NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.08
Volume:	182.865
LogP:	1.147
LogD:	1.348
LogS:	-1.627
# Rotatable Bonds:	1
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	3.102
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.5
MDCK Permeability:	1.0191515684709884e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.735
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.36

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	53.49498748779297%
Volume Distribution (VD):	0.741
Pgp-substrate:	34.71241760253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.844
CYP1A2-substrate:	0.854
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.735
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	16.786
Half-life (T1/2):	0.804

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.635
Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.861
Carcinogencity:	0.911
Eye Corrosion:	0.01
Eye Irritation:	0.902
Respiratory Toxicity:	0.141

Download Data

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

Natural Product: NPC96423

Natural Product ID:	NPC96423
*Common Name:**	5-Hydroxy-3S-Hydroxymethyl-6-Methyl-2,3-Dihydrobenzofuran
IUPAC Name:	(3S)-3-(hydroxymethyl)-6-methyl-2,3-dihydro-1-benzofuran-5-ol
Synonyms:
Standard InCHIKey:	XNGDDFPFJFPWRU-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C10H12O3/c1-6-2-10-8(3-9(6)12)7(4-11)5-13-10/h2-3,7,11-12H,4-5H2,1H3/t7-/m0/s1
SMILES:	OC[C@H]1COc2c1cc(O)c(c2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079035
PubChem CID:	44253995
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004189] Coumarans

*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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	50000.0	nM	PMID[451741]
NPT35	Others	n.a.		IC50	=	177000.0	nM	PMID[451741]

☑ 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 NPC96423 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	335
0.1-0.2	1506
0.2-0.3	4460
0.3-0.4	12552
0.4-0.5	6078
0.5-0.6	5649
0.6-0.7	9402
0.7-0.8	2469
0.8-0.85	204
0.85-0.9	41
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8992	High Similarity	NPC475529
0.888	High Similarity	NPC325003
0.872	High Similarity	NPC38604
0.872	High Similarity	NPC211179
0.8678	High Similarity	NPC473875
0.8651	High Similarity	NPC266868
0.8651	High Similarity	NPC472795
0.8651	High Similarity	NPC472797
0.8651	High Similarity	NPC472796
0.8629	High Similarity	NPC81641
0.8629	High Similarity	NPC476254
0.8629	High Similarity	NPC131397
0.8618	High Similarity	NPC261992
0.8595	High Similarity	NPC474131
0.8594	High Similarity	NPC51262
0.8583	High Similarity	NPC196193
0.8583	High Similarity	NPC283616
0.8537	High Similarity	NPC188997
0.8522	High Similarity	NPC241549
0.8512	High Similarity	NPC471449
0.8512	High Similarity	NPC32152
0.8512	High Similarity	NPC51341
0.8509	High Similarity	NPC30416
0.8492	Intermediate Similarity	NPC469386
0.8487	Intermediate Similarity	NPC301321
0.848	Intermediate Similarity	NPC252962
0.8473	Intermediate Similarity	NPC327735
0.8468	Intermediate Similarity	NPC96940
0.8462	Intermediate Similarity	NPC275627
0.8455	Intermediate Similarity	NPC48623
0.8455	Intermediate Similarity	NPC212965
0.8455	Intermediate Similarity	NPC168707
0.8443	Intermediate Similarity	NPC232295
0.8438	Intermediate Similarity	NPC11089
0.8435	Intermediate Similarity	NPC233320
0.8425	Intermediate Similarity	NPC19694
0.8417	Intermediate Similarity	NPC154256
0.8417	Intermediate Similarity	NPC290470
0.8413	Intermediate Similarity	NPC245060
0.839	Intermediate Similarity	NPC228452
0.839	Intermediate Similarity	NPC98372
0.8387	Intermediate Similarity	NPC120638
0.8387	Intermediate Similarity	NPC150026
0.8387	Intermediate Similarity	NPC18128
0.8387	Intermediate Similarity	NPC77789
0.8385	Intermediate Similarity	NPC105554
0.8374	Intermediate Similarity	NPC45663
0.8374	Intermediate Similarity	NPC218753
0.8372	Intermediate Similarity	NPC472590
0.837	Intermediate Similarity	NPC477616
0.8347	Intermediate Similarity	NPC187993
0.8347	Intermediate Similarity	NPC238176
0.8346	Intermediate Similarity	NPC98395
0.8333	Intermediate Similarity	NPC126101
0.8333	Intermediate Similarity	NPC232165
0.8308	Intermediate Similarity	NPC18842
0.8308	Intermediate Similarity	NPC472798
0.8281	Intermediate Similarity	NPC47283
0.8281	Intermediate Similarity	NPC39064
0.8268	Intermediate Similarity	NPC262573
0.8268	Intermediate Similarity	NPC471215
0.8264	Intermediate Similarity	NPC69539
0.825	Intermediate Similarity	NPC470837
0.8244	Intermediate Similarity	NPC26394
0.824	Intermediate Similarity	NPC204535
0.824	Intermediate Similarity	NPC46586
0.8235	Intermediate Similarity	NPC474920
0.8226	Intermediate Similarity	NPC277798
0.8226	Intermediate Similarity	NPC100108
0.8222	Intermediate Similarity	NPC311530
0.822	Intermediate Similarity	NPC168657
0.8217	Intermediate Similarity	NPC97326
0.8211	Intermediate Similarity	NPC184302
0.8211	Intermediate Similarity	NPC137294
0.8211	Intermediate Similarity	NPC85895
0.8209	Intermediate Similarity	NPC292882
0.8197	Intermediate Similarity	NPC244816
0.8197	Intermediate Similarity	NPC50521
0.8197	Intermediate Similarity	NPC221549
0.8195	Intermediate Similarity	NPC54743
0.8195	Intermediate Similarity	NPC476698
0.8195	Intermediate Similarity	NPC10737
0.8195	Intermediate Similarity	NPC475628
0.8195	Intermediate Similarity	NPC263367
0.8195	Intermediate Similarity	NPC177160
0.8195	Intermediate Similarity	NPC472800
0.8195	Intermediate Similarity	NPC477939
0.8195	Intermediate Similarity	NPC141717
0.8195	Intermediate Similarity	NPC29799
0.8195	Intermediate Similarity	NPC209985
0.8195	Intermediate Similarity	NPC156502
0.8189	Intermediate Similarity	NPC470726
0.8189	Intermediate Similarity	NPC293801
0.8182	Intermediate Similarity	NPC16485
0.8182	Intermediate Similarity	NPC473718
0.8175	Intermediate Similarity	NPC474130
0.8174	Intermediate Similarity	NPC475225
0.8174	Intermediate Similarity	NPC130817
0.8168	Intermediate Similarity	NPC230219
0.816	Intermediate Similarity	NPC193364
0.8154	Intermediate Similarity	NPC470727
0.8154	Intermediate Similarity	NPC27187
0.8154	Intermediate Similarity	NPC470225
0.8154	Intermediate Similarity	NPC220935
0.8151	Intermediate Similarity	NPC54373
0.8148	Intermediate Similarity	NPC27495
0.8148	Intermediate Similarity	NPC254759
0.8148	Intermediate Similarity	NPC160283
0.814	Intermediate Similarity	NPC63179
0.813	Intermediate Similarity	NPC139047
0.813	Intermediate Similarity	NPC329980
0.813	Intermediate Similarity	NPC190514
0.8125	Intermediate Similarity	NPC283049
0.8125	Intermediate Similarity	NPC50315
0.8125	Intermediate Similarity	NPC230479
0.8125	Intermediate Similarity	NPC470724
0.8125	Intermediate Similarity	NPC26879
0.812	Intermediate Similarity	NPC66834
0.812	Intermediate Similarity	NPC134968
0.8115	Intermediate Similarity	NPC150624
0.811	Intermediate Similarity	NPC61685
0.811	Intermediate Similarity	NPC248557
0.8106	Intermediate Similarity	NPC269528
0.8106	Intermediate Similarity	NPC211352
0.8103	Intermediate Similarity	NPC8302
0.8099	Intermediate Similarity	NPC161696
0.8092	Intermediate Similarity	NPC207892
0.8092	Intermediate Similarity	NPC118114
0.8092	Intermediate Similarity	NPC300875
0.8092	Intermediate Similarity	NPC17343
0.8092	Intermediate Similarity	NPC196765
0.8092	Intermediate Similarity	NPC236014
0.8092	Intermediate Similarity	NPC150011
0.8092	Intermediate Similarity	NPC271945
0.8092	Intermediate Similarity	NPC129106
0.8092	Intermediate Similarity	NPC164574
0.8092	Intermediate Similarity	NPC268917
0.8092	Intermediate Similarity	NPC153019
0.8092	Intermediate Similarity	NPC228369
0.8092	Intermediate Similarity	NPC12875
0.8092	Intermediate Similarity	NPC206224
0.8092	Intermediate Similarity	NPC129784
0.8092	Intermediate Similarity	NPC476166
0.8092	Intermediate Similarity	NPC181497
0.8092	Intermediate Similarity	NPC280653
0.8088	Intermediate Similarity	NPC247291
0.8087	Intermediate Similarity	NPC12870
0.8087	Intermediate Similarity	NPC235762
0.8087	Intermediate Similarity	NPC24327
0.8087	Intermediate Similarity	NPC471228
0.808	Intermediate Similarity	NPC129176
0.8077	Intermediate Similarity	NPC96719
0.8077	Intermediate Similarity	NPC222108
0.8074	Intermediate Similarity	NPC183781
0.8074	Intermediate Similarity	NPC471388
0.807	Intermediate Similarity	NPC174911
0.807	Intermediate Similarity	NPC130103
0.8065	Intermediate Similarity	NPC121866
0.8062	Intermediate Similarity	NPC46978
0.806	Intermediate Similarity	NPC173660
0.8049	Intermediate Similarity	NPC476266
0.8049	Intermediate Similarity	NPC33270
0.8049	Intermediate Similarity	NPC69261
0.8045	Intermediate Similarity	NPC49603
0.8045	Intermediate Similarity	NPC187616
0.8045	Intermediate Similarity	NPC193026
0.8034	Intermediate Similarity	NPC164576
0.8033	Intermediate Similarity	NPC167934
0.8033	Intermediate Similarity	NPC808
0.803	Intermediate Similarity	NPC289624
0.803	Intermediate Similarity	NPC27578
0.803	Intermediate Similarity	NPC13005
0.8029	Intermediate Similarity	NPC107161
0.8016	Intermediate Similarity	NPC285289
0.8015	Intermediate Similarity	NPC64201
0.8015	Intermediate Similarity	NPC42300
0.8015	Intermediate Similarity	NPC241522
0.8015	Intermediate Similarity	NPC187998
0.8015	Intermediate Similarity	NPC257582
0.8015	Intermediate Similarity	NPC77040
0.8015	Intermediate Similarity	NPC242807
0.8015	Intermediate Similarity	NPC174495
0.8015	Intermediate Similarity	NPC153739
0.8015	Intermediate Similarity	NPC92164
0.8015	Intermediate Similarity	NPC229231
0.8015	Intermediate Similarity	NPC145305
0.8	Intermediate Similarity	NPC53986
0.8	Intermediate Similarity	NPC40377
0.8	Intermediate Similarity	NPC255068
0.8	Intermediate Similarity	NPC14177
0.8	Intermediate Similarity	NPC81261
0.8	Intermediate Similarity	NPC477938
0.8	Intermediate Similarity	NPC38664
0.8	Intermediate Similarity	NPC470084
0.7985	Intermediate Similarity	NPC327382
0.7985	Intermediate Similarity	NPC475011
0.7985	Intermediate Similarity	NPC201357
0.7985	Intermediate Similarity	NPC281521
0.7985	Intermediate Similarity	NPC195022
0.7985	Intermediate Similarity	NPC255147

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 NPC96423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	950
0.2-0.3	1838
0.3-0.4	2738
0.4-0.5	1622
0.5-0.6	1052
0.6-0.7	557
0.7-0.8	82
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8699	High Similarity	NPD6696	Suspended
0.8492	Intermediate Similarity	NPD2861	Phase 2
0.8468	Intermediate Similarity	NPD4749	Approved
0.8438	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6671	Approved
0.816	Intermediate Similarity	NPD1610	Phase 2
0.8125	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD968	Approved
0.8017	Intermediate Similarity	NPD1398	Phase 1
0.7967	Intermediate Similarity	NPD7340	Approved
0.7966	Intermediate Similarity	NPD290	Approved
0.7939	Intermediate Similarity	NPD4625	Phase 3
0.7863	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD1778	Approved
0.784	Intermediate Similarity	NPD1548	Phase 1
0.7807	Intermediate Similarity	NPD288	Approved
0.7795	Intermediate Similarity	NPD3496	Discontinued
0.7761	Intermediate Similarity	NPD1613	Approved
0.7761	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD4750	Phase 3
0.7652	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1712	Approved
0.7652	Intermediate Similarity	NPD2237	Approved
0.7609	Intermediate Similarity	NPD6099	Approved
0.7609	Intermediate Similarity	NPD6100	Approved
0.7603	Intermediate Similarity	NPD2684	Approved
0.7597	Intermediate Similarity	NPD1611	Approved
0.7597	Intermediate Similarity	NPD1091	Approved
0.7594	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD844	Approved
0.7554	Intermediate Similarity	NPD6005	Phase 3
0.7554	Intermediate Similarity	NPD6002	Phase 3
0.7554	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6004	Phase 3
0.7538	Intermediate Similarity	NPD1608	Approved
0.7462	Intermediate Similarity	NPD422	Phase 1
0.746	Intermediate Similarity	NPD7157	Approved
0.7442	Intermediate Similarity	NPD4626	Approved
0.7431	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5762	Approved
0.7429	Intermediate Similarity	NPD5763	Approved
0.7419	Intermediate Similarity	NPD228	Approved
0.7407	Intermediate Similarity	NPD3027	Phase 3
0.7405	Intermediate Similarity	NPD2231	Phase 2
0.7405	Intermediate Similarity	NPD2235	Phase 2
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2238	Phase 2
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7364	Intermediate Similarity	NPD5691	Approved
0.736	Intermediate Similarity	NPD7843	Approved
0.736	Intermediate Similarity	NPD7635	Approved
0.7348	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD600	Approved
0.7333	Intermediate Similarity	NPD596	Approved
0.7328	Intermediate Similarity	NPD3705	Approved
0.7319	Intermediate Similarity	NPD5735	Approved
0.7313	Intermediate Similarity	NPD558	Phase 2
0.7308	Intermediate Similarity	NPD17	Approved
0.7293	Intermediate Similarity	NPD8651	Approved
0.7273	Intermediate Similarity	NPD2232	Approved
0.7273	Intermediate Similarity	NPD2233	Approved
0.7273	Intermediate Similarity	NPD2230	Approved
0.7273	Intermediate Similarity	NPD3892	Phase 2
0.7266	Intermediate Similarity	NPD2157	Approved
0.7266	Intermediate Similarity	NPD6653	Approved
0.726	Intermediate Similarity	NPD6090	Discontinued
0.7246	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD821	Approved
0.7218	Intermediate Similarity	NPD5327	Phase 3
0.7209	Intermediate Similarity	NPD7644	Approved
0.7203	Intermediate Similarity	NPD6674	Discontinued
0.7193	Intermediate Similarity	NPD9295	Approved
0.7185	Intermediate Similarity	NPD3691	Phase 2
0.7185	Intermediate Similarity	NPD3690	Phase 2
0.7185	Intermediate Similarity	NPD6584	Phase 3
0.7174	Intermediate Similarity	NPD840	Approved
0.7174	Intermediate Similarity	NPD839	Approved
0.7163	Intermediate Similarity	NPD7033	Discontinued
0.7154	Intermediate Similarity	NPD1182	Approved
0.7143	Intermediate Similarity	NPD4097	Suspended
0.7143	Intermediate Similarity	NPD1840	Phase 2
0.7122	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3620	Phase 2
0.7111	Intermediate Similarity	NPD2797	Approved
0.7107	Intermediate Similarity	NPD846	Approved
0.7107	Intermediate Similarity	NPD940	Approved
0.7101	Intermediate Similarity	NPD7985	Registered
0.7099	Intermediate Similarity	NPD5585	Approved
0.7099	Intermediate Similarity	NPD1357	Approved
0.7094	Intermediate Similarity	NPD845	Approved
0.7075	Intermediate Similarity	NPD2534	Approved
0.7075	Intermediate Similarity	NPD2533	Approved
0.7075	Intermediate Similarity	NPD2532	Approved
0.7054	Intermediate Similarity	NPD709	Approved
0.7037	Intermediate Similarity	NPD1283	Approved
0.7031	Intermediate Similarity	NPD5283	Phase 1
0.7021	Intermediate Similarity	NPD6353	Approved
0.7014	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7037	Approved
0.6993	Remote Similarity	NPD1551	Phase 2
0.6986	Remote Similarity	NPD2677	Approved
0.6985	Remote Similarity	NPD6362	Approved
0.6978	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3444	Approved
0.697	Remote Similarity	NPD3445	Approved
0.697	Remote Similarity	NPD3443	Approved
0.6963	Remote Similarity	NPD6582	Phase 2
0.6963	Remote Similarity	NPD6583	Phase 3
0.6963	Remote Similarity	NPD3685	Discontinued
0.6953	Remote Similarity	NPD1138	Approved
0.695	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6355	Discontinued
0.695	Remote Similarity	NPD5124	Phase 1
0.6944	Remote Similarity	NPD1375	Discontinued
0.6942	Remote Similarity	NPD3020	Approved
0.694	Remote Similarity	NPD1535	Discovery
0.694	Remote Similarity	NPD776	Approved
0.6939	Remote Similarity	NPD6667	Approved
0.6939	Remote Similarity	NPD6666	Approved
0.6934	Remote Similarity	NPD4624	Approved
0.6933	Remote Similarity	NPD1653	Approved
0.6929	Remote Similarity	NPD3162	Approved
0.6929	Remote Similarity	NPD3163	Approved
0.6928	Remote Similarity	NPD5929	Approved
0.6923	Remote Similarity	NPD5588	Approved
0.6923	Remote Similarity	NPD2557	Approved
0.6923	Remote Similarity	NPD9365	Approved
0.6918	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4628	Phase 3
0.6913	Remote Similarity	NPD2676	Approved
0.6913	Remote Similarity	NPD2675	Approved
0.6901	Remote Similarity	NPD1607	Approved
0.6894	Remote Similarity	NPD3091	Approved
0.6891	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1481	Phase 2
0.6883	Remote Similarity	NPD2563	Approved
0.6883	Remote Similarity	NPD2560	Approved
0.6879	Remote Similarity	NPD1558	Phase 1
0.6875	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD1139	Approved
0.6875	Remote Similarity	NPD1137	Approved
0.6863	Remote Similarity	NPD37	Approved
0.6861	Remote Similarity	NPD4098	Discontinued
0.6861	Remote Similarity	NPD3094	Phase 2
0.6857	Remote Similarity	NPD411	Approved
0.6857	Remote Similarity	NPD3268	Approved
0.6853	Remote Similarity	NPD4536	Approved
0.6853	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4538	Approved
0.6846	Remote Similarity	NPD1578	Phase 2
0.6842	Remote Similarity	NPD1651	Approved
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4966	Approved
0.6839	Remote Similarity	NPD4965	Approved
0.6838	Remote Similarity	NPD4359	Approved
0.6833	Remote Similarity	NPD1809	Phase 2
0.6829	Remote Similarity	NPD291	Approved
0.6828	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2342	Discontinued
0.6824	Remote Similarity	NPD5058	Phase 3
0.6815	Remote Similarity	NPD3092	Approved
0.6815	Remote Similarity	NPD1281	Approved
0.6803	Remote Similarity	NPD7466	Approved
0.68	Remote Similarity	NPD9697	Approved
0.6791	Remote Similarity	NPD5125	Phase 3
0.6791	Remote Similarity	NPD2667	Approved
0.6791	Remote Similarity	NPD5846	Approved
0.6791	Remote Similarity	NPD2668	Approved
0.6791	Remote Similarity	NPD5126	Approved
0.6791	Remote Similarity	NPD6516	Phase 2
0.6788	Remote Similarity	NPD3225	Approved
0.6781	Remote Similarity	NPD1549	Phase 2
0.6781	Remote Similarity	NPD2424	Discontinued
0.6776	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3226	Approved
0.6769	Remote Similarity	NPD1241	Discontinued
0.6769	Remote Similarity	NPD592	Approved
0.6769	Remote Similarity	NPD594	Approved
0.6765	Remote Similarity	NPD9717	Approved
0.6761	Remote Similarity	NPD1240	Approved
0.6759	Remote Similarity	NPD6032	Approved
0.6759	Remote Similarity	NPD2161	Phase 2
0.6753	Remote Similarity	NPD1934	Approved
0.6752	Remote Similarity	NPD6234	Discontinued
0.6748	Remote Similarity	NPD1242	Phase 1
0.6746	Remote Similarity	NPD3134	Approved
0.6746	Remote Similarity	NPD1445	Approved
0.6746	Remote Similarity	NPD1444	Approved
0.6739	Remote Similarity	NPD1794	Approved
0.6739	Remote Similarity	NPD987	Approved
0.6738	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2200	Suspended
0.6736	Remote Similarity	NPD696	Discontinued

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