NPASS Compound

Structure

NPC198209 OpenBabel07101718322D 28 32 0 0 1 0 0 0 0 0999 V2000 0.1142 -3.1594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5120 -2.8685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8943 -3.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1288 -3.2695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5860 -3.1163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 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 2.6831 -0.6910 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 0.0000 2.0000 0.0000 S 0 0 1 0 0 0 0 0 0 0 0 0 5 6 1 0 0 0 0 5 7 2 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 19 1 0 0 0 0 9 28 1 0 0 0 0 10 17 1 0 0 0 0 11 21 2 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 1 0 0 0 13 17 1 1 0 0 0 13 18 1 0 0 0 0 14 20 1 1 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 6 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 20 10 1 6 0 0 0 20 27 1 0 0 0 0 24 28 2 0 0 0 0 28 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.12
Volume:	381.189
LogP:	1.321
LogD:	-0.029
LogS:	-4.059
# Rotatable Bonds:	3
TPSA:	108.42
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	6.522
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.478
MDCK Permeability:	1.8665063180378638e-05
Pgp-inhibitor:	0.446
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.79
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	34.109901428222656%
Volume Distribution (VD):	1.381
Pgp-substrate:	49.536865234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.542
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.523
CYP3A4-substrate:	0.671

ADMET: Excretion

Clearance (CL):	1.929
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.098
AMES Toxicity:	0.861
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.397
Carcinogencity:	0.942
Eye Corrosion:	0.085
Eye Irritation:	0.035
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC198209

Natural Product ID:	NPC198209
*Common Name:**	JBOCKXJDIJBMIP-QLNKURTRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JBOCKXJDIJBMIP-QLNKURTRSA-N
Standard InCHI:	InChI=1S/C20H24O7S/c1-17-6-5-7-18(2)13(17)12(26-16(18)22)14-20(27-14)10(17)8-11(21)25-15(20)19(3,23)9-28(4)24/h5,7-8,12-15,23H,6,9H2,1-4H3/t12-,13+,14+,15+,17+,18-,19-,20-,28-/m0/s1
SMILES:	C[C@@]12CC=C[C@@]3(C)[C@@H]2[C@@H]([C@@H]2[C@]4(C1=CC(=O)O[C@@H]4[C@](C)(C[S@@](=O)C)O)O2)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460334
PubChem CID:	10364100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO27558.1	Podocarpus macrophyllus var. maki	Varieties	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608867]
NPO27558.1	Podocarpus macrophyllus var. maki	Varieties	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27558.1	Podocarpus macrophyllus var. maki	Varieties	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.52	ug.mL-1	PMID[533856]
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.23	ug.mL-1	PMID[533857]

☑ 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 NPC198209 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	233
0.1-0.2	1452
0.2-0.3	4565
0.3-0.4	7986
0.4-0.5	14335
0.5-0.6	8287
0.6-0.7	4939
0.7-0.8	868
0.8-0.85	28
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8696	High Similarity	NPC469370
0.8655	High Similarity	NPC469684
0.8583	High Similarity	NPC284707
0.8547	High Similarity	NPC469655
0.8547	High Similarity	NPC469656
0.8547	High Similarity	NPC474846
0.85	High Similarity	NPC53396
0.85	High Similarity	NPC98249
0.8362	Intermediate Similarity	NPC180744
0.8347	Intermediate Similarity	NPC58662
0.8347	Intermediate Similarity	NPC13713
0.8305	Intermediate Similarity	NPC253906
0.816	Intermediate Similarity	NPC170538
0.811	Intermediate Similarity	NPC293112
0.811	Intermediate Similarity	NPC473635
0.8095	Intermediate Similarity	NPC11895
0.8049	Intermediate Similarity	NPC478204
0.8031	Intermediate Similarity	NPC81736
0.8031	Intermediate Similarity	NPC172154
0.8017	Intermediate Similarity	NPC222834
0.8017	Intermediate Similarity	NPC472002
0.8017	Intermediate Similarity	NPC269530
0.8	Intermediate Similarity	NPC5103
0.7984	Intermediate Similarity	NPC478205
0.7984	Intermediate Similarity	NPC108581
0.7984	Intermediate Similarity	NPC478206
0.7967	Intermediate Similarity	NPC179626
0.7966	Intermediate Similarity	NPC469607
0.7953	Intermediate Similarity	NPC469789
0.7951	Intermediate Similarity	NPC471204
0.7951	Intermediate Similarity	NPC475966
0.7934	Intermediate Similarity	NPC179798
0.7934	Intermediate Similarity	NPC304180
0.7903	Intermediate Similarity	NPC473590
0.7891	Intermediate Similarity	NPC8369
0.7857	Intermediate Similarity	NPC143755
0.7851	Intermediate Similarity	NPC472215
0.7851	Intermediate Similarity	NPC472214
0.7823	Intermediate Similarity	NPC270478
0.7815	Intermediate Similarity	NPC102352
0.7812	Intermediate Similarity	NPC67251
0.7805	Intermediate Similarity	NPC56448
0.7805	Intermediate Similarity	NPC49451
0.7805	Intermediate Similarity	NPC477126
0.7805	Intermediate Similarity	NPC469463
0.7805	Intermediate Similarity	NPC469454
0.7805	Intermediate Similarity	NPC478212
0.7805	Intermediate Similarity	NPC469496
0.7805	Intermediate Similarity	NPC25909
0.7795	Intermediate Similarity	NPC310511
0.7795	Intermediate Similarity	NPC67569
0.7787	Intermediate Similarity	NPC188738
0.7787	Intermediate Similarity	NPC97939
0.7787	Intermediate Similarity	NPC247031
0.7787	Intermediate Similarity	NPC132790
0.7787	Intermediate Similarity	NPC100329
0.7778	Intermediate Similarity	NPC472667
0.7778	Intermediate Similarity	NPC475041
0.7778	Intermediate Similarity	NPC470186
0.7769	Intermediate Similarity	NPC299590
0.7769	Intermediate Similarity	NPC478210
0.776	Intermediate Similarity	NPC473968
0.7752	Intermediate Similarity	NPC24651
0.775	Intermediate Similarity	NPC230541
0.775	Intermediate Similarity	NPC3316
0.775	Intermediate Similarity	NPC67321
0.775	Intermediate Similarity	NPC144854
0.775	Intermediate Similarity	NPC187435
0.7742	Intermediate Similarity	NPC117712
0.7734	Intermediate Similarity	NPC470265
0.7734	Intermediate Similarity	NPC312833
0.7734	Intermediate Similarity	NPC23786
0.7731	Intermediate Similarity	NPC258532
0.7731	Intermediate Similarity	NPC146731
0.7724	Intermediate Similarity	NPC474516
0.7717	Intermediate Similarity	NPC154491
0.7717	Intermediate Similarity	NPC474585
0.7717	Intermediate Similarity	NPC268530
0.7717	Intermediate Similarity	NPC251226
0.7712	Intermediate Similarity	NPC469606
0.7712	Intermediate Similarity	NPC472552
0.7712	Intermediate Similarity	NPC31058
0.7712	Intermediate Similarity	NPC273005
0.7712	Intermediate Similarity	NPC295791
0.7705	Intermediate Similarity	NPC478211
0.7698	Intermediate Similarity	NPC124676
0.7698	Intermediate Similarity	NPC153440
0.7698	Intermediate Similarity	NPC146280
0.7686	Intermediate Similarity	NPC154608
0.7686	Intermediate Similarity	NPC192813
0.7686	Intermediate Similarity	NPC277017
0.7686	Intermediate Similarity	NPC469916
0.7686	Intermediate Similarity	NPC472439
0.7686	Intermediate Similarity	NPC189075
0.7686	Intermediate Similarity	NPC275539
0.768	Intermediate Similarity	NPC474734
0.768	Intermediate Similarity	NPC96312
0.768	Intermediate Similarity	NPC328374
0.768	Intermediate Similarity	NPC176840
0.768	Intermediate Similarity	NPC207217
0.768	Intermediate Similarity	NPC190286
0.768	Intermediate Similarity	NPC40632
0.768	Intermediate Similarity	NPC477509
0.768	Intermediate Similarity	NPC251236
0.7674	Intermediate Similarity	NPC105926
0.7674	Intermediate Similarity	NPC91693
0.7674	Intermediate Similarity	NPC265557
0.7674	Intermediate Similarity	NPC18945
0.7667	Intermediate Similarity	NPC477125
0.7656	Intermediate Similarity	NPC159456
0.7656	Intermediate Similarity	NPC102822
0.7656	Intermediate Similarity	NPC4021
0.7656	Intermediate Similarity	NPC477046
0.7647	Intermediate Similarity	NPC23584
0.7642	Intermediate Similarity	NPC474229
0.7638	Intermediate Similarity	NPC473636
0.7638	Intermediate Similarity	NPC5292
0.7638	Intermediate Similarity	NPC77689
0.7638	Intermediate Similarity	NPC475775
0.7638	Intermediate Similarity	NPC305260
0.7638	Intermediate Similarity	NPC476529
0.7638	Intermediate Similarity	NPC475520
0.7638	Intermediate Similarity	NPC270850
0.7638	Intermediate Similarity	NPC42673
0.7627	Intermediate Similarity	NPC472554
0.7623	Intermediate Similarity	NPC5475
0.7623	Intermediate Similarity	NPC143706
0.7623	Intermediate Similarity	NPC173905
0.7623	Intermediate Similarity	NPC141350
0.7623	Intermediate Similarity	NPC284828
0.7623	Intermediate Similarity	NPC472534
0.7623	Intermediate Similarity	NPC472216
0.7619	Intermediate Similarity	NPC470775
0.7619	Intermediate Similarity	NPC134430
0.7619	Intermediate Similarity	NPC284068
0.7619	Intermediate Similarity	NPC97908
0.7619	Intermediate Similarity	NPC470854
0.7619	Intermediate Similarity	NPC122033
0.7619	Intermediate Similarity	NPC474654
0.7619	Intermediate Similarity	NPC176513
0.7619	Intermediate Similarity	NPC23046
0.7619	Intermediate Similarity	NPC287343
0.7615	Intermediate Similarity	NPC476729
0.7607	Intermediate Similarity	NPC222303
0.7607	Intermediate Similarity	NPC216478
0.7603	Intermediate Similarity	NPC110496
0.76	Intermediate Similarity	NPC473798
0.76	Intermediate Similarity	NPC73314
0.7597	Intermediate Similarity	NPC269642
0.7583	Intermediate Similarity	NPC477127
0.7583	Intermediate Similarity	NPC296950
0.7583	Intermediate Similarity	NPC65523
0.7581	Intermediate Similarity	NPC476801
0.7581	Intermediate Similarity	NPC42658
0.7578	Intermediate Similarity	NPC79579
0.7578	Intermediate Similarity	NPC475003
0.7578	Intermediate Similarity	NPC475885
0.7578	Intermediate Similarity	NPC109607
0.7578	Intermediate Similarity	NPC107338
0.7563	Intermediate Similarity	NPC11956
0.7563	Intermediate Similarity	NPC476081
0.7561	Intermediate Similarity	NPC210005
0.7561	Intermediate Similarity	NPC478209
0.7561	Intermediate Similarity	NPC474567
0.7559	Intermediate Similarity	NPC50774
0.7559	Intermediate Similarity	NPC470776
0.7559	Intermediate Similarity	NPC251310
0.7559	Intermediate Similarity	NPC186525
0.7559	Intermediate Similarity	NPC240509
0.7559	Intermediate Similarity	NPC17772
0.7559	Intermediate Similarity	NPC709
0.7557	Intermediate Similarity	NPC120994
0.7557	Intermediate Similarity	NPC203702
0.7557	Intermediate Similarity	NPC181999
0.7557	Intermediate Similarity	NPC225049
0.7542	Intermediate Similarity	NPC47024
0.7541	Intermediate Similarity	NPC306265
0.7541	Intermediate Similarity	NPC94377
0.754	Intermediate Similarity	NPC478216
0.754	Intermediate Similarity	NPC471816
0.754	Intermediate Similarity	NPC154363
0.754	Intermediate Similarity	NPC471127
0.754	Intermediate Similarity	NPC234858
0.7538	Intermediate Similarity	NPC120724
0.7538	Intermediate Similarity	NPC473979
0.7521	Intermediate Similarity	NPC478208
0.7521	Intermediate Similarity	NPC470263
0.752	Intermediate Similarity	NPC51978
0.752	Intermediate Similarity	NPC317210
0.7519	Intermediate Similarity	NPC231529
0.7519	Intermediate Similarity	NPC473593
0.7519	Intermediate Similarity	NPC46570
0.7519	Intermediate Similarity	NPC470779
0.75	Intermediate Similarity	NPC236918
0.75	Intermediate Similarity	NPC230513
0.75	Intermediate Similarity	NPC156745
0.75	Intermediate Similarity	NPC211093
0.75	Intermediate Similarity	NPC317107
0.75	Intermediate Similarity	NPC61442
0.75	Intermediate Similarity	NPC159533

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 NPC198209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1510
0.2-0.3	3772
0.3-0.4	2476
0.4-0.5	782
0.5-0.6	264
0.6-0.7	144
0.7-0.8	6
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
0.7769	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD7115	Discovery
0.7459	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6008	Approved
0.712	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6317	Approved
0.7049	Intermediate Similarity	NPD5344	Discontinued
0.7025	Intermediate Similarity	NPD4225	Approved
0.6977	Remote Similarity	NPD4632	Approved
0.6953	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6319	Approved
0.6912	Remote Similarity	NPD7507	Approved
0.6885	Remote Similarity	NPD7638	Approved
0.6884	Remote Similarity	NPD7319	Approved
0.6866	Remote Similarity	NPD8513	Phase 3
0.685	Remote Similarity	NPD6686	Approved
0.6829	Remote Similarity	NPD7640	Approved
0.6829	Remote Similarity	NPD6648	Approved
0.6829	Remote Similarity	NPD7639	Approved
0.6772	Remote Similarity	NPD5697	Approved
0.6769	Remote Similarity	NPD8297	Approved
0.6769	Remote Similarity	NPD6053	Discontinued
0.6765	Remote Similarity	NPD6067	Discontinued
0.6744	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5135	Approved
0.6741	Remote Similarity	NPD8516	Approved
0.6741	Remote Similarity	NPD8515	Approved
0.6741	Remote Similarity	NPD8517	Approved
0.6723	Remote Similarity	NPD46	Approved
0.6723	Remote Similarity	NPD6698	Approved
0.6719	Remote Similarity	NPD6881	Approved
0.6719	Remote Similarity	NPD6899	Approved
0.6715	Remote Similarity	NPD7492	Approved
0.6693	Remote Similarity	NPD6675	Approved
0.6693	Remote Similarity	NPD7128	Approved
0.6693	Remote Similarity	NPD6402	Approved
0.6693	Remote Similarity	NPD5739	Approved
0.6692	Remote Similarity	NPD6649	Approved
0.6692	Remote Similarity	NPD6650	Approved
0.6692	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6642	Remote Similarity	NPD7604	Phase 2
0.6641	Remote Similarity	NPD5701	Approved
0.6619	Remote Similarity	NPD7078	Approved
0.6618	Remote Similarity	NPD6015	Approved
0.6618	Remote Similarity	NPD6016	Approved
0.6618	Remote Similarity	NPD5983	Phase 2
0.6615	Remote Similarity	NPD7290	Approved
0.6615	Remote Similarity	NPD6883	Approved
0.6615	Remote Similarity	NPD7102	Approved
0.6593	Remote Similarity	NPD7516	Approved
0.6589	Remote Similarity	NPD7320	Approved
0.6589	Remote Similarity	NPD6011	Approved
0.6581	Remote Similarity	NPD1694	Approved
0.6571	Remote Similarity	NPD7736	Approved
0.6569	Remote Similarity	NPD5988	Approved
0.6569	Remote Similarity	NPD6370	Approved
0.6565	Remote Similarity	NPD6847	Approved
0.6565	Remote Similarity	NPD6869	Approved
0.6565	Remote Similarity	NPD6617	Approved
0.6565	Remote Similarity	NPD8130	Phase 1
0.6544	Remote Similarity	NPD6059	Approved
0.6532	Remote Similarity	NPD7902	Approved
0.6522	Remote Similarity	NPD8328	Phase 3
0.6519	Remote Similarity	NPD7328	Approved
0.6519	Remote Similarity	NPD7327	Approved
0.6515	Remote Similarity	NPD6882	Approved
0.65	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD8074	Phase 3
0.6496	Remote Similarity	NPD7503	Approved
0.6496	Remote Similarity	NPD6921	Approved
0.6489	Remote Similarity	NPD4634	Approved
0.6489	Remote Similarity	NPD6371	Approved
0.6475	Remote Similarity	NPD6399	Phase 3
0.6457	Remote Similarity	NPD5211	Phase 2
0.6441	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD5286	Approved
0.6429	Remote Similarity	NPD6336	Discontinued
0.6429	Remote Similarity	NPD5285	Approved
0.6429	Remote Similarity	NPD4696	Approved
0.6423	Remote Similarity	NPD7748	Approved
0.6412	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6052	Approved
0.64	Remote Similarity	NPD4755	Approved
0.6385	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6412	Phase 2
0.6377	Remote Similarity	NPD8296	Approved
0.6377	Remote Similarity	NPD8380	Approved
0.6377	Remote Similarity	NPD8335	Approved
0.6377	Remote Similarity	NPD8379	Approved
0.6377	Remote Similarity	NPD8033	Approved
0.6377	Remote Similarity	NPD8378	Approved
0.6371	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5141	Approved
0.6341	Remote Similarity	NPD5778	Approved
0.6341	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD3573	Approved
0.6328	Remote Similarity	NPD5226	Approved
0.6328	Remote Similarity	NPD5224	Approved
0.6328	Remote Similarity	NPD4633	Approved
0.6328	Remote Similarity	NPD7632	Discontinued
0.6328	Remote Similarity	NPD5225	Approved
0.6324	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7838	Discovery
0.6304	Remote Similarity	NPD8294	Approved
0.6304	Remote Similarity	NPD8377	Approved
0.6299	Remote Similarity	NPD4700	Approved
0.629	Remote Similarity	NPD7900	Approved
0.629	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5174	Approved
0.6279	Remote Similarity	NPD5175	Approved
0.626	Remote Similarity	NPD6079	Approved
0.626	Remote Similarity	NPD6411	Approved
0.626	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD6422	Discontinued
0.625	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD5223	Approved
0.624	Remote Similarity	NPD5695	Phase 3
0.624	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD7101	Approved
0.6232	Remote Similarity	NPD7100	Approved
0.623	Remote Similarity	NPD5328	Approved
0.6222	Remote Similarity	NPD8133	Approved
0.622	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4697	Phase 3
0.619	Remote Similarity	NPD5221	Approved
0.619	Remote Similarity	NPD5222	Approved
0.6186	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7625	Phase 1
0.6164	Remote Similarity	NPD6845	Suspended
0.616	Remote Similarity	NPD5282	Discontinued
0.6159	Remote Similarity	NPD6313	Approved
0.6159	Remote Similarity	NPD6335	Approved
0.6159	Remote Similarity	NPD6314	Approved
0.6142	Remote Similarity	NPD6084	Phase 2
0.6142	Remote Similarity	NPD6083	Phase 2
0.6142	Remote Similarity	NPD5173	Approved
0.6129	Remote Similarity	NPD7983	Approved
0.6129	Remote Similarity	NPD5284	Approved
0.6129	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD6033	Approved
0.6098	Remote Similarity	NPD6101	Approved
0.6098	Remote Similarity	NPD1695	Approved
0.6098	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD5290	Discontinued
0.609	Remote Similarity	NPD4729	Approved
0.609	Remote Similarity	NPD4730	Approved
0.608	Remote Similarity	NPD4202	Approved
0.6061	Remote Similarity	NPD4767	Approved
0.6061	Remote Similarity	NPD4768	Approved
0.6032	Remote Similarity	NPD6001	Approved
0.6028	Remote Similarity	NPD6908	Approved
0.6028	Remote Similarity	NPD6909	Approved
0.6014	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD8034	Phase 2
0.6	Remote Similarity	NPD5250	Approved
0.6	Remote Similarity	NPD1700	Approved
0.6	Remote Similarity	NPD5248	Approved
0.6	Remote Similarity	NPD5247	Approved
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD5251	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD4159	Approved
0.6	Remote Similarity	NPD5249	Phase 3
0.5984	Remote Similarity	NPD5330	Approved
0.5984	Remote Similarity	NPD7521	Approved
0.5984	Remote Similarity	NPD6409	Approved
0.5984	Remote Similarity	NPD7146	Approved
0.5984	Remote Similarity	NPD7334	Approved
0.5984	Remote Similarity	NPD6684	Approved
0.597	Remote Similarity	NPD5128	Approved
0.5969	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD5217	Approved
0.5956	Remote Similarity	NPD5215	Approved
0.5956	Remote Similarity	NPD5216	Approved
0.5952	Remote Similarity	NPD7229	Phase 3
0.592	Remote Similarity	NPD5207	Approved
0.592	Remote Similarity	NPD7136	Phase 2
0.5917	Remote Similarity	NPD3667	Approved
0.5887	Remote Similarity	NPD7519	Approved
0.5887	Remote Similarity	NPD6672	Approved
0.5887	Remote Similarity	NPD7518	Approved
0.5887	Remote Similarity	NPD5737	Approved
0.5887	Remote Similarity	NPD6903	Approved
0.5887	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7517	Approved
0.5882	Remote Similarity	NPD5169	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