NPASS Compound

Structure

CID295339 OpenBabel06191716102D 24 26 0 0 1 0 0 0 0 0999 V2000 0.8660 2.5000 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 -2.5981 -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 -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 1.7321 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 1 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 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 0.8660 -0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 8 1 6 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 4 1 1 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 17 22 2 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.11
Volume:	328.501
LogP:	2.968
LogD:	1.488
LogS:	-3.578
# Rotatable Bonds:	4
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	3.211
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.098
MDCK Permeability:	1.4282860320236068e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.932
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	96.5612564086914%
Volume Distribution (VD):	0.759
Pgp-substrate:	7.439970016479492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.084
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	0.543
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.132
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	6.17
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.719
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.592
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.567
Skin Sensitization:	0.848
Carcinogencity:	0.703
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.357

Download Data

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

Natural Product: NPC295339

Natural Product ID:	NPC295339
*Common Name:**	Deoxyfrenolicin
IUPAC Name:	2-[(1R,3S)-9-hydroxy-5,10-dioxo-1-propyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
Synonyms:	deoxyfrenolicin
Standard InCHIKey:	XWXZEYLPRXYHQC-TVQRCGJNSA-N
Standard InCHI:	InChI=1S/C18H18O6/c1-2-4-13-16-11(7-9(24-13)8-14(20)21)17(22)10-5-3-6-12(19)15(10)18(16)23/h3,5-6,9,13,19H,2,4,7-8H2,1H3,(H,20,21)/t9-,13+/m0/s1
SMILES:	CCC[C@H]1O[C@H](CC(=O)O)CC2=C1C(=O)c1c(C2=O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444165
PubChem CID:	3084051
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones [CHEMONTID:0002355] Benzoisochromanequinones

*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
NPO33097	Streptomyces sp. RM-4-15	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23944931]

☑ 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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1070.0	nM	PMID[498283]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	330.0	nM	PMID[498282]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	=	424.0	nM	PMID[498282]

☑ 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 NPC295339 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	295
0.1-0.2	1239
0.2-0.3	2899
0.3-0.4	6578
0.4-0.5	11568
0.5-0.6	4916
0.6-0.7	8235
0.7-0.8	6386
0.8-0.85	454
0.85-0.9	95
0.9-0.95	29
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC61590
0.9706	High Similarity	NPC21873
0.9635	High Similarity	NPC103910
0.9559	High Similarity	NPC257003
0.9556	High Similarity	NPC111422
0.9556	High Similarity	NPC29771
0.9556	High Similarity	NPC306835
0.9556	High Similarity	NPC256463
0.9556	High Similarity	NPC299405
0.9556	High Similarity	NPC216312
0.9556	High Similarity	NPC476477
0.9556	High Similarity	NPC471602
0.9489	High Similarity	NPC474300
0.9485	High Similarity	NPC220496
0.9485	High Similarity	NPC37992
0.9485	High Similarity	NPC241349
0.9485	High Similarity	NPC32749
0.9485	High Similarity	NPC42262
0.9485	High Similarity	NPC327916
0.9485	High Similarity	NPC147542
0.942	High Similarity	NPC476473
0.9416	High Similarity	NPC471444
0.9214	High Similarity	NPC274085
0.9214	High Similarity	NPC89664
0.8978	High Similarity	NPC27407
0.8897	High Similarity	NPC246693
0.8897	High Similarity	NPC242358
0.8897	High Similarity	NPC110609
0.8859	High Similarity	NPC29552
0.8841	High Similarity	NPC142027
0.8828	High Similarity	NPC94781
0.8794	High Similarity	NPC156872
0.8794	High Similarity	NPC315578
0.8767	High Similarity	NPC120171
0.8767	High Similarity	NPC44378
0.8767	High Similarity	NPC280753
0.875	High Similarity	NPC474630
0.8741	High Similarity	NPC478202
0.8731	High Similarity	NPC3224
0.8723	High Similarity	NPC26924
0.8696	High Similarity	NPC43627
0.869	High Similarity	NPC147250
0.8686	High Similarity	NPC7012
0.8686	High Similarity	NPC214702
0.8686	High Similarity	NPC470831
0.8681	High Similarity	NPC42540
0.8681	High Similarity	NPC151607
0.8667	High Similarity	NPC472050
0.8667	High Similarity	NPC478027
0.8652	High Similarity	NPC33144
0.8652	High Similarity	NPC221104
0.8652	High Similarity	NPC478200
0.8652	High Similarity	NPC173980
0.8652	High Similarity	NPC191835
0.8643	High Similarity	NPC141934
0.8643	High Similarity	NPC291454
0.8639	High Similarity	NPC84142
0.8633	High Similarity	NPC474097
0.863	High Similarity	NPC119767
0.8621	High Similarity	NPC474309
0.8621	High Similarity	NPC475923
0.8611	High Similarity	NPC159721
0.8611	High Similarity	NPC471731
0.8601	High Similarity	NPC158634
0.8601	High Similarity	NPC470842
0.8601	High Similarity	NPC149533
0.8601	High Similarity	NPC313123
0.8601	High Similarity	NPC472603
0.8601	High Similarity	NPC478217
0.8601	High Similarity	NPC478201
0.8601	High Similarity	NPC53649
0.8601	High Similarity	NPC472035
0.8593	High Similarity	NPC231774
0.8593	High Similarity	NPC306765
0.8592	High Similarity	NPC1268
0.8591	High Similarity	NPC115249
0.8582	High Similarity	NPC301915
0.8582	High Similarity	NPC261292
0.8582	High Similarity	NPC71256
0.8582	High Similarity	NPC70380
0.8581	High Similarity	NPC164762
0.8581	High Similarity	NPC205766
0.8581	High Similarity	NPC472891
0.8571	High Similarity	NPC22222
0.8571	High Similarity	NPC228012
0.8571	High Similarity	NPC281513
0.8562	High Similarity	NPC470570
0.8552	High Similarity	NPC477409
0.8552	High Similarity	NPC475201
0.8542	High Similarity	NPC471733
0.8533	High Similarity	NPC137301
0.8533	High Similarity	NPC474621
0.8533	High Similarity	NPC474622
0.8531	High Similarity	NPC472601
0.8531	High Similarity	NPC472600
0.8523	High Similarity	NPC39819
0.8523	High Similarity	NPC91809
0.8521	High Similarity	NPC177307
0.8521	High Similarity	NPC197666
0.8521	High Similarity	NPC212693
0.8521	High Similarity	NPC472602
0.8521	High Similarity	NPC126739
0.8521	High Similarity	NPC9121
0.8521	High Similarity	NPC94248
0.8519	High Similarity	NPC167055
0.8519	High Similarity	NPC240744
0.8519	High Similarity	NPC103540
0.8511	High Similarity	NPC315275
0.8493	Intermediate Similarity	NPC34482
0.8489	Intermediate Similarity	NPC58685
0.8489	Intermediate Similarity	NPC309430
0.8489	Intermediate Similarity	NPC477406
0.8487	Intermediate Similarity	NPC472889
0.8485	Intermediate Similarity	NPC206778
0.8485	Intermediate Similarity	NPC285829
0.8483	Intermediate Similarity	NPC66593
0.8483	Intermediate Similarity	NPC277369
0.8483	Intermediate Similarity	NPC472006
0.8483	Intermediate Similarity	NPC215451
0.8478	Intermediate Similarity	NPC475741
0.8477	Intermediate Similarity	NPC472890
0.8472	Intermediate Similarity	NPC472604
0.8472	Intermediate Similarity	NPC283292
0.8472	Intermediate Similarity	NPC472605
0.8467	Intermediate Similarity	NPC76041
0.8467	Intermediate Similarity	NPC184284
0.8467	Intermediate Similarity	NPC165257
0.8467	Intermediate Similarity	NPC474533
0.8467	Intermediate Similarity	NPC282923
0.8467	Intermediate Similarity	NPC478224
0.8467	Intermediate Similarity	NPC474534
0.8462	Intermediate Similarity	NPC477408
0.8462	Intermediate Similarity	NPC268052
0.8462	Intermediate Similarity	NPC32360
0.8462	Intermediate Similarity	NPC103337
0.8462	Intermediate Similarity	NPC114620
0.8451	Intermediate Similarity	NPC474771
0.8451	Intermediate Similarity	NPC149372
0.8451	Intermediate Similarity	NPC474849
0.8451	Intermediate Similarity	NPC65837
0.8451	Intermediate Similarity	NPC305060
0.8451	Intermediate Similarity	NPC178467
0.8444	Intermediate Similarity	NPC265910
0.8444	Intermediate Similarity	NPC91475
0.844	Intermediate Similarity	NPC161632
0.844	Intermediate Similarity	NPC298900
0.844	Intermediate Similarity	NPC283088
0.8435	Intermediate Similarity	NPC472033
0.8433	Intermediate Similarity	NPC307174
0.8429	Intermediate Similarity	NPC115458
0.8429	Intermediate Similarity	NPC171968
0.8425	Intermediate Similarity	NPC210966
0.8425	Intermediate Similarity	NPC48762
0.8425	Intermediate Similarity	NPC193703
0.8425	Intermediate Similarity	NPC21599
0.8425	Intermediate Similarity	NPC477913
0.8425	Intermediate Similarity	NPC126882
0.8425	Intermediate Similarity	NPC478203
0.8421	Intermediate Similarity	NPC313299
0.8411	Intermediate Similarity	NPC182921
0.8411	Intermediate Similarity	NPC477691
0.8411	Intermediate Similarity	NPC474824
0.8411	Intermediate Similarity	NPC218870
0.8411	Intermediate Similarity	NPC470408
0.8411	Intermediate Similarity	NPC478231
0.8406	Intermediate Similarity	NPC99731
0.8406	Intermediate Similarity	NPC146647
0.8406	Intermediate Similarity	NPC34414
0.8403	Intermediate Similarity	NPC155205
0.8403	Intermediate Similarity	NPC168471
0.8403	Intermediate Similarity	NPC158472
0.84	Intermediate Similarity	NPC132990
0.84	Intermediate Similarity	NPC46882
0.84	Intermediate Similarity	NPC205918
0.8392	Intermediate Similarity	NPC472403
0.8392	Intermediate Similarity	NPC475974
0.8389	Intermediate Similarity	NPC70764
0.8389	Intermediate Similarity	NPC247219
0.838	Intermediate Similarity	NPC235115
0.8378	Intermediate Similarity	NPC471734
0.837	Intermediate Similarity	NPC375356
0.8369	Intermediate Similarity	NPC288089
0.8367	Intermediate Similarity	NPC257558
0.8367	Intermediate Similarity	NPC83272
0.8367	Intermediate Similarity	NPC472034
0.8366	Intermediate Similarity	NPC263483
0.8366	Intermediate Similarity	NPC208651
0.8366	Intermediate Similarity	NPC478225
0.8366	Intermediate Similarity	NPC206641
0.8357	Intermediate Similarity	NPC470160
0.8357	Intermediate Similarity	NPC70622
0.8357	Intermediate Similarity	NPC477407
0.8356	Intermediate Similarity	NPC472610
0.8355	Intermediate Similarity	NPC192219
0.8355	Intermediate Similarity	NPC174599
0.8355	Intermediate Similarity	NPC170189
0.8355	Intermediate Similarity	NPC69043
0.8355	Intermediate Similarity	NPC82190
0.8355	Intermediate Similarity	NPC317585
0.8355	Intermediate Similarity	NPC208173

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 NPC295339 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	840
0.2-0.3	1475
0.3-0.4	2474
0.4-0.5	2200
0.5-0.6	1253
0.6-0.7	513
0.7-0.8	131
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD1470	Approved
0.8267	Intermediate Similarity	NPD3226	Approved
0.8222	Intermediate Similarity	NPD1201	Approved
0.8182	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD2346	Discontinued
0.8095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD5408	Approved
0.8069	Intermediate Similarity	NPD5406	Approved
0.8069	Intermediate Similarity	NPD5405	Approved
0.8069	Intermediate Similarity	NPD5404	Approved
0.8052	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.7973	Intermediate Similarity	NPD3750	Approved
0.7958	Intermediate Similarity	NPD3764	Approved
0.7945	Intermediate Similarity	NPD2935	Discontinued
0.791	Intermediate Similarity	NPD9493	Approved
0.7832	Intermediate Similarity	NPD2313	Discontinued
0.7812	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7755	Intermediate Similarity	NPD2799	Discontinued
0.7755	Intermediate Similarity	NPD1510	Phase 2
0.7738	Intermediate Similarity	NPD8150	Discontinued
0.7733	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1551	Phase 2
0.7677	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2798	Approved
0.7673	Intermediate Similarity	NPD7075	Discontinued
0.7667	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8312	Approved
0.7665	Intermediate Similarity	NPD8313	Approved
0.7664	Intermediate Similarity	NPD9545	Approved
0.7658	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3748	Approved
0.7628	Intermediate Similarity	NPD4380	Phase 2
0.7616	Intermediate Similarity	NPD8166	Discontinued
0.761	Intermediate Similarity	NPD7768	Phase 2
0.76	Intermediate Similarity	NPD1549	Phase 2
0.7595	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2796	Approved
0.758	Intermediate Similarity	NPD7411	Suspended
0.7558	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5403	Approved
0.7544	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6801	Discontinued
0.7531	Intermediate Similarity	NPD6959	Discontinued
0.7518	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7483	Intermediate Similarity	NPD1240	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7468	Intermediate Similarity	NPD7390	Discontinued
0.7466	Intermediate Similarity	NPD411	Approved
0.7453	Intermediate Similarity	NPD3749	Approved
0.7448	Intermediate Similarity	NPD6832	Phase 2
0.7444	Intermediate Similarity	NPD74	Approved
0.7444	Intermediate Similarity	NPD9266	Approved
0.7438	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD230	Phase 1
0.7432	Intermediate Similarity	NPD447	Suspended
0.7421	Intermediate Similarity	NPD1934	Approved
0.7419	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5401	Approved
0.7415	Intermediate Similarity	NPD6663	Approved
0.7405	Intermediate Similarity	NPD6599	Discontinued
0.7403	Intermediate Similarity	NPD3300	Phase 2
0.74	Intermediate Similarity	NPD7033	Discontinued
0.74	Intermediate Similarity	NPD4308	Phase 3
0.7394	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7003	Approved
0.7379	Intermediate Similarity	NPD5736	Approved
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7375	Intermediate Similarity	NPD2801	Approved
0.7372	Intermediate Similarity	NPD6273	Approved
0.7368	Intermediate Similarity	NPD9264	Approved
0.7368	Intermediate Similarity	NPD9263	Approved
0.7368	Intermediate Similarity	NPD9267	Approved
0.7365	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD943	Approved
0.7361	Intermediate Similarity	NPD2797	Approved
0.7355	Intermediate Similarity	NPD6799	Approved
0.7347	Intermediate Similarity	NPD3268	Approved
0.7347	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7333	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3817	Phase 2
0.7324	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD2182	Approved
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4626	Approved
0.7305	Intermediate Similarity	NPD3818	Discontinued
0.7305	Intermediate Similarity	NPD2932	Approved
0.7303	Intermediate Similarity	NPD2344	Approved
0.7303	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3882	Suspended
0.7279	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1511	Approved
0.7234	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD6190	Approved
0.7225	Intermediate Similarity	NPD8434	Phase 2
0.7215	Intermediate Similarity	NPD920	Approved
0.7208	Intermediate Similarity	NPD2800	Approved
0.7202	Intermediate Similarity	NPD7177	Discontinued
0.7192	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3019	Approved
0.7181	Intermediate Similarity	NPD520	Approved
0.7176	Intermediate Similarity	NPD5953	Discontinued
0.7175	Intermediate Similarity	NPD6535	Approved
0.7175	Intermediate Similarity	NPD6534	Approved
0.7172	Intermediate Similarity	NPD1283	Approved
0.7171	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7008	Discontinued
0.7153	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7133	Intermediate Similarity	NPD4307	Phase 2
0.7125	Intermediate Similarity	NPD7458	Discontinued
0.7124	Intermediate Similarity	NPD6100	Approved
0.7124	Intermediate Similarity	NPD6099	Approved
0.7122	Intermediate Similarity	NPD9281	Approved
0.7122	Intermediate Similarity	NPD5951	Approved
0.7119	Intermediate Similarity	NPD6213	Phase 3
0.7119	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6212	Phase 3
0.7115	Intermediate Similarity	NPD2309	Approved
0.7104	Intermediate Similarity	NPD8319	Approved
0.7104	Intermediate Similarity	NPD8320	Phase 1
0.7099	Intermediate Similarity	NPD6844	Discontinued
0.7099	Intermediate Similarity	NPD37	Approved
0.7097	Intermediate Similarity	NPD1243	Approved
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6234	Discontinued
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6166	Phase 2
0.7078	Intermediate Similarity	NPD6002	Phase 3
0.7078	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6005	Phase 3
0.7078	Intermediate Similarity	NPD1471	Phase 3
0.7078	Intermediate Similarity	NPD6004	Phase 3
0.7075	Intermediate Similarity	NPD1019	Discontinued
0.7073	Intermediate Similarity	NPD4967	Phase 2
0.7073	Intermediate Similarity	NPD4966	Approved
0.7073	Intermediate Similarity	NPD4965	Approved
0.7072	Intermediate Similarity	NPD6782	Approved
0.7072	Intermediate Similarity	NPD6777	Approved
0.7072	Intermediate Similarity	NPD6779	Approved
0.7072	Intermediate Similarity	NPD6778	Approved
0.7072	Intermediate Similarity	NPD6781	Approved
0.7072	Intermediate Similarity	NPD6780	Approved
0.7072	Intermediate Similarity	NPD6776	Approved
0.707	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7236	Approved
0.7068	Intermediate Similarity	NPD9261	Approved
0.7063	Intermediate Similarity	NPD1778	Approved
0.7063	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7054	Approved
0.7056	Intermediate Similarity	NPD7700	Phase 2
0.7056	Intermediate Similarity	NPD7699	Phase 2
0.7039	Intermediate Similarity	NPD6651	Approved
0.702	Intermediate Similarity	NPD4060	Phase 1
0.702	Intermediate Similarity	NPD2979	Phase 3
0.7018	Intermediate Similarity	NPD7074	Phase 3
0.7018	Intermediate Similarity	NPD7472	Approved
0.7015	Intermediate Similarity	NPD164	Approved
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7012	Intermediate Similarity	NPD4288	Approved
0.7007	Intermediate Similarity	NPD3266	Approved
0.7007	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD919	Approved
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6797	Phase 2
0.6974	Remote Similarity	NPD1933	Approved
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7266	Discontinued
0.6968	Remote Similarity	NPD5763	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