved
0.6412	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2326	Approved
0.6398	Remote Similarity	NPD6913	Approved
0.6392	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD2380	Approved
0.6391	Remote Similarity	NPD2381	Approved
0.6391	Remote Similarity	NPD2382	Approved
0.638	Remote Similarity	NPD6063	Approved
0.6374	Remote Similarity	NPD6184	Discontinued
0.637	Remote Similarity	NPD9713	Approved
0.6369	Remote Similarity	NPD7418	Discontinued
0.6364	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD9609	Approved
0.6357	Remote Similarity	NPD9612	Approved
0.6357	Remote Similarity	NPD9611	Approved
0.6353	Remote Similarity	NPD6159	Phase 2
0.6352	Remote Similarity	NPD2328	Phase 2
0.6349	Remote Similarity	NPD752	Approved
0.6338	Remote Similarity	NPD7725	Approved
0.6338	Remote Similarity	NPD1525	Approved
0.6336	Remote Similarity	NPD4719	Phase 2
0.6336	Remote Similarity	NPD854	Approved
0.6336	Remote Similarity	NPD855	Approved
0.6336	Remote Similarity	NPD4818	Approved
0.6336	Remote Similarity	NPD4817	Approved
0.6333	Remote Similarity	NPD1106	Discontinued
0.6331	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD2622	Approved
0.6323	Remote Similarity	NPD1625	Approved
0.6322	Remote Similarity	NPD6557	Phase 2
0.6319	Remote Similarity	NPD5255	Approved
0.6319	Remote Similarity	NPD6283	Phase 2
0.6316	Remote Similarity	NPD564	Approved
0.6316	Remote Similarity	NPD563	Approved
0.6312	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD8011	Discontinued
0.6306	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3453	Discontinued
0.6301	Remote Similarity	NPD4103	Phase 2
0.6301	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD720	Approved
0.6299	Remote Similarity	NPD719	Approved
0.6296	Remote Similarity	NPD2679	Approved
0.6296	Remote Similarity	NPD2678	Approved
0.6296	Remote Similarity	NPD2527	Approved
0.6294	Remote Similarity	NPD9692	Approved
0.6294	Remote Similarity	NPD1236	Phase 3
0.6294	Remote Similarity	NPD9693	Approved
0.6289	Remote Similarity	NPD1405	Approved
0.6288	Remote Similarity	NPD3680	Approved
0.6288	Remote Similarity	NPD3682	Approved
0.6287	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4121	Phase 3
0.6273	Remote Similarity	NPD4120	Approved
0.6267	Remote Similarity	NPD7477	Discontinued
0.6264	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD7904	Phase 2
0.6258	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1107	Approved
0.625	Remote Similarity	NPD3277	Phase 3
0.625	Remote Similarity	NPD1108	Approved
0.6242	Remote Similarity	NPD3813	Approved
0.6242	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD311	Approved
0.6241	Remote Similarity	NPD10	Approved
0.6241	Remote Similarity	NPD314	Approved
0.6241	Remote Similarity	NPD254	Approved
0.6241	Remote Similarity	NPD315	Approved
0.6241	Remote Similarity	NPD309	Approved
0.6241	Remote Similarity	NPD7522	Discontinued
0.6241	Remote Similarity	NPD310	Approved
0.6235	Remote Similarity	NPD6492	Phase 2
0.6235	Remote Similarity	NPD5743	Approved
0.6235	Remote Similarity	NPD1514	Discontinued
0.6235	Remote Similarity	NPD5742	Approved
0.6235	Remote Similarity	NPD5741	Approved
0.6234	Remote Similarity	NPD3605	Approved
0.6234	Remote Similarity	NPD3068	Approved
0.6233	Remote Similarity	NPD1574	Approved
0.6226	Remote Similarity	NPD4888	Discontinued
0.6224	Remote Similarity	NPD5723	Approved
0.6224	Remote Similarity	NPD9272	Approved
0.6222	Remote Similarity	NPD6406	Approved
0.622	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6690	Approved
0.622	Remote Similarity	NPD4485	Approved
0.6218	Remote Similarity	NPD1592	Phase 3
0.6214	Remote Similarity	NPD9342	Approved
0.6212	Remote Similarity	NPD1419	Approved
0.6212	Remote Similarity	NPD1417	Approved
0.6207	Remote Similarity	NPD522	Approved
0.6207	Remote Similarity	NPD5596	Phase 2
0.6207	Remote Similarity	NPD7883	Discontinued
0.6194	Remote Similarity	NPD3069	Approved
0.6194	Remote Similarity	NPD999	Phase 2
0.6188	Remote Similarity	NPD6221	Approved
0.6188	Remote Similarity	NPD6222	Approved
0.6187	Remote Similarity	NPD1682	Approved
0.6187	Remote Similarity	NPD1681	Approved
0.6187	Remote Similarity	NPD1680	Approved
0.6187	Remote Similarity	NPD456	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