NPASS Compound

Structure

NPC188618 OpenBabel07101719512D 27 28 0 0 0 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 5.1962 -1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 -0.0000 -1.0000 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 3.4641 -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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 2.0000 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 8 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 27 1 0 0 0 0 12 16 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 27 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.06
Volume:	367.212
LogP:	3.998
LogD:	3.1
LogS:	-4.107
# Rotatable Bonds:	7
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	2.596
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.894
MDCK Permeability:	2.0292558474466205e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	99.10365295410156%
Volume Distribution (VD):	0.587
Pgp-substrate:	5.041897773742676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.879
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.937
CYP2C19-substrate:	0.181
CYP2C9-inhibitor:	0.856
CYP2C9-substrate:	0.884
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.556
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	11.656
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.571
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.482
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.345
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.677
Respiratory Toxicity:	0.486

Download Data

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

Natural Product: NPC188618

Natural Product ID:	NPC188618
*Common Name:**	Methyl Chloroasterrate
IUPAC Name:	methyl 3-chloro-2-hydroxy-6-(4-hydroxy-2-methoxy-6-methoxycarbonylphenoxy)-4-methylbenzoate
Synonyms:	Methyl Chloroasterrate
Standard InCHIKey:	XSBBWBWHNNKSSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H17ClO8/c1-8-5-11(13(18(23)26-4)15(21)14(8)19)27-16-10(17(22)25-3)6-9(20)7-12(16)24-2/h5-7,20-21H,1-4H3
SMILES:	COc1cc(O)cc(c1Oc1cc(C)c(c(c1C(=O)OC)O)Cl)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471279
PubChem CID:	10475888
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO32471	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809055]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
LD50	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT530	Organism	Caenorhabditis elegans	Caenorhabditis elegans	LD50	=	100.0	ppm	PMID[513287]
NPT2	Others	Unspecified		IC50	>	2000.0	nM	PMID[513288]

☑ 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 NPC188618 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	432
0.1-0.2	2354
0.2-0.3	6981
0.3-0.4	12249
0.4-0.5	4304
0.5-0.6	5569
0.6-0.7	7806
0.7-0.8	2942
0.8-0.85	30
0.85-0.9	23
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC28160
0.9006	High Similarity	NPC471801
0.8875	High Similarity	NPC285527
0.8875	High Similarity	NPC106334
0.882	High Similarity	NPC164527
0.882	High Similarity	NPC213382
0.882	High Similarity	NPC214901
0.8764	High Similarity	NPC220369
0.8701	High Similarity	NPC471804
0.8701	High Similarity	NPC471803
0.8701	High Similarity	NPC471812
0.8652	High Similarity	NPC39409
0.8626	High Similarity	NPC154720
0.8621	High Similarity	NPC471802
0.8619	High Similarity	NPC198163
0.8603	High Similarity	NPC471810
0.8603	High Similarity	NPC471807
0.8603	High Similarity	NPC471806
0.8547	High Similarity	NPC471813
0.8547	High Similarity	NPC121100
0.8547	High Similarity	NPC471805
0.8476	Intermediate Similarity	NPC225129
0.8457	Intermediate Similarity	NPC108278
0.8452	Intermediate Similarity	NPC287458
0.8448	Intermediate Similarity	NPC470422
0.8402	Intermediate Similarity	NPC98892
0.8315	Intermediate Similarity	NPC193676
0.8278	Intermediate Similarity	NPC471809
0.8278	Intermediate Similarity	NPC471811
0.8263	Intermediate Similarity	NPC289968
0.8249	Intermediate Similarity	NPC45072
0.8222	Intermediate Similarity	NPC471814
0.8222	Intermediate Similarity	NPC195675
0.8222	Intermediate Similarity	NPC471808
0.8218	Intermediate Similarity	NPC472032
0.8155	Intermediate Similarity	NPC75069
0.8125	Intermediate Similarity	NPC277865
0.809	Intermediate Similarity	NPC264922
0.8081	Intermediate Similarity	NPC130955
0.8079	Intermediate Similarity	NPC474857
0.8072	Intermediate Similarity	NPC46941
0.8068	Intermediate Similarity	NPC99613
0.8068	Intermediate Similarity	NPC49487
0.8059	Intermediate Similarity	NPC208197
0.8046	Intermediate Similarity	NPC300984
0.8035	Intermediate Similarity	NPC217950
0.8023	Intermediate Similarity	NPC124470
0.8023	Intermediate Similarity	NPC72696
0.8023	Intermediate Similarity	NPC109827
0.8012	Intermediate Similarity	NPC54928
0.8	Intermediate Similarity	NPC75279
0.8	Intermediate Similarity	NPC276409
0.8	Intermediate Similarity	NPC472915
0.8	Intermediate Similarity	NPC250822
0.8	Intermediate Similarity	NPC280937
0.7988	Intermediate Similarity	NPC208043
0.7988	Intermediate Similarity	NPC226973
0.7988	Intermediate Similarity	NPC308451
0.7978	Intermediate Similarity	NPC158226
0.7976	Intermediate Similarity	NPC294502
0.7976	Intermediate Similarity	NPC200221
0.7976	Intermediate Similarity	NPC328119
0.7964	Intermediate Similarity	NPC93034
0.7964	Intermediate Similarity	NPC119660
0.7957	Intermediate Similarity	NPC221185
0.7955	Intermediate Similarity	NPC29160
0.7955	Intermediate Similarity	NPC20216
0.7953	Intermediate Similarity	NPC4455
0.7953	Intermediate Similarity	NPC256612
0.7953	Intermediate Similarity	NPC471800
0.7953	Intermediate Similarity	NPC227325
0.7953	Intermediate Similarity	NPC201136
0.7953	Intermediate Similarity	NPC20830
0.7953	Intermediate Similarity	NPC183597
0.7953	Intermediate Similarity	NPC167815
0.7953	Intermediate Similarity	NPC92659
0.7953	Intermediate Similarity	NPC128863
0.7953	Intermediate Similarity	NPC280339
0.7953	Intermediate Similarity	NPC146165
0.7953	Intermediate Similarity	NPC138360
0.7953	Intermediate Similarity	NPC2476
0.7953	Intermediate Similarity	NPC163780
0.7953	Intermediate Similarity	NPC50715
0.7953	Intermediate Similarity	NPC196439
0.7944	Intermediate Similarity	NPC175804
0.7943	Intermediate Similarity	NPC474350
0.7943	Intermediate Similarity	NPC156082
0.7941	Intermediate Similarity	NPC199773
0.7933	Intermediate Similarity	NPC181523
0.7931	Intermediate Similarity	NPC303565
0.7931	Intermediate Similarity	NPC298401
0.7929	Intermediate Similarity	NPC179183
0.7929	Intermediate Similarity	NPC306821
0.7921	Intermediate Similarity	NPC246716
0.7921	Intermediate Similarity	NPC17219
0.7921	Intermediate Similarity	NPC10576
0.7919	Intermediate Similarity	NPC168616
0.7919	Intermediate Similarity	NPC83763
0.7919	Intermediate Similarity	NPC154304
0.7919	Intermediate Similarity	NPC190487
0.7919	Intermediate Similarity	NPC238381
0.7914	Intermediate Similarity	NPC247104
0.791	Intermediate Similarity	NPC234331
0.7907	Intermediate Similarity	NPC474520
0.7907	Intermediate Similarity	NPC472916
0.7907	Intermediate Similarity	NPC178854
0.7898	Intermediate Similarity	NPC58653
0.7898	Intermediate Similarity	NPC173352
0.7898	Intermediate Similarity	NPC112981
0.7898	Intermediate Similarity	NPC267153
0.7895	Intermediate Similarity	NPC246204
0.7895	Intermediate Similarity	NPC475895
0.7895	Intermediate Similarity	NPC47781
0.7895	Intermediate Similarity	NPC183878
0.7895	Intermediate Similarity	NPC274327
0.7895	Intermediate Similarity	NPC69394
0.7895	Intermediate Similarity	NPC160951
0.7895	Intermediate Similarity	NPC86485
0.7895	Intermediate Similarity	NPC22519
0.7895	Intermediate Similarity	NPC145379
0.7895	Intermediate Similarity	NPC255350
0.7895	Intermediate Similarity	NPC471981
0.7895	Intermediate Similarity	NPC231018
0.7895	Intermediate Similarity	NPC176775
0.7895	Intermediate Similarity	NPC298802
0.7889	Intermediate Similarity	NPC477568
0.7886	Intermediate Similarity	NPC473696
0.7886	Intermediate Similarity	NPC93739
0.7882	Intermediate Similarity	NPC474663
0.7882	Intermediate Similarity	NPC117579
0.7882	Intermediate Similarity	NPC149614
0.7879	Intermediate Similarity	NPC214919
0.7879	Intermediate Similarity	NPC124467
0.7874	Intermediate Similarity	NPC188967
0.787	Intermediate Similarity	NPC92722
0.787	Intermediate Similarity	NPC102003
0.7865	Intermediate Similarity	NPC165979
0.7865	Intermediate Similarity	NPC26568
0.7865	Intermediate Similarity	NPC280493
0.7865	Intermediate Similarity	NPC163130
0.7865	Intermediate Similarity	NPC476279
0.7861	Intermediate Similarity	NPC29841
0.7861	Intermediate Similarity	NPC189179
0.7861	Intermediate Similarity	NPC93376
0.7861	Intermediate Similarity	NPC75215
0.7861	Intermediate Similarity	NPC36852
0.7861	Intermediate Similarity	NPC227192
0.7861	Intermediate Similarity	NPC78302
0.7861	Intermediate Similarity	NPC7973
0.7861	Intermediate Similarity	NPC476981
0.7861	Intermediate Similarity	NPC235215
0.7861	Intermediate Similarity	NPC262286
0.7861	Intermediate Similarity	NPC224137
0.7861	Intermediate Similarity	NPC472438
0.7861	Intermediate Similarity	NPC181960
0.7857	Intermediate Similarity	NPC33265
0.7857	Intermediate Similarity	NPC62536
0.7853	Intermediate Similarity	NPC28669
0.7849	Intermediate Similarity	NPC32557
0.7849	Intermediate Similarity	NPC286052
0.7849	Intermediate Similarity	NPC189960
0.7849	Intermediate Similarity	NPC37392
0.7849	Intermediate Similarity	NPC472909
0.7849	Intermediate Similarity	NPC470099
0.7849	Intermediate Similarity	NPC213622
0.7849	Intermediate Similarity	NPC2928
0.7849	Intermediate Similarity	NPC470100
0.7841	Intermediate Similarity	NPC477689
0.7841	Intermediate Similarity	NPC284007
0.7841	Intermediate Similarity	NPC470081
0.7836	Intermediate Similarity	NPC39732
0.7836	Intermediate Similarity	NPC131624
0.7836	Intermediate Similarity	NPC162313
0.7836	Intermediate Similarity	NPC83508
0.7836	Intermediate Similarity	NPC275836
0.7836	Intermediate Similarity	NPC198826
0.7836	Intermediate Similarity	NPC120163
0.7836	Intermediate Similarity	NPC293183
0.7836	Intermediate Similarity	NPC301323
0.7836	Intermediate Similarity	NPC275722
0.7836	Intermediate Similarity	NPC188203
0.7836	Intermediate Similarity	NPC142540
0.7836	Intermediate Similarity	NPC222830
0.7836	Intermediate Similarity	NPC60972
0.7836	Intermediate Similarity	NPC134677
0.7836	Intermediate Similarity	NPC71334
0.7836	Intermediate Similarity	NPC256283
0.7836	Intermediate Similarity	NPC239128
0.7836	Intermediate Similarity	NPC187498
0.7836	Intermediate Similarity	NPC156222
0.7836	Intermediate Similarity	NPC212678
0.7836	Intermediate Similarity	NPC301123
0.7836	Intermediate Similarity	NPC100887
0.7836	Intermediate Similarity	NPC57030
0.7836	Intermediate Similarity	NPC101996
0.7836	Intermediate Similarity	NPC25270
0.7836	Intermediate Similarity	NPC241498
0.7829	Intermediate Similarity	NPC472405
0.7829	Intermediate Similarity	NPC66288
0.7824	Intermediate Similarity	NPC239363

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 NPC188618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	1142
0.2-0.3	2201
0.3-0.4	2717
0.4-0.5	1611
0.5-0.6	797
0.6-0.7	237
0.7-0.8	52
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD2801	Approved
0.7684	Intermediate Similarity	NPD6232	Discontinued
0.7683	Intermediate Similarity	NPD1551	Phase 2
0.7654	Intermediate Similarity	NPD447	Suspended
0.7644	Intermediate Similarity	NPD5402	Approved
0.7644	Intermediate Similarity	NPD3817	Phase 2
0.76	Intermediate Similarity	NPD3882	Suspended
0.76	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD2403	Approved
0.7556	Intermediate Similarity	NPD7473	Discontinued
0.7529	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5844	Phase 1
0.7418	Intermediate Similarity	NPD3818	Discontinued
0.7386	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6166	Phase 2
0.7288	Intermediate Similarity	NPD1465	Phase 2
0.7283	Intermediate Similarity	NPD7054	Approved
0.7283	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD6799	Approved
0.7263	Intermediate Similarity	NPD7075	Discontinued
0.7243	Intermediate Similarity	NPD7074	Phase 3
0.7243	Intermediate Similarity	NPD7472	Approved
0.7241	Intermediate Similarity	NPD5403	Approved
0.7229	Intermediate Similarity	NPD1933	Approved
0.7225	Intermediate Similarity	NPD1578	Phase 2
0.7216	Intermediate Similarity	NPD6599	Discontinued
0.7191	Intermediate Similarity	NPD7819	Suspended
0.7176	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD1203	Approved
0.7159	Intermediate Similarity	NPD3226	Approved
0.7151	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7808	Phase 3
0.7126	Intermediate Similarity	NPD1184	Approved
0.7126	Intermediate Similarity	NPD2532	Approved
0.7126	Intermediate Similarity	NPD230	Phase 1
0.7126	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2534	Approved
0.7126	Intermediate Similarity	NPD2533	Approved
0.7126	Intermediate Similarity	NPD5401	Approved
0.7112	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6797	Phase 2
0.7095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1607	Approved
0.7079	Intermediate Similarity	NPD7411	Suspended
0.7074	Intermediate Similarity	NPD7251	Discontinued
0.7072	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD6801	Discontinued
0.703	Intermediate Similarity	NPD6832	Phase 2
0.7024	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4380	Phase 2
0.7022	Intermediate Similarity	NPD4972	Discontinued
0.7018	Intermediate Similarity	NPD2346	Discontinued
0.7017	Intermediate Similarity	NPD7768	Phase 2
0.7006	Intermediate Similarity	NPD1653	Approved
0.6995	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD1549	Phase 2
0.6975	Remote Similarity	NPD9717	Approved
0.6973	Remote Similarity	NPD3926	Phase 2
0.6964	Remote Similarity	NPD1240	Approved
0.6957	Remote Similarity	NPD1247	Approved
0.6957	Remote Similarity	NPD6959	Discontinued
0.6949	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD37	Approved
0.694	Remote Similarity	NPD6234	Discontinued
0.694	Remote Similarity	NPD919	Approved
0.6932	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6919	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1510	Phase 2
0.6897	Remote Similarity	NPD4628	Phase 3
0.686	Remote Similarity	NPD2796	Approved
0.6845	Remote Similarity	NPD2313	Discontinued
0.6845	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8312	Approved
0.6823	Remote Similarity	NPD8313	Approved
0.6802	Remote Similarity	NPD4308	Phase 3
0.6802	Remote Similarity	NPD2799	Discontinued
0.6796	Remote Similarity	NPD958	Approved
0.6793	Remote Similarity	NPD3749	Approved
0.6776	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4363	Phase 3
0.6768	Remote Similarity	NPD4360	Phase 2
0.6766	Remote Similarity	NPD454	Approved
0.6765	Remote Similarity	NPD943	Approved
0.6761	Remote Similarity	NPD2354	Approved
0.6761	Remote Similarity	NPD6190	Approved
0.6754	Remote Similarity	NPD5953	Discontinued
0.6737	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD957	Approved
0.6705	Remote Similarity	NPD3748	Approved
0.6685	Remote Similarity	NPD5353	Approved
0.6685	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7199	Phase 2
0.6684	Remote Similarity	NPD7228	Approved
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD920	Approved
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.665	Remote Similarity	NPD4361	Phase 2
0.665	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5711	Approved
0.6649	Remote Similarity	NPD5710	Approved
0.6649	Remote Similarity	NPD7286	Phase 2
0.6648	Remote Similarity	NPD2800	Approved
0.6648	Remote Similarity	NPD1243	Approved
0.6648	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD9493	Approved
0.6629	Remote Similarity	NPD2353	Approved
0.6629	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5242	Approved
0.6614	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1019	Discontinued
0.66	Remote Similarity	NPD6312	Discontinued
0.6595	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3027	Phase 3
0.6582	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.657	Remote Similarity	NPD1613	Approved
0.657	Remote Similarity	NPD4307	Phase 2
0.6566	Remote Similarity	NPD9269	Phase 2
0.6556	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2797	Approved
0.6548	Remote Similarity	NPD8434	Phase 2
0.6548	Remote Similarity	NPD8150	Discontinued
0.6546	Remote Similarity	NPD7685	Pre-registration
0.6546	Remote Similarity	NPD7038	Approved
0.6546	Remote Similarity	NPD7039	Approved
0.6527	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD9268	Approved
0.6522	Remote Similarity	NPD6386	Approved
0.6522	Remote Similarity	NPD6385	Approved
0.652	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.651	Remote Similarity	NPD3751	Discontinued
0.6506	Remote Similarity	NPD422	Phase 1
0.6505	Remote Similarity	NPD7435	Discontinued
0.65	Remote Similarity	NPD4357	Discontinued
0.6497	Remote Similarity	NPD4534	Discontinued
0.6492	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3225	Approved
0.6486	Remote Similarity	NPD6844	Discontinued
0.6485	Remote Similarity	NPD1778	Approved
0.6471	Remote Similarity	NPD3018	Phase 2
0.6471	Remote Similarity	NPD9494	Approved
0.6467	Remote Similarity	NPD1608	Approved
0.6453	Remote Similarity	NPD3268	Approved
0.6453	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD3496	Discontinued
0.6444	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2344	Approved
0.6439	Remote Similarity	NPD6782	Approved
0.6439	Remote Similarity	NPD6779	Approved
0.6439	Remote Similarity	NPD6780	Approved
0.6439	Remote Similarity	NPD6776	Approved
0.6439	Remote Similarity	NPD6777	Approved
0.6439	Remote Similarity	NPD6781	Approved
0.6439	Remote Similarity	NPD6778	Approved
0.6429	Remote Similarity	NPD8151	Discontinued
0.6429	Remote Similarity	NPD4749	Approved
0.6429	Remote Similarity	NPD7549	Discontinued
0.6421	Remote Similarity	NPD8127	Discontinued
0.642	Remote Similarity	NPD7033	Discontinued
0.642	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6233	Phase 2
0.6412	Remote Similarity	NPD2798	Approved
0.6409	Remote Similarity	NPD7390	Discontinued
0.6404	Remote Similarity	NPD5958	Discontinued
0.64	Remote Similarity	NPD6651	Approved
0.6395	Remote Similarity	NPD4625	Phase 3
0.6387	Remote Similarity	NPD3787	Discontinued
0.6384	Remote Similarity	NPD5406	Approved
0.6384	Remote Similarity	NPD5405	Approved
0.6384	Remote Similarity	NPD5404	Approved
0.6384	Remote Similarity	NPD5408	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