NPASS Compound

Structure

NPC472330 OpenBabel07101718282D 40 43 0 0 1 0 0 0 0 0999 V2000 6.2213 -5.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9140 -5.2441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9140 -0.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8864 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3750 -3.7782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 2.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3626 3.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3626 2.6700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 4.1359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5163 2.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6700 3.6472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4432 -0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4659 -0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9091 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2213 -2.3123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3977 -0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3750 -1.8236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2213 -0.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0677 -4.7554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0677 -0.8463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9318 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6700 2.6700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9773 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0677 -1.8236 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4659 0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0677 -3.7782 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4432 0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6927 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4886 0.8463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9140 -3.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3750 -0.8463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9773 1.6927 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2213 -3.2895 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 2.9318 1.6927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4659 0.8463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7604 -3.7782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9773 2.6700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4886 2.5390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9140 -2.3123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 33 1 0 0 0 0 6 39 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 22 2 0 0 0 0 11 22 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 23 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 31 1 0 0 0 0 17 31 1 0 0 0 0 18 20 1 0 0 0 0 18 31 1 0 0 0 0 20 3 1 1 0 0 0 20 24 1 0 0 0 0 21 27 2 0 0 0 0 22 32 1 0 0 0 0 23 25 2 0 0 0 0 23 34 1 0 0 0 0 24 40 1 6 0 0 0 25 27 1 0 0 0 0 25 32 1 0 0 0 0 26 19 1 6 0 0 0 26 30 1 0 0 0 0 26 33 1 0 0 0 0 27 35 1 0 0 0 0 28 29 1 0 0 0 0 28 32 1 1 0 0 0 28 39 1 0 0 0 0 29 34 2 0 0 0 0 29 36 1 0 0 0 0 30 37 2 0 0 0 0 30 40 1 0 0 0 0 31 4 1 6 0 0 0 32 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.3
Volume:	578.809
LogP:	4.626
LogD:	3.691
LogS:	-4.083
# Rotatable Bonds:	9
TPSA:	117.45
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	5.117
Fsp3:	0.531
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.063
MDCK Permeability:	7.066976195346797e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.29
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.47
Plasma Protein Binding (PPB):	88.37708282470703%
Volume Distribution (VD):	1.859
Pgp-substrate:	10.168305397033691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.184
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	1.656
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.349
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.342
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.318
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC472330

Natural Product ID:	NPC472330
*Common Name:**	HXDOHVMCRWLYFS-XCNYLRODSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HXDOHVMCRWLYFS-XCNYLRODSA-N
Standard InCHI:	InChI=1S/C32H42N2O6/c1-19(2)26(33-5)30(37)40-24-15-17-31(4,18-20(24)3)16-14-21-12-13-23-25(27(21)35)32(38,22-10-8-7-9-11-22)28(39-6)29(36)34-23/h7-14,16,19-20,24,26,28,33,35,38H,15,17-18H2,1-6H3,(H,34,36)/b16-14+/t20-,24-,26+,28-,31-,32+/m1/s1
SMILES:	CC1CC(CCC1OC(=O)C(C(C)C)NC)(C)C=CC2=C(C3=C(C=C2)NC(=O)C(C3(C4=CC=CC=C4)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3359248
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	=	520.0	n.a.	PMID[557075]
NPT27	Others	Unspecified		TC50	=	22.0	uM	PMID[557075]
NPT70	Organism	Respiratory syncytial virus	Respiratory syncytial virus	IC50	=	42.0	nM	PMID[557075]

☑ 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 NPC472330 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	237
0.1-0.2	1119
0.2-0.3	4012
0.3-0.4	12659
0.4-0.5	12836
0.5-0.6	10401
0.6-0.7	1392
0.7-0.8	34
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472329
0.8516	High Similarity	NPC472331
0.8516	High Similarity	NPC274002
0.8516	High Similarity	NPC126515
0.8492	Intermediate Similarity	NPC257354
0.8202	Intermediate Similarity	NPC291359
0.8077	Intermediate Similarity	NPC19555
0.7821	Intermediate Similarity	NPC184161
0.7819	Intermediate Similarity	NPC168153
0.7273	Intermediate Similarity	NPC477391
0.7198	Intermediate Similarity	NPC232600
0.7165	Intermediate Similarity	NPC248670
0.705	Intermediate Similarity	NPC477392
0.705	Intermediate Similarity	NPC315934
0.7039	Intermediate Similarity	NPC303214
0.7037	Intermediate Similarity	NPC10875
0.7037	Intermediate Similarity	NPC10730
0.701	Intermediate Similarity	NPC28510
0.7	Intermediate Similarity	NPC469722
0.6985	Remote Similarity	NPC39822
0.6961	Remote Similarity	NPC474059
0.6954	Remote Similarity	NPC95412
0.6946	Remote Similarity	NPC469830
0.6944	Remote Similarity	NPC127996
0.6939	Remote Similarity	NPC83241
0.6937	Remote Similarity	NPC473667
0.6935	Remote Similarity	NPC45037
0.6919	Remote Similarity	NPC50016
0.6919	Remote Similarity	NPC311357
0.6904	Remote Similarity	NPC225381
0.6904	Remote Similarity	NPC273755
0.6891	Remote Similarity	NPC133470
0.6891	Remote Similarity	NPC191863
0.6891	Remote Similarity	NPC289776
0.6887	Remote Similarity	NPC473460
0.6881	Remote Similarity	NPC294951
0.6878	Remote Similarity	NPC140311
0.6869	Remote Similarity	NPC158277
0.6869	Remote Similarity	NPC473354
0.6869	Remote Similarity	NPC471165
0.6863	Remote Similarity	NPC94862
0.6853	Remote Similarity	NPC89831
0.6845	Remote Similarity	NPC203628
0.6831	Remote Similarity	NPC197921
0.6821	Remote Similarity	NPC15506
0.6818	Remote Similarity	NPC473837
0.6816	Remote Similarity	NPC106593
0.6806	Remote Similarity	NPC477160
0.6802	Remote Similarity	NPC274268
0.6793	Remote Similarity	NPC91953
0.6793	Remote Similarity	NPC469360
0.6786	Remote Similarity	NPC278887
0.6784	Remote Similarity	NPC476227
0.6782	Remote Similarity	NPC475962
0.6766	Remote Similarity	NPC269750
0.6766	Remote Similarity	NPC194671
0.6757	Remote Similarity	NPC223590
0.6753	Remote Similarity	NPC156348
0.6749	Remote Similarity	NPC471526
0.6732	Remote Similarity	NPC291759
0.672	Remote Similarity	NPC195788
0.672	Remote Similarity	NPC237901
0.6715	Remote Similarity	NPC163961
0.6715	Remote Similarity	NPC473305
0.6714	Remote Similarity	NPC214368
0.67	Remote Similarity	NPC26108
0.67	Remote Similarity	NPC476321
0.6698	Remote Similarity	NPC87714
0.6698	Remote Similarity	NPC473422
0.6697	Remote Similarity	NPC25961
0.6683	Remote Similarity	NPC230611
0.6683	Remote Similarity	NPC133591
0.6682	Remote Similarity	NPC474077
0.6667	Remote Similarity	NPC478008
0.6667	Remote Similarity	NPC6570
0.6651	Remote Similarity	NPC323662
0.6651	Remote Similarity	NPC477550
0.6651	Remote Similarity	NPC477552
0.665	Remote Similarity	NPC306804
0.6648	Remote Similarity	NPC197680
0.6648	Remote Similarity	NPC259098
0.6636	Remote Similarity	NPC119722
0.6634	Remote Similarity	NPC471049
0.6634	Remote Similarity	NPC471050
0.6634	Remote Similarity	NPC471048
0.6634	Remote Similarity	NPC320394
0.6633	Remote Similarity	NPC46009
0.6633	Remote Similarity	NPC72291
0.6633	Remote Similarity	NPC40234
0.6622	Remote Similarity	NPC330009
0.6619	Remote Similarity	NPC203972
0.6617	Remote Similarity	NPC159767
0.6617	Remote Similarity	NPC473402
0.6617	Remote Similarity	NPC155506
0.6617	Remote Similarity	NPC279871
0.6616	Remote Similarity	NPC294516
0.6616	Remote Similarity	NPC107938
0.6614	Remote Similarity	NPC260909
0.6608	Remote Similarity	NPC19175
0.6605	Remote Similarity	NPC475223
0.6589	Remote Similarity	NPC477551
0.6585	Remote Similarity	NPC469831
0.6584	Remote Similarity	NPC231371
0.658	Remote Similarity	NPC476741
0.6578	Remote Similarity	NPC478007
0.6574	Remote Similarity	NPC475448
0.6574	Remote Similarity	NPC246983
0.657	Remote Similarity	NPC207033
0.657	Remote Similarity	NPC38823
0.6562	Remote Similarity	NPC313582
0.656	Remote Similarity	NPC11708
0.6555	Remote Similarity	NPC61332
0.6555	Remote Similarity	NPC5630
0.6555	Remote Similarity	NPC240130
0.6555	Remote Similarity	NPC283207
0.6553	Remote Similarity	NPC469829
0.6552	Remote Similarity	NPC323752
0.654	Remote Similarity	NPC476565
0.654	Remote Similarity	NPC302715
0.6538	Remote Similarity	NPC326966
0.6535	Remote Similarity	NPC477394
0.6533	Remote Similarity	NPC222046
0.653	Remote Similarity	NPC478005
0.653	Remote Similarity	NPC257728
0.6528	Remote Similarity	NPC219383
0.6528	Remote Similarity	NPC476742
0.6524	Remote Similarity	NPC473378
0.6524	Remote Similarity	NPC473407
0.6524	Remote Similarity	NPC70340
0.6522	Remote Similarity	NPC52262
0.652	Remote Similarity	NPC97526
0.652	Remote Similarity	NPC203005
0.652	Remote Similarity	NPC119652
0.6515	Remote Similarity	NPC63931
0.6513	Remote Similarity	NPC477156
0.6513	Remote Similarity	NPC56635
0.6513	Remote Similarity	NPC477157
0.6511	Remote Similarity	NPC151171
0.651	Remote Similarity	NPC476744
0.6509	Remote Similarity	NPC321592
0.6509	Remote Similarity	NPC476257
0.6509	Remote Similarity	NPC476207
0.6509	Remote Similarity	NPC476205
0.6509	Remote Similarity	NPC476256
0.6509	Remote Similarity	NPC54803
0.6509	Remote Similarity	NPC476129
0.6509	Remote Similarity	NPC259791
0.6509	Remote Similarity	NPC476206
0.6509	Remote Similarity	NPC476212
0.6508	Remote Similarity	NPC471303
0.6508	Remote Similarity	NPC472103
0.6507	Remote Similarity	NPC24370
0.6507	Remote Similarity	NPC22928
0.6507	Remote Similarity	NPC319232
0.6502	Remote Similarity	NPC314817
0.6502	Remote Similarity	NPC66191
0.6502	Remote Similarity	NPC316297
0.65	Remote Similarity	NPC469462
0.65	Remote Similarity	NPC471561
0.6498	Remote Similarity	NPC469452
0.6496	Remote Similarity	NPC17160
0.6496	Remote Similarity	NPC313720
0.6495	Remote Similarity	NPC476268
0.6495	Remote Similarity	NPC306376
0.6493	Remote Similarity	NPC259350
0.6493	Remote Similarity	NPC223236
0.6492	Remote Similarity	NPC254798
0.6486	Remote Similarity	NPC64205
0.6485	Remote Similarity	NPC181138
0.6485	Remote Similarity	NPC298851
0.6485	Remote Similarity	NPC210415
0.6485	Remote Similarity	NPC276993
0.6485	Remote Similarity	NPC469734
0.6485	Remote Similarity	NPC21752
0.6485	Remote Similarity	NPC293255
0.6484	Remote Similarity	NPC257266
0.6483	Remote Similarity	NPC469450
0.6481	Remote Similarity	NPC323198
0.6479	Remote Similarity	NPC476218
0.6479	Remote Similarity	NPC108804
0.6478	Remote Similarity	NPC473458
0.6476	Remote Similarity	NPC477532
0.6476	Remote Similarity	NPC128476
0.6473	Remote Similarity	NPC74969
0.6471	Remote Similarity	NPC9475
0.6468	Remote Similarity	NPC475123
0.6468	Remote Similarity	NPC475204
0.6468	Remote Similarity	NPC68328
0.6468	Remote Similarity	NPC14339
0.6465	Remote Similarity	NPC317727
0.6465	Remote Similarity	NPC85651
0.6465	Remote Similarity	NPC472121
0.6463	Remote Similarity	NPC231924
0.6462	Remote Similarity	NPC314083
0.6462	Remote Similarity	NPC328763
0.6461	Remote Similarity	NPC314882
0.646	Remote Similarity	NPC37957
0.646	Remote Similarity	NPC153923
0.646	Remote Similarity	NPC108826
0.646	Remote Similarity	NPC288110

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 NPC472330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	442
0.2-0.3	742
0.3-0.4	1667
0.4-0.5	2896
0.5-0.6	2761
0.6-0.7	485
0.7-0.8	6
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
0.7426	Intermediate Similarity	NPD4604	Approved
0.7426	Intermediate Similarity	NPD4605	Approved
0.7292	Intermediate Similarity	NPD2216	Approved
0.7292	Intermediate Similarity	NPD2215	Approved
0.7286	Intermediate Similarity	NPD4951	Discontinued
0.7228	Intermediate Similarity	NPD5937	Approved
0.7206	Intermediate Similarity	NPD8249	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2845	Phase 2
0.7044	Intermediate Similarity	NPD2843	Phase 2
0.7	Intermediate Similarity	NPD7883	Discontinued
0.6961	Remote Similarity	NPD7628	Phase 3
0.6961	Remote Similarity	NPD7630	Phase 3
0.6961	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6072	Discontinued
0.6816	Remote Similarity	NPD8364	Approved
0.6816	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8363	Approved
0.6796	Remote Similarity	NPD5928	Phase 1
0.6787	Remote Similarity	NPD7293	Approved
0.6761	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6905	Phase 2
0.672	Remote Similarity	NPD8465	Approved
0.672	Remote Similarity	NPD8428	Approved
0.672	Remote Similarity	NPD8467	Approved
0.672	Remote Similarity	NPD8466	Approved
0.672	Remote Similarity	NPD8429	Approved
0.672	Remote Similarity	NPD8427	Approved
0.6719	Remote Similarity	NPD5617	Suspended
0.6714	Remote Similarity	NPD7476	Discontinued
0.6712	Remote Similarity	NPD7827	Phase 1
0.6712	Remote Similarity	NPD7301	Phase 3
0.6704	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6283	Phase 2
0.6699	Remote Similarity	NPD5150	Phase 2
0.6683	Remote Similarity	NPD7479	Phase 2
0.6682	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7256	Discontinued
0.6667	Remote Similarity	NPD6519	Phase 2
0.6667	Remote Similarity	NPD8025	Phase 2
0.6651	Remote Similarity	NPD4668	Phase 2
0.665	Remote Similarity	NPD6184	Discontinued
0.663	Remote Similarity	NPD3554	Approved
0.663	Remote Similarity	NPD3555	Approved
0.663	Remote Similarity	NPD3552	Approved
0.663	Remote Similarity	NPD3553	Approved
0.6619	Remote Similarity	NPD5610	Approved
0.6614	Remote Similarity	NPD8460	Approved
0.6614	Remote Similarity	NPD8425	Approved
0.6614	Remote Similarity	NPD8426	Approved
0.6614	Remote Similarity	NPD8459	Approved
0.6606	Remote Similarity	NPD7300	Phase 3
0.6606	Remote Similarity	NPD7302	Phase 3
0.6604	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD8167	Discontinued
0.6598	Remote Similarity	NPD7105	Phase 1
0.6598	Remote Similarity	NPD3778	Approved
0.6593	Remote Similarity	NPD6405	Approved
0.6593	Remote Similarity	NPD6407	Approved
0.6588	Remote Similarity	NPD4771	Phase 2
0.6582	Remote Similarity	NPD3558	Approved
0.6582	Remote Similarity	NPD3556	Approved
0.6582	Remote Similarity	NPD3560	Approved
0.6582	Remote Similarity	NPD3557	Approved
0.6582	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD8019	Approved
0.656	Remote Similarity	NPD6296	Discontinued
0.656	Remote Similarity	NPD7263	Phase 2
0.6542	Remote Similarity	NPD6874	Approved
0.653	Remote Similarity	NPD7585	Approved
0.6526	Remote Similarity	NPD5651	Approved
0.6526	Remote Similarity	NPD5652	Approved
0.6526	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5650	Approved
0.6524	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7978	Discontinued
0.6524	Remote Similarity	NPD7283	Approved
0.6522	Remote Similarity	NPD6045	Phase 3
0.652	Remote Similarity	NPD5190	Phase 2
0.6515	Remote Similarity	NPD3453	Discontinued
0.6515	Remote Similarity	NPD8070	Approved
0.6513	Remote Similarity	NPD2789	Approved
0.6508	Remote Similarity	NPD3400	Discontinued
0.6495	Remote Similarity	NPD5811	Approved
0.649	Remote Similarity	NPD3154	Approved
0.649	Remote Similarity	NPD6339	Approved
0.649	Remote Similarity	NPD3153	Approved
0.649	Remote Similarity	NPD6340	Approved
0.6489	Remote Similarity	NPD7292	Approved
0.6488	Remote Similarity	NPD5445	Approved
0.6484	Remote Similarity	NPD3136	Phase 2
0.6484	Remote Similarity	NPD7583	Approved
0.648	Remote Similarity	NPD7495	Discontinued
0.6477	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD42	Phase 2
0.6471	Remote Similarity	NPD6042	Phase 2
0.6471	Remote Similarity	NPD4603	Phase 2
0.6465	Remote Similarity	NPD5608	Approved
0.6465	Remote Similarity	NPD5609	Approved
0.645	Remote Similarity	NPD4666	Phase 3
0.6449	Remote Similarity	NPD6034	Phase 2
0.6449	Remote Similarity	NPD7282	Approved
0.6447	Remote Similarity	NPD4335	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4003	Phase 3
0.6438	Remote Similarity	NPD3003	Approved
0.6436	Remote Similarity	NPD4150	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4083	Discontinued
0.6429	Remote Similarity	NPD5903	Approved
0.6429	Remote Similarity	NPD5902	Approved
0.6429	Remote Similarity	NPD6677	Suspended
0.6425	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5599	Discontinued
0.6411	Remote Similarity	NPD6967	Phase 2
0.641	Remote Similarity	NPD6723	Discontinued
0.64	Remote Similarity	NPD5709	Phase 3
0.64	Remote Similarity	NPD8149	Discontinued
0.6393	Remote Similarity	NPD1294	Discontinued
0.6393	Remote Similarity	NPD7891	Discontinued
0.639	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7565	Approved
0.6389	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7262	Phase 1
0.6385	Remote Similarity	NPD5984	Phase 2
0.638	Remote Similarity	NPD2916	Discontinued
0.6379	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6346	Approved
0.6377	Remote Similarity	NPD5039	Approved
0.6373	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6807	Phase 3
0.6359	Remote Similarity	NPD4956	Approved
0.6355	Remote Similarity	NPD4523	Approved
0.6351	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7542	Phase 3
0.6343	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7558	Phase 2
0.634	Remote Similarity	NPD8489	Phase 1
0.6336	Remote Similarity	NPD4086	Phase 1
0.6332	Remote Similarity	NPD6063	Approved
0.6325	Remote Similarity	NPD8067	Phase 3
0.6324	Remote Similarity	NPD2246	Approved
0.6324	Remote Similarity	NPD2248	Approved
0.6316	Remote Similarity	NPD5035	Approved
0.6316	Remote Similarity	NPD8461	Discontinued
0.6316	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2177	Approved
0.6313	Remote Similarity	NPD2175	Phase 3
0.6313	Remote Similarity	NPD2176	Approved
0.6311	Remote Similarity	NPD3965	Phase 1
0.6311	Remote Similarity	NPD3793	Phase 3
0.6305	Remote Similarity	NPD7608	Discontinued
0.6305	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD3119	Phase 1
0.6303	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD5037	Approved
0.6303	Remote Similarity	NPD3120	Approved
0.6303	Remote Similarity	NPD5038	Approved
0.6302	Remote Similarity	NPD8131	Suspended
0.6302	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD8162	Phase 2
0.63	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6527	Approved
0.6296	Remote Similarity	NPD2941	Discontinued
0.6296	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD5939	Approved
0.6295	Remote Similarity	NPD5936	Approved
0.6294	Remote Similarity	NPD3296	Phase 1
0.6293	Remote Similarity	NPD5033	Approved
0.6293	Remote Similarity	NPD5466	Approved
0.629	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7956	Approved
0.629	Remote Similarity	NPD7955	Approved
0.6289	Remote Similarity	NPD3536	Discontinued
0.6287	Remote Similarity	NPD3587	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6557	Phase 2
0.6286	Remote Similarity	NPD6851	Approved
0.6286	Remote Similarity	NPD6853	Approved
0.6286	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7599	Phase 2
0.6279	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6852	Discontinued
0.6274	Remote Similarity	NPD1339	Discontinued
0.6274	Remote Similarity	NPD7906	Approved
0.6273	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD5632	Approved
0.6269	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD7554	Discontinued
0.6268	Remote Similarity	NPD4012	Approved
0.6268	Remote Similarity	NPD5032	Approved
0.6267	Remote Similarity	NPD5856	Discontinued
0.6263	Remote Similarity	NPD2469	Approved
0.6263	Remote Similarity	NPD6913	Approved
0.6263	Remote Similarity	NPD2468	Approved
0.6263	Remote Similarity	NPD6809	Clinical (unspecified phase)

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