NPASS Compound

Structure

NPC197972 OpenBabel07101718332D 45 51 0 0 1 0 0 0 0 0999 V2000 -7.2072 -1.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5925 -3.6837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2967 2.5511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9774 -0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6774 0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1063 -0.6646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9779 -1.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 -1.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3356 0.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9715 -1.9045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2383 -1.1335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3356 -0.6646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5925 -2.6773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4747 -1.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1063 0.3418 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5925 -0.6646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6183 -0.6561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 0.8450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3316 -1.7428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0182 0.5197 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0058 -0.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5925 0.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0590 -1.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9592 -0.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8494 0.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9779 0.8450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 0.8450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6001 -1.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3591 -0.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 -1.1677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2559 1.7587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8494 -0.6646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6591 -0.0341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4641 -2.1741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0758 -1.5524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4641 1.8514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3139 -2.5149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5607 1.4161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9779 1.8514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 1.8514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0576 -2.0721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2609 1.8107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2917 2.6031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7210 -2.1741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 43 1 0 0 0 0 4 5 2 0 0 0 0 4 17 1 0 0 0 0 5 20 1 0 0 0 0 6 7 2 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 32 1 0 0 0 0 13 34 2 0 0 0 0 13 44 1 0 0 0 0 14 21 1 0 0 0 0 15 6 1 1 0 0 0 15 21 1 0 0 0 0 15 26 1 0 0 0 0 16 22 2 0 0 0 0 16 30 1 0 0 0 0 17 24 2 0 0 0 0 17 35 1 0 0 0 0 18 22 1 0 0 0 0 18 36 1 0 0 0 0 19 23 2 0 0 0 0 19 37 1 0 0 0 0 20 33 1 6 0 0 0 20 38 1 0 0 0 0 21 29 2 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 25 32 1 0 0 0 0 26 39 2 0 0 0 0 27 40 1 0 0 0 0 28 41 2 0 0 0 0 29 45 1 0 0 0 0 30 32 1 1 0 0 0 30 44 1 0 0 0 0 31 42 2 0 0 0 0 31 43 1 0 0 0 0 32 7 1 1 0 0 0 33 31 1 6 0 0 0 33 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.14
Volume:	588.001
LogP:	3.307
LogD:	1.014
LogS:	-5.828
# Rotatable Bonds:	4
TPSA:	190.8
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	6.549
Fsp3:	0.333
Lipinski Rule-of-5:	Rejected
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:	-5.951
MDCK Permeability:	1.1205539522052277e-05
Pgp-inhibitor:	0.531
Pgp-substrate:	0.957
Human Intestinal Absorption (HIA):	0.756
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	89.55646514892578%
Volume Distribution (VD):	0.506
Pgp-substrate:	3.885579824447632%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.406
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.175
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	1.191
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.845
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.606
Rat Oral Acute Toxicity:	0.51
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.261
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.604

Download Data

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

Natural Product: NPC197972

Natural Product ID:	NPC197972
*Common Name:**	CJJVWWCXCQUGER-UAZACNSMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CJJVWWCXCQUGER-UAZACNSMSA-N
Standard InCHI:	InChI=1S/C33H26O12/c1-12-8-16-22(18(36)9-12)27(40)25-26(39)15-6-7-32(25,30(16)44-13(2)34)11-14-10-19(37)23-28(41)24-17(35)4-5-20(38)33(24,31(42)43-3)45-29(23)21(14)15/h4-10,15,20,30,35-38,40H,11H2,1-3H3/t15-,20+,30-,32-,33-/m0/s1
SMILES:	Cc1cc2c(c(c1)O)C(=C1C(=O)[C@H]3C=C[C@@]1(Cc1cc(c4C(=O)C5=C(C=C[C@H]([C@]5(C(=O)OC)Oc4c31)O)O)O)[C@H]2OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2408940
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO22864	Purpureocillium lilacinum	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23876004]
NPO22864	Purpureocillium lilacinum	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Kd	1
Others	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Activity	=	63.0	%	PMID[517606]
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Activity	=	47.0	%	PMID[517606]
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Ratio	=	70.0	n.a.	PMID[517606]
NPT1621	Individual Protein	Calmodulin	Homo sapiens	Kd	=	18.25	nM	PMID[517606]

☑ 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 NPC197972 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	419
0.1-0.2	1554
0.2-0.3	3327
0.3-0.4	7283
0.4-0.5	10511
0.5-0.6	5015
0.6-0.7	5769
0.7-0.8	7593
0.8-0.85	1126
0.85-0.9	77
0.9-0.95	13
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC477683
0.9474	High Similarity	NPC477682
0.9357	High Similarity	NPC232412
0.9357	High Similarity	NPC86809
0.9357	High Similarity	NPC98667
0.9302	High Similarity	NPC469345
0.9186	High Similarity	NPC154986
0.9106	High Similarity	NPC48474
0.907	High Similarity	NPC251144
0.907	High Similarity	NPC241387
0.9006	High Similarity	NPC178173
0.896	High Similarity	NPC241874
0.8927	High Similarity	NPC208069
0.8914	High Similarity	NPC294149
0.8908	High Similarity	NPC472620
0.8902	High Similarity	NPC207574
0.8902	High Similarity	NPC291795
0.8902	High Similarity	NPC297195
0.8876	High Similarity	NPC475656
0.8876	High Similarity	NPC475148
0.883	High Similarity	NPC473961
0.8793	High Similarity	NPC472619
0.8757	High Similarity	NPC324220
0.8757	High Similarity	NPC312630
0.875	High Similarity	NPC469393
0.8743	High Similarity	NPC315306
0.8743	High Similarity	NPC313717
0.8743	High Similarity	NPC193698
0.8736	High Similarity	NPC314672
0.8728	High Similarity	NPC71390
0.8686	High Similarity	NPC286074
0.8686	High Similarity	NPC54903
0.8686	High Similarity	NPC473095
0.8686	High Similarity	NPC473096
0.8655	High Similarity	NPC186113
0.8629	High Similarity	NPC472622
0.8629	High Similarity	NPC225419
0.8629	High Similarity	NPC473094
0.8621	High Similarity	NPC472057
0.8621	High Similarity	NPC472051
0.8613	High Similarity	NPC472059
0.8613	High Similarity	NPC473022
0.8611	High Similarity	NPC475161
0.8611	High Similarity	NPC477860
0.8603	High Similarity	NPC470334
0.8596	High Similarity	NPC68381
0.8588	High Similarity	NPC473113
0.8588	High Similarity	NPC237560
0.8571	High Similarity	NPC120857
0.8571	High Similarity	NPC472621
0.8571	High Similarity	NPC85047
0.8571	High Similarity	NPC17274
0.8571	High Similarity	NPC469394
0.8563	High Similarity	NPC472053
0.8556	High Similarity	NPC473607
0.8548	High Similarity	NPC470198
0.8548	High Similarity	NPC470194
0.8548	High Similarity	NPC470195
0.8548	High Similarity	NPC470197
0.8548	High Similarity	NPC470200
0.8548	High Similarity	NPC282474
0.8548	High Similarity	NPC316274
0.8548	High Similarity	NPC470196
0.8548	High Similarity	NPC470193
0.8547	High Similarity	NPC475246
0.8538	High Similarity	NPC154341
0.8531	High Similarity	NPC298778
0.8529	High Similarity	NPC135522
0.8523	High Similarity	NPC324522
0.8523	High Similarity	NPC470341
0.8523	High Similarity	NPC472058
0.8523	High Similarity	NPC105414
0.8523	High Similarity	NPC234497
0.8514	High Similarity	NPC316262
0.8514	High Similarity	NPC314653
0.8511	High Similarity	NPC131405
0.85	High Similarity	NPC476199
0.85	High Similarity	NPC233978
0.85	High Similarity	NPC476210
0.8497	Intermediate Similarity	NPC472618
0.8497	Intermediate Similarity	NPC472055
0.8495	Intermediate Similarity	NPC314020
0.8492	Intermediate Similarity	NPC470454
0.8492	Intermediate Similarity	NPC474345
0.8492	Intermediate Similarity	NPC3718
0.8492	Intermediate Similarity	NPC199533
0.8488	Intermediate Similarity	NPC246466
0.8483	Intermediate Similarity	NPC76128
0.8483	Intermediate Similarity	NPC315619
0.8483	Intermediate Similarity	NPC271385
0.8483	Intermediate Similarity	NPC5029
0.8483	Intermediate Similarity	NPC30432
0.8483	Intermediate Similarity	NPC118128
0.8483	Intermediate Similarity	NPC111536
0.848	Intermediate Similarity	NPC471116
0.848	Intermediate Similarity	NPC326910
0.8475	Intermediate Similarity	NPC217378
0.8475	Intermediate Similarity	NPC246274
0.8475	Intermediate Similarity	NPC20734
0.8471	Intermediate Similarity	NPC253904
0.8471	Intermediate Similarity	NPC321363
0.8471	Intermediate Similarity	NPC281272
0.8466	Intermediate Similarity	NPC125465
0.8462	Intermediate Similarity	NPC475662
0.8462	Intermediate Similarity	NPC182693
0.8462	Intermediate Similarity	NPC293227
0.8462	Intermediate Similarity	NPC473631
0.8462	Intermediate Similarity	NPC473717
0.8457	Intermediate Similarity	NPC469395
0.8453	Intermediate Similarity	NPC299149
0.8453	Intermediate Similarity	NPC114257
0.8453	Intermediate Similarity	NPC277710
0.8453	Intermediate Similarity	NPC245059
0.8453	Intermediate Similarity	NPC153578
0.8453	Intermediate Similarity	NPC244903
0.8453	Intermediate Similarity	NPC473729
0.8453	Intermediate Similarity	NPC84494
0.8448	Intermediate Similarity	NPC219686
0.8448	Intermediate Similarity	NPC117985
0.8444	Intermediate Similarity	NPC475233
0.8444	Intermediate Similarity	NPC98943
0.8444	Intermediate Similarity	NPC46958
0.8441	Intermediate Similarity	NPC314459
0.8441	Intermediate Similarity	NPC470199
0.8439	Intermediate Similarity	NPC474373
0.8439	Intermediate Similarity	NPC4950
0.8439	Intermediate Similarity	NPC470339
0.8436	Intermediate Similarity	NPC131862
0.8436	Intermediate Similarity	NPC472054
0.8436	Intermediate Similarity	NPC476139
0.8436	Intermediate Similarity	NPC229051
0.8436	Intermediate Similarity	NPC476229
0.8436	Intermediate Similarity	NPC476152
0.8436	Intermediate Similarity	NPC476311
0.843	Intermediate Similarity	NPC20530
0.843	Intermediate Similarity	NPC215917
0.843	Intermediate Similarity	NPC164427
0.843	Intermediate Similarity	NPC472050
0.843	Intermediate Similarity	NPC10754
0.8427	Intermediate Similarity	NPC313304
0.8424	Intermediate Similarity	NPC174486
0.8424	Intermediate Similarity	NPC105591
0.8418	Intermediate Similarity	NPC474024
0.8418	Intermediate Similarity	NPC76647
0.8418	Intermediate Similarity	NPC283041
0.8418	Intermediate Similarity	NPC63470
0.8415	Intermediate Similarity	NPC106700
0.8412	Intermediate Similarity	NPC46564
0.8412	Intermediate Similarity	NPC39819
0.8412	Intermediate Similarity	NPC207346
0.8409	Intermediate Similarity	NPC472049
0.8409	Intermediate Similarity	NPC178281
0.8407	Intermediate Similarity	NPC470452
0.8407	Intermediate Similarity	NPC315221
0.8407	Intermediate Similarity	NPC164047
0.8407	Intermediate Similarity	NPC470448
0.8407	Intermediate Similarity	NPC470453
0.84	Intermediate Similarity	NPC475106
0.84	Intermediate Similarity	NPC472402
0.8391	Intermediate Similarity	NPC313368
0.8391	Intermediate Similarity	NPC471976
0.8391	Intermediate Similarity	NPC470810
0.8389	Intermediate Similarity	NPC162248
0.8389	Intermediate Similarity	NPC63105
0.8389	Intermediate Similarity	NPC477991
0.8389	Intermediate Similarity	NPC477992
0.8389	Intermediate Similarity	NPC245975
0.8382	Intermediate Similarity	NPC472889
0.8382	Intermediate Similarity	NPC282390
0.8382	Intermediate Similarity	NPC44199
0.8382	Intermediate Similarity	NPC281137
0.8382	Intermediate Similarity	NPC158542
0.838	Intermediate Similarity	NPC477529
0.838	Intermediate Similarity	NPC477836
0.838	Intermediate Similarity	NPC476159
0.8372	Intermediate Similarity	NPC207809
0.8372	Intermediate Similarity	NPC304745
0.8372	Intermediate Similarity	NPC170189
0.8372	Intermediate Similarity	NPC476169
0.8372	Intermediate Similarity	NPC69043
0.8372	Intermediate Similarity	NPC217706
0.8372	Intermediate Similarity	NPC175192
0.8372	Intermediate Similarity	NPC48579
0.8372	Intermediate Similarity	NPC259710
0.8372	Intermediate Similarity	NPC111341
0.8372	Intermediate Similarity	NPC304207
0.8372	Intermediate Similarity	NPC478230
0.8372	Intermediate Similarity	NPC208173
0.8371	Intermediate Similarity	NPC177480
0.8371	Intermediate Similarity	NPC326877
0.8371	Intermediate Similarity	NPC259905
0.8371	Intermediate Similarity	NPC102810
0.8371	Intermediate Similarity	NPC222455
0.837	Intermediate Similarity	NPC221140
0.837	Intermediate Similarity	NPC475352
0.837	Intermediate Similarity	NPC475220
0.837	Intermediate Similarity	NPC87583
0.837	Intermediate Similarity	NPC229817
0.837	Intermediate Similarity	NPC473686
0.8363	Intermediate Similarity	NPC216035

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 NPC197972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	946
0.2-0.3	1865
0.3-0.4	2596
0.4-0.5	1866
0.5-0.6	924
0.6-0.7	419
0.7-0.8	144
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8525	High Similarity	NPD7879	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7075	Discontinued
0.8268	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD5402	Approved
0.8208	Intermediate Similarity	NPD7819	Suspended
0.8208	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD8150	Discontinued
0.8156	Intermediate Similarity	NPD7473	Discontinued
0.815	Intermediate Similarity	NPD6801	Discontinued
0.8142	Intermediate Similarity	NPD8312	Approved
0.8142	Intermediate Similarity	NPD8313	Approved
0.814	Intermediate Similarity	NPD6599	Discontinued
0.8136	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6166	Phase 2
0.809	Intermediate Similarity	NPD6232	Discontinued
0.8087	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8066	Intermediate Similarity	NPD5844	Phase 1
0.8035	Intermediate Similarity	NPD4380	Phase 2
0.8033	Intermediate Similarity	NPD6559	Discontinued
0.8011	Intermediate Similarity	NPD8434	Phase 2
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD7435	Discontinued
0.7989	Intermediate Similarity	NPD7808	Phase 3
0.7978	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD6797	Phase 2
0.7965	Intermediate Similarity	NPD5403	Approved
0.7955	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD3817	Phase 2
0.7935	Intermediate Similarity	NPD7251	Discontinued
0.7926	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD3751	Discontinued
0.7865	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD5401	Approved
0.7849	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD1934	Approved
0.7839	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7839	Intermediate Similarity	NPD7874	Approved
0.7835	Intermediate Similarity	NPD6781	Approved
0.7835	Intermediate Similarity	NPD6778	Approved
0.7835	Intermediate Similarity	NPD6782	Approved
0.7835	Intermediate Similarity	NPD6777	Approved
0.7835	Intermediate Similarity	NPD6780	Approved
0.7835	Intermediate Similarity	NPD6776	Approved
0.7835	Intermediate Similarity	NPD6779	Approved
0.7826	Intermediate Similarity	NPD7074	Phase 3
0.7809	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6799	Approved
0.7784	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD5494	Approved
0.7772	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD3226	Approved
0.7746	Intermediate Similarity	NPD2533	Approved
0.7746	Intermediate Similarity	NPD2532	Approved
0.7746	Intermediate Similarity	NPD2534	Approved
0.773	Intermediate Similarity	NPD7472	Approved
0.7719	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3750	Approved
0.7716	Intermediate Similarity	NPD7696	Phase 3
0.7716	Intermediate Similarity	NPD7697	Approved
0.7716	Intermediate Similarity	NPD7698	Approved
0.7709	Intermediate Similarity	NPD3882	Suspended
0.7709	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7677	Intermediate Similarity	NPD8320	Phase 1
0.7677	Intermediate Similarity	NPD8319	Approved
0.7677	Intermediate Similarity	NPD7871	Phase 2
0.7677	Intermediate Similarity	NPD7870	Phase 2
0.7672	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7701	Phase 2
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7624	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7783	Phase 2
0.7624	Intermediate Similarity	NPD7801	Approved
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD4628	Phase 3
0.7612	Intermediate Similarity	NPD8151	Discontinued
0.7577	Intermediate Similarity	NPD6535	Approved
0.7577	Intermediate Similarity	NPD6534	Approved
0.7571	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3749	Approved
0.7551	Intermediate Similarity	NPD7699	Phase 2
0.7551	Intermediate Similarity	NPD7700	Phase 2
0.7544	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.7487	Intermediate Similarity	NPD6823	Phase 2
0.7485	Intermediate Similarity	NPD2935	Discontinued
0.7464	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD37	Approved
0.7443	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6234	Discontinued
0.7427	Intermediate Similarity	NPD3748	Approved
0.7427	Intermediate Similarity	NPD2799	Discontinued
0.7418	Intermediate Similarity	NPD4967	Phase 2
0.7418	Intermediate Similarity	NPD4965	Approved
0.7418	Intermediate Similarity	NPD4966	Approved
0.7411	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4060	Phase 1
0.7386	Intermediate Similarity	NPD1511	Approved
0.7384	Intermediate Similarity	NPD6099	Approved
0.7384	Intermediate Similarity	NPD6100	Approved
0.7384	Intermediate Similarity	NPD1551	Phase 2
0.7356	Intermediate Similarity	NPD2800	Approved
0.7337	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7003	Approved
0.7312	Intermediate Similarity	NPD5711	Approved
0.7312	Intermediate Similarity	NPD5710	Approved
0.7308	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD6273	Approved
0.7288	Intermediate Similarity	NPD7390	Discontinued
0.7283	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD919	Approved
0.7225	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1510	Phase 2
0.7225	Intermediate Similarity	NPD5953	Discontinued
0.7209	Intermediate Similarity	NPD1607	Approved
0.7188	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6190	Approved
0.7166	Intermediate Similarity	NPD7199	Phase 2
0.7166	Intermediate Similarity	NPD1247	Approved
0.7166	Intermediate Similarity	NPD8127	Discontinued
0.7164	Intermediate Similarity	NPD8285	Discontinued
0.7159	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5124	Phase 1
0.7151	Intermediate Similarity	NPD6355	Discontinued
0.7151	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4625	Phase 3
0.711	Intermediate Similarity	NPD6651	Approved
0.7104	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1240	Approved
0.709	Intermediate Similarity	NPD3926	Phase 2
0.7086	Intermediate Similarity	NPD5405	Approved
0.7086	Intermediate Similarity	NPD5404	Approved
0.7086	Intermediate Similarity	NPD5408	Approved
0.7086	Intermediate Similarity	NPD5406	Approved
0.7085	Intermediate Similarity	NPD6213	Phase 3
0.7085	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6212	Phase 3
0.7076	Intermediate Similarity	NPD2313	Discontinued
0.7076	Intermediate Similarity	NPD6798	Discontinued
0.7076	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD920	Approved
0.707	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8366	Approved
0.7056	Intermediate Similarity	NPD7907	Approved
0.7056	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5762	Approved
0.7045	Intermediate Similarity	NPD5763	Approved
0.7039	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7229	Phase 3
0.7035	Intermediate Similarity	NPD6233	Phase 2
0.7031	Intermediate Similarity	NPD7286	Phase 2
0.7028	Intermediate Similarity	NPD8404	Phase 2
0.7022	Intermediate Similarity	NPD8166	Discontinued
0.7018	Intermediate Similarity	NPD7095	Approved
0.701	Intermediate Similarity	NPD7685	Pre-registration
0.6994	Remote Similarity	NPD1613	Approved
0.6994	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2438	Suspended
0.6977	Remote Similarity	NPD7985	Registered
0.6977	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7097	Phase 1
0.6966	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD4360	Phase 2
0.6965	Remote Similarity	NPD4363	Phase 3
0.6963	Remote Similarity	NPD4665	Approved
0.6963	Remote Similarity	NPD4111	Phase 1
0.6961	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4908	Phase 1
0.6955	Remote Similarity	NPD8067	Phase 3
0.6944	Remote Similarity	NPD3300	Phase 2
0.694	Remote Similarity	NPD1653	Approved
0.6927	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8491	Approved
0.6923	Remote Similarity	NPD6765	Approved
0.6923	Remote Similarity	NPD8368	Discontinued
0.6923	Remote Similarity	NPD6764	Approved
0.6923	Remote Similarity	NPD7584	Approved
0.6898	Remote Similarity	NPD4288	Approved
0.6895	Remote Similarity	NPD8059	Phase 3
0.6895	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7799	Discontinued
0.6879	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1243	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