NPASS Compound

Structure

CID197188 OpenBabel06191715582D 24 25 0 0 1 0 0 0 0 0999 V2000 5.6962 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9641 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8301 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0981 -5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.8301 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1090 -3.1540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 15 1 0 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 22 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.08
Volume:	293.597
LogP:	-0.66
LogD:	0.106
LogS:	-1.782
# Rotatable Bonds:	2
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	4.089
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.159
MDCK Permeability:	8.558767149224877e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.26
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.832

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.662
Plasma Protein Binding (PPB):	32.37486267089844%
Volume Distribution (VD):	0.684
Pgp-substrate:	54.158443450927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.271
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.343
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	4.946
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.675
AMES Toxicity:	0.231
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.107
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC197188

Natural Product ID:	NPC197188
*Common Name:**	3,4,8,10-Tetrahydroxy-2-(Hydroxymethyl)-9-Methoxy-3,4,4A,10B-Tetrahydro-2H-Pyrano[3,2-C]Isochromen-6-One;Hydrate
IUPAC Name:	3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one;hydrate
Synonyms:
Standard InCHIKey:	QCWSXSAFDSGKAT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16O9.H2O/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12;/h2,6,8,10,12-13,15-19H,3H2,1H3;1H2
SMILES:	COc1c(cc2c(c1O)C1C(C(C(C(CO)O1)O)O)OC2=O)O.O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1402585
PubChem CID:	6419883
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives

*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
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10316	Glechoma longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25902	Glechoma grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10316	Glechoma longituba	Species	Lamiaceae	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
Potency	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[496245]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	461.1	nM	PMID[496245]
NPT2	Others	Unspecified		Potency	=	23109.3	nM	PMID[496245]

☑ 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 NPC197188 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	350
0.1-0.2	1451
0.2-0.3	3331
0.3-0.4	7685
0.4-0.5	10283
0.5-0.6	4051
0.6-0.7	4891
0.7-0.8	7584
0.8-0.85	2508
0.85-0.9	523
0.9-0.95	31
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43872
1.0	High Similarity	NPC144801
1.0	High Similarity	NPC291510
1.0	High Similarity	NPC238672
1.0	High Similarity	NPC116850
0.9728	High Similarity	NPC228662
0.9669	High Similarity	NPC24627
0.9521	High Similarity	NPC268366
0.9467	High Similarity	NPC281477
0.9404	High Similarity	NPC82592
0.9404	High Similarity	NPC16082
0.9281	High Similarity	NPC77679
0.9281	High Similarity	NPC190020
0.9281	High Similarity	NPC84935
0.9281	High Similarity	NPC247713
0.9276	High Similarity	NPC199926
0.9221	High Similarity	NPC37502
0.9221	High Similarity	NPC40702
0.9221	High Similarity	NPC267627
0.9216	High Similarity	NPC150227
0.9161	High Similarity	NPC155101
0.9097	High Similarity	NPC87317
0.9091	High Similarity	NPC227062
0.9085	High Similarity	NPC178134
0.9079	High Similarity	NPC215921
0.9079	High Similarity	NPC70016
0.9068	High Similarity	NPC34436
0.9068	High Similarity	NPC46640
0.9068	High Similarity	NPC263119
0.9068	High Similarity	NPC219600
0.9068	High Similarity	NPC166674
0.9038	High Similarity	NPC53889
0.9026	High Similarity	NPC79998
0.9013	High Similarity	NPC96501
0.8968	High Similarity	NPC300845
0.8968	High Similarity	NPC250436
0.8968	High Similarity	NPC291948
0.8968	High Similarity	NPC88803
0.8968	High Similarity	NPC104983
0.8954	High Similarity	NPC75695
0.8951	High Similarity	NPC473550
0.8947	High Similarity	NPC270160
0.8947	High Similarity	NPC237440
0.8944	High Similarity	NPC181778
0.8924	High Similarity	NPC215612
0.8917	High Similarity	NPC24164
0.8912	High Similarity	NPC75763
0.8912	High Similarity	NPC105525
0.8912	High Similarity	NPC12218
0.8912	High Similarity	NPC225036
0.891	High Similarity	NPC289322
0.891	High Similarity	NPC160512
0.891	High Similarity	NPC472860
0.891	High Similarity	NPC474010
0.891	High Similarity	NPC114179
0.891	High Similarity	NPC156818
0.891	High Similarity	NPC135222
0.891	High Similarity	NPC38779
0.891	High Similarity	NPC68324
0.8896	High Similarity	NPC105827
0.8896	High Similarity	NPC295646
0.8896	High Similarity	NPC167903
0.8896	High Similarity	NPC310661
0.8875	High Similarity	NPC20237
0.8868	High Similarity	NPC249181
0.8846	High Similarity	NPC54928
0.8846	High Similarity	NPC318432
0.8841	High Similarity	NPC472723
0.8841	High Similarity	NPC297574
0.8831	High Similarity	NPC200773
0.8831	High Similarity	NPC240768
0.8824	High Similarity	NPC473091
0.882	High Similarity	NPC283041
0.8816	High Similarity	NPC81835
0.8812	High Similarity	NPC471788
0.8812	High Similarity	NPC191930
0.8805	High Similarity	NPC472964
0.8805	High Similarity	NPC42797
0.8805	High Similarity	NPC473445
0.8805	High Similarity	NPC41009
0.88	High Similarity	NPC469542
0.88	High Similarity	NPC226738
0.88	High Similarity	NPC190587
0.88	High Similarity	NPC121573
0.88	High Similarity	NPC22176
0.8797	High Similarity	NPC239966
0.8797	High Similarity	NPC472055
0.8797	High Similarity	NPC203020
0.8797	High Similarity	NPC472902
0.879	High Similarity	NPC1913
0.8782	High Similarity	NPC16286
0.8782	High Similarity	NPC145425
0.8782	High Similarity	NPC20541
0.8776	High Similarity	NPC25305
0.8776	High Similarity	NPC112068
0.8776	High Similarity	NPC110899
0.8776	High Similarity	NPC125417
0.8776	High Similarity	NPC95679
0.8773	High Similarity	NPC38438
0.8766	High Similarity	NPC179178
0.8766	High Similarity	NPC469619
0.8766	High Similarity	NPC469670
0.8758	High Similarity	NPC98809
0.8758	High Similarity	NPC476394
0.8758	High Similarity	NPC472452
0.8758	High Similarity	NPC13481
0.8758	High Similarity	NPC207575
0.8758	High Similarity	NPC477517
0.875	High Similarity	NPC67959
0.875	High Similarity	NPC260946
0.875	High Similarity	NPC291977
0.8742	High Similarity	NPC87431
0.8734	High Similarity	NPC329091
0.8734	High Similarity	NPC289811
0.8734	High Similarity	NPC160780
0.8734	High Similarity	NPC470339
0.8734	High Similarity	NPC45846
0.8727	High Similarity	NPC473713
0.8718	High Similarity	NPC281703
0.8718	High Similarity	NPC125487
0.8718	High Similarity	NPC192189
0.8718	High Similarity	NPC287504
0.8716	High Similarity	NPC239943
0.871	High Similarity	NPC272566
0.871	High Similarity	NPC204350
0.8704	High Similarity	NPC474024
0.8704	High Similarity	NPC6588
0.8704	High Similarity	NPC116745
0.8704	High Similarity	NPC298847
0.8704	High Similarity	NPC477154
0.8704	High Similarity	NPC117854
0.8696	High Similarity	NPC142614
0.8693	High Similarity	NPC476463
0.8693	High Similarity	NPC472969
0.8688	High Similarity	NPC291957
0.8688	High Similarity	NPC476371
0.8688	High Similarity	NPC220912
0.8688	High Similarity	NPC476372
0.8688	High Similarity	NPC14030
0.8683	High Similarity	NPC125352
0.8679	High Similarity	NPC119125
0.8679	High Similarity	NPC474770
0.8679	High Similarity	NPC166277
0.8679	High Similarity	NPC155302
0.8679	High Similarity	NPC36217
0.8679	High Similarity	NPC161947
0.8675	High Similarity	NPC51106
0.8675	High Similarity	NPC229036
0.8671	High Similarity	NPC179732
0.8671	High Similarity	NPC241904
0.8671	High Similarity	NPC300727
0.8671	High Similarity	NPC129684
0.8671	High Similarity	NPC299520
0.8667	High Similarity	NPC469354
0.8662	High Similarity	NPC67396
0.8662	High Similarity	NPC38898
0.8662	High Similarity	NPC99381
0.8659	High Similarity	NPC65333
0.8654	High Similarity	NPC475116
0.8654	High Similarity	NPC65591
0.8654	High Similarity	NPC474656
0.8654	High Similarity	NPC161159
0.8654	High Similarity	NPC178574
0.865	High Similarity	NPC229687
0.865	High Similarity	NPC183036
0.8645	High Similarity	NPC151473
0.8645	High Similarity	NPC225854
0.8636	High Similarity	NPC107636
0.8634	High Similarity	NPC7483
0.8634	High Similarity	NPC475985
0.8634	High Similarity	NPC474350
0.8634	High Similarity	NPC470898
0.8631	High Similarity	NPC123259
0.8631	High Similarity	NPC129533
0.8627	High Similarity	NPC32058
0.8627	High Similarity	NPC85734
0.8627	High Similarity	NPC30720
0.8627	High Similarity	NPC138978
0.8625	High Similarity	NPC474779
0.8625	High Similarity	NPC228383
0.8625	High Similarity	NPC112418
0.8625	High Similarity	NPC472859
0.8625	High Similarity	NPC25389
0.8625	High Similarity	NPC311803
0.8625	High Similarity	NPC134783
0.8623	High Similarity	NPC80956
0.8618	High Similarity	NPC280404
0.8618	High Similarity	NPC86373
0.8618	High Similarity	NPC469683
0.8618	High Similarity	NPC27106
0.8618	High Similarity	NPC207732
0.8618	High Similarity	NPC108455
0.8618	High Similarity	NPC210425
0.8618	High Similarity	NPC277426
0.8616	High Similarity	NPC315157
0.8616	High Similarity	NPC477410
0.8616	High Similarity	NPC476242
0.8614	High Similarity	NPC67629
0.8614	High Similarity	NPC79736
0.8609	High Similarity	NPC469579

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 NPC197188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	906
0.2-0.3	1850
0.3-0.4	2556
0.4-0.5	1881
0.5-0.6	968
0.6-0.7	514
0.7-0.8	140
0.8-0.85	38
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD1465	Phase 2
0.8968	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD7993	Clinical (unspecified phase)
0.8537	High Similarity	NPD5844	Phase 1
0.8535	High Similarity	NPD1934	Approved
0.8503	High Similarity	NPD230	Phase 1
0.8466	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD6166	Phase 2
0.8457	Intermediate Similarity	NPD6232	Discontinued
0.8373	Intermediate Similarity	NPD7074	Phase 3
0.8365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8313	Intermediate Similarity	NPD7054	Approved
0.8303	Intermediate Similarity	NPD7473	Discontinued
0.8289	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD6234	Discontinued
0.8263	Intermediate Similarity	NPD7472	Approved
0.8253	Intermediate Similarity	NPD7228	Approved
0.825	Intermediate Similarity	NPD2801	Approved
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD3817	Phase 2
0.8187	Intermediate Similarity	NPD37	Approved
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.8148	Intermediate Similarity	NPD4967	Phase 2
0.8148	Intermediate Similarity	NPD4965	Approved
0.8148	Intermediate Similarity	NPD4966	Approved
0.8148	Intermediate Similarity	NPD3882	Suspended
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8107	Intermediate Similarity	NPD6797	Phase 2
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8089	Intermediate Similarity	NPD2532	Approved
0.8089	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD2534	Approved
0.8059	Intermediate Similarity	NPD7251	Discontinued
0.805	Intermediate Similarity	NPD1653	Approved
0.8025	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD5494	Approved
0.7988	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6801	Discontinued
0.7952	Intermediate Similarity	NPD7199	Phase 2
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7925	Intermediate Similarity	NPD1512	Approved
0.7914	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6190	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7685	Pre-registration
0.7834	Intermediate Similarity	NPD3750	Approved
0.7834	Intermediate Similarity	NPD4628	Phase 3
0.7829	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1549	Phase 2
0.7758	Intermediate Similarity	NPD5353	Approved
0.7758	Intermediate Similarity	NPD5402	Approved
0.7756	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD9269	Phase 2
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD3027	Phase 3
0.7746	Intermediate Similarity	NPD7240	Approved
0.7742	Intermediate Similarity	NPD1510	Phase 2
0.774	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD9494	Approved
0.7688	Intermediate Similarity	NPD6799	Approved
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7674	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD447	Suspended
0.7654	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6559	Discontinued
0.7628	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.7616	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD943	Approved
0.7597	Intermediate Similarity	NPD1240	Approved
0.7588	Intermediate Similarity	NPD5711	Approved
0.7588	Intermediate Similarity	NPD5710	Approved
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5242	Approved
0.7532	Intermediate Similarity	NPD7266	Discontinued
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD919	Approved
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9268	Approved
0.7468	Intermediate Similarity	NPD2796	Approved
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8313	Approved
0.7458	Intermediate Similarity	NPD8312	Approved
0.7438	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5401	Approved
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7768	Phase 2
0.7358	Intermediate Similarity	NPD1551	Phase 2
0.7358	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD6099	Approved
0.7349	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3226	Approved
0.7341	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD8150	Discontinued
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD2800	Approved
0.7326	Intermediate Similarity	NPD8127	Discontinued
0.7326	Intermediate Similarity	NPD1247	Approved
0.7317	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9545	Approved
0.7296	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6385	Approved
0.7262	Intermediate Similarity	NPD6386	Approved
0.7249	Intermediate Similarity	NPD7680	Approved
0.7249	Intermediate Similarity	NPD7435	Discontinued
0.7244	Intermediate Similarity	NPD3764	Approved
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7222	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7184	Intermediate Similarity	NPD7229	Phase 3
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.717	Intermediate Similarity	NPD6651	Approved
0.7124	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1243	Approved
0.7108	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5124	Phase 1
0.7107	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD422	Phase 1
0.7095	Intermediate Similarity	NPD5953	Discontinued
0.7079	Intermediate Similarity	NPD7286	Phase 2
0.7077	Intermediate Similarity	NPD7783	Phase 2
0.7077	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8166	Discontinued
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7066	Intermediate Similarity	NPD6273	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7390	Discontinued
0.7044	Intermediate Similarity	NPD4060	Phase 1
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7035	Intermediate Similarity	NPD4288	Approved
0.7026	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7874	Approved
0.7025	Intermediate Similarity	NPD6798	Discontinued
0.7012	Intermediate Similarity	NPD6674	Discontinued
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD1610	Phase 2
0.6988	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7033	Discontinued
0.6975	Remote Similarity	NPD2799	Discontinued
0.697	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4110	Phase 3
0.697	Remote Similarity	NPD7003	Approved
0.6961	Remote Similarity	NPD7038	Approved
0.6961	Remote Similarity	NPD7039	Approved
0.6948	Remote Similarity	NPD9717	Approved
0.6943	Remote Similarity	NPD7871	Phase 2
0.6943	Remote Similarity	NPD8320	Phase 1
0.6943	Remote Similarity	NPD7870	Phase 2
0.6943	Remote Similarity	NPD8319	Approved
0.6941	Remote Similarity	NPD3455	Phase 2
0.6937	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3620	Phase 2
0.6933	Remote Similarity	NPD2438	Suspended
0.6931	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5005	Approved
0.6927	Remote Similarity	NPD5006	Approved
0.6927	Remote Similarity	NPD6823	Phase 2
0.6923	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD7549	Discontinued
0.6919	Remote Similarity	NPD6841	Approved
0.6919	Remote Similarity	NPD6842	Approved
0.6919	Remote Similarity	NPD6843	Phase 3
0.6918	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1699	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