NPASS Compound

Structure

CID226725 OpenBabel06191716022D 52 58 0 0 0 0 0 0 0 0999 V2000 3.4169 -0.9843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6892 0.4923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9382 -4.2711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5629 -1.4778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4166 0.0021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6893 1.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8349 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9246 -4.2712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4451 -3.4168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7085 -0.9849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5622 0.4950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8352 1.9720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9807 0.4926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4178 -3.4170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9383 -2.5627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8555 3.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5639 3.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8557 4.4393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5641 4.4389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8538 0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1268 1.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4179 -1.7085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8541 -2.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8547 -1.4798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7082 0.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9809 1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9247 -2.5627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7096 2.9596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7100 4.9323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8545 -1.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -2.9598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 -2.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -0.9864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8534 1.4808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2725 1.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9248 -0.8543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7094 1.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7093 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8550 1.4802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5640 1.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8546 0.4934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5639 0.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7103 5.9187 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -3.9778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7366 -2.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7075 1.9743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2723 0.4929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9384 -0.8542 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 -0.0009 1.9737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4183 1.9726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4181 -0.0001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 5 1 0 0 0 0 2 6 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 25 2 0 0 0 0 11 25 1 0 0 0 0 12 26 2 0 0 0 0 13 26 1 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 19 2 0 0 0 0 17 28 1 0 0 0 0 18 29 2 0 0 0 0 19 29 1 0 0 0 0 20 25 1 0 0 0 0 20 34 1 0 0 0 0 21 26 1 0 0 0 0 21 35 1 0 0 0 0 22 27 1 0 0 0 0 22 36 1 0 0 0 0 23 30 1 0 0 0 0 23 31 2 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 28 37 1 0 0 0 0 29 43 1 0 0 0 0 30 33 2 0 0 0 0 30 38 1 0 0 0 0 31 32 1 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 49 1 0 0 0 0 34 46 2 0 0 0 0 34 50 1 0 0 0 0 35 47 2 0 0 0 0 35 51 1 0 0 0 0 36 48 2 0 0 0 0 36 52 1 0 0 0 0 37 39 2 0 0 0 0 37 40 1 0 0 0 0 38 41 2 0 0 0 0 38 42 1 0 0 0 0 39 41 1 0 0 0 0 39 50 1 0 0 0 0 40 42 2 0 0 0 0 40 51 1 0 0 0 0 41 49 1 0 0 0 0 42 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	694.18
Volume:	707.629
LogP:	6.512
LogD:	4.655
LogS:	-4.462
# Rotatable Bonds:	13
TPSA:	152.73
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.073
Synthetic Accessibility Score:	3.073
Fsp3:	0.071
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.499
MDCK Permeability:	1.983775473490823e-05
Pgp-inhibitor:	0.335
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	102.73091888427734%
Volume Distribution (VD):	0.075
Pgp-substrate:	0.7661188840866089%

ADMET: Metabolism

CYP1A2-inhibitor:	0.594
CYP1A2-substrate:	0.021
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.201
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	9.495
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.009
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.569
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.326
Skin Sensitization:	0.911
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.879
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC226725

Natural Product ID:	NPC226725
*Common Name:**	Ganbajunin B
IUPAC Name:	[7,8-dihydroxy-3-(4-hydroxyphenyl)-1,2-bis[(2-phenylacetyl)oxy]dibenzofuran-4-yl] 2-phenylacetate
Synonyms:
Standard InCHIKey:	JJDLGUWMMXXQOA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C42H30O10/c43-29-18-16-28(17-19-29)37-39(50-34(46)20-25-10-4-1-5-11-25)41-38(30-23-31(44)32(45)24-33(30)49-41)42(52-36(48)22-27-14-8-3-9-15-27)40(37)51-35(47)21-26-12-6-2-7-13-26/h1-19,23-24,43-45H,20-22H2
SMILES:	Oc1ccc(cc1)c1c(OC(=O)Cc2ccccc2)c(OC(=O)Cc2ccccc2)c2c(c1OC(=O)Cc1ccccc1)oc1c2cc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL384074
PubChem CID:	44418271
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0002584] Phenylbenzofurans

*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
NPO22584	Thelephora vialis	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16901696]
NPO22584	Thelephora vialis	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22584	Thelephora vialis	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5475	Thelephora terrestris	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5475	Thelephora terrestris	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22584	Thelephora vialis	Species	Thelephoraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	IC50	=	5000.0	nM	PMID[486016]

☑ 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 NPC226725 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	473
0.1-0.2	2176
0.2-0.3	5077
0.3-0.4	10827
0.4-0.5	6684
0.5-0.6	4100
0.6-0.7	5714
0.7-0.8	5145
0.8-0.85	1877
0.85-0.9	589
0.9-0.95	30
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9941	High Similarity	NPC154527
0.9706	High Similarity	NPC47883
0.9588	High Similarity	NPC297807
0.9588	High Similarity	NPC98546
0.9483	High Similarity	NPC248315
0.9412	High Similarity	NPC149846
0.9298	High Similarity	NPC82217
0.9298	High Similarity	NPC476640
0.9298	High Similarity	NPC216842
0.929	High Similarity	NPC470704
0.9244	High Similarity	NPC287243
0.924	High Similarity	NPC230619
0.924	High Similarity	NPC54098
0.9191	High Similarity	NPC49667
0.9191	High Similarity	NPC8127
0.9181	High Similarity	NPC476641
0.9148	High Similarity	NPC71260
0.9128	High Similarity	NPC174700
0.9075	High Similarity	NPC65885
0.9012	High Similarity	NPC280493
0.8966	High Similarity	NPC473834
0.8947	High Similarity	NPC36320
0.8947	High Similarity	NPC45449
0.8944	High Similarity	NPC295436
0.8939	High Similarity	NPC269625
0.8908	High Similarity	NPC476370
0.8902	High Similarity	NPC476279
0.8889	High Similarity	NPC263092
0.8889	High Similarity	NPC1755
0.8889	High Similarity	NPC1706
0.8889	High Similarity	NPC59295
0.8889	High Similarity	NPC39305
0.8876	High Similarity	NPC36354
0.8864	High Similarity	NPC471841
0.8857	High Similarity	NPC476374
0.8851	High Similarity	NPC72696
0.8837	High Similarity	NPC29411
0.8837	High Similarity	NPC280893
0.883	High Similarity	NPC238995
0.883	High Similarity	NPC272722
0.883	High Similarity	NPC312056
0.883	High Similarity	NPC84515
0.882	High Similarity	NPC475996
0.8817	High Similarity	NPC185526
0.8817	High Similarity	NPC36077
0.8807	High Similarity	NPC99591
0.8793	High Similarity	NPC202470
0.8786	High Similarity	NPC272560
0.8772	High Similarity	NPC231758
0.8772	High Similarity	NPC196179
0.8772	High Similarity	NPC188486
0.8772	High Similarity	NPC34089
0.8757	High Similarity	NPC472461
0.8757	High Similarity	NPC137100
0.8757	High Similarity	NPC24258
0.875	High Similarity	NPC261471
0.875	High Similarity	NPC117450
0.8743	High Similarity	NPC476365
0.8743	High Similarity	NPC218533
0.8743	High Similarity	NPC78830
0.8736	High Similarity	NPC50394
0.8736	High Similarity	NPC86477
0.8728	High Similarity	NPC169471
0.8728	High Similarity	NPC259757
0.8713	High Similarity	NPC188967
0.8708	High Similarity	NPC475783
0.8703	High Similarity	NPC3474
0.8701	High Similarity	NPC227906
0.8693	High Similarity	NPC158226
0.8693	High Similarity	NPC247964
0.8686	High Similarity	NPC247136
0.8674	High Similarity	NPC469650
0.8671	High Similarity	NPC272064
0.8671	High Similarity	NPC67959
0.8671	High Similarity	NPC133065
0.8667	High Similarity	NPC471842
0.8655	High Similarity	NPC190487
0.8655	High Similarity	NPC287458
0.8655	High Similarity	NPC195832
0.8655	High Similarity	NPC196879
0.8655	High Similarity	NPC16935
0.8655	High Similarity	NPC154304
0.8652	High Similarity	NPC216307
0.8652	High Similarity	NPC164384
0.8644	High Similarity	NPC37606
0.8644	High Similarity	NPC233956
0.8644	High Similarity	NPC310794
0.8636	High Similarity	NPC17884
0.8636	High Similarity	NPC19273
0.8629	High Similarity	NPC247973
0.8629	High Similarity	NPC253730
0.8629	High Similarity	NPC286230
0.8626	High Similarity	NPC73929
0.8626	High Similarity	NPC139683
0.8626	High Similarity	NPC260521
0.8626	High Similarity	NPC174486
0.8626	High Similarity	NPC47905
0.8626	High Similarity	NPC469649
0.8621	High Similarity	NPC39306
0.8619	High Similarity	NPC476170
0.8619	High Similarity	NPC470416
0.8613	High Similarity	NPC174311
0.8605	High Similarity	NPC130955
0.8605	High Similarity	NPC98892
0.8603	High Similarity	NPC77179
0.8603	High Similarity	NPC23553
0.8603	High Similarity	NPC476773
0.8603	High Similarity	NPC265380
0.8602	High Similarity	NPC189312
0.8596	High Similarity	NPC112954
0.8588	High Similarity	NPC28589
0.8588	High Similarity	NPC248593
0.8588	High Similarity	NPC289396
0.8588	High Similarity	NPC212038
0.8588	High Similarity	NPC125709
0.8588	High Similarity	NPC47386
0.8588	High Similarity	NPC292385
0.8588	High Similarity	NPC271848
0.8588	High Similarity	NPC81332
0.8588	High Similarity	NPC262580
0.858	High Similarity	NPC125300
0.858	High Similarity	NPC186100
0.858	High Similarity	NPC99613
0.858	High Similarity	NPC49487
0.858	High Similarity	NPC165979
0.858	High Similarity	NPC163130
0.858	High Similarity	NPC41494
0.858	High Similarity	NPC216403
0.8579	High Similarity	NPC477081
0.8579	High Similarity	NPC223534
0.8579	High Similarity	NPC477083
0.8579	High Similarity	NPC290289
0.8579	High Similarity	NPC158214
0.8579	High Similarity	NPC240200
0.8571	High Similarity	NPC111490
0.8571	High Similarity	NPC261623
0.8571	High Similarity	NPC277480
0.8571	High Similarity	NPC112380
0.8571	High Similarity	NPC304322
0.8564	High Similarity	NPC297503
0.8564	High Similarity	NPC97119
0.8564	High Similarity	NPC240508
0.8564	High Similarity	NPC135831
0.8564	High Similarity	NPC36138
0.8563	High Similarity	NPC89131
0.8556	High Similarity	NPC324742
0.8556	High Similarity	NPC476273
0.8556	High Similarity	NPC185275
0.8547	High Similarity	NPC115798
0.8547	High Similarity	NPC253634
0.8547	High Similarity	NPC18607
0.8547	High Similarity	NPC288669
0.8547	High Similarity	NPC143828
0.8547	High Similarity	NPC18772
0.8547	High Similarity	NPC25495
0.8547	High Similarity	NPC107244
0.8547	High Similarity	NPC261004
0.8547	High Similarity	NPC154741
0.8547	High Similarity	NPC4481
0.8547	High Similarity	NPC130894
0.8547	High Similarity	NPC300943
0.8547	High Similarity	NPC7846
0.8547	High Similarity	NPC191459
0.8547	High Similarity	NPC176300
0.8547	High Similarity	NPC296018
0.8547	High Similarity	NPC105242
0.8547	High Similarity	NPC193842
0.8547	High Similarity	NPC152166
0.8547	High Similarity	NPC22472
0.8547	High Similarity	NPC204854
0.8547	High Similarity	NPC19687
0.8547	High Similarity	NPC156955
0.8547	High Similarity	NPC9609
0.8539	High Similarity	NPC59491
0.8539	High Similarity	NPC24748
0.8538	High Similarity	NPC45131
0.8533	High Similarity	NPC93065
0.8533	High Similarity	NPC472720
0.8533	High Similarity	NPC201814
0.8533	High Similarity	NPC472724
0.8533	High Similarity	NPC187632
0.8533	High Similarity	NPC160543
0.8533	High Similarity	NPC472721
0.8533	High Similarity	NPC469652
0.8533	High Similarity	NPC31208
0.8531	High Similarity	NPC124470
0.8531	High Similarity	NPC281835
0.8531	High Similarity	NPC180768
0.8531	High Similarity	NPC109827
0.8525	High Similarity	NPC65489
0.8525	High Similarity	NPC475179
0.8523	High Similarity	NPC76482
0.8523	High Similarity	NPC14662
0.8523	High Similarity	NPC234331
0.8523	High Similarity	NPC295082
0.8523	High Similarity	NPC243877
0.8523	High Similarity	NPC473818
0.8516	High Similarity	NPC231254
0.8514	High Similarity	NPC477840
0.8514	High Similarity	NPC142614

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 NPC226725 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	1064
0.2-0.3	1995
0.3-0.4	2704
0.4-0.5	1704
0.5-0.6	838
0.6-0.7	269
0.7-0.8	113
0.8-0.85	20
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8483	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD3882	Suspended
0.8415	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD6166	Phase 2
0.8389	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD3749	Approved
0.8324	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD2801	Approved
0.8295	Intermediate Similarity	NPD6232	Discontinued
0.8268	Intermediate Similarity	NPD5844	Phase 1
0.8266	Intermediate Similarity	NPD3817	Phase 2
0.8258	Intermediate Similarity	NPD7473	Discontinued
0.8212	Intermediate Similarity	NPD3818	Discontinued
0.8208	Intermediate Similarity	NPD1465	Phase 2
0.8118	Intermediate Similarity	NPD1512	Approved
0.8057	Intermediate Similarity	NPD5402	Approved
0.8046	Intermediate Similarity	NPD1934	Approved
0.8045	Intermediate Similarity	NPD3926	Phase 2
0.8023	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1511	Approved
0.7989	Intermediate Similarity	NPD7808	Phase 3
0.7978	Intermediate Similarity	NPD5494	Approved
0.7978	Intermediate Similarity	NPD6797	Phase 2
0.7966	Intermediate Similarity	NPD7075	Discontinued
0.7937	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD7251	Discontinued
0.7935	Intermediate Similarity	NPD6559	Discontinued
0.7933	Intermediate Similarity	NPD1247	Approved
0.7933	Intermediate Similarity	NPD6959	Discontinued
0.7931	Intermediate Similarity	NPD6599	Discontinued
0.7923	Intermediate Similarity	NPD7074	Phase 3
0.7898	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7054	Approved
0.7826	Intermediate Similarity	NPD7472	Approved
0.7809	Intermediate Similarity	NPD7768	Phase 2
0.7797	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6799	Approved
0.7766	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD8312	Approved
0.7754	Intermediate Similarity	NPD8313	Approved
0.774	Intermediate Similarity	NPD6801	Discontinued
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7684	Intermediate Similarity	NPD7411	Suspended
0.7676	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD5403	Approved
0.765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD7390	Discontinued
0.7571	Intermediate Similarity	NPD3226	Approved
0.7556	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD5401	Approved
0.7539	Intermediate Similarity	NPD8434	Phase 2
0.7527	Intermediate Similarity	NPD3751	Discontinued
0.7514	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7471	Intermediate Similarity	NPD6190	Approved
0.7461	Intermediate Similarity	NPD4287	Approved
0.7458	Intermediate Similarity	NPD920	Approved
0.7457	Intermediate Similarity	NPD1243	Approved
0.745	Intermediate Similarity	NPD7435	Discontinued
0.7446	Intermediate Similarity	NPD7199	Phase 2
0.7443	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD2534	Approved
0.7443	Intermediate Similarity	NPD2533	Approved
0.7443	Intermediate Similarity	NPD2532	Approved
0.7442	Intermediate Similarity	NPD2344	Approved
0.7438	Intermediate Similarity	NPD8151	Discontinued
0.7432	Intermediate Similarity	NPD6234	Discontinued
0.7399	Intermediate Similarity	NPD1549	Phase 2
0.7396	Intermediate Similarity	NPD943	Approved
0.7358	Intermediate Similarity	NPD8150	Discontinued
0.7353	Intermediate Similarity	NPD447	Suspended
0.7341	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7228	Approved
0.733	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7870	Phase 2
0.7327	Intermediate Similarity	NPD7871	Phase 2
0.7326	Intermediate Similarity	NPD1510	Phase 2
0.7317	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7874	Approved
0.731	Intermediate Similarity	NPD1607	Approved
0.73	Intermediate Similarity	NPD6779	Approved
0.73	Intermediate Similarity	NPD6781	Approved
0.73	Intermediate Similarity	NPD6777	Approved
0.73	Intermediate Similarity	NPD6776	Approved
0.73	Intermediate Similarity	NPD6780	Approved
0.73	Intermediate Similarity	NPD6778	Approved
0.73	Intermediate Similarity	NPD6782	Approved
0.7288	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2935	Discontinued
0.7283	Intermediate Similarity	NPD1551	Phase 2
0.7283	Intermediate Similarity	NPD5408	Approved
0.7283	Intermediate Similarity	NPD5404	Approved
0.7283	Intermediate Similarity	NPD5405	Approved
0.7283	Intermediate Similarity	NPD5406	Approved
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD2309	Approved
0.7253	Intermediate Similarity	NPD37	Approved
0.7247	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4966	Approved
0.7228	Intermediate Similarity	NPD4965	Approved
0.7228	Intermediate Similarity	NPD4967	Phase 2
0.7225	Intermediate Similarity	NPD3748	Approved
0.7225	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1653	Approved
0.7216	Intermediate Similarity	NPD4628	Phase 3
0.72	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1240	Approved
0.7192	Intermediate Similarity	NPD7698	Approved
0.7192	Intermediate Similarity	NPD7697	Approved
0.7192	Intermediate Similarity	NPD7696	Phase 3
0.7184	Intermediate Similarity	NPD2796	Approved
0.7159	Intermediate Similarity	NPD2800	Approved
0.7159	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD230	Phase 1
0.7151	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD8455	Phase 2
0.7098	Intermediate Similarity	NPD7685	Pre-registration
0.7088	Intermediate Similarity	NPD7458	Discontinued
0.7074	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6535	Approved
0.705	Intermediate Similarity	NPD6534	Approved
0.7033	Intermediate Similarity	NPD7801	Approved
0.703	Intermediate Similarity	NPD7700	Phase 2
0.703	Intermediate Similarity	NPD7699	Phase 2
0.7029	Intermediate Similarity	NPD2799	Discontinued
0.7029	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8320	Phase 1
0.699	Remote Similarity	NPD8319	Approved
0.6982	Remote Similarity	NPD1203	Approved
0.6979	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7907	Approved
0.6977	Remote Similarity	NPD3764	Approved
0.6977	Remote Similarity	NPD2313	Discontinued
0.6974	Remote Similarity	NPD7549	Discontinued
0.6959	Remote Similarity	NPD5953	Discontinued
0.6949	Remote Similarity	NPD1471	Phase 3
0.6947	Remote Similarity	NPD5711	Approved
0.6947	Remote Similarity	NPD5710	Approved
0.6947	Remote Similarity	NPD7229	Phase 3
0.6936	Remote Similarity	NPD6233	Phase 2
0.6927	Remote Similarity	NPD8166	Discontinued
0.6923	Remote Similarity	NPD7240	Approved
0.6897	Remote Similarity	NPD1613	Approved
0.6897	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6099	Approved
0.6893	Remote Similarity	NPD6100	Approved
0.6893	Remote Similarity	NPD6823	Phase 2
0.6891	Remote Similarity	NPD7177	Discontinued
0.6879	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6798	Discontinued
0.6878	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7680	Approved
0.6857	Remote Similarity	NPD1933	Approved
0.6856	Remote Similarity	NPD7286	Phase 2
0.6854	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4308	Phase 3
0.6835	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD5242	Approved
0.6809	Remote Similarity	NPD2296	Approved
0.6806	Remote Similarity	NPD4665	Approved
0.6806	Remote Similarity	NPD4111	Phase 1
0.6805	Remote Similarity	NPD9269	Phase 2
0.6789	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2403	Approved
0.6788	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD3268	Approved
0.6782	Remote Similarity	NPD411	Approved
0.6763	Remote Similarity	NPD6832	Phase 2
0.6761	Remote Similarity	NPD6355	Discontinued
0.6751	Remote Similarity	NPD7039	Approved
0.6751	Remote Similarity	NPD7038	Approved
0.6739	Remote Similarity	NPD6273	Approved
0.6724	Remote Similarity	NPD3027	Phase 3
0.6724	Remote Similarity	NPD7095	Approved
0.672	Remote Similarity	NPD4288	Approved
0.6718	Remote Similarity	NPD2163	Approved
0.6717	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD9717	Approved
0.6703	Remote Similarity	NPD2354	Approved
0.6686	Remote Similarity	NPD2797	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