NPASS Compound

Structure

CID29472 OpenBabel06191715352D 24 28 0 0 0 0 0 0 0 0999 V2000 1.6150 -5.5207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2292 -2.7245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -3.6331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5738 -3.6329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7869 -1.3624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3595 -1.3630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6644 -3.7088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7872 -4.0872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7871 -2.2705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5729 -0.9084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -0.9081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5738 -2.7246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3593 -2.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7861 -1.3627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7859 -2.2708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5725 -2.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5730 -0.0003 0.0000 C 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 -2.2378 0.6642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7873 -5.0429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4014 -2.2467 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0341 -2.8791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7611 -3.6136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 8 2 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 23 1 0 0 0 0 7 24 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 16 2 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.08
Volume:	310.958
LogP:	4.498
LogD:	3.224
LogS:	-7.797
# Rotatable Bonds:	2
TPSA:	66.02
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.733
Synthetic Accessibility Score:	2.759
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.022
MDCK Permeability:	3.6336114135337994e-05
Pgp-inhibitor:	0.138
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	88.80668640136719%
Volume Distribution (VD):	0.952
Pgp-substrate:	7.664941310882568%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.77
CYP2C19-substrate:	0.613
CYP2C9-inhibitor:	0.593
CYP2C9-substrate:	0.908
CYP2D6-inhibitor:	0.812
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.7
CYP3A4-substrate:	0.091

ADMET: Excretion

Clearance (CL):	9.953
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.773
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.698
Carcinogencity:	0.888
Eye Corrosion:	0.004
Eye Irritation:	0.364
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC29472

Natural Product ID:	NPC29472
*Common Name:**	IVQJJWTYXXUJQG-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IVQJJWTYXXUJQG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13NO5/c1-21-8-3-10-9(13(4-8)22-2)5-12-15-11(18(20)19-12)6-14-17(16(10)15)24-7-23-14/h3-6H,7H2,1-2H3,(H,19,20)
SMILES:	COc1cc2c(cc3c4c(cc5c(c24)OCO5)C(=N3)O)c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598535
PubChem CID:	5319404
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002663] Aristolactams

*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
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	amniotic fluid	n.a.	Database[Article]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7557	Aristolochia mollissima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	15000.0	nM	PMID[552767]

☑ 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 NPC29472 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	457
0.1-0.2	2119
0.2-0.3	9044
0.3-0.4	8952
0.4-0.5	6653
0.5-0.6	11599
0.6-0.7	3447
0.7-0.8	392
0.8-0.85	14
0.85-0.9	4
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9653	High Similarity	NPC296742
0.9595	High Similarity	NPC224293
0.954	High Similarity	NPC112676
0.9538	High Similarity	NPC69213
0.9425	High Similarity	NPC180253
0.9425	High Similarity	NPC219170
0.9422	High Similarity	NPC276060
0.9261	High Similarity	NPC22928
0.9249	High Similarity	NPC260118
0.9195	High Similarity	NPC215747
0.9195	High Similarity	NPC192939
0.9191	High Similarity	NPC265383
0.9091	High Similarity	NPC28425
0.9034	High Similarity	NPC119579
0.9027	High Similarity	NPC159101
0.8977	High Similarity	NPC311936
0.8895	High Similarity	NPC294244
0.8232	Intermediate Similarity	NPC228040
0.8182	Intermediate Similarity	NPC312531
0.8125	Intermediate Similarity	NPC235628
0.81	Intermediate Similarity	NPC290227
0.8063	Intermediate Similarity	NPC162653
0.806	Intermediate Similarity	NPC240684
0.8033	Intermediate Similarity	NPC474051
0.7989	Intermediate Similarity	NPC474904
0.7968	Intermediate Similarity	NPC249405
0.7956	Intermediate Similarity	NPC68328
0.788	Intermediate Similarity	NPC231371
0.785	Intermediate Similarity	NPC85661
0.7842	Intermediate Similarity	NPC57036
0.7842	Intermediate Similarity	NPC320088
0.7829	Intermediate Similarity	NPC77359
0.7807	Intermediate Similarity	NPC190461
0.78	Intermediate Similarity	NPC46679
0.7784	Intermediate Similarity	NPC19520
0.7784	Intermediate Similarity	NPC149090
0.7772	Intermediate Similarity	NPC302001
0.7761	Intermediate Similarity	NPC121510
0.7761	Intermediate Similarity	NPC171882
0.7725	Intermediate Similarity	NPC179704
0.7714	Intermediate Similarity	NPC16436
0.7708	Intermediate Similarity	NPC476576
0.7708	Intermediate Similarity	NPC186546
0.768	Intermediate Similarity	NPC78284
0.7672	Intermediate Similarity	NPC258695
0.7672	Intermediate Similarity	NPC470879
0.7668	Intermediate Similarity	NPC82763
0.766	Intermediate Similarity	NPC287588
0.7656	Intermediate Similarity	NPC214116
0.765	Intermediate Similarity	NPC38961
0.7647	Intermediate Similarity	NPC91234
0.7644	Intermediate Similarity	NPC33902
0.7644	Intermediate Similarity	NPC276674
0.7632	Intermediate Similarity	NPC32413
0.7632	Intermediate Similarity	NPC474506
0.7619	Intermediate Similarity	NPC114364
0.7619	Intermediate Similarity	NPC320223
0.7606	Intermediate Similarity	NPC229166
0.7606	Intermediate Similarity	NPC128560
0.7606	Intermediate Similarity	NPC199465
0.7598	Intermediate Similarity	NPC18614
0.7594	Intermediate Similarity	NPC168153
0.7586	Intermediate Similarity	NPC168250
0.7581	Intermediate Similarity	NPC182257
0.7562	Intermediate Similarity	NPC156728
0.7562	Intermediate Similarity	NPC244606
0.7553	Intermediate Similarity	NPC285941
0.7542	Intermediate Similarity	NPC52475
0.7527	Intermediate Similarity	NPC210918
0.7527	Intermediate Similarity	NPC247389
0.7526	Intermediate Similarity	NPC23219
0.7525	Intermediate Similarity	NPC261388
0.7514	Intermediate Similarity	NPC302527
0.7514	Intermediate Similarity	NPC167546
0.7514	Intermediate Similarity	NPC16805
0.75	Intermediate Similarity	NPC248642
0.75	Intermediate Similarity	NPC117717
0.75	Intermediate Similarity	NPC239775
0.7474	Intermediate Similarity	NPC112575
0.7473	Intermediate Similarity	NPC476432
0.7473	Intermediate Similarity	NPC24264
0.7473	Intermediate Similarity	NPC219341
0.7461	Intermediate Similarity	NPC156576
0.7461	Intermediate Similarity	NPC135772
0.746	Intermediate Similarity	NPC110374
0.746	Intermediate Similarity	NPC289743
0.7448	Intermediate Similarity	NPC312918
0.7448	Intermediate Similarity	NPC477561
0.7448	Intermediate Similarity	NPC155442
0.7448	Intermediate Similarity	NPC476574
0.7433	Intermediate Similarity	NPC298979
0.7432	Intermediate Similarity	NPC195766
0.7432	Intermediate Similarity	NPC206736
0.7429	Intermediate Similarity	NPC148409
0.7427	Intermediate Similarity	NPC186569
0.7427	Intermediate Similarity	NPC61731
0.7421	Intermediate Similarity	NPC477558
0.7419	Intermediate Similarity	NPC225774
0.7413	Intermediate Similarity	NPC295676
0.7409	Intermediate Similarity	NPC116284
0.74	Intermediate Similarity	NPC212163
0.7396	Intermediate Similarity	NPC126284
0.7391	Intermediate Similarity	NPC329837
0.7391	Intermediate Similarity	NPC69360
0.7383	Intermediate Similarity	NPC200888
0.7382	Intermediate Similarity	NPC1291
0.7382	Intermediate Similarity	NPC115343
0.7356	Intermediate Similarity	NPC227361
0.7356	Intermediate Similarity	NPC124658
0.7354	Intermediate Similarity	NPC168753
0.7354	Intermediate Similarity	NPC6152
0.7354	Intermediate Similarity	NPC118274
0.734	Intermediate Similarity	NPC304846
0.7333	Intermediate Similarity	NPC211296
0.7326	Intermediate Similarity	NPC89199
0.7326	Intermediate Similarity	NPC54125
0.7324	Intermediate Similarity	NPC122463
0.7324	Intermediate Similarity	NPC118121
0.7318	Intermediate Similarity	NPC33832
0.7312	Intermediate Similarity	NPC24954
0.7306	Intermediate Similarity	NPC474507
0.7299	Intermediate Similarity	NPC204446
0.7296	Intermediate Similarity	NPC475919
0.7296	Intermediate Similarity	NPC474009
0.7296	Intermediate Similarity	NPC474661
0.7288	Intermediate Similarity	NPC191231
0.7278	Intermediate Similarity	NPC116019
0.7268	Intermediate Similarity	NPC10730
0.7268	Intermediate Similarity	NPC10875
0.7264	Intermediate Similarity	NPC193906
0.7264	Intermediate Similarity	NPC108826
0.7264	Intermediate Similarity	NPC23080
0.7263	Intermediate Similarity	NPC474953
0.7263	Intermediate Similarity	NPC152212
0.7258	Intermediate Similarity	NPC306902
0.7258	Intermediate Similarity	NPC266753
0.7258	Intermediate Similarity	NPC477559
0.7258	Intermediate Similarity	NPC232924
0.7258	Intermediate Similarity	NPC160298
0.7257	Intermediate Similarity	NPC266006
0.7254	Intermediate Similarity	NPC148693
0.7254	Intermediate Similarity	NPC294790
0.7254	Intermediate Similarity	NPC118633
0.7249	Intermediate Similarity	NPC117188
0.7249	Intermediate Similarity	NPC145832
0.7249	Intermediate Similarity	NPC205421
0.7249	Intermediate Similarity	NPC81218
0.7249	Intermediate Similarity	NPC158376
0.7249	Intermediate Similarity	NPC474931
0.7249	Intermediate Similarity	NPC204947
0.7249	Intermediate Similarity	NPC306555
0.7249	Intermediate Similarity	NPC12053
0.724	Intermediate Similarity	NPC187678
0.7238	Intermediate Similarity	NPC235076
0.7234	Intermediate Similarity	NPC196447
0.7234	Intermediate Similarity	NPC212794
0.7234	Intermediate Similarity	NPC136508
0.7234	Intermediate Similarity	NPC13504
0.7234	Intermediate Similarity	NPC306843
0.7234	Intermediate Similarity	NPC477563
0.7234	Intermediate Similarity	NPC78222
0.7234	Intermediate Similarity	NPC253043
0.7234	Intermediate Similarity	NPC96603
0.7231	Intermediate Similarity	NPC476575
0.7216	Intermediate Similarity	NPC475794
0.7216	Intermediate Similarity	NPC77572
0.7216	Intermediate Similarity	NPC105847
0.7216	Intermediate Similarity	NPC243759
0.7216	Intermediate Similarity	NPC218131
0.7212	Intermediate Similarity	NPC188420
0.7202	Intermediate Similarity	NPC476577
0.7202	Intermediate Similarity	NPC283999
0.7202	Intermediate Similarity	NPC148709
0.7202	Intermediate Similarity	NPC173416
0.72	Intermediate Similarity	NPC254610
0.7198	Intermediate Similarity	NPC329329
0.7198	Intermediate Similarity	NPC90185
0.7198	Intermediate Similarity	NPC317709
0.7198	Intermediate Similarity	NPC265473
0.7198	Intermediate Similarity	NPC276665
0.7193	Intermediate Similarity	NPC183537
0.719	Intermediate Similarity	NPC474594
0.7183	Intermediate Similarity	NPC256422
0.7183	Intermediate Similarity	NPC46451
0.7181	Intermediate Similarity	NPC19555
0.7181	Intermediate Similarity	NPC324144
0.7179	Intermediate Similarity	NPC474607
0.7175	Intermediate Similarity	NPC308768
0.7175	Intermediate Similarity	NPC12668
0.7159	Intermediate Similarity	NPC151656
0.7159	Intermediate Similarity	NPC230919
0.7159	Intermediate Similarity	NPC200935
0.7159	Intermediate Similarity	NPC196420
0.7159	Intermediate Similarity	NPC266453
0.7159	Intermediate Similarity	NPC22902
0.7157	Intermediate Similarity	NPC9867
0.7151	Intermediate Similarity	NPC476572
0.715	Intermediate Similarity	NPC174049
0.7143	Intermediate Similarity	NPC474650
0.7143	Intermediate Similarity	NPC251160

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 NPC29472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	788
0.2-0.3	1041
0.3-0.4	2240
0.4-0.5	2667
0.5-0.6	1723
0.6-0.7	375
0.7-0.8	14
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
0.7432	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4005	Discontinued
0.7202	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3763	Approved
0.7172	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4055	Discovery
0.712	Intermediate Similarity	NPD5617	Suspended
0.7105	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8067	Phase 3
0.7083	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5811	Approved
0.7011	Intermediate Similarity	NPD2883	Discontinued
0.6984	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7827	Phase 1
0.698	Remote Similarity	NPD7125	Discontinued
0.6979	Remote Similarity	NPD4083	Discontinued
0.6951	Remote Similarity	NPD6723	Discontinued
0.695	Remote Similarity	NPD3349	Phase 2
0.6939	Remote Similarity	NPD6184	Discontinued
0.6935	Remote Similarity	NPD4675	Approved
0.6935	Remote Similarity	NPD4678	Approved
0.6911	Remote Similarity	NPD1850	Phase 3
0.6862	Remote Similarity	NPD37	Approved
0.6842	Remote Similarity	NPD4967	Phase 2
0.6842	Remote Similarity	NPD4966	Approved
0.6842	Remote Similarity	NPD4965	Approved
0.6832	Remote Similarity	NPD2843	Phase 2
0.6832	Remote Similarity	NPD2845	Phase 2
0.6829	Remote Similarity	NPD5582	Discontinued
0.6809	Remote Similarity	NPD3778	Approved
0.6806	Remote Similarity	NPD3453	Discontinued
0.6802	Remote Similarity	NPD3920	Phase 2
0.6793	Remote Similarity	NPD4357	Discontinued
0.6782	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6234	Discontinued
0.6755	Remote Similarity	NPD3296	Phase 1
0.675	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7263	Phase 2
0.6744	Remote Similarity	NPD3815	Phase 1
0.6744	Remote Similarity	NPD3816	Phase 1
0.6738	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5604	Discontinued
0.6716	Remote Similarity	NPD5641	Discontinued
0.6716	Remote Similarity	NPD8054	Approved
0.6716	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8053	Approved
0.6714	Remote Similarity	NPD4859	Phase 1
0.6714	Remote Similarity	NPD3515	Approved
0.6714	Remote Similarity	NPD3516	Approved
0.6713	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2821	Approved
0.67	Remote Similarity	NPD7906	Approved
0.6685	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4123	Phase 3
0.6667	Remote Similarity	NPD3051	Approved
0.6651	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4951	Discontinued
0.6649	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4003	Phase 3
0.6649	Remote Similarity	NPD6746	Phase 2
0.6635	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2970	Approved
0.6633	Remote Similarity	NPD2969	Approved
0.6632	Remote Similarity	NPD5090	Approved
0.6632	Remote Similarity	NPD3236	Phase 3
0.6632	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD2789	Approved
0.6632	Remote Similarity	NPD5089	Approved
0.6618	Remote Similarity	NPD1898	Discontinued
0.6617	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8099	Discontinued
0.6616	Remote Similarity	NPD8252	Approved
0.6616	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD8251	Approved
0.6611	Remote Similarity	NPD4097	Suspended
0.661	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4577	Approved
0.6584	Remote Similarity	NPD4578	Approved
0.6583	Remote Similarity	NPD5810	Discontinued
0.6583	Remote Similarity	NPD8156	Discontinued
0.6569	Remote Similarity	NPD4663	Approved
0.6566	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1375	Discontinued
0.6555	Remote Similarity	NPD7034	Discontinued
0.6555	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7479	Phase 2
0.6543	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6612	Phase 2
0.6538	Remote Similarity	NPD4108	Discontinued
0.6537	Remote Similarity	NPD6842	Approved
0.6537	Remote Similarity	NPD5800	Discontinued
0.6537	Remote Similarity	NPD6843	Phase 3
0.6537	Remote Similarity	NPD6841	Approved
0.6537	Remote Similarity	NPD3398	Discontinued
0.6533	Remote Similarity	NPD7228	Approved
0.6531	Remote Similarity	NPD7199	Phase 2
0.6531	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD5599	Discontinued
0.6522	Remote Similarity	NPD3923	Approved
0.6522	Remote Similarity	NPD3921	Approved
0.6522	Remote Similarity	NPD3922	Approved
0.6522	Remote Similarity	NPD3924	Approved
0.6517	Remote Similarity	NPD7007	Discovery
0.6515	Remote Similarity	NPD2489	Approved
0.6515	Remote Similarity	NPD27	Approved
0.6515	Remote Similarity	NPD677	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6625	Approved
0.6507	Remote Similarity	NPD6494	Phase 2
0.6502	Remote Similarity	NPD7312	Approved
0.6502	Remote Similarity	NPD7311	Approved
0.6502	Remote Similarity	NPD7310	Approved
0.6502	Remote Similarity	NPD7313	Approved
0.6498	Remote Similarity	NPD8367	Approved
0.6497	Remote Similarity	NPD6232	Discontinued
0.6495	Remote Similarity	NPD6788	Approved
0.649	Remote Similarity	NPD7262	Phase 1
0.6486	Remote Similarity	NPD6674	Discontinued
0.6479	Remote Similarity	NPD5006	Approved
0.6479	Remote Similarity	NPD5005	Approved
0.6473	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7309	Approved
0.6465	Remote Similarity	NPD5530	Phase 1
0.6465	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8492	Approved
0.6452	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6331	Phase 2
0.6448	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD2674	Phase 3
0.6443	Remote Similarity	NPD2563	Approved
0.6443	Remote Similarity	NPD2560	Approved
0.6442	Remote Similarity	NPD3963	Phase 1
0.644	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4481	Phase 3
0.6429	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7546	Discontinued
0.6417	Remote Similarity	NPD5241	Discontinued
0.6417	Remote Similarity	NPD3301	Approved
0.6413	Remote Similarity	NPD2161	Phase 2
0.641	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6502	Phase 2
0.6404	Remote Similarity	NPD7654	Discontinued
0.6402	Remote Similarity	NPD4584	Approved
0.64	Remote Similarity	NPD7473	Discontinued
0.6398	Remote Similarity	NPD4604	Approved
0.6398	Remote Similarity	NPD4605	Approved
0.6398	Remote Similarity	NPD6527	Approved
0.6396	Remote Similarity	NPD5164	Discontinued
0.6396	Remote Similarity	NPD6037	Discontinued
0.6392	Remote Similarity	NPD2978	Approved
0.6392	Remote Similarity	NPD2977	Approved
0.6381	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD8151	Discontinued
0.6373	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD4420	Approved
0.6364	Remote Similarity	NPD3983	Phase 3
0.6364	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD6339	Approved
0.6359	Remote Similarity	NPD6340	Approved
0.6356	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD2421	Approved
0.6349	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD2420	Approved
0.6343	Remote Similarity	NPD3705	Approved
0.634	Remote Similarity	NPD7417	Discontinued
0.6337	Remote Similarity	NPD5844	Phase 1
0.6333	Remote Similarity	NPD4625	Phase 3
0.6333	Remote Similarity	NPD3027	Phase 3
0.6332	Remote Similarity	NPD6071	Discontinued
0.633	Remote Similarity	NPD2219	Phase 1
0.6324	Remote Similarity	NPD7240	Approved
0.6321	Remote Similarity	NPD2973	Approved
0.6321	Remote Similarity	NPD2975	Approved
0.6321	Remote Similarity	NPD2974	Approved
0.6318	Remote Similarity	NPD4502	Phase 2
0.6313	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD5929	Approved
0.6298	Remote Similarity	NPD3144	Approved
0.6298	Remote Similarity	NPD3145	Approved
0.6294	Remote Similarity	NPD7833	Phase 2
0.6294	Remote Similarity	NPD7831	Phase 2
0.6294	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3634	Approved
0.6286	Remote Similarity	NPD3633	Approved
0.6284	Remote Similarity	NPD5429	Discontinued
0.6282	Remote Similarity	NPD5805	Approved
0.6279	Remote Similarity	NPD3452	Approved
0.6279	Remote Similarity	NPD2493	Approved
0.6279	Remote Similarity	NPD2494	Approved
0.6279	Remote Similarity	NPD3450	Approved
0.6278	Remote Similarity	NPD1529	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