NPASS Compound

Structure

NPC473136 OpenBabel07101719242D 24 26 0 0 0 0 0 0 0 0999 V2000 -2.7470 -1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8421 1.9854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2697 -1.1781 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 -3.6130 -1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3771 1.9453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6790 -0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3553 1.1518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8809 -0.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0680 1.4099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8809 -1.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4773 1.5921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7470 0.4140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5211 0.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6130 -0.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6792 1.5021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2258 -0.5754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0462 0.6164 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 -4.4790 0.4140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6681 1.6511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6004 -1.1388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9094 0.9112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9888 -0.1490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 11 1 0 0 0 0 2 6 2 0 0 0 0 2 12 1 0 0 0 0 3 7 1 0 0 0 0 3 11 1 0 0 0 0 4 8 1 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	334.37
LogP:	2.108
LogD:	1.34
LogS:	-3.841
# Rotatable Bonds:	0
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.645
Synthetic Accessibility Score:	4.423
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.77
MDCK Permeability:	1.4340340385388117e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.25
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	89.92035675048828%
Volume Distribution (VD):	0.669
Pgp-substrate:	6.895224571228027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.599
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.595
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.78
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	10.306
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.617
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.219
Carcinogencity:	0.169
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC473136

Natural Product ID:	NPC473136
*Common Name:**	XLFPSTUJYBEZIQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XLFPSTUJYBEZIQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O5/c20-15-5-1-11-3-7-17(22)19(24)18(23)8-4-12-2-6-16(21)14(10-12)13(15)9-11/h1-2,5-6,9-10,19-21,24H,3-4,7-8H2
SMILES:	C1CC(=O)C(C(=O)CCC2=CC(=C(C=C2)O)C3=C(C=CC1=C3)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3617765
PubChem CID:	86295273
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15361	Alnus japonica	Species	Betulaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	11.6	%	PMID[496704]

☑ 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 NPC473136 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	271
0.1-0.2	1256
0.2-0.3	3123
0.3-0.4	9438
0.4-0.5	10275
0.5-0.6	6269
0.6-0.7	9824
0.7-0.8	2125
0.8-0.85	86
0.85-0.9	20
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9652	High Similarity	NPC31936
0.9561	High Similarity	NPC182240
0.9407	High Similarity	NPC231767
0.9328	High Similarity	NPC127975
0.9286	High Similarity	NPC286222
0.8929	High Similarity	NPC262365
0.886	High Similarity	NPC177576
0.886	High Similarity	NPC308689
0.8772	High Similarity	NPC252544
0.8772	High Similarity	NPC44732
0.8772	High Similarity	NPC321252
0.875	High Similarity	NPC188677
0.8632	High Similarity	NPC473137
0.8632	High Similarity	NPC12656
0.8632	High Similarity	NPC285350
0.8571	High Similarity	NPC8931
0.8571	High Similarity	NPC120693
0.8571	High Similarity	NPC261573
0.8571	High Similarity	NPC288411
0.8525	High Similarity	NPC295034
0.8522	High Similarity	NPC88141
0.8509	High Similarity	NPC228737
0.8496	Intermediate Similarity	NPC138942
0.8482	Intermediate Similarity	NPC168829
0.8468	Intermediate Similarity	NPC474803
0.8462	Intermediate Similarity	NPC228988
0.8443	Intermediate Similarity	NPC216216
0.8435	Intermediate Similarity	NPC317305
0.843	Intermediate Similarity	NPC473767
0.8421	Intermediate Similarity	NPC70843
0.8403	Intermediate Similarity	NPC23402
0.8387	Intermediate Similarity	NPC471187
0.8361	Intermediate Similarity	NPC265454
0.8361	Intermediate Similarity	NPC34634
0.8321	Intermediate Similarity	NPC61153
0.8321	Intermediate Similarity	NPC70859
0.8321	Intermediate Similarity	NPC130899
0.8321	Intermediate Similarity	NPC283590
0.832	Intermediate Similarity	NPC181334
0.8306	Intermediate Similarity	NPC176208
0.8293	Intermediate Similarity	NPC164852
0.8291	Intermediate Similarity	NPC21162
0.8261	Intermediate Similarity	NPC95178
0.8261	Intermediate Similarity	NPC29989
0.8261	Intermediate Similarity	NPC69332
0.8254	Intermediate Similarity	NPC87985
0.824	Intermediate Similarity	NPC198014
0.823	Intermediate Similarity	NPC91461
0.823	Intermediate Similarity	NPC7686
0.823	Intermediate Similarity	NPC40258
0.8214	Intermediate Similarity	NPC78119
0.8214	Intermediate Similarity	NPC51333
0.8214	Intermediate Similarity	NPC132078
0.8214	Intermediate Similarity	NPC216468
0.8205	Intermediate Similarity	NPC326187
0.8197	Intermediate Similarity	NPC249435
0.8182	Intermediate Similarity	NPC28951
0.8182	Intermediate Similarity	NPC325646
0.8168	Intermediate Similarity	NPC139074
0.8168	Intermediate Similarity	NPC40524
0.8168	Intermediate Similarity	NPC213485
0.8167	Intermediate Similarity	NPC474050
0.8167	Intermediate Similarity	NPC474114
0.8167	Intermediate Similarity	NPC473931
0.816	Intermediate Similarity	NPC86900
0.8151	Intermediate Similarity	NPC228425
0.8145	Intermediate Similarity	NPC98305
0.8145	Intermediate Similarity	NPC259703
0.8145	Intermediate Similarity	NPC32322
0.8142	Intermediate Similarity	NPC213730
0.8136	Intermediate Similarity	NPC296683
0.8125	Intermediate Similarity	NPC262936
0.8125	Intermediate Similarity	NPC30491
0.811	Intermediate Similarity	NPC477213
0.8103	Intermediate Similarity	NPC54765
0.8099	Intermediate Similarity	NPC322197
0.8087	Intermediate Similarity	NPC323810
0.8083	Intermediate Similarity	NPC296144
0.8083	Intermediate Similarity	NPC28784
0.808	Intermediate Similarity	NPC253627
0.8065	Intermediate Similarity	NPC478121
0.8062	Intermediate Similarity	NPC217431
0.8053	Intermediate Similarity	NPC128723
0.8049	Intermediate Similarity	NPC104514
0.8049	Intermediate Similarity	NPC184527
0.8047	Intermediate Similarity	NPC71610
0.8031	Intermediate Similarity	NPC474766
0.8031	Intermediate Similarity	NPC164014
0.803	Intermediate Similarity	NPC314048
0.803	Intermediate Similarity	NPC78307
0.8017	Intermediate Similarity	NPC13495
0.8016	Intermediate Similarity	NPC11250
0.8016	Intermediate Similarity	NPC475192
0.8016	Intermediate Similarity	NPC121168
0.8015	Intermediate Similarity	NPC85342
0.8015	Intermediate Similarity	NPC475042
0.8	Intermediate Similarity	NPC120488
0.8	Intermediate Similarity	NPC241001
0.8	Intermediate Similarity	NPC102829
0.8	Intermediate Similarity	NPC68269
0.7986	Intermediate Similarity	NPC474799
0.7984	Intermediate Similarity	NPC151197
0.7984	Intermediate Similarity	NPC319422
0.7984	Intermediate Similarity	NPC476020
0.7984	Intermediate Similarity	NPC477214
0.7984	Intermediate Similarity	NPC477211
0.7984	Intermediate Similarity	NPC477212
0.7983	Intermediate Similarity	NPC475018
0.7983	Intermediate Similarity	NPC63345
0.7982	Intermediate Similarity	NPC294741
0.7967	Intermediate Similarity	NPC325295
0.7967	Intermediate Similarity	NPC76308
0.7966	Intermediate Similarity	NPC95344
0.7965	Intermediate Similarity	NPC260000
0.7953	Intermediate Similarity	NPC273683
0.7949	Intermediate Similarity	NPC271274
0.7939	Intermediate Similarity	NPC245395
0.7937	Intermediate Similarity	NPC251259
0.7937	Intermediate Similarity	NPC154696
0.7934	Intermediate Similarity	NPC141003
0.7934	Intermediate Similarity	NPC242136
0.7934	Intermediate Similarity	NPC35344
0.7926	Intermediate Similarity	NPC475957
0.7923	Intermediate Similarity	NPC96024
0.7923	Intermediate Similarity	NPC476024
0.792	Intermediate Similarity	NPC473662
0.792	Intermediate Similarity	NPC7151
0.792	Intermediate Similarity	NPC216297
0.792	Intermediate Similarity	NPC223451
0.7917	Intermediate Similarity	NPC95716
0.7917	Intermediate Similarity	NPC212718
0.791	Intermediate Similarity	NPC103082
0.791	Intermediate Similarity	NPC152209
0.7907	Intermediate Similarity	NPC269598
0.7903	Intermediate Similarity	NPC328694
0.7895	Intermediate Similarity	NPC471749
0.7895	Intermediate Similarity	NPC280869
0.7895	Intermediate Similarity	NPC52407
0.7891	Intermediate Similarity	NPC74507
0.7891	Intermediate Similarity	NPC152525
0.7891	Intermediate Similarity	NPC234890
0.7891	Intermediate Similarity	NPC68756
0.7886	Intermediate Similarity	NPC299252
0.7886	Intermediate Similarity	NPC277394
0.7886	Intermediate Similarity	NPC308828
0.7886	Intermediate Similarity	NPC61062
0.7881	Intermediate Similarity	NPC141523
0.7879	Intermediate Similarity	NPC474143
0.7879	Intermediate Similarity	NPC471851
0.7879	Intermediate Similarity	NPC93015
0.7879	Intermediate Similarity	NPC474246
0.7876	Intermediate Similarity	NPC132271
0.7876	Intermediate Similarity	NPC216520
0.7876	Intermediate Similarity	NPC292730
0.7876	Intermediate Similarity	NPC82664
0.7863	Intermediate Similarity	NPC154899
0.7863	Intermediate Similarity	NPC233396
0.7863	Intermediate Similarity	NPC474546
0.7863	Intermediate Similarity	NPC276238
0.7857	Intermediate Similarity	NPC128062
0.7857	Intermediate Similarity	NPC151715
0.7857	Intermediate Similarity	NPC131868
0.7852	Intermediate Similarity	NPC475549
0.7851	Intermediate Similarity	NPC48525
0.7851	Intermediate Similarity	NPC46940
0.7842	Intermediate Similarity	NPC148545
0.7842	Intermediate Similarity	NPC478164
0.784	Intermediate Similarity	NPC79933
0.784	Intermediate Similarity	NPC31296
0.784	Intermediate Similarity	NPC473974
0.784	Intermediate Similarity	NPC258366
0.7836	Intermediate Similarity	NPC202225
0.7833	Intermediate Similarity	NPC222905
0.7833	Intermediate Similarity	NPC147634
0.7833	Intermediate Similarity	NPC132720
0.7833	Intermediate Similarity	NPC116842
0.7833	Intermediate Similarity	NPC120982
0.7833	Intermediate Similarity	NPC226401
0.7833	Intermediate Similarity	NPC79793
0.7833	Intermediate Similarity	NPC174096
0.7833	Intermediate Similarity	NPC208229
0.7829	Intermediate Similarity	NPC137750
0.7826	Intermediate Similarity	NPC225506
0.7823	Intermediate Similarity	NPC477136
0.7823	Intermediate Similarity	NPC299180
0.782	Intermediate Similarity	NPC173034
0.7815	Intermediate Similarity	NPC31274
0.7815	Intermediate Similarity	NPC279887
0.7815	Intermediate Similarity	NPC68260
0.7807	Intermediate Similarity	NPC77492
0.7805	Intermediate Similarity	NPC474486
0.7805	Intermediate Similarity	NPC147179
0.7803	Intermediate Similarity	NPC253488
0.7803	Intermediate Similarity	NPC123
0.7803	Intermediate Similarity	NPC470725
0.7803	Intermediate Similarity	NPC199253
0.7803	Intermediate Similarity	NPC475880
0.7803	Intermediate Similarity	NPC27659
0.7803	Intermediate Similarity	NPC136588
0.7803	Intermediate Similarity	NPC163169

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 NPC473136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	895
0.2-0.3	1326
0.3-0.4	2579
0.4-0.5	2214
0.5-0.6	1243
0.6-0.7	587
0.7-0.8	65
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7895	Intermediate Similarity	NPD3020	Approved
0.7826	Intermediate Similarity	NPD3400	Discontinued
0.7788	Intermediate Similarity	NPD2860	Approved
0.7788	Intermediate Similarity	NPD2859	Approved
0.7778	Intermediate Similarity	NPD2932	Approved
0.7778	Intermediate Similarity	NPD3019	Approved
0.7699	Intermediate Similarity	NPD2933	Approved
0.7699	Intermediate Similarity	NPD2934	Approved
0.7692	Intermediate Similarity	NPD1164	Approved
0.763	Intermediate Similarity	NPD6355	Discontinued
0.7627	Intermediate Similarity	NPD1237	Approved
0.7561	Intermediate Similarity	NPD7635	Approved
0.7559	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD1651	Approved
0.7537	Intermediate Similarity	NPD6798	Discontinued
0.7519	Intermediate Similarity	NPD1201	Approved
0.7478	Intermediate Similarity	NPD1809	Phase 2
0.7464	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD3022	Approved
0.7459	Intermediate Similarity	NPD3021	Approved
0.7456	Intermediate Similarity	NPD845	Approved
0.7438	Intermediate Similarity	NPD2342	Discontinued
0.7426	Intermediate Similarity	NPD4060	Phase 1
0.7424	Intermediate Similarity	NPD1470	Approved
0.741	Intermediate Similarity	NPD2935	Discontinued
0.7391	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6663	Approved
0.7348	Intermediate Similarity	NPD1283	Approved
0.7344	Intermediate Similarity	NPD3091	Approved
0.7339	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD5736	Approved
0.7308	Intermediate Similarity	NPD3023	Approved
0.7308	Intermediate Similarity	NPD3026	Approved
0.7302	Intermediate Similarity	NPD2629	Approved
0.7287	Intermediate Similarity	NPD3024	Approved
0.7287	Intermediate Similarity	NPD3025	Approved
0.7286	Intermediate Similarity	NPD5408	Approved
0.7286	Intermediate Similarity	NPD5404	Approved
0.7286	Intermediate Similarity	NPD5405	Approved
0.7286	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4380	Phase 2
0.7227	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6233	Phase 2
0.7214	Intermediate Similarity	NPD2799	Discontinued
0.7203	Intermediate Similarity	NPD9495	Approved
0.7188	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD844	Approved
0.7174	Intermediate Similarity	NPD2979	Phase 3
0.7172	Intermediate Similarity	NPD7390	Discontinued
0.7167	Intermediate Similarity	NPD846	Approved
0.7167	Intermediate Similarity	NPD940	Approved
0.7164	Intermediate Similarity	NPD3094	Phase 2
0.7163	Intermediate Similarity	NPD4477	Approved
0.7163	Intermediate Similarity	NPD4476	Approved
0.7133	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1535	Discovery
0.7121	Intermediate Similarity	NPD1281	Approved
0.7121	Intermediate Similarity	NPD3092	Approved
0.7119	Intermediate Similarity	NPD288	Approved
0.7113	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6405	Approved
0.7101	Intermediate Similarity	NPD4062	Phase 3
0.7101	Intermediate Similarity	NPD6407	Approved
0.7099	Intermediate Similarity	NPD4589	Approved
0.7099	Intermediate Similarity	NPD3095	Discontinued
0.7092	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1510	Phase 2
0.7087	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7003	Approved
0.7077	Intermediate Similarity	NPD1894	Discontinued
0.7077	Intermediate Similarity	NPD5303	Approved
0.7077	Intermediate Similarity	NPD5304	Approved
0.7068	Intermediate Similarity	NPD1481	Phase 2
0.7068	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD2861	Phase 2
0.705	Intermediate Similarity	NPD943	Approved
0.7045	Intermediate Similarity	NPD3847	Discontinued
0.7037	Intermediate Similarity	NPD2797	Approved
0.7034	Intermediate Similarity	NPD6190	Approved
0.7029	Intermediate Similarity	NPD2313	Discontinued
0.7029	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3764	Approved
0.7029	Intermediate Similarity	NPD3268	Approved
0.7015	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6005	Phase 3
0.6993	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6002	Phase 3
0.6993	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6004	Phase 3
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3300	Phase 2
0.6985	Remote Similarity	NPD2798	Approved
0.6977	Remote Similarity	NPD256	Approved
0.6977	Remote Similarity	NPD255	Approved
0.6974	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8455	Phase 2
0.697	Remote Similarity	NPD4626	Approved
0.697	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2286	Discontinued
0.6966	Remote Similarity	NPD4628	Phase 3
0.6966	Remote Similarity	NPD8166	Discontinued
0.6963	Remote Similarity	NPD1876	Approved
0.6953	Remote Similarity	NPD2228	Approved
0.6953	Remote Similarity	NPD2234	Approved
0.6953	Remote Similarity	NPD2229	Approved
0.6949	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7075	Discontinued
0.6947	Remote Similarity	NPD1759	Phase 1
0.6944	Remote Similarity	NPD4534	Discontinued
0.6944	Remote Similarity	NPD1549	Phase 2
0.6944	Remote Similarity	NPD5958	Discontinued
0.6944	Remote Similarity	NPD2424	Discontinued
0.6942	Remote Similarity	NPD3028	Approved
0.6942	Remote Similarity	NPD1242	Phase 1
0.6934	Remote Similarity	NPD4208	Discontinued
0.6933	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7458	Discontinued
0.6929	Remote Similarity	NPD1240	Approved
0.6928	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD2309	Approved
0.6918	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4750	Phase 3
0.6903	Remote Similarity	NPD111	Approved
0.6899	Remote Similarity	NPD497	Approved
0.6892	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1755	Approved
0.6884	Remote Similarity	NPD4908	Phase 1
0.688	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1758	Phase 1
0.6866	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1610	Phase 2
0.6863	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7033	Discontinued
0.6853	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD3750	Approved
0.6835	Remote Similarity	NPD3027	Phase 3
0.6835	Remote Similarity	NPD7095	Approved
0.6831	Remote Similarity	NPD1607	Approved
0.6829	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1929	Approved
0.6829	Remote Similarity	NPD1930	Approved
0.6825	Remote Similarity	NPD74	Approved
0.6825	Remote Similarity	NPD9266	Approved
0.6822	Remote Similarity	NPD1241	Discontinued
0.6822	Remote Similarity	NPD495	Approved
0.6822	Remote Similarity	NPD498	Approved
0.6822	Remote Similarity	NPD496	Approved
0.6818	Remote Similarity	NPD9545	Approved
0.6806	Remote Similarity	NPD2531	Phase 2
0.68	Remote Similarity	NPD968	Approved
0.6797	Remote Similarity	NPD6801	Discontinued
0.6794	Remote Similarity	NPD9568	Approved
0.6794	Remote Similarity	NPD9493	Approved
0.6788	Remote Similarity	NPD4103	Phase 2
0.6788	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7768	Phase 2
0.6772	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5951	Approved
0.6767	Remote Similarity	NPD5691	Approved
0.6767	Remote Similarity	NPD4093	Discontinued
0.6765	Remote Similarity	NPD4659	Approved
0.6759	Remote Similarity	NPD2346	Discontinued
0.6746	Remote Similarity	NPD9264	Approved
0.6746	Remote Similarity	NPD9263	Approved
0.6746	Remote Similarity	NPD9267	Approved
0.6742	Remote Similarity	NPD5536	Phase 2
0.6741	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5048	Discontinued
0.6719	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7157	Approved
0.6718	Remote Similarity	NPD6671	Approved
0.6716	Remote Similarity	NPD4059	Approved
0.6712	Remote Similarity	NPD2897	Discontinued
0.6709	Remote Similarity	NPD6959	Discontinued
0.6695	Remote Similarity	NPD1239	Approved
0.6694	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2684	Approved
0.6693	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5283	Phase 1
0.6692	Remote Similarity	NPD7330	Discontinued
0.6692	Remote Similarity	NPD1548	Phase 1
0.6691	Remote Similarity	NPD1608	Approved
0.6691	Remote Similarity	NPD2561	Approved
0.6691	Remote Similarity	NPD2562	Approved
0.669	Remote Similarity	NPD1613	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