NPASS Compound

Structure

NPC219923 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -4.0862 -2.2882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6977 -3.0085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2330 -1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6488 -3.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1840 -1.6702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 -1.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4898 -2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3920 -2.6483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -2.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 0.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0933 1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3430 -2.9574 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 22 1 0 0 0 0 2 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 8 1 1 0 0 0 17 23 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	3.451
LogD:	3.28
LogS:	-3.445
# Rotatable Bonds:	4
TPSA:	83.06
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.685
Synthetic Accessibility Score:	2.58
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	1.1999827620456927e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.76
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.472
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	99.8540267944336%
Volume Distribution (VD):	0.639
Pgp-substrate:	0.8336547017097473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.899
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.854
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	11.289
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.422
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.539
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.102
Skin Sensitization:	0.194
Carcinogencity:	0.219
Eye Corrosion:	0.003
Eye Irritation:	0.281
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC219923

Natural Product ID:	NPC219923
*Common Name:**	(R)-4-(2,4-Dihydroxyphenyl)-5-(4-Methoxybenzyl)Furan-2(5H)-One
IUPAC Name:	(2R)-3-(2,4-dihydroxyphenyl)-2-[(4-methoxyphenyl)methyl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	BIOLMNGHEQESDD-QGZVFWFLSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-22-13-5-2-11(3-6-13)8-17-15(10-18(21)23-17)14-7-4-12(19)9-16(14)20/h2-7,9-10,17,19-20H,8H2,1H3/t17-/m1/s1
SMILES:	COc1ccc(cc1)C[C@@H]1C(=CC(=O)O1)c1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375517
PubChem CID:	71713865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO33423	dalea formosa	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[23631483]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	=	244.0	ug.mL-1	PMID[483306]

☑ 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 NPC219923 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	270
0.1-0.2	1276
0.2-0.3	3985
0.3-0.4	9914
0.4-0.5	8541
0.5-0.6	4052
0.6-0.7	7706
0.7-0.8	6428
0.8-0.85	479
0.85-0.9	44
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9141	High Similarity	NPC250727
0.8915	High Similarity	NPC32463
0.8855	High Similarity	NPC31849
0.8855	High Similarity	NPC163557
0.8843	High Similarity	NPC296526
0.8828	High Similarity	NPC258567
0.8828	High Similarity	NPC121740
0.8828	High Similarity	NPC224774
0.8819	High Similarity	NPC168259
0.881	High Similarity	NPC38761
0.881	High Similarity	NPC76465
0.8779	High Similarity	NPC194277
0.877	High Similarity	NPC229147
0.877	High Similarity	NPC85292
0.877	High Similarity	NPC54507
0.876	High Similarity	NPC469453
0.873	High Similarity	NPC36016
0.873	High Similarity	NPC100099
0.8689	High Similarity	NPC464
0.8689	High Similarity	NPC185541
0.8682	High Similarity	NPC243688
0.8672	High Similarity	NPC103420
0.8672	High Similarity	NPC188022
0.8672	High Similarity	NPC17809
0.8672	High Similarity	NPC102540
0.8672	High Similarity	NPC285040
0.8661	High Similarity	NPC474160
0.8661	High Similarity	NPC315807
0.8657	High Similarity	NPC38099
0.8657	High Similarity	NPC26954
0.8657	High Similarity	NPC223616
0.8651	High Similarity	NPC52247
0.8651	High Similarity	NPC187868
0.8647	High Similarity	NPC204353
0.8647	High Similarity	NPC326600
0.8647	High Similarity	NPC131950
0.8647	High Similarity	NPC50896
0.8629	High Similarity	NPC131118
0.8626	High Similarity	NPC113098
0.8623	High Similarity	NPC471824
0.8615	High Similarity	NPC87224
0.8615	High Similarity	NPC274717
0.8615	High Similarity	NPC222572
0.8615	High Similarity	NPC39064
0.8615	High Similarity	NPC47283
0.8605	High Similarity	NPC50315
0.8605	High Similarity	NPC230479
0.8605	High Similarity	NPC276212
0.8605	High Similarity	NPC283049
0.8605	High Similarity	NPC26879
0.8594	High Similarity	NPC246648
0.8594	High Similarity	NPC134195
0.8594	High Similarity	NPC197351
0.8594	High Similarity	NPC106914
0.8594	High Similarity	NPC86502
0.8571	High Similarity	NPC185777
0.8571	High Similarity	NPC215037
0.8561	High Similarity	NPC29734
0.8561	High Similarity	NPC12875
0.8561	High Similarity	NPC17343
0.8561	High Similarity	NPC207892
0.8561	High Similarity	NPC280653
0.8561	High Similarity	NPC300875
0.8561	High Similarity	NPC150011
0.8561	High Similarity	NPC272650
0.8561	High Similarity	NPC226722
0.8561	High Similarity	NPC267336
0.8561	High Similarity	NPC118114
0.8561	High Similarity	NPC129106
0.8561	High Similarity	NPC162801
0.8561	High Similarity	NPC196765
0.8561	High Similarity	NPC268917
0.8561	High Similarity	NPC206224
0.8561	High Similarity	NPC228369
0.8561	High Similarity	NPC164574
0.8561	High Similarity	NPC129784
0.8561	High Similarity	NPC476166
0.8561	High Similarity	NPC236014
0.855	High Similarity	NPC168710
0.854	High Similarity	NPC310370
0.854	High Similarity	NPC183642
0.8529	High Similarity	NPC278600
0.8529	High Similarity	NPC327612
0.8529	High Similarity	NPC37428
0.8529	High Similarity	NPC144512
0.8529	High Similarity	NPC137262
0.8529	High Similarity	NPC73078
0.8529	High Similarity	NPC151946
0.8529	High Similarity	NPC47040
0.8529	High Similarity	NPC148738
0.8529	High Similarity	NPC319870
0.8529	High Similarity	NPC279573
0.8529	High Similarity	NPC35501
0.8527	High Similarity	NPC244495
0.8527	High Similarity	NPC93219
0.8507	High Similarity	NPC213173
0.8507	High Similarity	NPC62366
0.8507	High Similarity	NPC180716
0.8507	High Similarity	NPC224475
0.8504	High Similarity	NPC476633
0.8504	High Similarity	NPC54972
0.8496	Intermediate Similarity	NPC13005
0.8492	Intermediate Similarity	NPC258979
0.8492	Intermediate Similarity	NPC8283
0.8492	Intermediate Similarity	NPC93398
0.8485	Intermediate Similarity	NPC27187
0.8485	Intermediate Similarity	NPC470225
0.8485	Intermediate Similarity	NPC469929
0.8473	Intermediate Similarity	NPC185066
0.8473	Intermediate Similarity	NPC38664
0.8473	Intermediate Similarity	NPC53986
0.8462	Intermediate Similarity	NPC471215
0.8462	Intermediate Similarity	NPC262573
0.8456	Intermediate Similarity	NPC155963
0.8456	Intermediate Similarity	NPC131198
0.8456	Intermediate Similarity	NPC474886
0.845	Intermediate Similarity	NPC73413
0.845	Intermediate Similarity	NPC140521
0.845	Intermediate Similarity	NPC201667
0.8444	Intermediate Similarity	NPC33986
0.8444	Intermediate Similarity	NPC472525
0.8438	Intermediate Similarity	NPC18128
0.8438	Intermediate Similarity	NPC77789
0.8433	Intermediate Similarity	NPC85435
0.8433	Intermediate Similarity	NPC469449
0.8433	Intermediate Similarity	NPC2363
0.8429	Intermediate Similarity	NPC108994
0.8429	Intermediate Similarity	NPC101255
0.8429	Intermediate Similarity	NPC43716
0.8429	Intermediate Similarity	NPC475719
0.8429	Intermediate Similarity	NPC106126
0.8425	Intermediate Similarity	NPC163200
0.8425	Intermediate Similarity	NPC180006
0.8425	Intermediate Similarity	NPC302107
0.8425	Intermediate Similarity	NPC235190
0.8421	Intermediate Similarity	NPC103799
0.8421	Intermediate Similarity	NPC181497
0.8421	Intermediate Similarity	NPC271945
0.8413	Intermediate Similarity	NPC172253
0.8413	Intermediate Similarity	NPC59561
0.8413	Intermediate Similarity	NPC295259
0.8409	Intermediate Similarity	NPC134360
0.8409	Intermediate Similarity	NPC474289
0.8409	Intermediate Similarity	NPC93962
0.8406	Intermediate Similarity	NPC195357
0.8406	Intermediate Similarity	NPC152771
0.8406	Intermediate Similarity	NPC170812
0.84	Intermediate Similarity	NPC474933
0.84	Intermediate Similarity	NPC33270
0.84	Intermediate Similarity	NPC69261
0.8397	Intermediate Similarity	NPC66331
0.8397	Intermediate Similarity	NPC149796
0.8397	Intermediate Similarity	NPC257947
0.8394	Intermediate Similarity	NPC211110
0.8387	Intermediate Similarity	NPC808
0.8385	Intermediate Similarity	NPC167571
0.8385	Intermediate Similarity	NPC278552
0.8385	Intermediate Similarity	NPC249836
0.8385	Intermediate Similarity	NPC207179
0.8382	Intermediate Similarity	NPC246177
0.8382	Intermediate Similarity	NPC317045
0.8372	Intermediate Similarity	NPC273772
0.8372	Intermediate Similarity	NPC472518
0.8372	Intermediate Similarity	NPC109675
0.837	Intermediate Similarity	NPC225696
0.837	Intermediate Similarity	NPC198154
0.837	Intermediate Similarity	NPC124085
0.837	Intermediate Similarity	NPC307412
0.837	Intermediate Similarity	NPC296915
0.837	Intermediate Similarity	NPC55149
0.837	Intermediate Similarity	NPC223008
0.837	Intermediate Similarity	NPC98179
0.837	Intermediate Similarity	NPC115335
0.837	Intermediate Similarity	NPC253574
0.837	Intermediate Similarity	NPC97834
0.837	Intermediate Similarity	NPC117048
0.8369	Intermediate Similarity	NPC40222
0.8369	Intermediate Similarity	NPC268515
0.8358	Intermediate Similarity	NPC307289
0.8358	Intermediate Similarity	NPC475008
0.8358	Intermediate Similarity	NPC186097
0.8358	Intermediate Similarity	NPC475009
0.8358	Intermediate Similarity	NPC128348
0.8358	Intermediate Similarity	NPC112192
0.8358	Intermediate Similarity	NPC469956
0.8358	Intermediate Similarity	NPC164236
0.8358	Intermediate Similarity	NPC189106
0.8358	Intermediate Similarity	NPC309717
0.8358	Intermediate Similarity	NPC14248
0.8358	Intermediate Similarity	NPC66384
0.8347	Intermediate Similarity	NPC79543
0.8346	Intermediate Similarity	NPC476399
0.8346	Intermediate Similarity	NPC80170
0.8346	Intermediate Similarity	NPC247553
0.8346	Intermediate Similarity	NPC12694
0.8333	Intermediate Similarity	NPC71903
0.8333	Intermediate Similarity	NPC74821
0.8333	Intermediate Similarity	NPC96705
0.8333	Intermediate Similarity	NPC190514
0.8333	Intermediate Similarity	NPC199204

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 NPC219923 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	829
0.2-0.3	1602
0.3-0.4	2610
0.4-0.5	1898
0.5-0.6	1175
0.6-0.7	642
0.7-0.8	156
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8651	High Similarity	NPD422	Phase 1
0.8485	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4908	Phase 1
0.8333	Intermediate Similarity	NPD1548	Phase 1
0.8296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD5124	Phase 1
0.8217	Intermediate Similarity	NPD1610	Phase 2
0.8209	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD3027	Phase 3
0.8014	Intermediate Similarity	NPD1652	Phase 2
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD2797	Approved
0.7958	Intermediate Similarity	NPD3750	Approved
0.7956	Intermediate Similarity	NPD1613	Approved
0.7956	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD1240	Approved
0.7943	Intermediate Similarity	NPD1549	Phase 2
0.7929	Intermediate Similarity	NPD2935	Discontinued
0.7863	Intermediate Similarity	NPD3496	Discontinued
0.7862	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7033	Discontinued
0.7857	Intermediate Similarity	NPD5535	Approved
0.7857	Intermediate Similarity	NPD1510	Phase 2
0.7852	Intermediate Similarity	NPD2861	Phase 2
0.7842	Intermediate Similarity	NPD1607	Approved
0.7826	Intermediate Similarity	NPD4060	Phase 1
0.781	Intermediate Similarity	NPD3268	Approved
0.781	Intermediate Similarity	NPD6798	Discontinued
0.7805	Intermediate Similarity	NPD3134	Approved
0.7801	Intermediate Similarity	NPD1551	Phase 2
0.7794	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6799	Approved
0.7786	Intermediate Similarity	NPD4626	Approved
0.7785	Intermediate Similarity	NPD7411	Suspended
0.7785	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6355	Discontinued
0.7769	Intermediate Similarity	NPD940	Approved
0.7769	Intermediate Similarity	NPD846	Approved
0.7763	Intermediate Similarity	NPD7075	Discontinued
0.7762	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD3225	Approved
0.7742	Intermediate Similarity	NPD1358	Approved
0.7727	Intermediate Similarity	NPD3847	Discontinued
0.7721	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4380	Phase 2
0.771	Intermediate Similarity	NPD5691	Approved
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD2796	Approved
0.7664	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6233	Phase 2
0.7619	Intermediate Similarity	NPD2533	Approved
0.7619	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD6801	Discontinued
0.7616	Intermediate Similarity	NPD1934	Approved
0.7609	Intermediate Similarity	NPD4625	Phase 3
0.7606	Intermediate Similarity	NPD3748	Approved
0.76	Intermediate Similarity	NPD6599	Discontinued
0.7586	Intermediate Similarity	NPD4628	Phase 3
0.7586	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD1653	Approved
0.7574	Intermediate Similarity	NPD1203	Approved
0.7566	Intermediate Similarity	NPD7819	Suspended
0.7556	Intermediate Similarity	NPD4749	Approved
0.7554	Intermediate Similarity	NPD1296	Phase 2
0.7551	Intermediate Similarity	NPD7213	Phase 3
0.7551	Intermediate Similarity	NPD7212	Phase 2
0.7537	Intermediate Similarity	NPD1091	Approved
0.7537	Intermediate Similarity	NPD1535	Discovery
0.7536	Intermediate Similarity	NPD6832	Phase 2
0.7532	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD968	Approved
0.7518	Intermediate Similarity	NPD4340	Discontinued
0.7517	Intermediate Similarity	NPD5403	Approved
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD1894	Discontinued
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6234	Discontinued
0.7481	Intermediate Similarity	NPD1481	Phase 2
0.7468	Intermediate Similarity	NPD4965	Approved
0.7468	Intermediate Similarity	NPD4966	Approved
0.7468	Intermediate Similarity	NPD4967	Phase 2
0.7448	Intermediate Similarity	NPD2424	Discontinued
0.7445	Intermediate Similarity	NPD3266	Approved
0.7445	Intermediate Similarity	NPD3267	Approved
0.7432	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7097	Phase 1
0.7405	Intermediate Similarity	NPD6671	Approved
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7402	Intermediate Similarity	NPD2684	Approved
0.7391	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7447	Phase 1
0.7383	Intermediate Similarity	NPD5401	Approved
0.7383	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7266	Discontinued
0.7379	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5762	Approved
0.7379	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6002	Phase 3
0.7379	Intermediate Similarity	NPD5763	Approved
0.7379	Intermediate Similarity	NPD6005	Phase 3
0.7379	Intermediate Similarity	NPD6004	Phase 3
0.7376	Intermediate Similarity	NPD4062	Phase 3
0.7368	Intermediate Similarity	NPD9545	Approved
0.7361	Intermediate Similarity	NPD2799	Discontinued
0.7361	Intermediate Similarity	NPD4308	Phase 3
0.7358	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2859	Approved
0.7355	Intermediate Similarity	NPD3882	Suspended
0.7355	Intermediate Similarity	NPD2860	Approved
0.7353	Intermediate Similarity	NPD9717	Approved
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD3018	Phase 2
0.7338	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD5844	Phase 1
0.7324	Intermediate Similarity	NPD4140	Approved
0.7323	Intermediate Similarity	NPD290	Approved
0.7315	Intermediate Similarity	NPD1511	Approved
0.731	Intermediate Similarity	NPD6032	Approved
0.7308	Intermediate Similarity	NPD7843	Approved
0.7308	Intermediate Similarity	NPD3749	Approved
0.7305	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD9697	Approved
0.7301	Intermediate Similarity	NPD6559	Discontinued
0.7299	Intermediate Similarity	NPD6583	Phase 3
0.7299	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6582	Phase 2
0.729	Intermediate Similarity	NPD5402	Approved
0.7285	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD2933	Approved
0.7273	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD2934	Approved
0.7267	Intermediate Similarity	NPD3818	Discontinued
0.7259	Intermediate Similarity	NPD1778	Approved
0.7258	Intermediate Similarity	NPD1242	Phase 1
0.725	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6166	Phase 2
0.7248	Intermediate Similarity	NPD6667	Approved
0.7248	Intermediate Similarity	NPD6666	Approved
0.7234	Intermediate Similarity	NPD7095	Approved
0.7234	Intermediate Similarity	NPD5163	Phase 2
0.7233	Intermediate Similarity	NPD7229	Phase 3
0.7226	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD7286	Phase 2
0.7222	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1512	Approved
0.7218	Intermediate Similarity	NPD9493	Approved
0.7209	Intermediate Similarity	NPD5451	Approved
0.7209	Intermediate Similarity	NPD4750	Phase 3
0.7205	Intermediate Similarity	NPD7473	Discontinued
0.7203	Intermediate Similarity	NPD2238	Phase 2
0.72	Intermediate Similarity	NPD4357	Discontinued
0.7197	Intermediate Similarity	NPD6971	Discontinued
0.7194	Intermediate Similarity	NPD6362	Approved
0.7192	Intermediate Similarity	NPD6099	Approved
0.7192	Intermediate Similarity	NPD4477	Approved
0.7192	Intermediate Similarity	NPD4476	Approved
0.7192	Intermediate Similarity	NPD6100	Approved
0.7185	Intermediate Similarity	NPD5585	Approved
0.7183	Intermediate Similarity	NPD2313	Discontinued
0.7183	Intermediate Similarity	NPD1048	Approved
0.7178	Intermediate Similarity	NPD7074	Phase 3
0.7177	Intermediate Similarity	NPD3020	Approved
0.7174	Intermediate Similarity	NPD2982	Phase 2
0.7174	Intermediate Similarity	NPD2983	Phase 2
0.7172	Intermediate Similarity	NPD4538	Approved
0.7172	Intermediate Similarity	NPD4536	Approved
0.7172	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6959	Discontinued
0.717	Intermediate Similarity	NPD7199	Phase 2
0.7162	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1243	Approved
0.7162	Intermediate Similarity	NPD2800	Approved
0.716	Intermediate Similarity	NPD7228	Approved
0.7153	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1611	Approved
0.7152	Intermediate Similarity	NPD3536	Discontinued
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7134	Intermediate Similarity	NPD5953	Discontinued
0.7134	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5588	Approved
0.7122	Intermediate Similarity	NPD1283	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