NPASS Compound

Structure

NPC472629 OpenBabel07101718292D 31 33 0 0 1 0 0 0 0 0999 V2000 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -0.5000 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 -1.7321 -0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -2.5981 -0.5000 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 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 1 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 -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 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1.7321 -2.0000 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 15 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 16 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 12 23 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 15 19 1 0 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 25 2 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 24 1 0 0 0 0 21 29 2 0 0 0 0 22 16 1 1 0 0 0 22 31 1 0 0 0 0 23 24 2 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.19
Volume:	444.3
LogP:	4.866
LogD:	3.364
LogS:	-3.563
# Rotatable Bonds:	7
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	3.834
Fsp3:	0.32
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:	-4.91
MDCK Permeability:	1.085013627744047e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.327
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	96.69300079345703%
Volume Distribution (VD):	0.966
Pgp-substrate:	1.7261013984680176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.226
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.689
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.352
CYP3A4-substrate:	0.196

ADMET: Excretion

Clearance (CL):	14.376
Half-life (T1/2):	0.252

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.715
Drug-inuced Liver Injury (DILI):	0.741
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.772
Maximum Recommended Daily Dose:	0.465
Skin Sensitization:	0.774
Carcinogencity:	0.441
Eye Corrosion:	0.003
Eye Irritation:	0.796
Respiratory Toxicity:	0.853

Download Data

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

Natural Product: NPC472629

Natural Product ID:	NPC472629
*Common Name:**	GPHIDEIQYPAQLK-BPARTEKVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GPHIDEIQYPAQLK-BPARTEKVSA-N
Standard InCHI:	InChI=1S/C25H28O6/c1-14(2)5-4-6-15(3)19(27)11-18-20(28)12-23-24(25(18)30)21(29)13-22(31-23)16-7-9-17(26)10-8-16/h5,7-10,12,19,22,26-28,30H,3-4,6,11,13H2,1-2H3/t19?,22-/m0/s1
SMILES:	CC(=CCCC(=C)C(Cc1c(O)cc2c(c1O)C(=O)C[C@H](O2)c1ccc(cc1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581349
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	>	11400.0	nM	PMID[509818]

☑ 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 NPC472629 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	362
0.1-0.2	1410
0.2-0.3	3520
0.3-0.4	8641
0.4-0.5	9995
0.5-0.6	3472
0.6-0.7	5311
0.7-0.8	5397
0.8-0.85	2370
0.85-0.9	1369
0.9-0.95	657
0.95-1	193

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC470890
0.9928	High Similarity	NPC124780
0.9928	High Similarity	NPC87486
0.9786	High Similarity	NPC224714
0.9784	High Similarity	NPC125855
0.9784	High Similarity	NPC107572
0.9784	High Similarity	NPC220998
0.9784	High Similarity	NPC265040
0.9784	High Similarity	NPC227579
0.9784	High Similarity	NPC10937
0.9784	High Similarity	NPC324436
0.9784	High Similarity	NPC223500
0.9784	High Similarity	NPC40833
0.9784	High Similarity	NPC167624
0.9784	High Similarity	NPC1089
0.9784	High Similarity	NPC76372
0.9784	High Similarity	NPC161506
0.9784	High Similarity	NPC78
0.9784	High Similarity	NPC66515
0.9784	High Similarity	NPC166482
0.9784	High Similarity	NPC194432
0.9784	High Similarity	NPC32739
0.9784	High Similarity	NPC328164
0.9784	High Similarity	NPC64915
0.9784	High Similarity	NPC148757
0.9784	High Similarity	NPC324134
0.9784	High Similarity	NPC228504
0.9784	High Similarity	NPC182852
0.9784	High Similarity	NPC296917
0.9784	High Similarity	NPC37496
0.9784	High Similarity	NPC166934
0.9784	High Similarity	NPC177354
0.9784	High Similarity	NPC76338
0.9784	High Similarity	NPC306829
0.9716	High Similarity	NPC24136
0.9716	High Similarity	NPC187282
0.9716	High Similarity	NPC290133
0.9714	High Similarity	NPC68104
0.9714	High Similarity	NPC164980
0.9714	High Similarity	NPC185276
0.9714	High Similarity	NPC75049
0.9714	High Similarity	NPC257097
0.9714	High Similarity	NPC278249
0.9714	High Similarity	NPC107177
0.9714	High Similarity	NPC149026
0.9714	High Similarity	NPC221432
0.9714	High Similarity	NPC214166
0.9714	High Similarity	NPC77794
0.9714	High Similarity	NPC169591
0.9714	High Similarity	NPC39329
0.9714	High Similarity	NPC125894
0.9714	High Similarity	NPC91560
0.9714	High Similarity	NPC143896
0.9714	High Similarity	NPC223812
0.9714	High Similarity	NPC175504
0.9714	High Similarity	NPC85162
0.9714	High Similarity	NPC316816
0.9714	High Similarity	NPC310130
0.9714	High Similarity	NPC478086
0.9714	High Similarity	NPC150408
0.9714	High Similarity	NPC81697
0.9712	High Similarity	NPC258630
0.9712	High Similarity	NPC213322
0.9712	High Similarity	NPC17170
0.9712	High Similarity	NPC110038
0.9712	High Similarity	NPC156190
0.9712	High Similarity	NPC324386
0.9712	High Similarity	NPC4743
0.9712	High Similarity	NPC166689
0.9712	High Similarity	NPC312391
0.9712	High Similarity	NPC96408
0.9712	High Similarity	NPC279650
0.9712	High Similarity	NPC248372
0.9653	High Similarity	NPC472422
0.9653	High Similarity	NPC471677
0.9653	High Similarity	NPC263384
0.9653	High Similarity	NPC319910
0.9653	High Similarity	NPC254412
0.9653	High Similarity	NPC471676
0.9653	High Similarity	NPC262038
0.9653	High Similarity	NPC244577
0.9653	High Similarity	NPC262039
0.9653	High Similarity	NPC278476
0.9653	High Similarity	NPC472420
0.965	High Similarity	NPC5173
0.9648	High Similarity	NPC296998
0.9648	High Similarity	NPC473077
0.9648	High Similarity	NPC300988
0.9648	High Similarity	NPC308200
0.9648	High Similarity	NPC472627
0.9648	High Similarity	NPC10990
0.9645	High Similarity	NPC473013
0.9645	High Similarity	NPC197252
0.9645	High Similarity	NPC235217
0.9645	High Similarity	NPC473014
0.9645	High Similarity	NPC209040
0.9645	High Similarity	NPC473015
0.9645	High Similarity	NPC131568
0.9645	High Similarity	NPC236766
0.9645	High Similarity	NPC131579
0.9645	High Similarity	NPC271288
0.964	High Similarity	NPC6407
0.964	High Similarity	NPC110228
0.964	High Similarity	NPC188243
0.9586	High Similarity	NPC171651
0.9586	High Similarity	NPC35567
0.9586	High Similarity	NPC216035
0.9586	High Similarity	NPC217149
0.9586	High Similarity	NPC138288
0.9586	High Similarity	NPC10807
0.9586	High Similarity	NPC150123
0.9586	High Similarity	NPC475790
0.9586	High Similarity	NPC244583
0.9586	High Similarity	NPC243171
0.9586	High Similarity	NPC161881
0.9586	High Similarity	NPC56232
0.9583	High Similarity	NPC61258
0.9583	High Similarity	NPC37348
0.9583	High Similarity	NPC105136
0.9583	High Similarity	NPC472633
0.958	High Similarity	NPC168085
0.958	High Similarity	NPC145467
0.958	High Similarity	NPC39195
0.9577	High Similarity	NPC470132
0.9577	High Similarity	NPC312973
0.9577	High Similarity	NPC267375
0.9577	High Similarity	NPC88964
0.9577	High Similarity	NPC285630
0.9577	High Similarity	NPC470647
0.9577	High Similarity	NPC470133
0.9577	High Similarity	NPC475052
0.9577	High Similarity	NPC127059
0.9577	High Similarity	NPC470131
0.9577	High Similarity	NPC111786
0.9577	High Similarity	NPC67805
0.9577	High Similarity	NPC473078
0.9577	High Similarity	NPC195621
0.9577	High Similarity	NPC54577
0.9577	High Similarity	NPC83357
0.9577	High Similarity	NPC109183
0.9577	High Similarity	NPC246948
0.9577	High Similarity	NPC142405
0.9577	High Similarity	NPC214774
0.9577	High Similarity	NPC301276
0.9577	High Similarity	NPC470134
0.9577	High Similarity	NPC176229
0.9577	High Similarity	NPC20488
0.9574	High Similarity	NPC106985
0.9574	High Similarity	NPC471621
0.9574	High Similarity	NPC166138
0.9574	High Similarity	NPC51887
0.9574	High Similarity	NPC475705
0.9574	High Similarity	NPC117836
0.9574	High Similarity	NPC476178
0.9574	High Similarity	NPC18585
0.9571	High Similarity	NPC470087
0.9571	High Similarity	NPC3188
0.9571	High Similarity	NPC321980
0.9568	High Similarity	NPC265871
0.9568	High Similarity	NPC150648
0.9568	High Similarity	NPC310135
0.9568	High Similarity	NPC225153
0.9568	High Similarity	NPC20709
0.9568	High Similarity	NPC222342
0.9568	High Similarity	NPC140890
0.9568	High Similarity	NPC329203
0.9568	High Similarity	NPC274784
0.9521	High Similarity	NPC223701
0.9521	High Similarity	NPC293286
0.9521	High Similarity	NPC7989
0.9521	High Similarity	NPC472583
0.9517	High Similarity	NPC474023
0.9517	High Similarity	NPC289774
0.9517	High Similarity	NPC472636
0.9517	High Similarity	NPC328740
0.9517	High Similarity	NPC209846
0.9517	High Similarity	NPC474021
0.9517	High Similarity	NPC477897
0.9514	High Similarity	NPC317492
0.9514	High Similarity	NPC471114
0.9514	High Similarity	NPC472628
0.9514	High Similarity	NPC473016
0.9514	High Similarity	NPC89442
0.9514	High Similarity	NPC470461
0.951	High Similarity	NPC23728
0.951	High Similarity	NPC110303
0.951	High Similarity	NPC283234
0.9507	High Similarity	NPC273538
0.9507	High Similarity	NPC311144
0.9507	High Similarity	NPC319752
0.9507	High Similarity	NPC216538
0.9507	High Similarity	NPC470136
0.9507	High Similarity	NPC470135
0.9507	High Similarity	NPC39045
0.9504	High Similarity	NPC73028
0.9504	High Similarity	NPC147145
0.9504	High Similarity	NPC144499
0.95	High Similarity	NPC76445
0.95	High Similarity	NPC129853
0.95	High Similarity	NPC284550

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 NPC472629 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	882
0.2-0.3	1541
0.3-0.4	2522
0.4-0.5	1961
0.5-0.6	1164
0.6-0.7	512
0.7-0.8	173
0.8-0.85	38
0.85-0.9	21
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9507	High Similarity	NPD4378	Clinical (unspecified phase)
0.9424	High Similarity	NPD1552	Clinical (unspecified phase)
0.9424	High Similarity	NPD1550	Clinical (unspecified phase)
0.9388	High Similarity	NPD2393	Clinical (unspecified phase)
0.9357	High Similarity	NPD1549	Phase 2
0.9315	High Similarity	NPD4380	Phase 2
0.9195	High Similarity	NPD8443	Clinical (unspecified phase)
0.9078	High Similarity	NPD2796	Approved
0.9073	High Similarity	NPD7075	Discontinued
0.906	High Similarity	NPD1934	Approved
0.9007	High Similarity	NPD1510	Phase 2
0.9	High Similarity	NPD7096	Clinical (unspecified phase)
0.8993	High Similarity	NPD7411	Suspended
0.8973	High Similarity	NPD7410	Clinical (unspecified phase)
0.8947	High Similarity	NPD4381	Clinical (unspecified phase)
0.8874	High Similarity	NPD7819	Suspended
0.8857	High Similarity	NPD1240	Approved
0.8808	High Similarity	NPD6801	Discontinued
0.8797	High Similarity	NPD7804	Clinical (unspecified phase)
0.8774	High Similarity	NPD6959	Discontinued
0.8732	High Similarity	NPD1607	Approved
0.8726	High Similarity	NPD6166	Phase 2
0.8726	High Similarity	NPD6167	Clinical (unspecified phase)
0.8726	High Similarity	NPD6168	Clinical (unspecified phase)
0.8649	High Similarity	NPD1511	Approved
0.8627	High Similarity	NPD2801	Approved
0.8608	High Similarity	NPD7852	Clinical (unspecified phase)
0.8533	High Similarity	NPD1512	Approved
0.8523	High Similarity	NPD6799	Approved
0.8516	High Similarity	NPD7768	Phase 2
0.8509	High Similarity	NPD7074	Phase 3
0.8503	High Similarity	NPD7421	Clinical (unspecified phase)
0.8503	High Similarity	NPD2800	Approved
0.8471	Intermediate Similarity	NPD5494	Approved
0.8447	Intermediate Similarity	NPD7054	Approved
0.8405	Intermediate Similarity	NPD6559	Discontinued
0.8397	Intermediate Similarity	NPD3882	Suspended
0.8395	Intermediate Similarity	NPD7472	Approved
0.8385	Intermediate Similarity	NPD3818	Discontinued
0.8344	Intermediate Similarity	NPD6797	Phase 2
0.8333	Intermediate Similarity	NPD3817	Phase 2
0.8322	Intermediate Similarity	NPD3750	Approved
0.8322	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD6599	Discontinued
0.8299	Intermediate Similarity	NPD1551	Phase 2
0.8299	Intermediate Similarity	NPD2935	Discontinued
0.8293	Intermediate Similarity	NPD7251	Discontinued
0.828	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7808	Phase 3
0.8242	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5403	Approved
0.8235	Intermediate Similarity	NPD920	Approved
0.8228	Intermediate Similarity	NPD3749	Approved
0.8224	Intermediate Similarity	NPD2534	Approved
0.8224	Intermediate Similarity	NPD2533	Approved
0.8224	Intermediate Similarity	NPD2532	Approved
0.8221	Intermediate Similarity	NPD5844	Phase 1
0.8219	Intermediate Similarity	NPD6651	Approved
0.8194	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6232	Discontinued
0.8133	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1243	Approved
0.8121	Intermediate Similarity	NPD5953	Discontinued
0.811	Intermediate Similarity	NPD7286	Phase 2
0.8108	Intermediate Similarity	NPD2799	Discontinued
0.8105	Intermediate Similarity	NPD5401	Approved
0.8105	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5402	Approved
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8092	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD4360	Phase 2
0.8081	Intermediate Similarity	NPD4363	Phase 3
0.8079	Intermediate Similarity	NPD4628	Phase 3
0.8079	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD2313	Discontinued
0.8056	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD2344	Approved
0.7987	Intermediate Similarity	NPD7033	Discontinued
0.7987	Intermediate Similarity	NPD3748	Approved
0.7943	Intermediate Similarity	NPD1610	Phase 2
0.7933	Intermediate Similarity	NPD6100	Approved
0.7933	Intermediate Similarity	NPD6099	Approved
0.7911	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5124	Phase 1
0.7904	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3226	Approved
0.7881	Intermediate Similarity	NPD2346	Discontinued
0.7867	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1203	Approved
0.7838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1613	Approved
0.7808	Intermediate Similarity	NPD6832	Phase 2
0.7806	Intermediate Similarity	NPD7390	Discontinued
0.7792	Intermediate Similarity	NPD2309	Approved
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7756	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1247	Approved
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4361	Phase 2
0.7718	Intermediate Similarity	NPD943	Approved
0.7703	Intermediate Similarity	NPD3268	Approved
0.7697	Intermediate Similarity	NPD5711	Approved
0.7697	Intermediate Similarity	NPD5710	Approved
0.7684	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2798	Approved
0.7657	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD9717	Approved
0.7635	Intermediate Similarity	NPD4625	Phase 3
0.7603	Intermediate Similarity	NPD2797	Approved
0.7597	Intermediate Similarity	NPD2424	Discontinued
0.7596	Intermediate Similarity	NPD7584	Approved
0.7593	Intermediate Similarity	NPD1465	Phase 2
0.7569	Intermediate Similarity	NPD422	Phase 1
0.7568	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD8312	Approved
0.7558	Intermediate Similarity	NPD8313	Approved
0.755	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2654	Approved
0.7545	Intermediate Similarity	NPD3926	Phase 2
0.7531	Intermediate Similarity	NPD6844	Discontinued
0.7529	Intermediate Similarity	NPD1729	Discontinued
0.7517	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD4308	Phase 3
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7485	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7467	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6798	Discontinued
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1652	Phase 2
0.7434	Intermediate Similarity	NPD230	Phase 1
0.7434	Intermediate Similarity	NPD1933	Approved
0.7419	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6005	Phase 3
0.7419	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6002	Phase 3
0.7419	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6004	Phase 3
0.7415	Intermediate Similarity	NPD3225	Approved
0.7413	Intermediate Similarity	NPD9545	Approved
0.7397	Intermediate Similarity	NPD3972	Approved
0.7397	Intermediate Similarity	NPD1608	Approved
0.7384	Intermediate Similarity	NPD3823	Discontinued
0.7378	Intermediate Similarity	NPD5761	Phase 2
0.7378	Intermediate Similarity	NPD5760	Phase 2
0.7365	Intermediate Similarity	NPD3266	Approved
0.7365	Intermediate Similarity	NPD3267	Approved
0.7363	Intermediate Similarity	NPD6780	Approved
0.7363	Intermediate Similarity	NPD6776	Approved
0.7363	Intermediate Similarity	NPD6778	Approved
0.7363	Intermediate Similarity	NPD6777	Approved
0.7363	Intermediate Similarity	NPD6781	Approved
0.7363	Intermediate Similarity	NPD6782	Approved
0.7363	Intermediate Similarity	NPD6779	Approved
0.7362	Intermediate Similarity	NPD5890	Approved
0.7362	Intermediate Similarity	NPD5889	Approved
0.7347	Intermediate Similarity	NPD4749	Approved
0.7341	Intermediate Similarity	NPD6104	Discontinued
0.7333	Intermediate Similarity	NPD4288	Approved
0.733	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1201	Approved
0.7325	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD37	Approved
0.7315	Intermediate Similarity	NPD1019	Discontinued
0.7312	Intermediate Similarity	NPD4661	Approved
0.7312	Intermediate Similarity	NPD4662	Approved
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1241	Discontinued
0.7303	Intermediate Similarity	NPD6233	Phase 2
0.7289	Intermediate Similarity	NPD4965	Approved
0.7289	Intermediate Similarity	NPD4967	Phase 2
0.7289	Intermediate Similarity	NPD4966	Approved
0.7278	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD9493	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7255	Intermediate Similarity	NPD4307	Phase 2
0.725	Intermediate Similarity	NPD7213	Phase 3
0.725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7212	Phase 2
0.7248	Intermediate Similarity	NPD1470	Approved
0.7248	Intermediate Similarity	NPD1164	Approved
0.7247	Intermediate Similarity	NPD4287	Approved
0.7247	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5404	Approved
0.7244	Intermediate Similarity	NPD5406	Approved
0.7244	Intermediate Similarity	NPD5408	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data