NPASS Compound

Structure

NPC113906 OpenBabel07101718272D 30 32 0 0 0 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 29 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 10 17 2 0 0 0 0 11 18 2 0 0 0 0 11 19 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 21 27 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.17
Volume:	427.004
LogP:	6.16
LogD:	3.307
LogS:	-2.676
# Rotatable Bonds:	5
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.308
Synthetic Accessibility Score:	3.096
Fsp3:	0.292
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822
MDCK Permeability:	1.2226931175973732e-05
Pgp-inhibitor:	0.697
Pgp-substrate:	0.821
Human Intestinal Absorption (HIA):	0.227
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.315

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	80.47936248779297%
Volume Distribution (VD):	0.873
Pgp-substrate:	18.779651641845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.435
CYP1A2-substrate:	0.433
CYP2C19-inhibitor:	0.756
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.816
CYP2C9-substrate:	0.877
CYP2D6-inhibitor:	0.432
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	9.324
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.286
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.352
Skin Sensitization:	0.932
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.659
Respiratory Toxicity:	0.328

Download Data

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

Natural Product: NPC113906

Natural Product ID:	NPC113906
*Common Name:**	Cudratricusxanthone K
IUPAC Name:	1,6,7-trihydroxy-3-methoxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms:	cudratricusxanthone K
Standard InCHIKey:	NHJUGTUGZNCOKP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H26O6/c1-12(2)6-8-14-21(27)20-22(28)16-10-17(25)18(26)11-19(16)30-24(20)15(23(14)29-5)9-7-13(3)4/h6-7,10-11,25-27H,8-9H2,1-5H3
SMILES:	COc1c(CC=C(C)C)c2oc3cc(O)c(cc3c(=O)c2c(c1CC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228335
PubChem CID:	16757289
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 [CHEMONTID:0003518] 4-prenylated 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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	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	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT892	Individual Protein	Monoamine oxidase A	Mus musculus	IC50	>	150000.0	nM	PMID[475246]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[475247]

☑ 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 NPC113906 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	435
0.1-0.2	1802
0.2-0.3	4560
0.3-0.4	11037
0.4-0.5	6867
0.5-0.6	3713
0.6-0.7	4911
0.7-0.8	4822
0.8-0.85	2286
0.85-0.9	1479
0.9-0.95	695
0.95-1	90

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC262286
0.9866	High Similarity	NPC36852
0.9799	High Similarity	NPC138243
0.9733	High Similarity	NPC78225
0.9671	High Similarity	NPC472275
0.9669	High Similarity	NPC172770
0.9669	High Similarity	NPC185258
0.9667	High Similarity	NPC191146
0.9667	High Similarity	NPC68093
0.9667	High Similarity	NPC142339
0.9608	High Similarity	NPC83922
0.9608	High Similarity	NPC472448
0.9605	High Similarity	NPC56085
0.9605	High Similarity	NPC228785
0.9605	High Similarity	NPC14353
0.9605	High Similarity	NPC476980
0.9603	High Similarity	NPC236796
0.9603	High Similarity	NPC223787
0.9603	High Similarity	NPC79053
0.96	High Similarity	NPC117992
0.96	High Similarity	NPC152951
0.96	High Similarity	NPC230149
0.96	High Similarity	NPC57674
0.96	High Similarity	NPC168247
0.9597	High Similarity	NPC106976
0.9597	High Similarity	NPC249570
0.9597	High Similarity	NPC101996
0.9595	High Similarity	NPC62042
0.9592	High Similarity	NPC194856
0.9545	High Similarity	NPC329669
0.9545	High Similarity	NPC473313
0.9545	High Similarity	NPC472278
0.9542	High Similarity	NPC266314
0.9542	High Similarity	NPC278052
0.9542	High Similarity	NPC167678
0.9542	High Similarity	NPC40491
0.9542	High Similarity	NPC61010
0.9542	High Similarity	NPC32694
0.9542	High Similarity	NPC258331
0.9542	High Similarity	NPC29876
0.9539	High Similarity	NPC95936
0.9539	High Similarity	NPC100123
0.9539	High Similarity	NPC250214
0.9536	High Similarity	NPC472916
0.9533	High Similarity	NPC33051
0.9533	High Similarity	NPC213896
0.9533	High Similarity	NPC167091
0.9533	High Similarity	NPC88645
0.9533	High Similarity	NPC476631
0.9533	High Similarity	NPC89474
0.9533	High Similarity	NPC292214
0.9533	High Similarity	NPC74924
0.9533	High Similarity	NPC49402
0.9533	High Similarity	NPC273462
0.9533	High Similarity	NPC70433
0.9533	High Similarity	NPC298692
0.9533	High Similarity	NPC206238
0.9533	High Similarity	NPC227337
0.9533	High Similarity	NPC192083
0.9533	High Similarity	NPC271779
0.953	High Similarity	NPC171010
0.9527	High Similarity	NPC266499
0.9524	High Similarity	NPC207729
0.9484	High Similarity	NPC37183
0.9481	High Similarity	NPC81679
0.9481	High Similarity	NPC220912
0.9481	High Similarity	NPC329760
0.9481	High Similarity	NPC470694
0.9477	High Similarity	NPC119224
0.9477	High Similarity	NPC204290
0.9477	High Similarity	NPC320359
0.9477	High Similarity	NPC246478
0.9477	High Similarity	NPC235018
0.9477	High Similarity	NPC45146
0.9474	High Similarity	NPC474836
0.9474	High Similarity	NPC217677
0.9474	High Similarity	NPC469584
0.9474	High Similarity	NPC472913
0.9474	High Similarity	NPC472910
0.9474	High Similarity	NPC241904
0.9474	High Similarity	NPC222814
0.9474	High Similarity	NPC48208
0.9474	High Similarity	NPC291508
0.9474	High Similarity	NPC96167
0.9474	High Similarity	NPC472914
0.9474	High Similarity	NPC476981
0.9474	High Similarity	NPC162869
0.9474	High Similarity	NPC156057
0.9474	High Similarity	NPC245758
0.9474	High Similarity	NPC99597
0.9474	High Similarity	NPC474208
0.9474	High Similarity	NPC472911
0.9474	High Similarity	NPC210084
0.9474	High Similarity	NPC475267
0.9474	High Similarity	NPC165977
0.9474	High Similarity	NPC300727
0.947	High Similarity	NPC321779
0.947	High Similarity	NPC477503
0.947	High Similarity	NPC256925
0.947	High Similarity	NPC20830
0.947	High Similarity	NPC200761
0.947	High Similarity	NPC470327
0.947	High Similarity	NPC208197
0.947	High Similarity	NPC256612
0.947	High Similarity	NPC134287
0.947	High Similarity	NPC45849
0.947	High Similarity	NPC2928
0.947	High Similarity	NPC130589
0.9467	High Similarity	NPC161277
0.9467	High Similarity	NPC199100
0.9467	High Similarity	NPC180234
0.9467	High Similarity	NPC471982
0.9467	High Similarity	NPC39007
0.9467	High Similarity	NPC120537
0.9463	High Similarity	NPC88804
0.9463	High Similarity	NPC184136
0.9463	High Similarity	NPC179183
0.9463	High Similarity	NPC3825
0.9459	High Similarity	NPC276930
0.9459	High Similarity	NPC37135
0.9459	High Similarity	NPC186397
0.9423	High Similarity	NPC277480
0.9419	High Similarity	NPC248638
0.9419	High Similarity	NPC236132
0.9419	High Similarity	NPC236521
0.9419	High Similarity	NPC41301
0.9419	High Similarity	NPC220313
0.9419	High Similarity	NPC152659
0.9419	High Similarity	NPC7483
0.9416	High Similarity	NPC259456
0.9416	High Similarity	NPC134783
0.9416	High Similarity	NPC228383
0.9412	High Similarity	NPC204879
0.9412	High Similarity	NPC476242
0.9412	High Similarity	NPC469658
0.9412	High Similarity	NPC329091
0.9408	High Similarity	NPC472626
0.9408	High Similarity	NPC255106
0.9408	High Similarity	NPC470328
0.9408	High Similarity	NPC291878
0.9408	High Similarity	NPC274730
0.9408	High Similarity	NPC235165
0.9408	High Similarity	NPC472455
0.9408	High Similarity	NPC35038
0.9408	High Similarity	NPC209614
0.9408	High Similarity	NPC278778
0.9408	High Similarity	NPC276444
0.9408	High Similarity	NPC195796
0.9404	High Similarity	NPC280937
0.9404	High Similarity	NPC231018
0.9404	High Similarity	NPC47781
0.9404	High Similarity	NPC22519
0.9404	High Similarity	NPC250822
0.9404	High Similarity	NPC176775
0.9404	High Similarity	NPC75279
0.9404	High Similarity	NPC160951
0.9404	High Similarity	NPC274327
0.9404	High Similarity	NPC69394
0.9404	High Similarity	NPC183878
0.9404	High Similarity	NPC472915
0.9404	High Similarity	NPC145379
0.9404	High Similarity	NPC255350
0.9404	High Similarity	NPC276409
0.94	High Similarity	NPC149614
0.94	High Similarity	NPC251110
0.94	High Similarity	NPC202157
0.94	High Similarity	NPC117579
0.94	High Similarity	NPC154345
0.94	High Similarity	NPC205046
0.94	High Similarity	NPC204515
0.94	High Similarity	NPC304295
0.94	High Similarity	NPC59162
0.9396	High Similarity	NPC223988
0.9359	High Similarity	NPC275780
0.9359	High Similarity	NPC472450
0.9359	High Similarity	NPC239752
0.9359	High Similarity	NPC473286
0.9359	High Similarity	NPC326520
0.9355	High Similarity	NPC261470
0.9355	High Similarity	NPC25152
0.9351	High Similarity	NPC474287
0.9351	High Similarity	NPC475886
0.9351	High Similarity	NPC80375
0.9346	High Similarity	NPC52889
0.9346	High Similarity	NPC180011
0.9346	High Similarity	NPC129684
0.9346	High Similarity	NPC27337
0.9346	High Similarity	NPC161960
0.9346	High Similarity	NPC304008
0.9346	High Similarity	NPC472598
0.9346	High Similarity	NPC187745
0.9346	High Similarity	NPC219867
0.9346	High Similarity	NPC218871
0.9346	High Similarity	NPC476630
0.9346	High Similarity	NPC78103
0.9346	High Similarity	NPC474681
0.9346	High Similarity	NPC181960
0.9346	High Similarity	NPC218313
0.9346	High Similarity	NPC299520
0.9346	High Similarity	NPC474055

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 NPC113906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	977
0.2-0.3	1809
0.3-0.4	2689
0.4-0.5	1772
0.5-0.6	992
0.6-0.7	351
0.7-0.8	109
0.8-0.85	45
0.85-0.9	11
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9533	High Similarity	NPD2393	Clinical (unspecified phase)
0.9404	High Similarity	NPD2801	Approved
0.9211	High Similarity	NPD1934	Approved
0.906	High Similarity	NPD1511	Approved
0.894	High Similarity	NPD1512	Approved
0.891	High Similarity	NPD3882	Suspended
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8861	High Similarity	NPD5494	Approved
0.879	High Similarity	NPD4868	Clinical (unspecified phase)
0.8758	High Similarity	NPD6166	Phase 2
0.8758	High Similarity	NPD6167	Clinical (unspecified phase)
0.8758	High Similarity	NPD6168	Clinical (unspecified phase)
0.871	High Similarity	NPD4380	Phase 2
0.865	High Similarity	NPD3818	Discontinued
0.8616	High Similarity	NPD7075	Discontinued
0.86	High Similarity	NPD1549	Phase 2
0.8545	High Similarity	NPD7074	Phase 3
0.8544	High Similarity	NPD7096	Clinical (unspecified phase)
0.8544	High Similarity	NPD7819	Suspended
0.8533	High Similarity	NPD1550	Clinical (unspecified phase)
0.8533	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD7410	Clinical (unspecified phase)
0.8503	High Similarity	NPD4338	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD3817	Phase 2
0.8485	Intermediate Similarity	NPD7054	Approved
0.8434	Intermediate Similarity	NPD7472	Approved
0.8418	Intermediate Similarity	NPD7411	Suspended
0.8405	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8385	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6797	Phase 2
0.8378	Intermediate Similarity	NPD1240	Approved
0.8378	Intermediate Similarity	NPD943	Approved
0.8375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5844	Phase 1
0.8364	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD2796	Approved
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD1465	Phase 2
0.8274	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD1247	Approved
0.8205	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD2800	Approved
0.8176	Intermediate Similarity	NPD7808	Phase 3
0.8155	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD5402	Approved
0.8118	Intermediate Similarity	NPD6559	Discontinued
0.8084	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD230	Phase 1
0.8041	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3749	Approved
0.7922	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3926	Phase 2
0.7898	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1613	Approved
0.7892	Intermediate Similarity	NPD919	Approved
0.784	Intermediate Similarity	NPD3226	Approved
0.7834	Intermediate Similarity	NPD1243	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7821	Intermediate Similarity	NPD2346	Discontinued
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2799	Discontinued
0.7797	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6651	Approved
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7756	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7756	Intermediate Similarity	NPD6100	Approved
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7727	Intermediate Similarity	NPD447	Suspended
0.7716	Intermediate Similarity	NPD5403	Approved
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2344	Approved
0.7705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7593	Intermediate Similarity	NPD5401	Approved
0.7582	Intermediate Similarity	NPD3027	Phase 3
0.758	Intermediate Similarity	NPD3748	Approved
0.7578	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1653	Approved
0.7557	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD9269	Phase 2
0.7451	Intermediate Similarity	NPD9494	Approved
0.7442	Intermediate Similarity	NPD3787	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.7423	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6782	Approved
0.7419	Intermediate Similarity	NPD6778	Approved
0.7419	Intermediate Similarity	NPD6777	Approved
0.7419	Intermediate Similarity	NPD6776	Approved
0.7419	Intermediate Similarity	NPD6779	Approved
0.7419	Intermediate Similarity	NPD6780	Approved
0.7419	Intermediate Similarity	NPD6781	Approved
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8312	Approved
0.7416	Intermediate Similarity	NPD8313	Approved
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.74	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7381	Intermediate Similarity	NPD6844	Discontinued
0.7381	Intermediate Similarity	NPD37	Approved
0.7371	Intermediate Similarity	NPD7228	Approved
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4360	Phase 2
0.7337	Intermediate Similarity	NPD4363	Phase 3
0.7321	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD8434	Phase 2
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2798	Approved
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD9717	Approved
0.7226	Intermediate Similarity	NPD2861	Phase 2
0.7211	Intermediate Similarity	NPD7698	Approved
0.7211	Intermediate Similarity	NPD7696	Phase 3
0.7211	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD1470	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7202	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9268	Approved
0.72	Intermediate Similarity	NPD5242	Approved
0.7197	Intermediate Similarity	NPD3268	Approved
0.7193	Intermediate Similarity	NPD5353	Approved
0.719	Intermediate Similarity	NPD4749	Approved
0.7188	Intermediate Similarity	NPD7584	Approved
0.7178	Intermediate Similarity	NPD2654	Approved
0.7173	Intermediate Similarity	NPD7871	Phase 2
0.7173	Intermediate Similarity	NPD7870	Phase 2
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2403	Approved
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7151	Intermediate Similarity	NPD6534	Approved
0.7151	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7124	Intermediate Similarity	NPD1608	Approved
0.7117	Intermediate Similarity	NPD2424	Discontinued
0.7112	Intermediate Similarity	NPD4361	Phase 2
0.7112	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7097	Intermediate Similarity	NPD2797	Approved
0.7095	Intermediate Similarity	NPD1729	Discontinued
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7874	Approved
0.7077	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.705	Intermediate Similarity	NPD2899	Discontinued

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