NPASS Compound

Structure

CID38219 OpenBabel06191715372D 27 30 0 0 0 0 0 0 0 0999 V2000 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 -0.5000 -1.8660 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 6.0622 0.5000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 4.3301 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 0.8660 0.5000 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 3.4641 2.0000 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 2.5981 0.5000 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 1.7321 3.0000 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 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 14 1 0 0 0 0 7 16 2 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 14 21 2 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 25 2 0 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.15
Volume:	383.571
LogP:	6.153
LogD:	4.37
LogS:	-3.729
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	3.094
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.748
MDCK Permeability:	1.654252082516905e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.123

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	90.30596160888672%
Volume Distribution (VD):	0.683
Pgp-substrate:	8.679491996765137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.89
CYP1A2-substrate:	0.273
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.906
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.754
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.532
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	3.006
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.548
Rat Oral Acute Toxicity:	0.692
Maximum Recommended Daily Dose:	0.72
Skin Sensitization:	0.706
Carcinogencity:	0.926
Eye Corrosion:	0.003
Eye Irritation:	0.059
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC38219

Natural Product ID:	NPC38219
*Common Name:**	Laurentixanthone A
IUPAC Name:	6-hydroxy-3,3-dimethyl-11-(3-methylbut-2-enyl)pyrano[2,3-c]xanthen-7-one
Synonyms:	Laurentixanthone A
Standard InCHIKey:	BCILHNDVVWKDBW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H22O4/c1-13(2)8-9-14-6-5-7-16-20(25)19-17(24)12-18-15(22(19)26-21(14)16)10-11-23(3,4)27-18/h5-8,10-12,24H,9H2,1-4H3
SMILES:	CC(=CCc1cccc2c(=O)c3c(cc4c(C=CC(C)(C)O4)c3oc12)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923853
PubChem CID:	16081685
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:0003518] 4-prenylated xanthones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14855	Vismia laurentii	Species	Hypericaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	2440.0	nM	PMID[544624]

☑ 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 NPC38219 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	410
0.1-0.2	1699
0.2-0.3	4387
0.3-0.4	11841
0.4-0.5	6331
0.5-0.6	4217
0.6-0.7	5984
0.7-0.8	4173
0.8-0.85	1875
0.85-0.9	1236
0.9-0.95	483
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC219915
0.9854	High Similarity	NPC147688
0.9854	High Similarity	NPC156590
0.9854	High Similarity	NPC205006
0.9854	High Similarity	NPC118840
0.9854	High Similarity	NPC64908
0.9786	High Similarity	NPC23728
0.9786	High Similarity	NPC110303
0.9783	High Similarity	NPC293852
0.9783	High Similarity	NPC11561
0.9783	High Similarity	NPC214236
0.9783	High Similarity	NPC62840
0.9783	High Similarity	NPC226636
0.9783	High Similarity	NPC59739
0.9783	High Similarity	NPC299080
0.9783	High Similarity	NPC78803
0.9783	High Similarity	NPC144499
0.9783	High Similarity	NPC217083
0.9781	High Similarity	NPC235239
0.9781	High Similarity	NPC261227
0.9781	High Similarity	NPC69769
0.9781	High Similarity	NPC475680
0.9781	High Similarity	NPC270883
0.9781	High Similarity	NPC305355
0.9781	High Similarity	NPC172986
0.9716	High Similarity	NPC160821
0.9716	High Similarity	NPC132592
0.9714	High Similarity	NPC54577
0.9714	High Similarity	NPC83357
0.9714	High Similarity	NPC214774
0.9714	High Similarity	NPC176229
0.9714	High Similarity	NPC142405
0.9714	High Similarity	NPC267375
0.9714	High Similarity	NPC301276
0.9714	High Similarity	NPC312973
0.9714	High Similarity	NPC20488
0.9714	High Similarity	NPC195621
0.9714	High Similarity	NPC475052
0.9714	High Similarity	NPC67805
0.9714	High Similarity	NPC246948
0.9714	High Similarity	NPC111786
0.9714	High Similarity	NPC88964
0.9714	High Similarity	NPC470647
0.9712	High Similarity	NPC18585
0.9712	High Similarity	NPC166138
0.9712	High Similarity	NPC106985
0.971	High Similarity	NPC110969
0.971	High Similarity	NPC103362
0.9708	High Similarity	NPC55018
0.9708	High Similarity	NPC96565
0.9708	High Similarity	NPC216978
0.9708	High Similarity	NPC303633
0.9708	High Similarity	NPC301217
0.9708	High Similarity	NPC220062
0.9645	High Similarity	NPC104406
0.9645	High Similarity	NPC296998
0.9645	High Similarity	NPC473077
0.9645	High Similarity	NPC79469
0.9645	High Similarity	NPC283234
0.9645	High Similarity	NPC201731
0.9645	High Similarity	NPC97716
0.9645	High Similarity	NPC237635
0.9645	High Similarity	NPC24673
0.9643	High Similarity	NPC209040
0.9643	High Similarity	NPC278175
0.9643	High Similarity	NPC234629
0.9643	High Similarity	NPC257236
0.9643	High Similarity	NPC311741
0.9638	High Similarity	NPC150522
0.9638	High Similarity	NPC241100
0.9638	High Similarity	NPC159275
0.9635	High Similarity	NPC201395
0.9577	High Similarity	NPC6511
0.9577	High Similarity	NPC296869
0.9577	High Similarity	NPC161191
0.9577	High Similarity	NPC266572
0.9574	High Similarity	NPC477955
0.9571	High Similarity	NPC68104
0.9571	High Similarity	NPC175504
0.9571	High Similarity	NPC257097
0.9571	High Similarity	NPC150408
0.9571	High Similarity	NPC221432
0.9571	High Similarity	NPC91560
0.9571	High Similarity	NPC478086
0.9571	High Similarity	NPC75049
0.9571	High Similarity	NPC39329
0.9571	High Similarity	NPC316816
0.9571	High Similarity	NPC149026
0.9571	High Similarity	NPC214166
0.9571	High Similarity	NPC310130
0.9571	High Similarity	NPC143896
0.9571	High Similarity	NPC164980
0.9571	High Similarity	NPC169591
0.9568	High Similarity	NPC282300
0.9568	High Similarity	NPC3188
0.9568	High Similarity	NPC14871
0.9565	High Similarity	NPC18260
0.9565	High Similarity	NPC78913
0.9565	High Similarity	NPC217186
0.9565	High Similarity	NPC53181
0.9507	High Similarity	NPC180477
0.9507	High Similarity	NPC14001
0.9507	High Similarity	NPC140120
0.9507	High Similarity	NPC166757
0.9504	High Similarity	NPC131568
0.9504	High Similarity	NPC197252
0.9504	High Similarity	NPC473015
0.9504	High Similarity	NPC319752
0.9504	High Similarity	NPC469953
0.9504	High Similarity	NPC131579
0.9504	High Similarity	NPC236766
0.9504	High Similarity	NPC473013
0.95	High Similarity	NPC296917
0.95	High Similarity	NPC147145
0.95	High Similarity	NPC166934
0.95	High Similarity	NPC328164
0.95	High Similarity	NPC223500
0.95	High Similarity	NPC265040
0.95	High Similarity	NPC125855
0.95	High Similarity	NPC306829
0.95	High Similarity	NPC227579
0.95	High Similarity	NPC228504
0.95	High Similarity	NPC200694
0.95	High Similarity	NPC107572
0.95	High Similarity	NPC40833
0.95	High Similarity	NPC194432
0.95	High Similarity	NPC76372
0.95	High Similarity	NPC10937
0.95	High Similarity	NPC166482
0.95	High Similarity	NPC148757
0.95	High Similarity	NPC37496
0.95	High Similarity	NPC76338
0.95	High Similarity	NPC324134
0.95	High Similarity	NPC220998
0.95	High Similarity	NPC177354
0.95	High Similarity	NPC324436
0.95	High Similarity	NPC78
0.95	High Similarity	NPC1089
0.95	High Similarity	NPC182852
0.95	High Similarity	NPC66515
0.95	High Similarity	NPC161506
0.95	High Similarity	NPC167624
0.95	High Similarity	NPC32739
0.95	High Similarity	NPC64915
0.9493	High Similarity	NPC470668
0.9493	High Similarity	NPC470669
0.9489	High Similarity	NPC13408
0.9444	High Similarity	NPC471115
0.9444	High Similarity	NPC472633
0.9444	High Similarity	NPC188403
0.9444	High Similarity	NPC120105
0.9444	High Similarity	NPC29777
0.9444	High Similarity	NPC101957
0.9441	High Similarity	NPC244407
0.9441	High Similarity	NPC189087
0.9441	High Similarity	NPC321623
0.9437	High Similarity	NPC470133
0.9437	High Similarity	NPC285630
0.9437	High Similarity	NPC470134
0.9437	High Similarity	NPC473078
0.9437	High Similarity	NPC476088
0.9437	High Similarity	NPC470131
0.9437	High Similarity	NPC220418
0.9437	High Similarity	NPC127059
0.9437	High Similarity	NPC470132
0.9437	High Similarity	NPC57470
0.9437	High Similarity	NPC474161
0.9437	High Similarity	NPC109183
0.9437	High Similarity	NPC124729
0.9433	High Similarity	NPC107177
0.9433	High Similarity	NPC125894
0.9433	High Similarity	NPC81697
0.9433	High Similarity	NPC9117
0.9433	High Similarity	NPC85162
0.9433	High Similarity	NPC24821
0.9433	High Similarity	NPC190637
0.9433	High Similarity	NPC278249
0.9433	High Similarity	NPC293053
0.9433	High Similarity	NPC77794
0.9433	High Similarity	NPC185276
0.9433	High Similarity	NPC223812
0.9433	High Similarity	NPC212932
0.9433	High Similarity	NPC11700
0.9429	High Similarity	NPC110038
0.9429	High Similarity	NPC17170
0.9429	High Similarity	NPC258630
0.9429	High Similarity	NPC4743
0.9429	High Similarity	NPC156190
0.9429	High Similarity	NPC324386
0.9429	High Similarity	NPC248372
0.9429	High Similarity	NPC96408
0.9429	High Similarity	NPC166689
0.9429	High Similarity	NPC279650
0.9429	High Similarity	NPC213322
0.9429	High Similarity	NPC312391
0.9424	High Similarity	NPC23257
0.942	High Similarity	NPC266597
0.942	High Similarity	NPC157855
0.942	High Similarity	NPC317119
0.942	High Similarity	NPC228661

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 NPC38219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	969
0.2-0.3	1447
0.3-0.4	2717
0.4-0.5	1946
0.5-0.6	1149
0.6-0.7	364
0.7-0.8	118
0.8-0.85	41
0.85-0.9	19
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9643	High Similarity	NPD7410	Clinical (unspecified phase)
0.9366	High Similarity	NPD4378	Clinical (unspecified phase)
0.9214	High Similarity	NPD1549	Phase 2
0.9143	High Similarity	NPD1552	Clinical (unspecified phase)
0.9143	High Similarity	NPD1550	Clinical (unspecified phase)
0.9116	High Similarity	NPD7411	Suspended
0.9048	High Similarity	NPD4380	Phase 2
0.9	High Similarity	NPD1510	Phase 2
0.8986	High Similarity	NPD1240	Approved
0.8936	High Similarity	NPD2796	Approved
0.8933	High Similarity	NPD8443	Clinical (unspecified phase)
0.8867	High Similarity	NPD2393	Clinical (unspecified phase)
0.8857	High Similarity	NPD1607	Approved
0.8816	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD7096	Clinical (unspecified phase)
0.8742	High Similarity	NPD7819	Suspended
0.8693	High Similarity	NPD4381	Clinical (unspecified phase)
0.869	High Similarity	NPD3750	Approved
0.8675	High Similarity	NPD6801	Discontinued
0.8639	High Similarity	NPD1511	Approved
0.8599	High Similarity	NPD7852	Clinical (unspecified phase)
0.8571	High Similarity	NPD3749	Approved
0.8553	High Similarity	NPD1934	Approved
0.8523	High Similarity	NPD1512	Approved
0.8514	High Similarity	NPD6799	Approved
0.8506	High Similarity	NPD7768	Phase 2
0.8497	Intermediate Similarity	NPD2801	Approved
0.8493	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6959	Discontinued
0.8367	Intermediate Similarity	NPD1243	Approved
0.8367	Intermediate Similarity	NPD2800	Approved
0.8345	Intermediate Similarity	NPD3748	Approved
0.8301	Intermediate Similarity	NPD6599	Discontinued
0.8269	Intermediate Similarity	NPD3882	Suspended
0.825	Intermediate Similarity	NPD6166	Phase 2
0.825	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD5494	Approved
0.8224	Intermediate Similarity	NPD5403	Approved
0.8219	Intermediate Similarity	NPD2799	Discontinued
0.8207	Intermediate Similarity	NPD6651	Approved
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2313	Discontinued
0.8176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD2935	Discontinued
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.8108	Intermediate Similarity	NPD2344	Approved
0.8105	Intermediate Similarity	NPD920	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD5401	Approved
0.8089	Intermediate Similarity	NPD3817	Phase 2
0.8085	Intermediate Similarity	NPD1203	Approved
0.8079	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7074	Phase 3
0.8049	Intermediate Similarity	NPD7472	Approved
0.8041	Intermediate Similarity	NPD6099	Approved
0.8041	Intermediate Similarity	NPD6100	Approved
0.8038	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5953	Discontinued
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7974	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6559	Discontinued
0.7952	Intermediate Similarity	NPD7251	Discontinued
0.7947	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3268	Approved
0.7929	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4908	Phase 1
0.7904	Intermediate Similarity	NPD7808	Phase 3
0.7902	Intermediate Similarity	NPD2798	Approved
0.7901	Intermediate Similarity	NPD6232	Discontinued
0.7895	Intermediate Similarity	NPD2309	Approved
0.7891	Intermediate Similarity	NPD5124	Phase 1
0.7891	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD3226	Approved
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7872	Intermediate Similarity	NPD9717	Approved
0.7867	Intermediate Similarity	NPD2346	Discontinued
0.7866	Intermediate Similarity	NPD7473	Discontinued
0.7862	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD2534	Approved
0.7857	Intermediate Similarity	NPD2532	Approved
0.7852	Intermediate Similarity	NPD4308	Phase 3
0.7852	Intermediate Similarity	NPD7033	Discontinued
0.7832	Intermediate Similarity	NPD2797	Approved
0.7823	Intermediate Similarity	NPD943	Approved
0.7801	Intermediate Similarity	NPD422	Phase 1
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6832	Phase 2
0.7792	Intermediate Similarity	NPD7390	Discontinued
0.777	Intermediate Similarity	NPD1548	Phase 1
0.7762	Intermediate Similarity	NPD3225	Approved
0.7759	Intermediate Similarity	NPD4363	Phase 3
0.7759	Intermediate Similarity	NPD4360	Phase 2
0.774	Intermediate Similarity	NPD4625	Phase 3
0.7722	Intermediate Similarity	NPD6585	Discontinued
0.7716	Intermediate Similarity	NPD919	Approved
0.7712	Intermediate Similarity	NPD4628	Phase 3
0.7688	Intermediate Similarity	NPD1465	Phase 2
0.7676	Intermediate Similarity	NPD1610	Phase 2
0.767	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4288	Approved
0.7622	Intermediate Similarity	NPD1247	Approved
0.7586	Intermediate Similarity	NPD3266	Approved
0.7586	Intermediate Similarity	NPD3267	Approved
0.7584	Intermediate Similarity	NPD4307	Phase 2
0.7574	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD5890	Approved
0.7562	Intermediate Similarity	NPD5889	Approved
0.7562	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1933	Approved
0.7532	Intermediate Similarity	NPD2654	Approved
0.753	Intermediate Similarity	NPD3926	Phase 2
0.7529	Intermediate Similarity	NPD4287	Approved
0.7515	Intermediate Similarity	NPD1729	Discontinued
0.7514	Intermediate Similarity	NPD4361	Phase 2
0.7514	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7584	Approved
0.7451	Intermediate Similarity	NPD5408	Approved
0.7451	Intermediate Similarity	NPD5406	Approved
0.7451	Intermediate Similarity	NPD5404	Approved
0.7451	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD1296	Phase 2
0.745	Intermediate Similarity	NPD3764	Approved
0.7448	Intermediate Similarity	NPD4749	Approved
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7458	Discontinued
0.7438	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD9545	Approved
0.7379	Intermediate Similarity	NPD1608	Approved
0.7376	Intermediate Similarity	NPD9493	Approved
0.7372	Intermediate Similarity	NPD7003	Approved
0.7365	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5710	Approved
0.7365	Intermediate Similarity	NPD5711	Approved
0.7358	Intermediate Similarity	NPD5049	Phase 3
0.7348	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1164	Approved
0.7347	Intermediate Similarity	NPD1470	Approved
0.7333	Intermediate Similarity	NPD411	Approved
0.7326	Intermediate Similarity	NPD6104	Discontinued
0.7325	Intermediate Similarity	NPD2354	Approved
0.7317	Intermediate Similarity	NPD2296	Approved
0.731	Intermediate Similarity	NPD1201	Approved
0.7303	Intermediate Similarity	NPD447	Suspended
0.7303	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7577	Discontinued
0.7301	Intermediate Similarity	NPD6844	Discontinued
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.729	Intermediate Similarity	NPD1471	Phase 3
0.7286	Intermediate Similarity	NPD1241	Discontinued
0.7278	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8313	Approved
0.7241	Intermediate Similarity	NPD8312	Approved
0.7237	Intermediate Similarity	NPD1613	Approved
0.7237	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7213	Phase 3
0.7233	Intermediate Similarity	NPD7212	Phase 2
0.7222	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6798	Discontinued
0.7219	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD230	Phase 1
0.7188	Intermediate Similarity	NPD7447	Phase 1
0.7181	Intermediate Similarity	NPD1019	Discontinued
0.7179	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2353	Approved
0.7172	Intermediate Similarity	NPD17	Approved
0.7161	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD3787	Discontinued
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3142	Approved
0.7124	Intermediate Similarity	NPD3140	Approved
0.7107	Intermediate Similarity	NPD3887	Approved
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7093	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1652	Phase 2

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