NPASS Compound

Structure

CID39929 OpenBabel06191715372D 22 24 0 0 0 0 0 0 0 0999 V2000 5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 3.0878 -1.6750 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 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 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 -0.0000 -1.6180 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 -2.6831 -1.3090 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 3.5878 -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 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 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.9230 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 3 12 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 13 17 2 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	310.921
LogP:	4.122
LogD:	3.173
LogS:	-4.789
# Rotatable Bonds:	5
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	2.207
Fsp3:	0.222
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:	-4.872
MDCK Permeability:	1.4571063729817979e-05
Pgp-inhibitor:	0.929
Pgp-substrate:	0.35
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	98.2481460571289%
Volume Distribution (VD):	0.693
Pgp-substrate:	1.7175064086914062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.91
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.315

ADMET: Excretion

Clearance (CL):	8.875
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.261
Rat Oral Acute Toxicity:	0.277
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.699
Carcinogencity:	0.168
Eye Corrosion:	0.004
Eye Irritation:	0.77
Respiratory Toxicity:	0.098

Download Data

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

Natural Product: NPC39929

Natural Product ID:	NPC39929
*Common Name:**	2-[5-(3-Hydroxypropyl)-1-Benzofuran-2-Yl]-5-Methoxyphenol
IUPAC Name:	2-[5-(3-hydroxypropyl)-1-benzofuran-2-yl]-5-methoxyphenol
Synonyms:
Standard InCHIKey:	DZMMGSFVLBBPIA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O4/c1-21-14-5-6-15(16(20)11-14)18-10-13-9-12(3-2-8-19)4-7-17(13)22-18/h4-7,9-11,19-20H,2-3,8H2,1H3
SMILES:	OCCCc1ccc2c(c1)cc(o2)c1ccc(cc1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2147419
PubChem CID:	14213211
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
NPO13392	Caiophora coronata	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695811]
NPO15400	Krameria lappacea	Species	Krameriaceae	Eukaryota	n.a.	root	n.a.	PMID[21800856]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15864	Skimmia wallichii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15400	Krameria lappacea	Species	Krameriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO558	Limnophila rugosa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3420	Alsomitra graciliflora	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13392	Caiophora coronata	Species	Loasaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5464	Baliospermum axillare	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9820	Nepeta erecta	Species	Lamiaceae	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	6
Others	12

Activity Type	# Activity
Individual Protein	5
Organism	11
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	>	50000.0	nM	PMID[557337]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	=	80.2	%	PMID[557337]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	27200.0	nM	PMID[557337]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	50000.0	nM	PMID[557337]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	42000.0	nM	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	32.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	25.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	50.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	67.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.36	umol/cm2	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	28.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	89.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	29.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	47.0	%	PMID[557337]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	24.0	%	PMID[557337]
NPT2	Others	Unspecified		IC50	=	5900.0	nM	PMID[557337]
NPT1	Others	Radical scavenging activity		IC50	=	42300.0	nM	PMID[557337]

☑ 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 NPC39929 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	363
0.1-0.2	1623
0.2-0.3	3867
0.3-0.4	10532
0.4-0.5	7923
0.5-0.6	3865
0.6-0.7	5933
0.7-0.8	4758
0.8-0.85	2182
0.85-0.9	1158
0.9-0.95	468
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296030
0.9859	High Similarity	NPC130581
0.9859	High Similarity	NPC12148
0.979	High Similarity	NPC135325
0.9789	High Similarity	NPC210826
0.9789	High Similarity	NPC300267
0.9789	High Similarity	NPC51641
0.9722	High Similarity	NPC226644
0.9722	High Similarity	NPC37226
0.9648	High Similarity	NPC225884
0.9648	High Similarity	NPC302181
0.9592	High Similarity	NPC122365
0.9592	High Similarity	NPC213608
0.9592	High Similarity	NPC1477
0.9589	High Similarity	NPC170169
0.9586	High Similarity	NPC221868
0.9586	High Similarity	NPC37208
0.958	High Similarity	NPC230943
0.9577	High Similarity	NPC53192
0.9527	High Similarity	NPC198490
0.9524	High Similarity	NPC5871
0.9521	High Similarity	NPC230713
0.9521	High Similarity	NPC78335
0.9517	High Similarity	NPC272194
0.9467	High Similarity	NPC476350
0.9467	High Similarity	NPC476349
0.9463	High Similarity	NPC247677
0.9463	High Similarity	NPC160015
0.9459	High Similarity	NPC183874
0.9452	High Similarity	NPC178202
0.94	High Similarity	NPC260902
0.94	High Similarity	NPC296957
0.94	High Similarity	NPC65504
0.9396	High Similarity	NPC148938
0.9392	High Similarity	NPC263676
0.9384	High Similarity	NPC168085
0.9338	High Similarity	NPC40583
0.9329	High Similarity	NPC235333
0.9329	High Similarity	NPC472462
0.9324	High Similarity	NPC116604
0.9324	High Similarity	NPC474744
0.9324	High Similarity	NPC156244
0.9324	High Similarity	NPC472423
0.9324	High Similarity	NPC474772
0.932	High Similarity	NPC317492
0.9315	High Similarity	NPC17816
0.9296	High Similarity	NPC124269
0.9272	High Similarity	NPC246647
0.9272	High Similarity	NPC212967
0.9272	High Similarity	NPC164110
0.9272	High Similarity	NPC96342
0.9267	High Similarity	NPC213936
0.9267	High Similarity	NPC297531
0.9262	High Similarity	NPC67654
0.9262	High Similarity	NPC285623
0.9262	High Similarity	NPC207624
0.9257	High Similarity	NPC472421
0.9257	High Similarity	NPC167576
0.9252	High Similarity	NPC6511
0.9247	High Similarity	NPC472629
0.9241	High Similarity	NPC166138
0.9241	High Similarity	NPC221432
0.9241	High Similarity	NPC175504
0.9241	High Similarity	NPC164980
0.9241	High Similarity	NPC18585
0.9241	High Similarity	NPC75049
0.9241	High Similarity	NPC169591
0.9241	High Similarity	NPC39329
0.9241	High Similarity	NPC149026
0.9241	High Similarity	NPC310130
0.9241	High Similarity	NPC143896
0.9241	High Similarity	NPC257097
0.9241	High Similarity	NPC91560
0.9241	High Similarity	NPC150408
0.9241	High Similarity	NPC106985
0.9241	High Similarity	NPC17262
0.9241	High Similarity	NPC68104
0.9236	High Similarity	NPC470087
0.9236	High Similarity	NPC110969
0.9236	High Similarity	NPC321980
0.9236	High Similarity	NPC3188
0.9231	High Similarity	NPC470211
0.9231	High Similarity	NPC37206
0.9225	High Similarity	NPC188879
0.9216	High Similarity	NPC45124
0.9216	High Similarity	NPC30655
0.9216	High Similarity	NPC74854
0.9205	High Similarity	NPC180924
0.9195	High Similarity	NPC318424
0.9195	High Similarity	NPC115324
0.9195	High Similarity	NPC23668
0.9195	High Similarity	NPC472580
0.9195	High Similarity	NPC58668
0.9195	High Similarity	NPC193976
0.9195	High Similarity	NPC106372
0.9184	High Similarity	NPC24673
0.9184	High Similarity	NPC237635
0.9184	High Similarity	NPC104406
0.9184	High Similarity	NPC79469
0.9184	High Similarity	NPC201731
0.9184	High Similarity	NPC97716
0.9178	High Similarity	NPC234629
0.9178	High Similarity	NPC155144
0.9178	High Similarity	NPC311741
0.9178	High Similarity	NPC87486
0.9178	High Similarity	NPC197252
0.9178	High Similarity	NPC473013
0.9178	High Similarity	NPC470890
0.9178	High Similarity	NPC271288
0.9178	High Similarity	NPC98926
0.9178	High Similarity	NPC124780
0.9178	High Similarity	NPC236766
0.9178	High Similarity	NPC473015
0.9178	High Similarity	NPC209040
0.9178	High Similarity	NPC224714
0.9172	High Similarity	NPC37496
0.9172	High Similarity	NPC107572
0.9172	High Similarity	NPC78
0.9172	High Similarity	NPC125855
0.9172	High Similarity	NPC166482
0.9172	High Similarity	NPC40833
0.9172	High Similarity	NPC76338
0.9172	High Similarity	NPC306829
0.9172	High Similarity	NPC76372
0.9172	High Similarity	NPC166934
0.9172	High Similarity	NPC64915
0.9172	High Similarity	NPC148757
0.9172	High Similarity	NPC226636
0.9172	High Similarity	NPC167624
0.9172	High Similarity	NPC1089
0.9172	High Similarity	NPC11561
0.9172	High Similarity	NPC194432
0.9172	High Similarity	NPC144499
0.9172	High Similarity	NPC220998
0.9172	High Similarity	NPC32739
0.9172	High Similarity	NPC10937
0.9172	High Similarity	NPC328164
0.9172	High Similarity	NPC227579
0.9172	High Similarity	NPC228504
0.9172	High Similarity	NPC324436
0.9172	High Similarity	NPC177354
0.9172	High Similarity	NPC223500
0.9172	High Similarity	NPC265040
0.9172	High Similarity	NPC296917
0.9172	High Similarity	NPC66515
0.9172	High Similarity	NPC324134
0.9172	High Similarity	NPC182852
0.9172	High Similarity	NPC161506
0.9167	High Similarity	NPC172986
0.9167	High Similarity	NPC261227
0.9167	High Similarity	NPC172250
0.9167	High Similarity	NPC215311
0.9167	High Similarity	NPC48624
0.9167	High Similarity	NPC326109
0.9167	High Similarity	NPC28337
0.9167	High Similarity	NPC219917
0.9167	High Similarity	NPC270883
0.9167	High Similarity	NPC213659
0.9167	High Similarity	NPC204985
0.9167	High Similarity	NPC69769
0.9167	High Similarity	NPC241100
0.9167	High Similarity	NPC259166
0.9167	High Similarity	NPC144118
0.9167	High Similarity	NPC80962
0.9167	High Similarity	NPC159275
0.9161	High Similarity	NPC21350
0.9156	High Similarity	NPC219861
0.9155	High Similarity	NPC477243
0.9155	High Similarity	NPC150399
0.9155	High Similarity	NPC98115
0.9155	High Similarity	NPC1486
0.9155	High Similarity	NPC477244
0.9155	High Similarity	NPC249606
0.9155	High Similarity	NPC477242
0.9155	High Similarity	NPC240593
0.9155	High Similarity	NPC168105
0.9155	High Similarity	NPC274109
0.9155	High Similarity	NPC186838
0.9155	High Similarity	NPC12165
0.9155	High Similarity	NPC41461
0.9155	High Similarity	NPC66349
0.9155	High Similarity	NPC25287
0.915	High Similarity	NPC220582
0.915	High Similarity	NPC115432
0.915	High Similarity	NPC260296
0.915	High Similarity	NPC304839
0.9145	High Similarity	NPC268360
0.9145	High Similarity	NPC269495
0.9133	High Similarity	NPC477957
0.9133	High Similarity	NPC473996
0.9133	High Similarity	NPC476238
0.9133	High Similarity	NPC142308
0.9133	High Similarity	NPC253872
0.9133	High Similarity	NPC327269
0.9133	High Similarity	NPC31627
0.9128	High Similarity	NPC321896
0.9128	High Similarity	NPC61258
0.9128	High Similarity	NPC476185
0.9122	High Similarity	NPC266572
0.9122	High Similarity	NPC39195

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 NPC39929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	976
0.2-0.3	1469
0.3-0.4	2612
0.4-0.5	1944
0.5-0.6	1215
0.6-0.7	400
0.7-0.8	126
0.8-0.85	40
0.85-0.9	26
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD4378	Clinical (unspecified phase)
0.8919	High Similarity	NPD7410	Clinical (unspecified phase)
0.8897	High Similarity	NPD1549	Phase 2
0.8828	High Similarity	NPD1552	Clinical (unspecified phase)
0.8828	High Similarity	NPD1550	Clinical (unspecified phase)
0.8819	High Similarity	NPD1510	Phase 2
0.8816	High Similarity	NPD7411	Suspended
0.8803	High Similarity	NPD1240	Approved
0.8766	High Similarity	NPD8443	Clinical (unspecified phase)
0.8759	High Similarity	NPD2796	Approved
0.875	High Similarity	NPD4380	Phase 2
0.8707	High Similarity	NPD1243	Approved
0.8701	High Similarity	NPD2393	Clinical (unspecified phase)
0.8699	High Similarity	NPD2344	Approved
0.8681	High Similarity	NPD1607	Approved
0.8675	High Similarity	NPD920	Approved
0.8658	High Similarity	NPD643	Clinical (unspecified phase)
0.8654	High Similarity	NPD3749	Approved
0.8654	High Similarity	NPD7075	Discontinued
0.859	High Similarity	NPD3882	Suspended
0.859	High Similarity	NPD7768	Phase 2
0.8589	High Similarity	NPD6559	Discontinued
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.8562	High Similarity	NPD7852	Clinical (unspecified phase)
0.8543	High Similarity	NPD642	Clinical (unspecified phase)
0.8516	High Similarity	NPD6801	Discontinued
0.8477	Intermediate Similarity	NPD6799	Approved
0.8467	Intermediate Similarity	NPD2309	Approved
0.8456	Intermediate Similarity	NPD2800	Approved
0.8456	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1934	Approved
0.8375	Intermediate Similarity	NPD6959	Discontinued
0.8269	Intermediate Similarity	NPD6599	Discontinued
0.8255	Intermediate Similarity	NPD1551	Phase 2
0.825	Intermediate Similarity	NPD919	Approved
0.8235	Intermediate Similarity	NPD1511	Approved
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8228	Intermediate Similarity	NPD2801	Approved
0.8221	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2532	Approved
0.8182	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD2533	Approved
0.816	Intermediate Similarity	NPD3926	Phase 2
0.8158	Intermediate Similarity	NPD3750	Approved
0.8151	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD1247	Approved
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8129	Intermediate Similarity	NPD1512	Approved
0.8084	Intermediate Similarity	NPD5953	Discontinued
0.8067	Intermediate Similarity	NPD2799	Discontinued
0.8054	Intermediate Similarity	NPD6651	Approved
0.8039	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7964	Intermediate Similarity	NPD7286	Phase 2
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7962	Intermediate Similarity	NPD5403	Approved
0.7961	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7473	Discontinued
0.795	Intermediate Similarity	NPD3817	Phase 2
0.7922	Intermediate Similarity	NPD4628	Phase 3
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7905	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7054	Approved
0.784	Intermediate Similarity	NPD2296	Approved
0.7834	Intermediate Similarity	NPD5401	Approved
0.7829	Intermediate Similarity	NPD3748	Approved
0.7811	Intermediate Similarity	NPD7472	Approved
0.7811	Intermediate Similarity	NPD1729	Discontinued
0.7808	Intermediate Similarity	NPD1203	Approved
0.7798	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2313	Discontinued
0.777	Intermediate Similarity	NPD4908	Phase 1
0.777	Intermediate Similarity	NPD6832	Phase 2
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.773	Intermediate Similarity	NPD5402	Approved
0.7719	Intermediate Similarity	NPD7251	Discontinued
0.7716	Intermediate Similarity	NPD6280	Approved
0.7716	Intermediate Similarity	NPD6279	Approved
0.7712	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7033	Discontinued
0.7697	Intermediate Similarity	NPD4361	Phase 2
0.7697	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD943	Approved
0.7674	Intermediate Similarity	NPD7808	Phase 3
0.7658	Intermediate Similarity	NPD7390	Discontinued
0.7655	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD2654	Approved
0.7625	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4287	Approved
0.7613	Intermediate Similarity	NPD1471	Phase 3
0.761	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD9717	Approved
0.7572	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6808	Phase 2
0.756	Intermediate Similarity	NPD7229	Phase 3
0.756	Intermediate Similarity	NPD5710	Approved
0.756	Intermediate Similarity	NPD5711	Approved
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6099	Approved
0.7548	Intermediate Similarity	NPD6100	Approved
0.7542	Intermediate Similarity	NPD4360	Phase 2
0.7542	Intermediate Similarity	NPD4363	Phase 3
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7531	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7471	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5760	Phase 2
0.7455	Intermediate Similarity	NPD5761	Phase 2
0.7434	Intermediate Similarity	NPD3268	Approved
0.7434	Intermediate Similarity	NPD3764	Approved
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7403	Intermediate Similarity	NPD5124	Phase 1
0.7403	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7379	Intermediate Similarity	NPD9545	Approved
0.7372	Intermediate Similarity	NPD4308	Phase 3
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7365	Intermediate Similarity	NPD3972	Approved
0.7358	Intermediate Similarity	NPD7003	Approved
0.7349	Intermediate Similarity	NPD1465	Phase 2
0.7333	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2797	Approved
0.7333	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD5406	Approved
0.7325	Intermediate Similarity	NPD5408	Approved
0.7325	Intermediate Similarity	NPD5405	Approved
0.7325	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD7458	Discontinued
0.729	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6005	Phase 3
0.7278	Intermediate Similarity	NPD6004	Phase 3
0.7278	Intermediate Similarity	NPD6002	Phase 3
0.7278	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1241	Discontinued
0.7248	Intermediate Similarity	NPD1608	Approved
0.7243	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9493	Approved
0.7238	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2424	Discontinued
0.7232	Intermediate Similarity	NPD8313	Approved
0.7232	Intermediate Similarity	NPD8312	Approved
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6104	Discontinued
0.7216	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6798	Discontinued
0.7208	Intermediate Similarity	NPD411	Approved
0.7202	Intermediate Similarity	NPD4288	Approved
0.7196	Intermediate Similarity	NPD7584	Approved
0.7184	Intermediate Similarity	NPD7177	Discontinued
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7179	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD447	Suspended
0.7179	Intermediate Similarity	NPD1933	Approved
0.7178	Intermediate Similarity	NPD4662	Approved
0.7178	Intermediate Similarity	NPD4661	Approved
0.7171	Intermediate Similarity	NPD1019	Discontinued
0.7168	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7134	Intermediate Similarity	NPD6273	Approved
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5889	Approved
0.7126	Intermediate Similarity	NPD5890	Approved
0.7118	Intermediate Similarity	NPD6971	Discontinued
0.7115	Intermediate Similarity	NPD4307	Phase 2
0.7107	Intermediate Similarity	NPD4477	Approved
0.7107	Intermediate Similarity	NPD4476	Approved
0.7105	Intermediate Similarity	NPD1470	Approved
0.7105	Intermediate Similarity	NPD3266	Approved
0.7105	Intermediate Similarity	NPD3267	Approved
0.7097	Intermediate Similarity	NPD1296	Phase 2
0.7097	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6844	Discontinued
0.7083	Intermediate Similarity	NPD37	Approved
0.7078	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD4966	Approved
0.7059	Intermediate Similarity	NPD4965	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