NPASS Compound

Structure

CID148938 OpenBabel06191715522D 30 32 0 0 0 0 0 0 0 0999 V2000 0.9122 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -4.2731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 2.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 3.5211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 2.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 11 1 0 0 0 0 7 16 2 0 0 0 0 8 12 1 0 0 0 0 8 17 2 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 25 2 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 18 22 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 30 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.21
Volume:	444.015
LogP:	7.35
LogD:	4.601
LogS:	-4.913
# Rotatable Bonds:	7
TPSA:	51.83
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	2.958
Fsp3:	0.308
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:	-4.827
MDCK Permeability:	1.4817711416981183e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.104
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	86.21842193603516%
Volume Distribution (VD):	5.254
Pgp-substrate:	14.854589462280273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.738
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.253
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.537
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	10.202
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.387
Human Hepatotoxicity (H-HT):	0.948
Drug-inuced Liver Injury (DILI):	0.856
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.661
Skin Sensitization:	0.408
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.523

Download Data

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

Natural Product: NPC148938

Natural Product ID:	NPC148938
*Common Name:**	Lakoochin A
IUPAC Name:	2-[3,5-dimethoxy-2,6-bis(3-methylbut-2-enyl)phenyl]-1-benzofuran-6-ol
Synonyms:
Standard InCHIKey:	CHDJBHWCUVZCGP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H30O4/c1-16(2)7-11-20-23(28-5)15-24(29-6)21(12-8-17(3)4)26(20)25-13-18-9-10-19(27)14-22(18)30-25/h7-10,13-15,27H,11-12H2,1-6H3
SMILES:	CC(=CCc1c(cc(c(CC=C(C)C)c1c1cc2ccc(cc2o1)O)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463296
PubChem CID:	3012524
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO40440	Artocarpus lakoocha	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043440]
NPO9272	Artocarpus lakoocha	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9272	Artocarpus lakoocha	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9272	Artocarpus lakoocha	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	3
MIC	1
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	=	13880.0	nM	PMID[531486]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	27420.0	nM	PMID[531486]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	12.5	ug.mL-1	PMID[531485]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.1	ug.mL-1	PMID[531485]
NPT2	Others	Unspecified		Ratio IC50	=	0.5	n.a.	PMID[531486]

☑ 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 NPC148938 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	407
0.1-0.2	1670
0.2-0.3	3799
0.3-0.4	10232
0.4-0.5	8211
0.5-0.6	3561
0.6-0.7	5429
0.7-0.8	5109
0.8-0.85	2528
0.85-0.9	1576
0.9-0.95	145
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC235333
0.9866	High Similarity	NPC164110
0.9866	High Similarity	NPC212967
0.9866	High Similarity	NPC246647
0.9866	High Similarity	NPC96342
0.9865	High Similarity	NPC297531
0.9865	High Similarity	NPC213936
0.9864	High Similarity	NPC207624
0.9799	High Similarity	NPC180924
0.9796	High Similarity	NPC106372
0.9796	High Similarity	NPC170169
0.9796	High Similarity	NPC115324
0.9796	High Similarity	NPC58668
0.9796	High Similarity	NPC23668
0.9796	High Similarity	NPC193976
0.9733	High Similarity	NPC268360
0.973	High Similarity	NPC142308
0.9728	High Similarity	NPC78335
0.9728	High Similarity	NPC230713
0.966	High Similarity	NPC178202
0.966	High Similarity	NPC226644
0.966	High Similarity	NPC37226
0.96	High Similarity	NPC198490
0.96	High Similarity	NPC99199
0.9592	High Similarity	NPC135325
0.9533	High Similarity	NPC213608
0.9533	High Similarity	NPC1477
0.9533	High Similarity	NPC472462
0.9533	High Similarity	NPC183874
0.9524	High Similarity	NPC17816
0.9524	High Similarity	NPC130581
0.9524	High Similarity	NPC12148
0.9467	High Similarity	NPC5871
0.9463	High Similarity	NPC13282
0.9463	High Similarity	NPC167576
0.9456	High Similarity	NPC210826
0.9456	High Similarity	NPC300267
0.9456	High Similarity	NPC51641
0.9423	High Similarity	NPC53640
0.9408	High Similarity	NPC247677
0.9408	High Similarity	NPC160015
0.9396	High Similarity	NPC296030
0.9396	High Similarity	NPC39929
0.9388	High Similarity	NPC230943
0.9388	High Similarity	NPC98926
0.9388	High Similarity	NPC155144
0.9346	High Similarity	NPC65504
0.9346	High Similarity	NPC296957
0.9346	High Similarity	NPC260902
0.932	High Similarity	NPC225884
0.932	High Similarity	NPC302181
0.9286	High Similarity	NPC40583
0.9286	High Similarity	NPC476349
0.9286	High Similarity	NPC476350
0.9276	High Similarity	NPC72370
0.9267	High Similarity	NPC221868
0.9267	High Similarity	NPC10027
0.9267	High Similarity	NPC65775
0.9267	High Similarity	NPC37208
0.9252	High Similarity	NPC53192
0.9226	High Similarity	NPC260296
0.9226	High Similarity	NPC220582
0.9226	High Similarity	NPC304839
0.9226	High Similarity	NPC115432
0.9211	High Similarity	NPC253872
0.9211	High Similarity	NPC263676
0.9211	High Similarity	NPC67654
0.9205	High Similarity	NPC227122
0.92	High Similarity	NPC272194
0.9184	High Similarity	NPC49108
0.9177	High Similarity	NPC277480
0.9172	High Similarity	NPC133065
0.9167	High Similarity	NPC30655
0.9167	High Similarity	NPC74854
0.9167	High Similarity	NPC45124
0.9161	High Similarity	NPC244750
0.9156	High Similarity	NPC137100
0.915	High Similarity	NPC122365
0.9145	High Similarity	NPC258249
0.9145	High Similarity	NPC156244
0.9145	High Similarity	NPC116604
0.9139	High Similarity	NPC65589
0.9139	High Similarity	NPC97029
0.9139	High Similarity	NPC288036
0.9139	High Similarity	NPC266499
0.9139	High Similarity	NPC158338
0.9139	High Similarity	NPC100985
0.9139	High Similarity	NPC317492
0.9139	High Similarity	NPC97028
0.9119	High Similarity	NPC50394
0.9119	High Similarity	NPC247973
0.9114	High Similarity	NPC474591
0.9114	High Similarity	NPC39306
0.9114	High Similarity	NPC37183
0.9108	High Similarity	NPC312056
0.9108	High Similarity	NPC84515
0.9108	High Similarity	NPC193998
0.9085	High Similarity	NPC154683
0.9085	High Similarity	NPC40356
0.9073	High Similarity	NPC7025
0.9073	High Similarity	NPC37135
0.9073	High Similarity	NPC256672
0.9073	High Similarity	NPC39195
0.9073	High Similarity	NPC186397
0.9073	High Similarity	NPC168085
0.9073	High Similarity	NPC27221
0.9051	High Similarity	NPC159508
0.9051	High Similarity	NPC155640
0.9048	High Similarity	NPC472366
0.9045	High Similarity	NPC188486
0.9045	High Similarity	NPC304387
0.9038	High Similarity	NPC472877
0.9032	High Similarity	NPC45131
0.9026	High Similarity	NPC178964
0.9026	High Similarity	NPC210942
0.9026	High Similarity	NPC329844
0.9026	High Similarity	NPC95842
0.9026	High Similarity	NPC280530
0.9026	High Similarity	NPC169990
0.902	High Similarity	NPC72958
0.902	High Similarity	NPC149526
0.902	High Similarity	NPC474417
0.902	High Similarity	NPC232645
0.9013	High Similarity	NPC223988
0.9007	High Similarity	NPC308200
0.9007	High Similarity	NPC17101
0.9007	High Similarity	NPC77903
0.9007	High Similarity	NPC123202
0.9007	High Similarity	NPC7943
0.9007	High Similarity	NPC22005
0.9006	High Similarity	NPC131866
0.9	High Similarity	NPC311741
0.9	High Similarity	NPC234629
0.9	High Similarity	NPC286230
0.9	High Similarity	NPC253730
0.8994	High Similarity	NPC169471
0.8994	High Similarity	NPC136641
0.8993	High Similarity	NPC226942
0.8993	High Similarity	NPC96791
0.8993	High Similarity	NPC470636
0.8993	High Similarity	NPC310340
0.8993	High Similarity	NPC84266
0.8987	High Similarity	NPC3448
0.8987	High Similarity	NPC219861
0.8987	High Similarity	NPC477239
0.8987	High Similarity	NPC272722
0.8981	High Similarity	NPC470810
0.8974	High Similarity	NPC196448
0.8968	High Similarity	NPC66508
0.8968	High Similarity	NPC226656
0.8961	High Similarity	NPC87708
0.8961	High Similarity	NPC474843
0.8961	High Similarity	NPC38361
0.8961	High Similarity	NPC130015
0.8954	High Similarity	NPC119929
0.8954	High Similarity	NPC202595
0.8954	High Similarity	NPC295036
0.8954	High Similarity	NPC470107
0.8954	High Similarity	NPC321896
0.8954	High Similarity	NPC476185
0.8954	High Similarity	NPC472406
0.8954	High Similarity	NPC472421
0.8947	High Similarity	NPC145467
0.8947	High Similarity	NPC216624
0.894	High Similarity	NPC290133
0.894	High Similarity	NPC187282
0.894	High Similarity	NPC477955
0.894	High Similarity	NPC24136
0.894	High Similarity	NPC299011
0.8933	High Similarity	NPC166138
0.8933	High Similarity	NPC106985
0.8933	High Similarity	NPC17262
0.8933	High Similarity	NPC262935
0.8933	High Similarity	NPC251182
0.8933	High Similarity	NPC18585
0.8933	High Similarity	NPC172182
0.8931	High Similarity	NPC472581
0.8931	High Similarity	NPC109180
0.8931	High Similarity	NPC38591
0.8926	High Similarity	NPC182255
0.8926	High Similarity	NPC94076
0.8926	High Similarity	NPC110969
0.8924	High Similarity	NPC18380
0.8924	High Similarity	NPC96031
0.8919	High Similarity	NPC477956
0.8917	High Similarity	NPC196879
0.8917	High Similarity	NPC324736
0.8917	High Similarity	NPC18699
0.8917	High Similarity	NPC16935
0.8917	High Similarity	NPC55443
0.8912	High Similarity	NPC62735
0.8912	High Similarity	NPC472419
0.891	High Similarity	NPC146211
0.8903	High Similarity	NPC135522
0.8896	High Similarity	NPC65885
0.8896	High Similarity	NPC474772
0.8896	High Similarity	NPC472423
0.8896	High Similarity	NPC310794
0.8896	High Similarity	NPC478148
0.8896	High Similarity	NPC474744

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 NPC148938 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	974
0.2-0.3	1483
0.3-0.4	2645
0.4-0.5	1907
0.5-0.6	1123
0.6-0.7	437
0.7-0.8	146
0.8-0.85	52
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8854	High Similarity	NPD3749	Approved
0.8782	High Similarity	NPD7819	Suspended
0.8688	High Similarity	NPD6959	Discontinued
0.8662	High Similarity	NPD2393	Clinical (unspecified phase)
0.8658	High Similarity	NPD2344	Approved
0.8627	High Similarity	NPD2532	Approved
0.8627	High Similarity	NPD2534	Approved
0.8627	High Similarity	NPD2533	Approved
0.8627	High Similarity	NPD7410	Clinical (unspecified phase)
0.8553	High Similarity	NPD3882	Suspended
0.8543	High Similarity	NPD2800	Approved
0.8519	High Similarity	NPD6232	Discontinued
0.8516	High Similarity	NPD920	Approved
0.8503	High Similarity	NPD1240	Approved
0.8491	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1549	Phase 2
0.8476	Intermediate Similarity	NPD7473	Discontinued
0.8443	Intermediate Similarity	NPD6559	Discontinued
0.8431	Intermediate Similarity	NPD2309	Approved
0.8428	Intermediate Similarity	NPD2801	Approved
0.8421	Intermediate Similarity	NPD1243	Approved
0.8418	Intermediate Similarity	NPD7411	Suspended
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8395	Intermediate Similarity	NPD5494	Approved
0.8389	Intermediate Similarity	NPD1607	Approved
0.8387	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD1934	Approved
0.8355	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8354	Intermediate Similarity	NPD3926	Phase 2
0.8344	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8323	Intermediate Similarity	NPD1511	Approved
0.8303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7075	Discontinued
0.8258	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD3750	Approved
0.8232	Intermediate Similarity	NPD1247	Approved
0.8224	Intermediate Similarity	NPD2935	Discontinued
0.8217	Intermediate Similarity	NPD1512	Approved
0.8204	Intermediate Similarity	NPD3818	Discontinued
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3226	Approved
0.8158	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD919	Approved
0.8089	Intermediate Similarity	NPD7390	Discontinued
0.8089	Intermediate Similarity	NPD6799	Approved
0.8084	Intermediate Similarity	NPD6166	Phase 2
0.8084	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2346	Discontinued
0.8049	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2799	Discontinued
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5710	Approved
0.7964	Intermediate Similarity	NPD5711	Approved
0.7964	Intermediate Similarity	NPD7229	Phase 3
0.7935	Intermediate Similarity	NPD1471	Phase 3
0.7935	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3817	Phase 2
0.7922	Intermediate Similarity	NPD3748	Approved
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7866	Intermediate Similarity	NPD1465	Phase 2
0.7861	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD5953	Discontinued
0.7836	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7286	Phase 2
0.7818	Intermediate Similarity	NPD2296	Approved
0.7797	Intermediate Similarity	NPD4287	Approved
0.7792	Intermediate Similarity	NPD6651	Approved
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7778	Intermediate Similarity	NPD943	Approved
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7756	Intermediate Similarity	NPD6099	Approved
0.7756	Intermediate Similarity	NPD6100	Approved
0.7733	Intermediate Similarity	NPD7054	Approved
0.7711	Intermediate Similarity	NPD5402	Approved
0.7697	Intermediate Similarity	NPD4625	Phase 3
0.7688	Intermediate Similarity	NPD7472	Approved
0.7674	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3764	Approved
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD5405	Approved
0.7643	Intermediate Similarity	NPD5404	Approved
0.7643	Intermediate Similarity	NPD5406	Approved
0.7643	Intermediate Similarity	NPD5408	Approved
0.7622	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7251	Discontinued
0.759	Intermediate Similarity	NPD6280	Approved
0.759	Intermediate Similarity	NPD6279	Approved
0.758	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.7557	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1203	Approved
0.755	Intermediate Similarity	NPD1470	Approved
0.7545	Intermediate Similarity	NPD5761	Phase 2
0.7545	Intermediate Similarity	NPD5760	Phase 2
0.7543	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.7486	Intermediate Similarity	NPD1729	Discontinued
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7453	Intermediate Similarity	NPD7003	Approved
0.7442	Intermediate Similarity	NPD6808	Phase 2
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.74	Intermediate Similarity	NPD1201	Approved
0.7399	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2654	Approved
0.7391	Intermediate Similarity	NPD4361	Phase 2
0.7391	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD447	Suspended
0.7389	Intermediate Similarity	NPD230	Phase 1
0.7386	Intermediate Similarity	NPD2798	Approved
0.7381	Intermediate Similarity	NPD37	Approved
0.7378	Intermediate Similarity	NPD5401	Approved
0.7371	Intermediate Similarity	NPD7177	Discontinued
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7353	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD4966	Approved
0.7351	Intermediate Similarity	NPD9717	Approved
0.7351	Intermediate Similarity	NPD1608	Approved
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7337	Intermediate Similarity	NPD4363	Phase 3
0.7337	Intermediate Similarity	NPD4360	Phase 2
0.7317	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1651	Approved
0.7308	Intermediate Similarity	NPD3268	Approved
0.7294	Intermediate Similarity	NPD4288	Approved
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2403	Approved
0.7255	Intermediate Similarity	NPD1283	Approved
0.7255	Intermediate Similarity	NPD1876	Approved
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7237	Intermediate Similarity	NPD3972	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7229	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7208	Intermediate Similarity	NPD2797	Approved
0.7208	Intermediate Similarity	NPD1164	Approved
0.7197	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD411	Approved
0.7193	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7871	Phase 2
0.7173	Intermediate Similarity	NPD7870	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.7166	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2861	Phase 2
0.7114	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6971	Discontinued
0.7107	Intermediate Similarity	NPD1613	Approved
0.7107	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2979	Phase 3
0.7104	Intermediate Similarity	NPD8150	Discontinued

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