NPASS Compound

Structure

NPC306321 OpenBabel07101719522D 29 32 0 0 0 0 0 0 0 0999 V2000 8.6603 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4282 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 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 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 5.1962 -0.0000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 4.3301 -0.5000 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 6.0622 -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 5.1962 -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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 6 2 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 22 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 23 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 20 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 21 2 0 0 0 0 14 25 1 0 0 0 0 15 16 2 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 19 2 0 0 0 0 17 22 1 0 0 0 0 18 26 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.14
Volume:	401.152
LogP:	5.368
LogD:	3.337
LogS:	-3.47
# 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:	0.43
Synthetic Accessibility Score:	3.544
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.943
MDCK Permeability:	1.8236500181956217e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.455
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	97.04647064208984%
Volume Distribution (VD):	0.801
Pgp-substrate:	8.21728229522705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.823
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.396
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.476
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	1.137
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.393
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.597
Carcinogencity:	0.838
Eye Corrosion:	0.003
Eye Irritation:	0.759
Respiratory Toxicity:	0.569

Download Data

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

Natural Product: NPC306321

Natural Product ID:	NPC306321
*Common Name:**	Isocudraxanthone K
IUPAC Name:	5,8,10-trihydroxy-3,3-dimethyl-9-(2-methylbut-3-en-2-yl)pyrano[2,3-c]xanthen-7-one
Synonyms:	Isocudraxanthone K
Standard InCHIKey:	DKKSZAXBHZPWMV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O6/c1-6-22(2,3)17-13(24)10-15-16(19(17)27)18(26)12-9-14(25)21-11(20(12)28-15)7-8-23(4,5)29-21/h6-10,24-25,27H,1H2,2-5H3
SMILES:	C=CC(c1c(O)cc2c(c1O)c(=O)c1c(o2)c2C=CC(Oc2c(c1)O)(C)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390040
PubChem CID:	44426653
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:0003521] Pyranoxanthones

*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	1

Activity Type	# Activity
Individual Protein	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[570926]

☑ 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 NPC306321 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	467
0.1-0.2	1981
0.2-0.3	4335
0.3-0.4	11077
0.4-0.5	6964
0.5-0.6	3776
0.6-0.7	5332
0.7-0.8	4995
0.8-0.85	2210
0.85-0.9	989
0.9-0.95	530
0.95-1	41

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC303460
0.9805	High Similarity	NPC188433
0.9742	High Similarity	NPC29876
0.9742	High Similarity	NPC57715
0.9742	High Similarity	NPC167678
0.9742	High Similarity	NPC234644
0.9686	High Similarity	NPC472276
0.9679	High Similarity	NPC472448
0.9679	High Similarity	NPC83922
0.9677	High Similarity	NPC204290
0.9675	High Similarity	NPC79053
0.9618	High Similarity	NPC23298
0.9618	High Similarity	NPC189473
0.9615	High Similarity	NPC259456
0.9613	High Similarity	NPC172770
0.9613	High Similarity	NPC185258
0.961	High Similarity	NPC115853
0.9557	High Similarity	NPC275780
0.9557	High Similarity	NPC472450
0.9557	High Similarity	NPC239752
0.9554	High Similarity	NPC329760
0.9554	High Similarity	NPC261470
0.9551	High Similarity	NPC476980
0.9551	High Similarity	NPC80375
0.9548	High Similarity	NPC187745
0.9548	High Similarity	NPC474681
0.9548	High Similarity	NPC180011
0.9548	High Similarity	NPC304008
0.9548	High Similarity	NPC219867
0.9548	High Similarity	NPC161960
0.9548	High Similarity	NPC218313
0.9545	High Similarity	NPC200246
0.95	High Similarity	NPC288813
0.9497	High Similarity	NPC39091
0.9497	High Similarity	NPC472449
0.9497	High Similarity	NPC37870
0.9494	High Similarity	NPC220313
0.949	High Similarity	NPC472275
0.9487	High Similarity	NPC204879
0.9484	High Similarity	NPC191146
0.9484	High Similarity	NPC5322
0.9484	High Similarity	NPC68093
0.9484	High Similarity	NPC138243
0.9484	High Similarity	NPC6633
0.9484	High Similarity	NPC470600
0.9484	High Similarity	NPC133970
0.9434	High Similarity	NPC50960
0.943	High Similarity	NPC474162
0.943	High Similarity	NPC229632
0.943	High Similarity	NPC474150
0.943	High Similarity	NPC78332
0.943	High Similarity	NPC25152
0.9427	High Similarity	NPC45146
0.9427	High Similarity	NPC139036
0.9427	High Similarity	NPC235018
0.9427	High Similarity	NPC471973
0.9423	High Similarity	NPC476981
0.9423	High Similarity	NPC78225
0.9423	High Similarity	NPC36852
0.9423	High Similarity	NPC262286
0.9419	High Similarity	NPC472280
0.9419	High Similarity	NPC256925
0.9371	High Similarity	NPC236521
0.9371	High Similarity	NPC152659
0.9371	High Similarity	NPC146134
0.9371	High Similarity	NPC472281
0.9371	High Similarity	NPC248638
0.9371	High Similarity	NPC207690
0.9371	High Similarity	NPC205265
0.9367	High Similarity	NPC61010
0.9367	High Similarity	NPC32694
0.9367	High Similarity	NPC258331
0.9363	High Similarity	NPC100123
0.9363	High Similarity	NPC235448
0.9363	High Similarity	NPC474290
0.9359	High Similarity	NPC276444
0.9359	High Similarity	NPC471985
0.9359	High Similarity	NPC472455
0.9355	High Similarity	NPC33051
0.9355	High Similarity	NPC227337
0.9355	High Similarity	NPC49402
0.9355	High Similarity	NPC273462
0.9355	High Similarity	NPC70433
0.9325	High Similarity	NPC310794
0.9317	High Similarity	NPC8965
0.9313	High Similarity	NPC472277
0.9308	High Similarity	NPC470694
0.9308	High Similarity	NPC206605
0.9304	High Similarity	NPC200746
0.9304	High Similarity	NPC192686
0.9304	High Similarity	NPC320359
0.9304	High Similarity	NPC228785
0.9304	High Similarity	NPC476280
0.9304	High Similarity	NPC118256
0.9304	High Similarity	NPC119209
0.9304	High Similarity	NPC14353
0.9304	High Similarity	NPC56085
0.9299	High Similarity	NPC218871
0.9299	High Similarity	NPC136674
0.9299	High Similarity	NPC52889
0.9299	High Similarity	NPC476630
0.9295	High Similarity	NPC57674
0.9295	High Similarity	NPC230149
0.9295	High Similarity	NPC168247
0.9295	High Similarity	NPC256612
0.9295	High Similarity	NPC234255
0.9295	High Similarity	NPC20830
0.9295	High Similarity	NPC152951
0.9295	High Similarity	NPC113906
0.9295	High Similarity	NPC117992
0.929	High Similarity	NPC161277
0.929	High Similarity	NPC166201
0.929	High Similarity	NPC237994
0.929	High Similarity	NPC39007
0.9286	High Similarity	NPC248102
0.9259	High Similarity	NPC177480
0.9255	High Similarity	NPC120593
0.925	High Similarity	NPC329669
0.925	High Similarity	NPC18100
0.925	High Similarity	NPC12461
0.925	High Similarity	NPC319200
0.925	High Similarity	NPC473313
0.925	High Similarity	NPC472278
0.925	High Similarity	NPC186686
0.925	High Similarity	NPC41301
0.925	High Similarity	NPC187491
0.9245	High Similarity	NPC278052
0.9245	High Similarity	NPC134783
0.9245	High Similarity	NPC474038
0.9245	High Similarity	NPC40037
0.9245	High Similarity	NPC472906
0.9245	High Similarity	NPC266314
0.9245	High Similarity	NPC40491
0.9241	High Similarity	NPC476242
0.9241	High Similarity	NPC74178
0.9241	High Similarity	NPC46736
0.9241	High Similarity	NPC95936
0.9241	High Similarity	NPC197856
0.9241	High Similarity	NPC184755
0.9241	High Similarity	NPC250214
0.9236	High Similarity	NPC472916
0.9236	High Similarity	NPC142339
0.9236	High Similarity	NPC274730
0.9236	High Similarity	NPC3980
0.9231	High Similarity	NPC170492
0.9231	High Similarity	NPC231018
0.9231	High Similarity	NPC274327
0.9231	High Similarity	NPC271779
0.9231	High Similarity	NPC183878
0.9231	High Similarity	NPC292214
0.9231	High Similarity	NPC88645
0.9231	High Similarity	NPC160951
0.9231	High Similarity	NPC206238
0.9231	High Similarity	NPC255350
0.9231	High Similarity	NPC167091
0.9231	High Similarity	NPC176775
0.9231	High Similarity	NPC69394
0.9231	High Similarity	NPC47781
0.9231	High Similarity	NPC145379
0.9231	High Similarity	NPC22519
0.9226	High Similarity	NPC154345
0.9226	High Similarity	NPC171010
0.9226	High Similarity	NPC251110
0.9198	High Similarity	NPC476306
0.9198	High Similarity	NPC117854
0.9198	High Similarity	NPC477154
0.9198	High Similarity	NPC6588
0.9193	High Similarity	NPC62261
0.9193	High Similarity	NPC234052
0.9193	High Similarity	NPC224280
0.9187	High Similarity	NPC81679
0.9187	High Similarity	NPC52204
0.9187	High Similarity	NPC474034
0.9187	High Similarity	NPC474033
0.9187	High Similarity	NPC220912
0.9182	High Similarity	NPC246478
0.9182	High Similarity	NPC28241
0.9182	High Similarity	NPC297212
0.9182	High Similarity	NPC475784
0.9182	High Similarity	NPC474960
0.9177	High Similarity	NPC165977
0.9177	High Similarity	NPC472914
0.9177	High Similarity	NPC284820
0.9177	High Similarity	NPC223787
0.9177	High Similarity	NPC129684
0.9177	High Similarity	NPC241904
0.9177	High Similarity	NPC99597
0.9177	High Similarity	NPC472911
0.9177	High Similarity	NPC162869
0.9177	High Similarity	NPC27337
0.9177	High Similarity	NPC236796
0.9177	High Similarity	NPC48208
0.9177	High Similarity	NPC156057
0.9177	High Similarity	NPC245758
0.9177	High Similarity	NPC210084
0.9177	High Similarity	NPC475267
0.9177	High Similarity	NPC222814
0.9177	High Similarity	NPC472910
0.9177	High Similarity	NPC300727
0.9177	High Similarity	NPC469584

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 NPC306321 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	1026
0.2-0.3	1842
0.3-0.4	2719
0.4-0.5	1736
0.5-0.6	914
0.6-0.7	341
0.7-0.8	109
0.8-0.85	33
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD2801	Approved
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.8924	High Similarity	NPD1934	Approved
0.8827	High Similarity	NPD5494	Approved
0.8774	High Similarity	NPD1511	Approved
0.8662	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD3882	Suspended
0.8614	High Similarity	NPD6166	Phase 2
0.8614	High Similarity	NPD6168	Clinical (unspecified phase)
0.8614	High Similarity	NPD6167	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8512	High Similarity	NPD3818	Discontinued
0.8481	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7054	Approved
0.8415	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7472	Approved
0.8412	Intermediate Similarity	NPD7074	Phase 3
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8274	Intermediate Similarity	NPD6232	Discontinued
0.8256	Intermediate Similarity	NPD6797	Phase 2
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7075	Discontinued
0.8235	Intermediate Similarity	NPD7473	Discontinued
0.8208	Intermediate Similarity	NPD7251	Discontinued
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8165	Intermediate Similarity	NPD2800	Approved
0.8161	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6801	Discontinued
0.8107	Intermediate Similarity	NPD1247	Approved
0.8107	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD1549	Phase 2
0.8061	Intermediate Similarity	NPD7411	Suspended
0.8038	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8024	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.8	Intermediate Similarity	NPD943	Approved
0.7975	Intermediate Similarity	NPD2796	Approved
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD3750	Approved
0.7885	Intermediate Similarity	NPD1240	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7861	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6799	Approved
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7797	Intermediate Similarity	NPD6559	Discontinued
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.7765	Intermediate Similarity	NPD7768	Phase 2
0.775	Intermediate Similarity	NPD6099	Approved
0.775	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3226	Approved
0.761	Intermediate Similarity	NPD447	Suspended
0.7606	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5403	Approved
0.7605	Intermediate Similarity	NPD920	Approved
0.7593	Intermediate Similarity	NPD2346	Discontinued
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7578	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD3748	Approved
0.7578	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD3751	Discontinued
0.7562	Intermediate Similarity	NPD6651	Approved
0.7561	Intermediate Similarity	NPD4628	Phase 3
0.7547	Intermediate Similarity	NPD1613	Approved
0.7547	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7456	Intermediate Similarity	NPD1653	Approved
0.7443	Intermediate Similarity	NPD3787	Discontinued
0.743	Intermediate Similarity	NPD7286	Phase 2
0.7425	Intermediate Similarity	NPD7390	Discontinued
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6782	Approved
0.7403	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD8434	Phase 2
0.7381	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6234	Discontinued
0.7363	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3027	Phase 3
0.7348	Intermediate Similarity	NPD5953	Discontinued
0.7322	Intermediate Similarity	NPD8312	Approved
0.7322	Intermediate Similarity	NPD8313	Approved
0.7317	Intermediate Similarity	NPD1551	Phase 2
0.7312	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7305	Intermediate Similarity	NPD2309	Approved
0.7305	Intermediate Similarity	NPD6190	Approved
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7288	Intermediate Similarity	NPD7199	Phase 2
0.7284	Intermediate Similarity	NPD1933	Approved
0.7278	Intermediate Similarity	NPD7228	Approved
0.7262	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4625	Phase 3
0.7249	Intermediate Similarity	NPD4360	Phase 2
0.7249	Intermediate Similarity	NPD4363	Phase 3
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD9494	Approved
0.7219	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7697	Approved
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7584	Approved
0.7188	Intermediate Similarity	NPD4908	Phase 1
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.7184	Intermediate Similarity	NPD37	Approved
0.7179	Intermediate Similarity	NPD7871	Phase 2
0.7179	Intermediate Similarity	NPD7870	Phase 2
0.7176	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7549	Discontinued
0.7173	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2798	Approved
0.7165	Intermediate Similarity	NPD6823	Phase 2
0.7159	Intermediate Similarity	NPD4966	Approved
0.7159	Intermediate Similarity	NPD4965	Approved
0.7159	Intermediate Similarity	NPD4967	Phase 2
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7151	Intermediate Similarity	NPD5710	Approved
0.7151	Intermediate Similarity	NPD5711	Approved
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7121	Intermediate Similarity	NPD8151	Discontinued
0.7111	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7099	Intermediate Similarity	NPD3268	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7874	Approved
0.7073	Intermediate Similarity	NPD7907	Approved
0.7072	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD4111	Phase 1
0.7059	Intermediate Similarity	NPD4665	Approved
0.705	Intermediate Similarity	NPD7801	Approved
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7037	Intermediate Similarity	NPD4287	Approved
0.7026	Intermediate Similarity	NPD2494	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7025	Intermediate Similarity	NPD9269	Phase 2
0.7011	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD4288	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD1470	Approved
0.7	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD2797	Approved
0.6994	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4749	Approved
0.6976	Remote Similarity	NPD2899	Discontinued
0.697	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5124	Phase 1
0.6962	Remote Similarity	NPD1610	Phase 2
0.6962	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7229	Phase 3
0.6949	Remote Similarity	NPD5761	Phase 2
0.6949	Remote Similarity	NPD5760	Phase 2
0.6946	Remote Similarity	NPD7033	Discontinued
0.6943	Remote Similarity	NPD4361	Phase 2
0.6943	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8166	Discontinued
0.6941	Remote Similarity	NPD7003	Approved
0.6939	Remote Similarity	NPD3450	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