NPASS Compound

Structure

CID61590 OpenBabel06191715402D 22 24 0 0 1 0 0 0 0 0999 V2000 -1.7321 1.0000 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 -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 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 -4.3301 -1.5000 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 -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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 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 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 8 1 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 7 1 1 1 0 0 0 7 13 1 0 0 0 0 7 22 1 0 0 0 0 8 6 1 6 0 0 0 8 22 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 14 16 1 0 0 0 0 15 20 2 0 0 0 0 16 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	1.892
LogD:	0.719
LogS:	-3.31
# Rotatable Bonds:	2
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	3.124
Fsp3:	0.188
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:	-5.208
MDCK Permeability:	3.356521119712852e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.921
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	91.1872329711914%
Volume Distribution (VD):	0.897
Pgp-substrate:	12.21117115020752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.81
CYP1A2-substrate:	0.843
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.152
CYP2C9-inhibitor:	0.306
CYP2C9-substrate:	0.689
CYP2D6-inhibitor:	0.364
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	7.213
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.25
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.523
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.567
Skin Sensitization:	0.857
Carcinogencity:	0.831
Eye Corrosion:	0.003
Eye Irritation:	0.06
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC61590

Natural Product ID:	NPC61590
*Common Name:**	Nanafrocin
IUPAC Name:	2-[(1S,3R)-9-hydroxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid
Synonyms:	Nanafrocin
Standard InCHIKey:	ZCJHPTKRISJQTN-JGVFFNPUSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m0/s1
SMILES:	C[C@H]1C2=C(C[C@H](CC(=O)O)O1)C(=O)c1cccc(c1C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2106789
PubChem CID:	442757
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
NPO29388	Euchresta strigillosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28746	Cynoglossum zeylanicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29388	Euchresta strigillosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29137	Anemone alpina	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29388	Euchresta strigillosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29299	Baccharis pingraea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28746	Cynoglossum zeylanicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29224	Eupatorium erythropappum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29195	Eucalyptus conglomerata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
LD50	1
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3537	Individual Protein	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens	IC50	=	500.0	nM	PMID[468880]
NPT3537	Individual Protein	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens	IC50	=	500.0	nM	PMID[468881]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	700.0	nM	PMID[468881]
NPT3537	Individual Protein	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens	IC50	=	1500.0	nM	PMID[468881]
NPT3537	Individual Protein	DNA (cytosine-5)-methyltransferase 3B	Homo sapiens	IC50	=	730.0	nM	PMID[468881]
NPT27	Others	Unspecified		LD50	=	28.0	mg.kg-1	PMID[468881]

☑ 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 NPC61590 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	NPC295339
0.9632	High Similarity	NPC21873
0.9562	High Similarity	NPC103910
0.9485	High Similarity	NPC257003
0.9481	High Similarity	NPC256463
0.9481	High Similarity	NPC471602
0.9481	High Similarity	NPC476477
0.9481	High Similarity	NPC216312
0.9481	High Similarity	NPC299405
0.9481	High Similarity	NPC29771
0.9481	High Similarity	NPC111422
0.9481	High Similarity	NPC306835
0.9416	High Similarity	NPC474300
0.9412	High Similarity	NPC32749
0.9412	High Similarity	NPC42262
0.9412	High Similarity	NPC37992
0.9412	High Similarity	NPC241349
0.9412	High Similarity	NPC327916
0.9412	High Similarity	NPC220496
0.9412	High Similarity	NPC147542
0.9348	High Similarity	NPC476473
0.9343	High Similarity	NPC471444
0.9143	High Similarity	NPC89664
0.9143	High Similarity	NPC274085
0.8905	High Similarity	NPC27407
0.8857	High Similarity	NPC156872
0.8824	High Similarity	NPC242358
0.8824	High Similarity	NPC246693
0.8824	High Similarity	NPC110609
0.8797	High Similarity	NPC3224
0.8792	High Similarity	NPC29552
0.8786	High Similarity	NPC26924
0.8768	High Similarity	NPC142027
0.8759	High Similarity	NPC94781
0.875	High Similarity	NPC214702
0.875	High Similarity	NPC470831
0.8723	High Similarity	NPC315578
0.8714	High Similarity	NPC173980
0.8714	High Similarity	NPC221104
0.8705	High Similarity	NPC291454
0.8705	High Similarity	NPC141934
0.8699	High Similarity	NPC44378
0.8699	High Similarity	NPC280753
0.8699	High Similarity	NPC120171
0.869	High Similarity	NPC119767
0.8681	High Similarity	NPC474630
0.8671	High Similarity	NPC478202
0.8662	High Similarity	NPC149533
0.8662	High Similarity	NPC470842
0.8657	High Similarity	NPC231774
0.8652	High Similarity	NPC1268
0.8643	High Similarity	NPC301915
0.8643	High Similarity	NPC261292
0.863	High Similarity	NPC228012
0.8623	High Similarity	NPC43627
0.8621	High Similarity	NPC147250
0.8613	High Similarity	NPC7012
0.8611	High Similarity	NPC151607
0.8611	High Similarity	NPC42540
0.8611	High Similarity	NPC475201
0.86	High Similarity	NPC472050
0.86	High Similarity	NPC478027
0.8582	High Similarity	NPC197666
0.8582	High Similarity	NPC33144
0.8582	High Similarity	NPC478200
0.8582	High Similarity	NPC103540
0.8582	High Similarity	NPC126739
0.8582	High Similarity	NPC191835
0.8581	High Similarity	NPC39819
0.8571	High Similarity	NPC315275
0.8571	High Similarity	NPC84142
0.8561	High Similarity	NPC474097
0.8552	High Similarity	NPC475923
0.8552	High Similarity	NPC474309
0.8551	High Similarity	NPC309430
0.8551	High Similarity	NPC477406
0.855	High Similarity	NPC206778
0.855	High Similarity	NPC285829
0.8542	High Similarity	NPC471731
0.8542	High Similarity	NPC159721
0.8542	High Similarity	NPC66593
0.854	High Similarity	NPC475741
0.8531	High Similarity	NPC283292
0.8531	High Similarity	NPC53649
0.8531	High Similarity	NPC478201
0.8531	High Similarity	NPC472603
0.8531	High Similarity	NPC478217
0.8531	High Similarity	NPC472035
0.8531	High Similarity	NPC313123
0.8531	High Similarity	NPC158634
0.8529	High Similarity	NPC282923
0.8529	High Similarity	NPC165257
0.8523	High Similarity	NPC115249
0.8521	High Similarity	NPC114620
0.8521	High Similarity	NPC268052
0.8521	High Similarity	NPC103337
0.8519	High Similarity	NPC306765
0.8514	High Similarity	NPC472891
0.8514	High Similarity	NPC205766
0.8514	High Similarity	NPC164762
0.8511	High Similarity	NPC305060
0.8511	High Similarity	NPC71256
0.8511	High Similarity	NPC70380
0.8507	High Similarity	NPC265910
0.8507	High Similarity	NPC91475
0.85	High Similarity	NPC22222
0.85	High Similarity	NPC161632
0.85	High Similarity	NPC281513
0.8496	Intermediate Similarity	NPC307174
0.8493	Intermediate Similarity	NPC470570
0.8489	Intermediate Similarity	NPC171968
0.8483	Intermediate Similarity	NPC193703
0.8483	Intermediate Similarity	NPC48762
0.8483	Intermediate Similarity	NPC477409
0.8483	Intermediate Similarity	NPC21599
0.8477	Intermediate Similarity	NPC313299
0.8472	Intermediate Similarity	NPC471733
0.8467	Intermediate Similarity	NPC146647
0.8467	Intermediate Similarity	NPC99731
0.8467	Intermediate Similarity	NPC137301
0.8467	Intermediate Similarity	NPC474622
0.8467	Intermediate Similarity	NPC34414
0.8467	Intermediate Similarity	NPC474621
0.8462	Intermediate Similarity	NPC472600
0.8462	Intermediate Similarity	NPC472601
0.8462	Intermediate Similarity	NPC155205
0.8456	Intermediate Similarity	NPC91809
0.8451	Intermediate Similarity	NPC9121
0.8451	Intermediate Similarity	NPC94248
0.8451	Intermediate Similarity	NPC177307
0.8451	Intermediate Similarity	NPC212693
0.8451	Intermediate Similarity	NPC472602
0.8446	Intermediate Similarity	NPC70764
0.8444	Intermediate Similarity	NPC167055
0.8444	Intermediate Similarity	NPC240744
0.844	Intermediate Similarity	NPC235115
0.8433	Intermediate Similarity	NPC375356
0.8429	Intermediate Similarity	NPC288089
0.8425	Intermediate Similarity	NPC34482
0.8421	Intermediate Similarity	NPC472889
0.8417	Intermediate Similarity	NPC58685
0.8417	Intermediate Similarity	NPC477407
0.8417	Intermediate Similarity	NPC70622
0.8414	Intermediate Similarity	NPC277369
0.8414	Intermediate Similarity	NPC472006
0.8414	Intermediate Similarity	NPC215451
0.8411	Intermediate Similarity	NPC472890
0.8403	Intermediate Similarity	NPC472605
0.8403	Intermediate Similarity	NPC472604
0.8403	Intermediate Similarity	NPC124365
0.84	Intermediate Similarity	NPC474533
0.84	Intermediate Similarity	NPC184284
0.84	Intermediate Similarity	NPC76041
0.84	Intermediate Similarity	NPC474534
0.84	Intermediate Similarity	NPC478224
0.84	Intermediate Similarity	NPC281272
0.8394	Intermediate Similarity	NPC237225
0.8392	Intermediate Similarity	NPC52358
0.8392	Intermediate Similarity	NPC32360
0.8392	Intermediate Similarity	NPC92655
0.8392	Intermediate Similarity	NPC88269
0.8392	Intermediate Similarity	NPC477408
0.8389	Intermediate Similarity	NPC295036
0.838	Intermediate Similarity	NPC65837
0.838	Intermediate Similarity	NPC149372
0.838	Intermediate Similarity	NPC474771
0.838	Intermediate Similarity	NPC474849
0.838	Intermediate Similarity	NPC178467
0.8378	Intermediate Similarity	NPC153417
0.837	Intermediate Similarity	NPC234890
0.837	Intermediate Similarity	NPC74507
0.837	Intermediate Similarity	NPC310540
0.8369	Intermediate Similarity	NPC298900
0.8369	Intermediate Similarity	NPC283088
0.8367	Intermediate Similarity	NPC300540
0.8367	Intermediate Similarity	NPC472033
0.8358	Intermediate Similarity	NPC300274
0.8358	Intermediate Similarity	NPC46634
0.8358	Intermediate Similarity	NPC217756
0.8357	Intermediate Similarity	NPC153783
0.8357	Intermediate Similarity	NPC254603
0.8357	Intermediate Similarity	NPC115458
0.8356	Intermediate Similarity	NPC126882
0.8356	Intermediate Similarity	NPC477913
0.8356	Intermediate Similarity	NPC478203
0.8356	Intermediate Similarity	NPC210966
0.8345	Intermediate Similarity	NPC244699
0.8345	Intermediate Similarity	NPC205992
0.8344	Intermediate Similarity	NPC218870
0.8344	Intermediate Similarity	NPC474824
0.8344	Intermediate Similarity	NPC470408
0.8344	Intermediate Similarity	NPC478231
0.8344	Intermediate Similarity	NPC182921
0.8344	Intermediate Similarity	NPC477691
0.8333	Intermediate Similarity	NPC109007
0.8333	Intermediate Similarity	NPC132990
0.8333	Intermediate Similarity	NPC46882
0.8333	Intermediate Similarity	NPC205918
0.8333	Intermediate Similarity	NPC168471
0.8333	Intermediate Similarity	NPC183345

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 NPC61590 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
0.8582	High Similarity	NPD1470	Approved
0.8322	Intermediate Similarity	NPD3226	Approved
0.8284	Intermediate Similarity	NPD1201	Approved
0.8244	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2346	Discontinued
0.8151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD3750	Approved
0.8014	Intermediate Similarity	NPD3764	Approved
0.8	Intermediate Similarity	NPD5408	Approved
0.8	Intermediate Similarity	NPD5405	Approved
0.8	Intermediate Similarity	NPD5404	Approved
0.8	Intermediate Similarity	NPD5406	Approved
0.7987	Intermediate Similarity	NPD7819	Suspended
0.797	Intermediate Similarity	NPD9493	Approved
0.7933	Intermediate Similarity	NPD2532	Approved
0.7933	Intermediate Similarity	NPD2533	Approved
0.7933	Intermediate Similarity	NPD2534	Approved
0.7887	Intermediate Similarity	NPD2313	Discontinued
0.7877	Intermediate Similarity	NPD2935	Discontinued
0.7808	Intermediate Similarity	NPD1510	Phase 2
0.7755	Intermediate Similarity	NPD1551	Phase 2
0.775	Intermediate Similarity	NPD6232	Discontinued
0.7721	Intermediate Similarity	NPD9545	Approved
0.7716	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD3748	Approved
0.7687	Intermediate Similarity	NPD2799	Discontinued
0.7679	Intermediate Similarity	NPD8150	Discontinued
0.7667	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1549	Phase 2
0.7613	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7075	Discontinued
0.7606	Intermediate Similarity	NPD2798	Approved
0.7605	Intermediate Similarity	NPD8313	Approved
0.7605	Intermediate Similarity	NPD8312	Approved
0.76	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5402	Approved
0.7584	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD9717	Approved
0.7564	Intermediate Similarity	NPD4380	Phase 2
0.7551	Intermediate Similarity	NPD1607	Approved
0.755	Intermediate Similarity	NPD8166	Discontinued
0.7547	Intermediate Similarity	NPD7768	Phase 2
0.7535	Intermediate Similarity	NPD1203	Approved
0.7535	Intermediate Similarity	NPD1164	Approved
0.7534	Intermediate Similarity	NPD1240	Approved
0.7532	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2796	Approved
0.7517	Intermediate Similarity	NPD411	Approved
0.7516	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD74	Approved
0.75	Intermediate Similarity	NPD9266	Approved
0.75	Intermediate Similarity	NPD3749	Approved
0.7485	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5403	Approved
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7469	Intermediate Similarity	NPD6959	Discontinued
0.7468	Intermediate Similarity	NPD5401	Approved
0.7468	Intermediate Similarity	NPD6801	Discontinued
0.7468	Intermediate Similarity	NPD1934	Approved
0.745	Intermediate Similarity	NPD4308	Phase 3
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7424	Intermediate Similarity	NPD9264	Approved
0.7424	Intermediate Similarity	NPD9263	Approved
0.7424	Intermediate Similarity	NPD9267	Approved
0.7415	Intermediate Similarity	NPD943	Approved
0.7403	Intermediate Similarity	NPD7390	Discontinued
0.7379	Intermediate Similarity	NPD6832	Phase 2
0.7376	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2344	Approved
0.7347	Intermediate Similarity	NPD6663	Approved
0.7342	Intermediate Similarity	NPD6599	Discontinued
0.7338	Intermediate Similarity	NPD3300	Phase 2
0.7333	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7003	Approved
0.7317	Intermediate Similarity	NPD5711	Approved
0.7317	Intermediate Similarity	NPD5710	Approved
0.7312	Intermediate Similarity	NPD2801	Approved
0.731	Intermediate Similarity	NPD5736	Approved
0.7308	Intermediate Similarity	NPD6273	Approved
0.7305	Intermediate Similarity	NPD5844	Phase 1
0.7292	Intermediate Similarity	NPD2797	Approved
0.729	Intermediate Similarity	NPD6799	Approved
0.729	Intermediate Similarity	NPD1511	Approved
0.7284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3268	Approved
0.7279	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6559	Discontinued
0.7267	Intermediate Similarity	NPD3817	Phase 2
0.7261	Intermediate Similarity	NPD920	Approved
0.7259	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2800	Approved
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7244	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2182	Approved
0.7234	Intermediate Similarity	NPD4626	Approved
0.7234	Intermediate Similarity	NPD2932	Approved
0.723	Intermediate Similarity	NPD520	Approved
0.7222	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7211	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1608	Approved
0.7197	Intermediate Similarity	NPD1512	Approved
0.7181	Intermediate Similarity	NPD4307	Phase 2
0.7174	Intermediate Similarity	NPD9281	Approved
0.7168	Intermediate Similarity	NPD8434	Phase 2
0.7163	Intermediate Similarity	NPD5691	Approved
0.7161	Intermediate Similarity	NPD2309	Approved
0.7161	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD1243	Approved
0.7134	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1471	Phase 3
0.7123	Intermediate Similarity	NPD1019	Discontinued
0.7123	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD9261	Approved
0.7119	Intermediate Similarity	NPD6534	Approved
0.7119	Intermediate Similarity	NPD6535	Approved
0.7118	Intermediate Similarity	NPD5953	Discontinued
0.7115	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3019	Approved
0.7105	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7008	Discontinued
0.7091	Intermediate Similarity	NPD5494	Approved
0.7088	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD164	Approved
0.7063	Intermediate Similarity	NPD7458	Discontinued
0.7062	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6213	Phase 3
0.7062	Intermediate Similarity	NPD6212	Phase 3
0.7059	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD6100	Approved
0.7055	Intermediate Similarity	NPD3267	Approved
0.7055	Intermediate Similarity	NPD3266	Approved
0.7055	Intermediate Similarity	NPD4288	Approved
0.705	Intermediate Similarity	NPD5951	Approved
0.7049	Intermediate Similarity	NPD8319	Approved
0.7049	Intermediate Similarity	NPD8320	Phase 1
0.7041	Intermediate Similarity	NPD3751	Discontinued
0.7037	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6844	Discontinued
0.7037	Intermediate Similarity	NPD37	Approved
0.7035	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD919	Approved
0.703	Intermediate Similarity	NPD6234	Discontinued
0.7024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6166	Phase 2
0.7024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1933	Approved
0.7017	Intermediate Similarity	NPD6778	Approved
0.7017	Intermediate Similarity	NPD6776	Approved
0.7017	Intermediate Similarity	NPD6782	Approved
0.7017	Intermediate Similarity	NPD6780	Approved
0.7017	Intermediate Similarity	NPD6777	Approved
0.7017	Intermediate Similarity	NPD6779	Approved
0.7017	Intermediate Similarity	NPD6781	Approved
0.7014	Intermediate Similarity	NPD1281	Approved
0.7013	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6005	Phase 3
0.7013	Intermediate Similarity	NPD6004	Phase 3
0.7013	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6002	Phase 3
0.7012	Intermediate Similarity	NPD4965	Approved
0.7012	Intermediate Similarity	NPD4967	Phase 2
0.7012	Intermediate Similarity	NPD4966	Approved
0.7006	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD7700	Phase 2
0.6994	Remote Similarity	NPD1465	Phase 2
0.6993	Remote Similarity	NPD1778	Approved
0.6993	Remote Similarity	NPD17	Approved
0.6993	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3225	Approved
0.6986	Remote Similarity	NPD1876	Approved
0.6985	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6651	Approved
0.6959	Remote Similarity	NPD7074	Phase 3
0.6959	Remote Similarity	NPD7472	Approved
0.6954	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD4060	Phase 1
0.6948	Remote Similarity	NPD2438	Suspended
0.6941	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6859	Clinical (unspecified phase)

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