NPASS Compound

Structure

NPC472636 OpenBabel07101718182D 31 34 0 0 1 0 0 0 0 0999 V2000 -6.9049 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9049 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9049 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4049 0.7321 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9049 -0.1340 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 2.5981 -0.5000 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 -6.4049 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 3 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4049 -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 -1.8171 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 17 1 0 0 0 0 11 22 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 15 19 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 23 1 0 0 0 0 18 27 2 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 23 2 0 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 0 0 0 0 23 24 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.19
Volume:	438.38
LogP:	5.254
LogD:	3.491
LogS:	-3.745
# Rotatable Bonds:	5
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.607
Synthetic Accessibility Score:	4.03
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.799
MDCK Permeability:	1.2737814358843025e-05
Pgp-inhibitor:	0.229
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.369

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	98.93798065185547%
Volume Distribution (VD):	0.596
Pgp-substrate:	2.9342241287231445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.201
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.904
CYP2C19-substrate:	0.342
CYP2C9-inhibitor:	0.898
CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.562
CYP3A4-inhibitor:	0.574
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	16.982
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.569
Drug-inuced Liver Injury (DILI):	0.429
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.751
Carcinogencity:	0.217
Eye Corrosion:	0.003
Eye Irritation:	0.276
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC472636

Natural Product ID:	NPC472636
*Common Name:**	WTGUNSGYPQJOLT-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WTGUNSGYPQJOLT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H28O6/c1-14(2)5-4-10-25(3,29)22-11-17-20(31-22)13-21-23(24(17)28)18(27)12-19(30-21)15-6-8-16(26)9-7-15/h5-9,13,19,22,26,28-29H,4,10-12H2,1-3H3
SMILES:	CC(=CCCC(C1Cc2c(O1)cc1c(c2O)C(=O)CC(O1)c1ccc(cc1)O)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581359
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[541317]

☑ 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 NPC472636 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	375
0.1-0.2	1439
0.2-0.3	3483
0.3-0.4	8755
0.4-0.5	9835
0.5-0.6	3579
0.6-0.7	5247
0.7-0.8	5589
0.8-0.85	2566
0.85-0.9	1242
0.9-0.95	513
0.95-1	74

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC473996
0.9862	High Similarity	NPC471675
0.9862	High Similarity	NPC472580
0.9795	High Similarity	NPC476238
0.9795	High Similarity	NPC327269
0.9795	High Similarity	NPC31627
0.9795	High Similarity	NPC477957
0.9793	High Similarity	NPC472421
0.9726	High Similarity	NPC263384
0.9726	High Similarity	NPC472420
0.9726	High Similarity	NPC472423
0.9726	High Similarity	NPC472422
0.9726	High Similarity	NPC471677
0.9726	High Similarity	NPC474744
0.9726	High Similarity	NPC471676
0.9726	High Similarity	NPC244577
0.9726	High Similarity	NPC474772
0.966	High Similarity	NPC285623
0.966	High Similarity	NPC475790
0.9595	High Similarity	NPC472583
0.9595	High Similarity	NPC223701
0.9595	High Similarity	NPC7989
0.9592	High Similarity	NPC262038
0.9592	High Similarity	NPC254412
0.9592	High Similarity	NPC319910
0.9592	High Similarity	NPC278476
0.9592	High Similarity	NPC474023
0.9592	High Similarity	NPC474021
0.9592	High Similarity	NPC262039
0.9589	High Similarity	NPC472628
0.9586	High Similarity	NPC14875
0.9586	High Similarity	NPC472627
0.9536	High Similarity	NPC472624
0.953	High Similarity	NPC108937
0.953	High Similarity	NPC304207
0.953	High Similarity	NPC279218
0.953	High Similarity	NPC259710
0.953	High Similarity	NPC207809
0.953	High Similarity	NPC217706
0.953	High Similarity	NPC48579
0.953	High Similarity	NPC477958
0.9527	High Similarity	NPC35567
0.9527	High Similarity	NPC217149
0.9527	High Similarity	NPC161881
0.9527	High Similarity	NPC150123
0.9527	High Similarity	NPC216035
0.9527	High Similarity	NPC10807
0.9527	High Similarity	NPC243171
0.9527	High Similarity	NPC138288
0.9527	High Similarity	NPC56232
0.9527	High Similarity	NPC244583
0.9527	High Similarity	NPC171651
0.9527	High Similarity	NPC210597
0.9524	High Similarity	NPC105136
0.9521	High Similarity	NPC168085
0.9517	High Similarity	NPC472629
0.9514	High Similarity	NPC316816
0.9514	High Similarity	NPC478086
0.9514	High Similarity	NPC214166
0.9467	High Similarity	NPC109967
0.9467	High Similarity	NPC215917
0.9467	High Similarity	NPC474609
0.9467	High Similarity	NPC469936
0.9467	High Similarity	NPC20530
0.9467	High Similarity	NPC129053
0.9467	High Similarity	NPC78554
0.9467	High Similarity	NPC475797
0.9467	High Similarity	NPC474738
0.9467	High Similarity	NPC321372
0.9467	High Similarity	NPC10754
0.9463	High Similarity	NPC293286
0.9463	High Similarity	NPC311579
0.9463	High Similarity	NPC180301
0.9463	High Similarity	NPC236756
0.9463	High Similarity	NPC248793
0.9463	High Similarity	NPC100134
0.9463	High Similarity	NPC469405
0.9463	High Similarity	NPC209760
0.9459	High Similarity	NPC289774
0.9459	High Similarity	NPC209846
0.9459	High Similarity	NPC328740
0.9459	High Similarity	NPC477897
0.9456	High Similarity	NPC89442
0.9456	High Similarity	NPC317492
0.9452	High Similarity	NPC473077
0.9452	High Similarity	NPC296998
0.9452	High Similarity	NPC470670
0.9452	High Similarity	NPC47388
0.9452	High Similarity	NPC473133
0.9452	High Similarity	NPC472918
0.9452	High Similarity	NPC202494
0.9452	High Similarity	NPC85773
0.9452	High Similarity	NPC91902
0.9448	High Similarity	NPC470890
0.9448	High Similarity	NPC87486
0.9448	High Similarity	NPC131568
0.9448	High Similarity	NPC209040
0.9448	High Similarity	NPC131579
0.9448	High Similarity	NPC124780
0.9444	High Similarity	NPC66515
0.9444	High Similarity	NPC306829
0.9444	High Similarity	NPC32739
0.9444	High Similarity	NPC76372
0.9444	High Similarity	NPC166934
0.9444	High Similarity	NPC107572
0.9444	High Similarity	NPC324134
0.9444	High Similarity	NPC296917
0.9444	High Similarity	NPC324436
0.9444	High Similarity	NPC194432
0.9444	High Similarity	NPC265040
0.9444	High Similarity	NPC37496
0.9444	High Similarity	NPC177354
0.9444	High Similarity	NPC167624
0.9444	High Similarity	NPC227579
0.9444	High Similarity	NPC228504
0.9444	High Similarity	NPC220998
0.9444	High Similarity	NPC78
0.9444	High Similarity	NPC166482
0.9444	High Similarity	NPC223500
0.9444	High Similarity	NPC76338
0.9444	High Similarity	NPC161506
0.9444	High Similarity	NPC10937
0.9444	High Similarity	NPC40833
0.9444	High Similarity	NPC64915
0.9444	High Similarity	NPC328164
0.9444	High Similarity	NPC182852
0.9444	High Similarity	NPC1089
0.9444	High Similarity	NPC125855
0.9444	High Similarity	NPC148757
0.9412	High Similarity	NPC472635
0.9408	High Similarity	NPC328102
0.9404	High Similarity	NPC27337
0.94	High Similarity	NPC304745
0.94	High Similarity	NPC111341
0.94	High Similarity	NPC470681
0.94	High Similarity	NPC476169
0.94	High Similarity	NPC471116
0.9392	High Similarity	NPC476185
0.9392	High Similarity	NPC321896
0.9392	High Similarity	NPC472633
0.9388	High Similarity	NPC10097
0.9384	High Similarity	NPC67805
0.9384	High Similarity	NPC176229
0.9384	High Similarity	NPC316769
0.9384	High Similarity	NPC187282
0.9384	High Similarity	NPC195621
0.9384	High Similarity	NPC214774
0.9384	High Similarity	NPC290133
0.9384	High Similarity	NPC474302
0.9384	High Similarity	NPC285630
0.9384	High Similarity	NPC142405
0.9384	High Similarity	NPC312973
0.9384	High Similarity	NPC267375
0.9384	High Similarity	NPC475052
0.9384	High Similarity	NPC246948
0.9384	High Similarity	NPC88964
0.9384	High Similarity	NPC83357
0.9384	High Similarity	NPC470647
0.9384	High Similarity	NPC127059
0.9384	High Similarity	NPC301276
0.9384	High Similarity	NPC54577
0.9384	High Similarity	NPC111786
0.9384	High Similarity	NPC20488
0.9384	High Similarity	NPC24136
0.9379	High Similarity	NPC149026
0.9379	High Similarity	NPC310130
0.9379	High Similarity	NPC257097
0.9379	High Similarity	NPC81697
0.9379	High Similarity	NPC85162
0.9379	High Similarity	NPC106985
0.9379	High Similarity	NPC150408
0.9379	High Similarity	NPC68104
0.9379	High Similarity	NPC278249
0.9379	High Similarity	NPC143896
0.9379	High Similarity	NPC166138
0.9379	High Similarity	NPC75049
0.9379	High Similarity	NPC185276
0.9379	High Similarity	NPC18585
0.9379	High Similarity	NPC91560
0.9379	High Similarity	NPC221432
0.9379	High Similarity	NPC175504
0.9379	High Similarity	NPC125894
0.9379	High Similarity	NPC107177
0.9379	High Similarity	NPC223812
0.9379	High Similarity	NPC164980
0.9379	High Similarity	NPC39329
0.9379	High Similarity	NPC169591
0.9379	High Similarity	NPC77794
0.9375	High Similarity	NPC96408
0.9375	High Similarity	NPC4743
0.9375	High Similarity	NPC258630
0.9375	High Similarity	NPC17170
0.9375	High Similarity	NPC156190
0.9375	High Similarity	NPC74397
0.9375	High Similarity	NPC279650
0.9375	High Similarity	NPC248372
0.9375	High Similarity	NPC312391
0.9375	High Similarity	NPC213322
0.9375	High Similarity	NPC110038
0.9375	High Similarity	NPC166689

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 NPC472636 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	861
0.2-0.3	1598
0.3-0.4	2589
0.4-0.5	1947
0.5-0.6	1145
0.6-0.7	477
0.7-0.8	160
0.8-0.85	32
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD2393	Clinical (unspecified phase)
0.9262	High Similarity	NPD4380	Phase 2
0.9184	High Similarity	NPD4378	Clinical (unspecified phase)
0.915	High Similarity	NPD7075	Discontinued
0.9139	High Similarity	NPD1934	Approved
0.9097	High Similarity	NPD1552	Clinical (unspecified phase)
0.9097	High Similarity	NPD1550	Clinical (unspecified phase)
0.9079	High Similarity	NPD7096	Clinical (unspecified phase)
0.9034	High Similarity	NPD1549	Phase 2
0.8903	High Similarity	NPD4381	Clinical (unspecified phase)
0.8896	High Similarity	NPD8443	Clinical (unspecified phase)
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8767	High Similarity	NPD2796	Approved
0.8766	High Similarity	NPD6801	Discontinued
0.8758	High Similarity	NPD7804	Clinical (unspecified phase)
0.8718	High Similarity	NPD3882	Suspended
0.871	High Similarity	NPD2801	Approved
0.8701	High Similarity	NPD7411	Suspended
0.8699	High Similarity	NPD1510	Phase 2
0.8688	High Similarity	NPD6168	Clinical (unspecified phase)
0.8688	High Similarity	NPD6166	Phase 2
0.8688	High Similarity	NPD6167	Clinical (unspecified phase)
0.8671	High Similarity	NPD5494	Approved
0.8609	High Similarity	NPD6799	Approved
0.8609	High Similarity	NPD1511	Approved
0.8598	High Similarity	NPD6559	Discontinued
0.859	High Similarity	NPD7819	Suspended
0.858	High Similarity	NPD3818	Discontinued
0.8552	High Similarity	NPD1240	Approved
0.85	High Similarity	NPD6959	Discontinued
0.8497	Intermediate Similarity	NPD1512	Approved
0.8476	Intermediate Similarity	NPD7074	Phase 3
0.8467	Intermediate Similarity	NPD2800	Approved
0.8435	Intermediate Similarity	NPD1607	Approved
0.8418	Intermediate Similarity	NPD3817	Phase 2
0.8415	Intermediate Similarity	NPD7054	Approved
0.8397	Intermediate Similarity	NPD6599	Discontinued
0.8365	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8313	Intermediate Similarity	NPD3749	Approved
0.8263	Intermediate Similarity	NPD7251	Discontinued
0.825	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7808	Phase 3
0.8205	Intermediate Similarity	NPD920	Approved
0.8205	Intermediate Similarity	NPD5403	Approved
0.8194	Intermediate Similarity	NPD2532	Approved
0.8194	Intermediate Similarity	NPD2533	Approved
0.8194	Intermediate Similarity	NPD2534	Approved
0.811	Intermediate Similarity	NPD6232	Discontinued
0.8107	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1243	Approved
0.8084	Intermediate Similarity	NPD5844	Phase 1
0.8077	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5401	Approved
0.8075	Intermediate Similarity	NPD5402	Approved
0.8072	Intermediate Similarity	NPD7473	Discontinued
0.8065	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD4628	Phase 3
0.8052	Intermediate Similarity	NPD3750	Approved
0.8041	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.8026	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD2344	Approved
0.7947	Intermediate Similarity	NPD6651	Approved
0.7939	Intermediate Similarity	NPD1247	Approved
0.7927	Intermediate Similarity	NPD919	Approved
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD5953	Discontinued
0.7882	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7286	Phase 2
0.7843	Intermediate Similarity	NPD7033	Discontinued
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.7815	Intermediate Similarity	NPD1613	Approved
0.7815	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2424	Discontinued
0.78	Intermediate Similarity	NPD2313	Discontinued
0.7793	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7785	Intermediate Similarity	NPD4908	Phase 1
0.7771	Intermediate Similarity	NPD2309	Approved
0.7753	Intermediate Similarity	NPD4360	Phase 2
0.7753	Intermediate Similarity	NPD4363	Phase 3
0.774	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3926	Phase 2
0.7727	Intermediate Similarity	NPD3748	Approved
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD943	Approved
0.7683	Intermediate Similarity	NPD1465	Phase 2
0.7679	Intermediate Similarity	NPD5710	Approved
0.7679	Intermediate Similarity	NPD5711	Approved
0.7676	Intermediate Similarity	NPD7584	Approved
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.7669	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD5124	Phase 1
0.7647	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7614	Intermediate Similarity	NPD8434	Phase 2
0.7613	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4361	Phase 2
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.76	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1203	Approved
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7566	Intermediate Similarity	NPD6798	Discontinued
0.7562	Intermediate Similarity	NPD7390	Discontinued
0.755	Intermediate Similarity	NPD6832	Phase 2
0.7543	Intermediate Similarity	NPD8313	Approved
0.7543	Intermediate Similarity	NPD8312	Approved
0.7532	Intermediate Similarity	NPD2654	Approved
0.7532	Intermediate Similarity	NPD6355	Discontinued
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7514	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7485	Intermediate Similarity	NPD2403	Approved
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.7471	Intermediate Similarity	NPD3823	Discontinued
0.747	Intermediate Similarity	NPD8455	Phase 2
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3268	Approved
0.7446	Intermediate Similarity	NPD6777	Approved
0.7446	Intermediate Similarity	NPD6780	Approved
0.7446	Intermediate Similarity	NPD6778	Approved
0.7446	Intermediate Similarity	NPD6782	Approved
0.7446	Intermediate Similarity	NPD6781	Approved
0.7446	Intermediate Similarity	NPD6776	Approved
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6779	Approved
0.7439	Intermediate Similarity	NPD7458	Discontinued
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1652	Phase 2
0.7419	Intermediate Similarity	NPD1933	Approved
0.7419	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD2798	Approved
0.741	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6233	Phase 2
0.7389	Intermediate Similarity	NPD4308	Phase 3
0.7383	Intermediate Similarity	NPD9717	Approved
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7365	Intermediate Similarity	NPD5760	Phase 2
0.7365	Intermediate Similarity	NPD5761	Phase 2
0.7351	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD3764	Approved
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4287	Approved
0.7326	Intermediate Similarity	NPD7435	Discontinued
0.7318	Intermediate Similarity	NPD8150	Discontinued
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD447	Suspended
0.7301	Intermediate Similarity	NPD4662	Approved
0.7301	Intermediate Similarity	NPD4661	Approved
0.7299	Intermediate Similarity	NPD7228	Approved
0.7299	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6002	Phase 3
0.7296	Intermediate Similarity	NPD6005	Phase 3
0.7296	Intermediate Similarity	NPD6004	Phase 3
0.7296	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5058	Phase 3
0.7278	Intermediate Similarity	NPD5588	Approved
0.7263	Intermediate Similarity	NPD7585	Approved
0.7256	Intermediate Similarity	NPD5049	Phase 3
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.724	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7783	Phase 2
0.7234	Intermediate Similarity	NPD7697	Approved
0.7234	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD7696	Phase 3
0.7226	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8151	Discontinued
0.7222	Intermediate Similarity	NPD3887	Approved
0.7222	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD2354	Approved
0.7219	Intermediate Similarity	NPD4749	Approved
0.7219	Intermediate Similarity	NPD2296	Approved
0.7215	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4536	Approved
0.7215	Intermediate Similarity	NPD4538	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