NPASS Compound

Structure

NPC130581 OpenBabel07101718202D 24 26 0 0 0 0 0 0 0 0999 V2000 6.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 2.6551 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 4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 0.9230 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 2.0878 0.0570 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 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0878 1.7891 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 -0.9511 -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 1.5878 -0.8090 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 -0.9511 -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 0.5878 -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 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 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 12 1 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.14
Volume:	342.876
LogP:	5.39
LogD:	3.771
LogS:	-4.336
# Rotatable Bonds:	4
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	2.569
Fsp3:	0.2
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:	-4.831
MDCK Permeability:	1.4378889318322763e-05
Pgp-inhibitor:	0.434
Pgp-substrate:	0.619
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	97.59357452392578%
Volume Distribution (VD):	1.106
Pgp-substrate:	4.41997766494751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.769
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.768
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.829
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	11.568
Half-life (T1/2):	0.397

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.471
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.634
Carcinogencity:	0.072
Eye Corrosion:	0.003
Eye Irritation:	0.868
Respiratory Toxicity:	0.546

Download Data

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

Natural Product: NPC130581

Natural Product ID:	NPC130581
*Common Name:**	Addisofuran A
IUPAC Name:	2-[4-hydroxy-2-methoxy-5-(3-methylbut-2-enyl)phenyl]-1-benzofuran-6-ol
Synonyms:
Standard InCHIKey:	XQVKBMIVACNFLX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-12(2)4-5-13-8-16(19(23-3)11-17(13)22)20-9-14-6-7-15(21)10-18(14)24-20/h4,6-11,21-22H,5H2,1-3H3
SMILES:	COc1cc(O)c(cc1c1cc2c(o1)cc(cc2)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL233142
PubChem CID:	44432363
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
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[12828487]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17517504]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	Barks	n.a.	n.a.	PMID[18302333]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20934335]
NPO27387	Erythrina addisoniae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23022281]
NPO27387	Erythrina addisoniae	Species	Fabaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	17500.0	nM	PMID[464575]

☑ 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 NPC130581 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	380
0.1-0.2	1693
0.2-0.3	4189
0.3-0.4	11197
0.4-0.5	6933
0.5-0.6	3989
0.6-0.7	5874
0.7-0.8	4692
0.8-0.85	2026
0.85-0.9	1175
0.9-0.95	519
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12148
0.9929	High Similarity	NPC300267
0.9929	High Similarity	NPC135325
0.9929	High Similarity	NPC210826
0.9929	High Similarity	NPC51641
0.9859	High Similarity	NPC226644
0.9859	High Similarity	NPC37226
0.9859	High Similarity	NPC296030
0.9859	High Similarity	NPC39929
0.9786	High Similarity	NPC302181
0.9786	High Similarity	NPC225884
0.9722	High Similarity	NPC170169
0.972	High Similarity	NPC37208
0.972	High Similarity	NPC221868
0.9716	High Similarity	NPC230943
0.9714	High Similarity	NPC53192
0.9653	High Similarity	NPC78335
0.9653	High Similarity	NPC230713
0.965	High Similarity	NPC272194
0.9589	High Similarity	NPC213608
0.9589	High Similarity	NPC122365
0.9589	High Similarity	NPC1477
0.9583	High Similarity	NPC178202
0.9524	High Similarity	NPC148938
0.9524	High Similarity	NPC198490
0.9521	High Similarity	NPC5871
0.9459	High Similarity	NPC247677
0.9459	High Similarity	NPC160015
0.9456	High Similarity	NPC472462
0.9456	High Similarity	NPC235333
0.9456	High Similarity	NPC183874
0.9444	High Similarity	NPC17816
0.9396	High Similarity	NPC212967
0.9396	High Similarity	NPC164110
0.9396	High Similarity	NPC260902
0.9396	High Similarity	NPC65504
0.9396	High Similarity	NPC96342
0.9396	High Similarity	NPC246647
0.9396	High Similarity	NPC296957
0.9392	High Similarity	NPC213936
0.9392	High Similarity	NPC297531
0.9388	High Similarity	NPC207624
0.9388	High Similarity	NPC263676
0.9384	High Similarity	NPC167576
0.9379	High Similarity	NPC168085
0.9371	High Similarity	NPC106985
0.9371	High Similarity	NPC166138
0.9371	High Similarity	NPC17262
0.9371	High Similarity	NPC18585
0.9366	High Similarity	NPC110969
0.9333	High Similarity	NPC40583
0.9333	High Similarity	NPC476350
0.9333	High Similarity	NPC476349
0.9329	High Similarity	NPC180924
0.932	High Similarity	NPC23668
0.932	High Similarity	NPC116604
0.932	High Similarity	NPC106372
0.932	High Similarity	NPC156244
0.932	High Similarity	NPC115324
0.932	High Similarity	NPC193976
0.932	High Similarity	NPC58668
0.9315	High Similarity	NPC317492
0.9306	High Similarity	NPC234629
0.9306	High Similarity	NPC311741
0.9306	High Similarity	NPC155144
0.9306	High Similarity	NPC98926
0.9301	High Similarity	NPC226636
0.9301	High Similarity	NPC144499
0.9301	High Similarity	NPC11561
0.9296	High Similarity	NPC270883
0.9296	High Similarity	NPC28337
0.9296	High Similarity	NPC69769
0.9296	High Similarity	NPC159275
0.9296	High Similarity	NPC241100
0.9296	High Similarity	NPC172986
0.9296	High Similarity	NPC261227
0.9291	High Similarity	NPC21350
0.9291	High Similarity	NPC124269
0.9286	High Similarity	NPC12165
0.9286	High Similarity	NPC98115
0.9286	High Similarity	NPC41461
0.9286	High Similarity	NPC25287
0.9286	High Similarity	NPC477242
0.9286	High Similarity	NPC150399
0.9286	High Similarity	NPC1486
0.9286	High Similarity	NPC274109
0.9286	High Similarity	NPC168105
0.9286	High Similarity	NPC477244
0.9286	High Similarity	NPC66349
0.9286	High Similarity	NPC249606
0.9286	High Similarity	NPC477243
0.9286	High Similarity	NPC186838
0.9272	High Similarity	NPC115432
0.9272	High Similarity	NPC260296
0.9267	High Similarity	NPC268360
0.9257	High Similarity	NPC67654
0.9257	High Similarity	NPC142308
0.9252	High Similarity	NPC472421
0.9241	High Similarity	NPC477955
0.9236	High Similarity	NPC310130
0.9236	High Similarity	NPC164980
0.9236	High Similarity	NPC68104
0.9236	High Similarity	NPC91560
0.9236	High Similarity	NPC75049
0.9236	High Similarity	NPC169591
0.9236	High Similarity	NPC175504
0.9236	High Similarity	NPC143896
0.9236	High Similarity	NPC149026
0.9236	High Similarity	NPC257097
0.9236	High Similarity	NPC39329
0.9236	High Similarity	NPC150408
0.9236	High Similarity	NPC221432
0.9231	High Similarity	NPC147688
0.9231	High Similarity	NPC103362
0.9231	High Similarity	NPC205006
0.9231	High Similarity	NPC3188
0.9231	High Similarity	NPC156590
0.9231	High Similarity	NPC118840
0.9231	High Similarity	NPC64908
0.9231	High Similarity	NPC282300
0.9225	High Similarity	NPC96565
0.9225	High Similarity	NPC18260
0.9225	High Similarity	NPC220062
0.9225	High Similarity	NPC55018
0.9225	High Similarity	NPC301217
0.9225	High Similarity	NPC303633
0.9225	High Similarity	NPC53181
0.9225	High Similarity	NPC217186
0.9225	High Similarity	NPC216978
0.9225	High Similarity	NPC477956
0.9225	High Similarity	NPC78913
0.922	High Similarity	NPC153979
0.922	High Similarity	NPC188879
0.922	High Similarity	NPC62735
0.922	High Similarity	NPC472419
0.922	High Similarity	NPC317119
0.9214	High Similarity	NPC131039
0.9214	High Similarity	NPC13575
0.9214	High Similarity	NPC163029
0.9214	High Similarity	NPC156092
0.9205	High Similarity	NPC244750
0.9195	High Similarity	NPC72370
0.9189	High Similarity	NPC472423
0.9189	High Similarity	NPC474744
0.9189	High Similarity	NPC472580
0.9189	High Similarity	NPC318424
0.9189	High Similarity	NPC474772
0.9178	High Similarity	NPC97716
0.9178	High Similarity	NPC237635
0.9178	High Similarity	NPC79469
0.9178	High Similarity	NPC104406
0.9178	High Similarity	NPC24673
0.9178	High Similarity	NPC201731
0.9172	High Similarity	NPC473013
0.9172	High Similarity	NPC271288
0.9172	High Similarity	NPC216538
0.9172	High Similarity	NPC197252
0.9172	High Similarity	NPC236766
0.9172	High Similarity	NPC473015
0.9172	High Similarity	NPC273538
0.9172	High Similarity	NPC209040
0.9167	High Similarity	NPC166482
0.9167	High Similarity	NPC220998
0.9167	High Similarity	NPC32739
0.9167	High Similarity	NPC265040
0.9167	High Similarity	NPC228504
0.9167	High Similarity	NPC227579
0.9167	High Similarity	NPC324436
0.9167	High Similarity	NPC223500
0.9167	High Similarity	NPC296917
0.9167	High Similarity	NPC64915
0.9167	High Similarity	NPC66515
0.9167	High Similarity	NPC324134
0.9167	High Similarity	NPC182852
0.9167	High Similarity	NPC161506
0.9167	High Similarity	NPC37496
0.9167	High Similarity	NPC107572
0.9167	High Similarity	NPC78
0.9167	High Similarity	NPC76338
0.9167	High Similarity	NPC76372
0.9167	High Similarity	NPC40833
0.9167	High Similarity	NPC166934
0.9167	High Similarity	NPC306829
0.9167	High Similarity	NPC177354
0.9167	High Similarity	NPC10937
0.9167	High Similarity	NPC148757
0.9167	High Similarity	NPC125855
0.9167	High Similarity	NPC167624
0.9167	High Similarity	NPC328164
0.9167	High Similarity	NPC1089
0.9167	High Similarity	NPC194432
0.9161	High Similarity	NPC172250
0.9161	High Similarity	NPC235239
0.9161	High Similarity	NPC150522
0.9161	High Similarity	NPC305355
0.9161	High Similarity	NPC215311
0.9161	High Similarity	NPC80962
0.9161	High Similarity	NPC48624
0.9161	High Similarity	NPC326109
0.9161	High Similarity	NPC11056

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 NPC130581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	986
0.2-0.3	1460
0.3-0.4	2644
0.4-0.5	1919
0.5-0.6	1206
0.6-0.7	386
0.7-0.8	122
0.8-0.85	48
0.85-0.9	22
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9172	High Similarity	NPD4378	Clinical (unspecified phase)
0.9041	High Similarity	NPD7410	Clinical (unspecified phase)
0.8929	High Similarity	NPD1240	Approved
0.8889	High Similarity	NPD1549	Phase 2
0.8828	High Similarity	NPD1243	Approved
0.8819	High Similarity	NPD2344	Approved
0.8819	High Similarity	NPD1550	Clinical (unspecified phase)
0.8819	High Similarity	NPD1552	Clinical (unspecified phase)
0.8811	High Similarity	NPD1510	Phase 2
0.8808	High Similarity	NPD7411	Suspended
0.8803	High Similarity	NPD1607	Approved
0.8766	High Similarity	NPD3749	Approved
0.8758	High Similarity	NPD8443	Clinical (unspecified phase)
0.875	High Similarity	NPD2796	Approved
0.8693	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD920	Approved
0.8649	High Similarity	NPD643	Clinical (unspecified phase)
0.8645	High Similarity	NPD7075	Discontinued
0.8618	High Similarity	NPD4380	Phase 2
0.8581	High Similarity	NPD3882	Suspended
0.8581	High Similarity	NPD7768	Phase 2
0.8581	High Similarity	NPD2309	Approved
0.8571	High Similarity	NPD7096	Clinical (unspecified phase)
0.8571	High Similarity	NPD7819	Suspended
0.8571	High Similarity	NPD2800	Approved
0.8553	High Similarity	NPD7852	Clinical (unspecified phase)
0.8533	High Similarity	NPD642	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6799	Approved
0.8466	Intermediate Similarity	NPD6559	Discontinued
0.8446	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1934	Approved
0.8387	Intermediate Similarity	NPD6801	Discontinued
0.8365	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD2801	Approved
0.8291	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD3750	Approved
0.8261	Intermediate Similarity	NPD3926	Phase 2
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.8243	Intermediate Similarity	NPD1551	Phase 2
0.8243	Intermediate Similarity	NPD2935	Discontinued
0.8239	Intermediate Similarity	NPD919	Approved
0.8235	Intermediate Similarity	NPD1512	Approved
0.8187	Intermediate Similarity	NPD5494	Approved
0.8176	Intermediate Similarity	NPD2799	Discontinued
0.817	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD2532	Approved
0.817	Intermediate Similarity	NPD2533	Approved
0.8163	Intermediate Similarity	NPD6651	Approved
0.8138	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3818	Discontinued
0.8098	Intermediate Similarity	NPD6166	Phase 2
0.8098	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6232	Discontinued
0.8084	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5953	Discontinued
0.8061	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7473	Discontinued
0.7952	Intermediate Similarity	NPD7286	Phase 2
0.7947	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2296	Approved
0.7937	Intermediate Similarity	NPD3817	Phase 2
0.7933	Intermediate Similarity	NPD3748	Approved
0.7917	Intermediate Similarity	NPD1203	Approved
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7888	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7834	Intermediate Similarity	NPD5403	Approved
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1729	Discontinued
0.7798	Intermediate Similarity	NPD7074	Phase 3
0.7792	Intermediate Similarity	NPD4628	Phase 3
0.7785	Intermediate Similarity	NPD943	Approved
0.7784	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7390	Discontinued
0.7755	Intermediate Similarity	NPD4908	Phase 1
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7738	Intermediate Similarity	NPD7054	Approved
0.7736	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD2654	Approved
0.7722	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1471	Phase 3
0.7708	Intermediate Similarity	NPD9717	Approved
0.7707	Intermediate Similarity	NPD5401	Approved
0.7702	Intermediate Similarity	NPD6280	Approved
0.7702	Intermediate Similarity	NPD6279	Approved
0.7701	Intermediate Similarity	NPD4287	Approved
0.7692	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD6100	Approved
0.7647	Intermediate Similarity	NPD6099	Approved
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2798	Approved
0.7607	Intermediate Similarity	NPD5402	Approved
0.7602	Intermediate Similarity	NPD7251	Discontinued
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7584	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4361	Phase 2
0.7582	Intermediate Similarity	NPD7033	Discontinued
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7808	Phase 3
0.7545	Intermediate Similarity	NPD5710	Approved
0.7545	Intermediate Similarity	NPD6808	Phase 2
0.7545	Intermediate Similarity	NPD5711	Approved
0.7545	Intermediate Similarity	NPD7229	Phase 3
0.7533	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD3268	Approved
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD1610	Phase 2
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7467	Intermediate Similarity	NPD4625	Phase 3
0.7466	Intermediate Similarity	NPD3972	Approved
0.7457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7003	Approved
0.7444	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7432	Intermediate Similarity	NPD2797	Approved
0.7432	Intermediate Similarity	NPD1164	Approved
0.743	Intermediate Similarity	NPD4360	Phase 2
0.743	Intermediate Similarity	NPD4363	Phase 3
0.7421	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5406	Approved
0.7419	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD5408	Approved
0.7419	Intermediate Similarity	NPD5404	Approved
0.7407	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1608	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7333	Intermediate Similarity	NPD5760	Phase 2
0.7333	Intermediate Similarity	NPD5761	Phase 2
0.7317	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD411	Approved
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7289	Intermediate Similarity	NPD4288	Approved
0.7288	Intermediate Similarity	NPD8434	Phase 2
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1933	Approved
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7251	Intermediate Similarity	NPD2403	Approved
0.7248	Intermediate Similarity	NPD1876	Approved
0.7248	Intermediate Similarity	NPD3225	Approved
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4307	Phase 2
0.7202	Intermediate Similarity	NPD6971	Discontinued
0.72	Intermediate Similarity	NPD1470	Approved
0.72	Intermediate Similarity	NPD6104	Discontinued
0.72	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3266	Approved
0.72	Intermediate Similarity	NPD3267	Approved
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6798	Discontinued
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7171	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7177	Discontinued
0.7162	Intermediate Similarity	NPD1201	Approved
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8313	Approved
0.7119	Intermediate Similarity	NPD8312	Approved
0.7117	Intermediate Similarity	NPD5049	Phase 3
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5889	Approved
0.7108	Intermediate Similarity	NPD5890	Approved
0.7107	Intermediate Similarity	NPD2424	Discontinued
0.7105	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1613	Approved
0.709	Intermediate Similarity	NPD7584	Approved
0.7089	Intermediate Similarity	NPD4477	Approved
0.7089	Intermediate Similarity	NPD4476	Approved
0.7081	Intermediate Similarity	NPD2354	Approved
0.7075	Intermediate Similarity	NPD1651	Approved
0.7075	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7067	Intermediate Similarity	NPD4749	Approved
0.7055	Intermediate Similarity	NPD4661	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