NPASS Compound

Structure

NPC473286 OpenBabel07101718182D 29 32 0 0 1 0 0 0 0 0999 V2000 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9889 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -1.0827 0.0000 C 0 0 3 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 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 2.5981 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 0.8660 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 -2.5981 1.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -0.9781 0.0000 C 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 -3.4641 -0.0000 0.0000 O 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 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -0.1691 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 7 1 0 0 0 0 6 10 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 11 23 1 0 0 0 0 11 28 1 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 19 2 0 0 0 0 16 28 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 27 2 0 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	403.788
LogP:	5.507
LogD:	3.132
LogS:	-3.419
# Rotatable Bonds:	2
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	3.834
Fsp3:	0.348
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:	-4.87
MDCK Permeability:	1.209962101711426e-05
Pgp-inhibitor:	0.199
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.09
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	89.09952545166016%
Volume Distribution (VD):	0.902
Pgp-substrate:	11.504155158996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.572
CYP1A2-substrate:	0.561
CYP2C19-inhibitor:	0.568
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.811
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.282
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	3.528
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.565
Rat Oral Acute Toxicity:	0.454
Maximum Recommended Daily Dose:	0.657
Skin Sensitization:	0.873
Carcinogencity:	0.442
Eye Corrosion:	0.004
Eye Irritation:	0.89
Respiratory Toxicity:	0.378

Download Data

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

Natural Product: NPC473286

Natural Product ID:	NPC473286
*Common Name:**	Cudratricusxanthone J
IUPAC Name:	5,8,9-trihydroxy-1,1,2-trimethyl-7-(3-methylbut-2-enyl)-2H-furo[2,3-c]xanthen-6-one
Synonyms:	cudratricusxanthone J
Standard InCHIKey:	GIEMQAXHAKGAAH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-10(2)6-7-12-17-15(9-14(25)20(12)26)29-22-18(21(17)27)13(24)8-16-19(22)23(4,5)11(3)28-16/h6,8-9,11,24-26H,7H2,1-5H3
SMILES:	CC(=CCc1c2c(cc(c1O)O)oc1c(c(cc3c1C(C)(C)C(C)O3)O)c2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL395246
PubChem CID:	16757393
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:0003519] 8-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]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[25051453]
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]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27420919]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8797	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8797	Cudrania tricuspidata	Species	Moraceae	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
EC50	2
IC50	1

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2

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[548934]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	8100.0	nM	PMID[548935]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	50000.0	nM	PMID[548935]

☑ 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 NPC473286 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	439
0.1-0.2	1696
0.2-0.3	3640
0.3-0.4	9341
0.4-0.5	9324
0.5-0.6	3737
0.6-0.7	5058
0.7-0.8	5355
0.8-0.85	2570
0.85-0.9	1251
0.9-0.95	259
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC473313
0.9808	High Similarity	NPC472278
0.9808	High Similarity	NPC329669
0.9745	High Similarity	NPC326520
0.9684	High Similarity	NPC170245
0.9679	High Similarity	NPC32694
0.9615	High Similarity	NPC235018
0.9615	High Similarity	NPC45146
0.9557	High Similarity	NPC475985
0.9557	High Similarity	NPC220313
0.9557	High Similarity	NPC18100
0.9551	High Similarity	NPC329091
0.9548	High Similarity	NPC142339
0.9497	High Similarity	NPC472277
0.9494	High Similarity	NPC470694
0.949	High Similarity	NPC476283
0.949	High Similarity	NPC56085
0.949	High Similarity	NPC80375
0.949	High Similarity	NPC228785
0.949	High Similarity	NPC14353
0.9487	High Similarity	NPC236796
0.9434	High Similarity	NPC205265
0.9434	High Similarity	NPC7483
0.9434	High Similarity	NPC472281
0.943	High Similarity	NPC187354
0.943	High Similarity	NPC278052
0.943	High Similarity	NPC474186
0.943	High Similarity	NPC40491
0.943	High Similarity	NPC61010
0.943	High Similarity	NPC472275
0.9427	High Similarity	NPC210459
0.9427	High Similarity	NPC172770
0.9427	High Similarity	NPC185258
0.9427	High Similarity	NPC85121
0.9427	High Similarity	NPC100123
0.9419	High Similarity	NPC89474
0.9383	High Similarity	NPC472276
0.9379	High Similarity	NPC477154
0.9379	High Similarity	NPC117854
0.9379	High Similarity	NPC6588
0.9375	High Similarity	NPC37183
0.9371	High Similarity	NPC81679
0.9367	High Similarity	NPC321399
0.9367	High Similarity	NPC320359
0.9367	High Similarity	NPC475886
0.9367	High Similarity	NPC474287
0.9367	High Similarity	NPC119224
0.9367	High Similarity	NPC36217
0.9363	High Similarity	NPC165977
0.9363	High Similarity	NPC79053
0.9363	High Similarity	NPC217677
0.9363	High Similarity	NPC300727
0.9363	High Similarity	NPC196448
0.9363	High Similarity	NPC223787
0.9363	High Similarity	NPC241904
0.9359	High Similarity	NPC67396
0.9359	High Similarity	NPC113906
0.9355	High Similarity	NPC106976
0.9321	High Similarity	NPC288813
0.9317	High Similarity	NPC472452
0.9317	High Similarity	NPC277480
0.9313	High Similarity	NPC236521
0.9313	High Similarity	NPC152659
0.9313	High Similarity	NPC197168
0.9313	High Similarity	NPC236132
0.9313	High Similarity	NPC273959
0.9313	High Similarity	NPC248638
0.9308	High Similarity	NPC474351
0.9308	High Similarity	NPC475883
0.9308	High Similarity	NPC474187
0.9304	High Similarity	NPC250214
0.9304	High Similarity	NPC95936
0.9304	High Similarity	NPC235448
0.9304	High Similarity	NPC476242
0.9299	High Similarity	NPC24640
0.9299	High Similarity	NPC274730
0.9295	High Similarity	NPC192083
0.9295	High Similarity	NPC298692
0.9295	High Similarity	NPC74924
0.9295	High Similarity	NPC213896
0.929	High Similarity	NPC202157
0.9255	High Similarity	NPC275780
0.9255	High Similarity	NPC25361
0.9255	High Similarity	NPC239752
0.9255	High Similarity	NPC472450
0.925	High Similarity	NPC211107
0.925	High Similarity	NPC472402
0.925	High Similarity	NPC201800
0.925	High Similarity	NPC329760
0.925	High Similarity	NPC25152
0.9245	High Similarity	NPC472624
0.9241	High Similarity	NPC162869
0.9241	High Similarity	NPC156057
0.9241	High Similarity	NPC474208
0.9241	High Similarity	NPC48208
0.9241	High Similarity	NPC78225
0.9241	High Similarity	NPC262286
0.9241	High Similarity	NPC36852
0.9241	High Similarity	NPC475267
0.9241	High Similarity	NPC474836
0.9241	High Similarity	NPC469584
0.9236	High Similarity	NPC45849
0.9236	High Similarity	NPC200761
0.9236	High Similarity	NPC470327
0.9236	High Similarity	NPC321779
0.9236	High Similarity	NPC477503
0.9198	High Similarity	NPC39091
0.9193	High Similarity	NPC124038
0.9193	High Similarity	NPC270837
0.9193	High Similarity	NPC23298
0.9193	High Similarity	NPC207690
0.9193	High Similarity	NPC189473
0.9193	High Similarity	NPC186686
0.9193	High Similarity	NPC476295
0.9193	High Similarity	NPC475055
0.9193	High Similarity	NPC41301
0.9187	High Similarity	NPC266314
0.9182	High Similarity	NPC469658
0.9177	High Similarity	NPC470328
0.9177	High Similarity	NPC235165
0.9177	High Similarity	NPC195796
0.9177	High Similarity	NPC209614
0.9177	High Similarity	NPC191146
0.9177	High Similarity	NPC138243
0.9177	High Similarity	NPC35038
0.9177	High Similarity	NPC68093
0.9177	High Similarity	NPC278778
0.9177	High Similarity	NPC255106
0.9177	High Similarity	NPC291878
0.9177	High Similarity	NPC472626
0.9167	High Similarity	NPC204515
0.9136	High Similarity	NPC293319
0.9136	High Similarity	NPC300053
0.9136	High Similarity	NPC108433
0.9136	High Similarity	NPC475888
0.913	High Similarity	NPC229632
0.913	High Similarity	NPC472635
0.913	High Similarity	NPC294965
0.913	High Similarity	NPC220912
0.9125	High Similarity	NPC328102
0.9125	High Similarity	NPC470810
0.9125	High Similarity	NPC297212
0.9125	High Similarity	NPC200746
0.9125	High Similarity	NPC299436
0.9119	High Similarity	NPC472914
0.9119	High Similarity	NPC245758
0.9119	High Similarity	NPC27337
0.9119	High Similarity	NPC222814
0.9119	High Similarity	NPC187745
0.9119	High Similarity	NPC472911
0.9119	High Similarity	NPC219867
0.9119	High Similarity	NPC161960
0.9119	High Similarity	NPC210084
0.9119	High Similarity	NPC472910
0.9119	High Similarity	NPC304008
0.9119	High Similarity	NPC136674
0.9119	High Similarity	NPC180011
0.9119	High Similarity	NPC472598
0.9119	High Similarity	NPC99597
0.9119	High Similarity	NPC291508
0.9119	High Similarity	NPC471209
0.9119	High Similarity	NPC472913
0.9119	High Similarity	NPC96167
0.9119	High Similarity	NPC474055
0.9119	High Similarity	NPC111969
0.9114	High Similarity	NPC37392
0.9108	High Similarity	NPC249570
0.9108	High Similarity	NPC474843
0.9103	High Similarity	NPC227122
0.9103	High Similarity	NPC62042
0.9091	High Similarity	NPC307286
0.9085	High Similarity	NPC152477
0.9085	High Similarity	NPC165456
0.908	High Similarity	NPC37870
0.908	High Similarity	NPC235610
0.908	High Similarity	NPC43319
0.908	High Similarity	NPC128293
0.908	High Similarity	NPC472449
0.908	High Similarity	NPC173292
0.9074	High Similarity	NPC146134
0.9074	High Similarity	NPC173587
0.9074	High Similarity	NPC474350
0.9074	High Similarity	NPC303460
0.9074	High Similarity	NPC474240
0.9074	High Similarity	NPC12461
0.9074	High Similarity	NPC306321
0.9074	High Similarity	NPC133065
0.9074	High Similarity	NPC208120
0.9068	High Similarity	NPC278427
0.9068	High Similarity	NPC66288
0.9068	High Similarity	NPC228383
0.9068	High Similarity	NPC134783
0.9062	High Similarity	NPC46736
0.9062	High Similarity	NPC197856
0.9062	High Similarity	NPC22192
0.9057	High Similarity	NPC13779
0.9057	High Similarity	NPC115853
0.9057	High Similarity	NPC3980
0.9057	High Similarity	NPC475799
0.9057	High Similarity	NPC472916

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 NPC473286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	952
0.2-0.3	1792
0.3-0.4	2649
0.4-0.5	1881
0.5-0.6	923
0.6-0.7	408
0.7-0.8	118
0.8-0.85	39
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9295	High Similarity	NPD2393	Clinical (unspecified phase)
0.8987	High Similarity	NPD1934	Approved
0.8931	High Similarity	NPD2801	Approved
0.8889	High Similarity	NPD5494	Approved
0.8704	High Similarity	NPD3882	Suspended
0.8599	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD3818	Discontinued
0.8563	High Similarity	NPD6168	Clinical (unspecified phase)
0.8563	High Similarity	NPD6166	Phase 2
0.8563	High Similarity	NPD6167	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD6959	Discontinued
0.8491	Intermediate Similarity	NPD1512	Approved
0.8476	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7819	Suspended
0.8428	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8363	Intermediate Similarity	NPD7074	Phase 3
0.8344	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD2534	Approved
0.8313	Intermediate Similarity	NPD2533	Approved
0.8313	Intermediate Similarity	NPD2532	Approved
0.8304	Intermediate Similarity	NPD7054	Approved
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8256	Intermediate Similarity	NPD7472	Approved
0.8242	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8208	Intermediate Similarity	NPD6797	Phase 2
0.8193	Intermediate Similarity	NPD3817	Phase 2
0.8161	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD1247	Approved
0.8057	Intermediate Similarity	NPD6559	Discontinued
0.8038	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3749	Approved
0.7975	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1510	Phase 2
0.7964	Intermediate Similarity	NPD6801	Discontinued
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.7941	Intermediate Similarity	NPD6234	Discontinued
0.7937	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5402	Approved
0.7845	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1240	Approved
0.7834	Intermediate Similarity	NPD943	Approved
0.7816	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6100	Approved
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD6099	Approved
0.7805	Intermediate Similarity	NPD6799	Approved
0.7803	Intermediate Similarity	NPD5710	Approved
0.7803	Intermediate Similarity	NPD5711	Approved
0.776	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3926	Phase 2
0.7751	Intermediate Similarity	NPD37	Approved
0.775	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1607	Approved
0.7733	Intermediate Similarity	NPD919	Approved
0.773	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD7228	Approved
0.7722	Intermediate Similarity	NPD1613	Approved
0.7722	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD4967	Phase 2
0.7719	Intermediate Similarity	NPD4966	Approved
0.7719	Intermediate Similarity	NPD4965	Approved
0.7719	Intermediate Similarity	NPD7768	Phase 2
0.768	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3226	Approved
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7665	Intermediate Similarity	NPD920	Approved
0.766	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2346	Discontinued
0.7644	Intermediate Similarity	NPD7199	Phase 2
0.764	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD8434	Phase 2
0.7628	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD3751	Discontinued
0.7625	Intermediate Similarity	NPD6651	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7611	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3787	Discontinued
0.759	Intermediate Similarity	NPD7390	Discontinued
0.758	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1243	Approved
0.7557	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2344	Approved
0.7545	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7229	Phase 3
0.7474	Intermediate Similarity	NPD6778	Approved
0.7474	Intermediate Similarity	NPD6779	Approved
0.7474	Intermediate Similarity	NPD6780	Approved
0.7474	Intermediate Similarity	NPD6782	Approved
0.7474	Intermediate Similarity	NPD6781	Approved
0.7474	Intermediate Similarity	NPD6777	Approved
0.7474	Intermediate Similarity	NPD6776	Approved
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.7456	Intermediate Similarity	NPD5403	Approved
0.7456	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3748	Approved
0.7423	Intermediate Similarity	NPD2799	Discontinued
0.7421	Intermediate Similarity	NPD3027	Phase 3
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7378	Intermediate Similarity	NPD1551	Phase 2
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2309	Approved
0.7358	Intermediate Similarity	NPD7435	Discontinued
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7347	Intermediate Similarity	NPD8151	Discontinued
0.7337	Intermediate Similarity	NPD5401	Approved
0.7312	Intermediate Similarity	NPD4625	Phase 3
0.731	Intermediate Similarity	NPD1653	Approved
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7299	Intermediate Similarity	NPD5760	Phase 2
0.7299	Intermediate Similarity	NPD5761	Phase 2
0.7296	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7783	Phase 2
0.7268	Intermediate Similarity	NPD7240	Approved
0.7268	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7698	Approved
0.7268	Intermediate Similarity	NPD7697	Approved
0.7268	Intermediate Similarity	NPD7696	Phase 3
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6190	Approved
0.7254	Intermediate Similarity	NPD2493	Approved
0.7254	Intermediate Similarity	NPD2494	Approved
0.725	Intermediate Similarity	NPD4908	Phase 1
0.7239	Intermediate Similarity	NPD447	Suspended
0.7231	Intermediate Similarity	NPD7871	Phase 2
0.7231	Intermediate Similarity	NPD7870	Phase 2
0.7216	Intermediate Similarity	NPD6823	Phase 2
0.7211	Intermediate Similarity	NPD6535	Approved
0.7211	Intermediate Similarity	NPD6534	Approved
0.7208	Intermediate Similarity	NPD7701	Phase 2
0.7206	Intermediate Similarity	NPD7907	Approved
0.7202	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6273	Approved
0.7192	Intermediate Similarity	NPD4665	Approved
0.7192	Intermediate Similarity	NPD4111	Phase 1
0.7184	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7685	Pre-registration
0.7173	Intermediate Similarity	NPD4361	Phase 2
0.7173	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD3452	Approved
0.7165	Intermediate Similarity	NPD3450	Approved
0.716	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4583	Approved
0.7143	Intermediate Similarity	NPD4582	Approved
0.7143	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7136	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7874	Approved
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD2403	Approved
0.7126	Intermediate Similarity	NPD1471	Phase 3
0.7108	Intermediate Similarity	NPD7033	Discontinued
0.7107	Intermediate Similarity	NPD6696	Suspended
0.71	Intermediate Similarity	NPD7801	Approved
0.7098	Intermediate Similarity	NPD7699	Phase 2
0.7098	Intermediate Similarity	NPD7700	Phase 2
0.7092	Intermediate Similarity	NPD4002	Approved
0.7092	Intermediate Similarity	NPD4004	Approved
0.709	Intermediate Similarity	NPD4287	Approved
0.7083	Intermediate Similarity	NPD2424	Discontinued
0.7081	Intermediate Similarity	NPD9494	Approved
0.7073	Intermediate Similarity	NPD4060	Phase 1
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7063	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD3764	Approved
0.7053	Intermediate Similarity	NPD2490	Approved
0.7053	Intermediate Similarity	NPD2488	Approved
0.7047	Intermediate Similarity	NPD2975	Approved
0.7047	Intermediate Similarity	NPD2973	Approved
0.7047	Intermediate Similarity	NPD2974	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