NPASS Compound

Structure

NPC472331 OpenBabel07101718282D 32 35 0 0 1 0 0 0 0 0999 V2000 7.8731 -1.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8611 -1.6839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4583 2.5259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3401 3.6284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3401 2.6562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 4.1145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 2.1700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6562 3.6284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4306 -0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4583 -0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8889 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1892 0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3750 -0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3472 0.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1892 -1.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0312 -0.8420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9167 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6562 2.6562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9722 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0312 0.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4583 0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4306 0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6839 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4861 0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3472 -0.8420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9722 1.6839 0.0000 C 0 0 2 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 7.8731 0.6164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9167 1.6839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4583 0.8420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9722 2.6562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4861 2.5259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 32 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 1 1 6 0 0 0 16 20 1 0 0 0 0 17 22 2 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 19 27 1 0 0 0 0 20 28 2 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 1 0 0 0 23 32 1 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 25 2 1 1 0 0 0 26 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	435.2
Volume:	455.246
LogP:	3.067
LogD:	2.377
LogS:	-3.915
# Rotatable Bonds:	4
TPSA:	96.19
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.769
Synthetic Accessibility Score:	4.764
Fsp3:	0.423
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:	-4.667
MDCK Permeability:	2.693683018151205e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.201
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.592
Plasma Protein Binding (PPB):	95.93138885498047%
Volume Distribution (VD):	0.731
Pgp-substrate:	2.5253002643585205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.308
CYP2D6-inhibitor:	0.08
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.434
CYP3A4-substrate:	0.891

ADMET: Excretion

Clearance (CL):	0.904
Half-life (T1/2):	0.422

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.357
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.605
Carcinogencity:	0.655
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.316

Download Data

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

Natural Product: NPC472331

Natural Product ID:	NPC472331
*Common Name:**	QWVOGENNJWSIPL-DGRAQUCUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QWVOGENNJWSIPL-DGRAQUCUSA-N
Standard InCHI:	InChI=1S/C26H29NO5/c1-16-15-25(2,14-12-20(16)28)13-11-17-9-10-19-21(22(17)29)26(31,18-7-5-4-6-8-18)23(32-3)24(30)27-19/h4-11,13,16,23,29,31H,12,14-15H2,1-3H3,(H,27,30)/b13-11+/t16-,23-,25-,26+/m1/s1
SMILES:	CO[C@@H]1C(=Nc2c([C@@]1(O)c1ccccc1)c(O)c(cc2)/C=C/[C@]1(C)CCC(=O)[C@@H](C1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359249
PubChem CID:	n.a.
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
NPO33330	aspergillus sp. xs-20090b15	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25420212]

☑ 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	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		TI	=	4.0	n.a.	PMID[525280]
NPT27	Others	Unspecified		TC50	=	27.0	uM	PMID[525280]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	6600.0	nM	PMID[525280]

☑ 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 NPC472331 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	257
0.1-0.2	1134
0.2-0.3	3246
0.3-0.4	11627
0.4-0.5	8015
0.5-0.6	17238
0.6-0.7	1146
0.7-0.8	24
0.8-0.85	1
0.85-0.9	4
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126515
1.0	High Similarity	NPC274002
0.9379	High Similarity	NPC257354
0.9182	High Similarity	NPC291359
0.8902	High Similarity	NPC19555
0.875	High Similarity	NPC184161
0.8588	High Similarity	NPC168153
0.8516	High Similarity	NPC472330
0.8516	High Similarity	NPC472329
0.7719	Intermediate Similarity	NPC10730
0.7719	Intermediate Similarity	NPC10875
0.7438	Intermediate Similarity	NPC197680
0.7438	Intermediate Similarity	NPC259098
0.7173	Intermediate Similarity	NPC28510
0.7164	Intermediate Similarity	NPC25961
0.7143	Intermediate Similarity	NPC219383
0.7083	Intermediate Similarity	NPC70340
0.7083	Intermediate Similarity	NPC166667
0.7068	Intermediate Similarity	NPC22928
0.7065	Intermediate Similarity	NPC225381
0.7059	Intermediate Similarity	NPC39822
0.7043	Intermediate Similarity	NPC9475
0.7037	Intermediate Similarity	NPC325013
0.7016	Intermediate Similarity	NPC180253
0.7016	Intermediate Similarity	NPC219170
0.7	Intermediate Similarity	NPC276060
0.7	Intermediate Similarity	NPC28425
0.7	Intermediate Similarity	NPC132751
0.6984	Remote Similarity	NPC192939
0.6984	Remote Similarity	NPC311936
0.6984	Remote Similarity	NPC215747
0.6963	Remote Similarity	NPC288854
0.6947	Remote Similarity	NPC477392
0.6947	Remote Similarity	NPC315934
0.6947	Remote Similarity	NPC119579
0.694	Remote Similarity	NPC278887
0.6935	Remote Similarity	NPC232600
0.6931	Remote Similarity	NPC475962
0.6931	Remote Similarity	NPC260118
0.6927	Remote Similarity	NPC116178
0.6911	Remote Similarity	NPC477391
0.6898	Remote Similarity	NPC231371
0.6893	Remote Similarity	NPC217903
0.6878	Remote Similarity	NPC265383
0.6868	Remote Similarity	NPC72291
0.6845	Remote Similarity	NPC95412
0.6816	Remote Similarity	NPC474077
0.6812	Remote Similarity	NPC321166
0.6793	Remote Similarity	NPC15506
0.6788	Remote Similarity	NPC291759
0.6786	Remote Similarity	NPC294244
0.6774	Remote Similarity	NPC68328
0.6769	Remote Similarity	NPC474059
0.6768	Remote Similarity	NPC303214
0.6751	Remote Similarity	NPC203972
0.6749	Remote Similarity	NPC301292
0.6749	Remote Similarity	NPC313112
0.6749	Remote Similarity	NPC14339
0.6738	Remote Similarity	NPC83241
0.6736	Remote Similarity	NPC133591
0.6701	Remote Similarity	NPC38823
0.6701	Remote Similarity	NPC207033
0.67	Remote Similarity	NPC159101
0.6684	Remote Similarity	NPC112676
0.6684	Remote Similarity	NPC296742
0.6683	Remote Similarity	NPC198160
0.6683	Remote Similarity	NPC127996
0.6667	Remote Similarity	NPC133156
0.6667	Remote Similarity	NPC103250
0.6667	Remote Similarity	NPC329830
0.665	Remote Similarity	NPC15987
0.6649	Remote Similarity	NPC204867
0.6649	Remote Similarity	NPC313886
0.6649	Remote Similarity	NPC310894
0.6649	Remote Similarity	NPC126676
0.6649	Remote Similarity	NPC469671
0.6633	Remote Similarity	NPC476256
0.6633	Remote Similarity	NPC476257
0.6633	Remote Similarity	NPC29472
0.6633	Remote Similarity	NPC259791
0.6633	Remote Similarity	NPC476212
0.6633	Remote Similarity	NPC476129
0.6633	Remote Similarity	NPC224293
0.6633	Remote Similarity	NPC476206
0.6633	Remote Similarity	NPC476205
0.6633	Remote Similarity	NPC476207
0.663	Remote Similarity	NPC235628
0.663	Remote Similarity	NPC156348
0.6617	Remote Similarity	NPC17677
0.6615	Remote Similarity	NPC298320
0.6614	Remote Similarity	NPC293255
0.6614	Remote Similarity	NPC181138
0.6614	Remote Similarity	NPC298851
0.6614	Remote Similarity	NPC210415
0.6614	Remote Similarity	NPC276993
0.6614	Remote Similarity	NPC21752
0.6601	Remote Similarity	NPC471489
0.66	Remote Similarity	NPC476218
0.66	Remote Similarity	NPC108804
0.6598	Remote Similarity	NPC320394
0.6595	Remote Similarity	NPC191863
0.6595	Remote Similarity	NPC133470
0.6595	Remote Similarity	NPC289776
0.6593	Remote Similarity	NPC114808
0.659	Remote Similarity	NPC126637
0.6584	Remote Similarity	NPC317727
0.6582	Remote Similarity	NPC69213
0.6575	Remote Similarity	NPC227033
0.6571	Remote Similarity	NPC314113
0.6569	Remote Similarity	NPC288759
0.6566	Remote Similarity	NPC203628
0.6559	Remote Similarity	NPC313757
0.6554	Remote Similarity	NPC323798
0.6548	Remote Similarity	NPC320088
0.6545	Remote Similarity	NPC129624
0.6536	Remote Similarity	NPC315829
0.6531	Remote Similarity	NPC150308
0.6529	Remote Similarity	NPC316746
0.6527	Remote Similarity	NPC474926
0.6522	Remote Similarity	NPC211525
0.6522	Remote Similarity	NPC153694
0.6517	Remote Similarity	NPC170333
0.6515	Remote Similarity	NPC471196
0.6515	Remote Similarity	NPC471195
0.6513	Remote Similarity	NPC245741
0.6508	Remote Similarity	NPC469915
0.6507	Remote Similarity	NPC303951
0.6507	Remote Similarity	NPC474366
0.6505	Remote Similarity	NPC472121
0.6503	Remote Similarity	NPC275027
0.6495	Remote Similarity	NPC153923
0.6495	Remote Similarity	NPC37957
0.649	Remote Similarity	NPC205926
0.6488	Remote Similarity	NPC311357
0.6482	Remote Similarity	NPC1820
0.6481	Remote Similarity	NPC106593
0.648	Remote Similarity	NPC470579
0.6476	Remote Similarity	NPC220241
0.6476	Remote Similarity	NPC295479
0.6476	Remote Similarity	NPC23294
0.6473	Remote Similarity	NPC476106
0.6467	Remote Similarity	NPC477157
0.6467	Remote Similarity	NPC477156
0.6465	Remote Similarity	NPC140311
0.6464	Remote Similarity	NPC144691
0.6462	Remote Similarity	NPC176113
0.6459	Remote Similarity	NPC477160
0.6458	Remote Similarity	NPC88378
0.6458	Remote Similarity	NPC211713
0.6458	Remote Similarity	NPC477115
0.6453	Remote Similarity	NPC234933
0.6452	Remote Similarity	NPC206736
0.6452	Remote Similarity	NPC473667
0.6452	Remote Similarity	NPC195766
0.645	Remote Similarity	NPC206109
0.645	Remote Similarity	NPC204970
0.645	Remote Similarity	NPC114039
0.6447	Remote Similarity	NPC33902
0.6447	Remote Similarity	NPC282092
0.6447	Remote Similarity	NPC276674
0.6441	Remote Similarity	NPC301702
0.6438	Remote Similarity	NPC13249
0.6437	Remote Similarity	NPC175870
0.6436	Remote Similarity	NPC470069
0.6436	Remote Similarity	NPC52059
0.6435	Remote Similarity	NPC7560
0.6429	Remote Similarity	NPC190007
0.6429	Remote Similarity	NPC477816
0.6425	Remote Similarity	NPC87714
0.6425	Remote Similarity	NPC477187
0.6422	Remote Similarity	NPC241263
0.6422	Remote Similarity	NPC473449
0.6418	Remote Similarity	NPC79293
0.6418	Remote Similarity	NPC279401
0.6417	Remote Similarity	NPC476231
0.6417	Remote Similarity	NPC475983
0.6415	Remote Similarity	NPC30749
0.6414	Remote Similarity	NPC295531
0.6409	Remote Similarity	NPC170055
0.6398	Remote Similarity	NPC263709
0.6398	Remote Similarity	NPC148468
0.6398	Remote Similarity	NPC63210
0.6398	Remote Similarity	NPC310403
0.6398	Remote Similarity	NPC471203
0.6398	Remote Similarity	NPC97380
0.6398	Remote Similarity	NPC243673
0.6396	Remote Similarity	NPC94943
0.6396	Remote Similarity	NPC49184
0.6395	Remote Similarity	NPC45191
0.6395	Remote Similarity	NPC275538
0.6394	Remote Similarity	NPC475768
0.6393	Remote Similarity	NPC285254
0.6393	Remote Similarity	NPC200888
0.6391	Remote Similarity	NPC127975
0.6391	Remote Similarity	NPC87985
0.6384	Remote Similarity	NPC473187
0.6383	Remote Similarity	NPC292143
0.6383	Remote Similarity	NPC139506
0.6379	Remote Similarity	NPC113325
0.6379	Remote Similarity	NPC279045

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 NPC472331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	570
0.2-0.3	783
0.3-0.4	1694
0.4-0.5	3002
0.5-0.6	2617
0.6-0.7	283
0.7-0.8	1
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
0.7356	Intermediate Similarity	NPD5617	Suspended
0.7316	Intermediate Similarity	NPD5937	Approved
0.7157	Intermediate Similarity	NPD5848	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6184	Discontinued
0.6931	Remote Similarity	NPD6296	Discontinued
0.6927	Remote Similarity	NPD3778	Approved
0.6927	Remote Similarity	NPD4951	Discontinued
0.6872	Remote Similarity	NPD3296	Phase 1
0.6831	Remote Similarity	NPD3453	Discontinued
0.6828	Remote Similarity	NPD2216	Approved
0.6828	Remote Similarity	NPD2215	Approved
0.6818	Remote Similarity	NPD4605	Approved
0.6818	Remote Similarity	NPD4604	Approved
0.6796	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5811	Approved
0.6683	Remote Similarity	NPD4931	Phase 2
0.6667	Remote Similarity	NPD5610	Approved
0.6667	Remote Similarity	NPD4003	Phase 3
0.665	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5928	Phase 1
0.6598	Remote Similarity	NPD7546	Discontinued
0.6597	Remote Similarity	NPD3793	Phase 3
0.6584	Remote Similarity	NPD5609	Approved
0.6584	Remote Similarity	NPD5608	Approved
0.6578	Remote Similarity	NPD3251	Approved
0.6575	Remote Similarity	NPD8067	Phase 3
0.6562	Remote Similarity	NPD5190	Phase 2
0.6554	Remote Similarity	NPD3400	Discontinued
0.6553	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2821	Approved
0.6535	Remote Similarity	NPD4668	Phase 2
0.6527	Remote Similarity	NPD1036	Approved
0.6524	Remote Similarity	NPD7301	Phase 3
0.6515	Remote Similarity	NPD2845	Phase 2
0.6515	Remote Similarity	NPD2843	Phase 2
0.651	Remote Similarity	NPD4603	Phase 2
0.6503	Remote Similarity	NPD6502	Phase 2
0.6502	Remote Similarity	NPD6874	Approved
0.649	Remote Similarity	NPD7302	Phase 3
0.649	Remote Similarity	NPD2916	Discontinued
0.649	Remote Similarity	NPD7300	Phase 3
0.6486	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6807	Phase 3
0.6467	Remote Similarity	NPD2672	Discontinued
0.6467	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2789	Approved
0.6465	Remote Similarity	NPD8025	Phase 2
0.6455	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1543	Discontinued
0.6443	Remote Similarity	NPD3823	Discontinued
0.6441	Remote Similarity	NPD75	Approved
0.6441	Remote Similarity	NPD9277	Approved
0.6432	Remote Similarity	NPD7630	Phase 3
0.6432	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7628	Phase 3
0.6425	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5038	Approved
0.6414	Remote Similarity	NPD5037	Approved
0.641	Remote Similarity	NPD5039	Approved
0.6406	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4956	Approved
0.6384	Remote Similarity	NPD9276	Approved
0.6384	Remote Similarity	NPD9275	Approved
0.6384	Remote Similarity	NPD9278	Suspended
0.6384	Remote Similarity	NPD9274	Approved
0.6383	Remote Similarity	NPD955	Approved
0.6378	Remote Similarity	NPD2366	Approved
0.6378	Remote Similarity	NPD6072	Discontinued
0.6378	Remote Similarity	NPD7883	Discontinued
0.6372	Remote Similarity	NPD7293	Approved
0.6364	Remote Similarity	NPD5599	Discontinued
0.6364	Remote Similarity	NPD7263	Phase 2
0.6364	Remote Similarity	NPD5036	Approved
0.6354	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD3252	Approved
0.6348	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5035	Approved
0.634	Remote Similarity	NPD3965	Phase 1
0.6337	Remote Similarity	NPD4539	Phase 1
0.6337	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6213	Phase 3
0.6337	Remote Similarity	NPD6212	Phase 3
0.6332	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7324	Discontinued
0.6321	Remote Similarity	NPD5033	Approved
0.6318	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5823	Approved
0.6311	Remote Similarity	NPD2339	Phase 3
0.6308	Remote Similarity	NPD7479	Phase 2
0.6307	Remote Similarity	NPD8363	Approved
0.6307	Remote Similarity	NPD8364	Approved
0.6305	Remote Similarity	NPD4771	Phase 2
0.6298	Remote Similarity	NPD3141	Discontinued
0.6296	Remote Similarity	NPD7292	Approved
0.6294	Remote Similarity	NPD4954	Approved
0.6294	Remote Similarity	NPD5028	Approved
0.6294	Remote Similarity	NPD5026	Approved
0.6294	Remote Similarity	NPD36	Approved
0.6294	Remote Similarity	NPD5034	Approved
0.6294	Remote Similarity	NPD2802	Phase 3
0.6294	Remote Similarity	NPD4955	Approved
0.6294	Remote Similarity	NPD5032	Approved
0.6292	Remote Similarity	NPD6789	Approved
0.629	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3236	Phase 3
0.6287	Remote Similarity	NPD8146	Phase 2
0.6286	Remote Similarity	NPD7584	Approved
0.6281	Remote Similarity	NPD3153	Approved
0.6281	Remote Similarity	NPD3154	Approved
0.628	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD1196	Approved
0.6276	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD5984	Phase 2
0.6256	Remote Similarity	NPD6159	Phase 2
0.6255	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5030	Phase 2
0.6244	Remote Similarity	NPD5031	Approved
0.6244	Remote Similarity	NPD5029	Approved
0.6244	Remote Similarity	NPD5027	Approved
0.6244	Remote Similarity	NPD6527	Approved
0.6244	Remote Similarity	NPD6161	Approved
0.6244	Remote Similarity	NPD6162	Approved
0.6244	Remote Similarity	NPD6104	Discontinued
0.6243	Remote Similarity	NPD7295	Approved
0.6238	Remote Similarity	NPD2490	Approved
0.6238	Remote Similarity	NPD2488	Approved
0.6237	Remote Similarity	NPD3684	Discontinued
0.6235	Remote Similarity	NPD6320	Approved
0.623	Remote Similarity	NPD7129	Suspended
0.623	Remote Similarity	NPD6746	Phase 2
0.6223	Remote Similarity	NPD6283	Phase 2
0.6222	Remote Similarity	NPD1195	Approved
0.6219	Remote Similarity	NPD1898	Discontinued
0.6219	Remote Similarity	NPD2792	Approved
0.6214	Remote Similarity	NPD2727	Phase 2
0.6211	Remote Similarity	NPD8070	Approved
0.6207	Remote Similarity	NPD2322	Discovery
0.6207	Remote Similarity	NPD4302	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5968	Phase 3
0.6204	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD8461	Discontinued
0.6203	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD6913	Approved
0.6202	Remote Similarity	NPD2494	Approved
0.6202	Remote Similarity	NPD7476	Discontinued
0.6202	Remote Similarity	NPD2493	Approved
0.6202	Remote Similarity	NPD3450	Approved
0.6202	Remote Similarity	NPD3452	Approved
0.6199	Remote Similarity	NPD1593	Approved
0.6193	Remote Similarity	NPD5445	Approved
0.6193	Remote Similarity	NPD5496	Approved
0.6193	Remote Similarity	NPD2899	Discontinued
0.619	Remote Similarity	NPD6063	Approved
0.619	Remote Similarity	NPD4582	Approved
0.619	Remote Similarity	NPD4583	Approved
0.6186	Remote Similarity	NPD1220	Phase 1
0.6179	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD1221	Approved
0.6171	Remote Similarity	NPD7477	Discontinued
0.6169	Remote Similarity	NPD8150	Discontinued
0.6169	Remote Similarity	NPD3120	Approved
0.6169	Remote Similarity	NPD3119	Phase 1
0.6165	Remote Similarity	NPD2941	Discontinued
0.6161	Remote Similarity	NPD6905	Phase 2
0.6154	Remote Similarity	NPD8428	Approved
0.6154	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1835	Phase 1
0.6154	Remote Similarity	NPD8466	Approved
0.6154	Remote Similarity	NPD8465	Approved
0.6154	Remote Similarity	NPD8429	Approved
0.6154	Remote Similarity	NPD8467	Approved
0.6154	Remote Similarity	NPD8427	Approved
0.6146	Remote Similarity	NPD1850	Phase 3
0.6146	Remote Similarity	NPD7256	Discontinued
0.6145	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD4004	Approved
0.6143	Remote Similarity	NPD4002	Approved
0.6135	Remote Similarity	NPD5194	Approved
0.6135	Remote Similarity	NPD5196	Approved
0.6135	Remote Similarity	NPD5197	Approved
0.6135	Remote Similarity	NPD181	Approved
0.6134	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5429	Discontinued
0.6131	Remote Similarity	NPD4012	Approved
0.6131	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD3819	Phase 2
0.6126	Remote Similarity	NPD3925	Approved
0.6124	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.612	Remote Similarity	NPD3300	Phase 2
0.6119	Remote Similarity	NPD5565	Discontinued
0.6117	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7654	Discontinued
0.6114	Remote Similarity	NPD3298	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