NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.09
Volume:	200.161
LogP:	1.978
LogD:	1.619
LogS:	-1.686
# 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:	0.711
Synthetic Accessibility Score:	3.005
Fsp3:	0.455
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:	-4.462
MDCK Permeability:	1.6065172530943528e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.37
Plasma Protein Binding (PPB):	69.02779388427734%
Volume Distribution (VD):	1.69
Pgp-substrate:	20.373504638671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.231
CYP1A2-substrate:	0.237
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.72
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.435
CYP2D6-substrate:	0.849
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.277

ADMET: Excretion

Clearance (CL):	11.35
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.148
Skin Sensitization:	0.515
Carcinogencity:	0.523
Eye Corrosion:	0.057
Eye Irritation:	0.892
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC475529

Natural Product ID:	NPC475529
*Common Name:**	2-(1-Hydroxy-1-Methyl)-2,3-Dihydrobenzofuran-5-Ol
IUPAC Name:	2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-5-ol
Synonyms:
Standard InCHIKey:	RKKRVILMZZPTOV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O3/c1-11(2,13)10-6-7-5-8(12)3-4-9(7)14-10/h3-5,10,12-13H,6H2,1-2H3
SMILES:	Oc1ccc2c(c1)CC(O2)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507380
PubChem CID:	10442610
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	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ 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	7

Activity Type	# Activity
NON-MOLECULAR	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-11.8	%	PMID[468979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	15.9	%	PMID[468979]
NPT1	Others	Radical scavenging activity		Activity	=	35.3	%	PMID[468979]
NPT1	Others	Radical scavenging activity		Activity	=	85.8	%	PMID[468979]
NPT1	Others	Radical scavenging activity		Activity	=	89.1	%	PMID[468979]
NPT1	Others	Radical scavenging activity		Activity	=	90.2	%	PMID[468979]
NPT1	Others	Radical scavenging activity		Activity	=	90.4	%	PMID[468979]

☑ 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 NPC475529 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	336
0.1-0.2	1504
0.2-0.3	4780
0.3-0.4	12350
0.4-0.5	5815
0.5-0.6	5202
0.6-0.7	9407
0.7-0.8	2906
0.8-0.85	364
0.85-0.9	28
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC473875
0.9052	High Similarity	NPC154256
0.9052	High Similarity	NPC290470
0.9024	High Similarity	NPC19694
0.8992	High Similarity	NPC96423
0.888	High Similarity	NPC11089
0.877	High Similarity	NPC474130
0.8739	High Similarity	NPC283616
0.8689	High Similarity	NPC204535
0.8689	High Similarity	NPC46586
0.8682	High Similarity	NPC134968
0.8651	High Similarity	NPC97326
0.864	High Similarity	NPC469386
0.8596	High Similarity	NPC233320
0.8595	High Similarity	NPC232295
0.8583	High Similarity	NPC220935
0.8547	High Similarity	NPC474920
0.8527	High Similarity	NPC105554
0.8512	High Similarity	NPC32152
0.8487	Intermediate Similarity	NPC473718
0.8485	Intermediate Similarity	NPC292882
0.848	Intermediate Similarity	NPC476254
0.848	Intermediate Similarity	NPC131397
0.8473	Intermediate Similarity	NPC126101
0.8462	Intermediate Similarity	NPC264956
0.8462	Intermediate Similarity	NPC193026
0.8462	Intermediate Similarity	NPC187616
0.8462	Intermediate Similarity	NPC49603
0.8462	Intermediate Similarity	NPC275627
0.8448	Intermediate Similarity	NPC473524
0.8443	Intermediate Similarity	NPC474131
0.8438	Intermediate Similarity	NPC325003
0.8435	Intermediate Similarity	NPC194034
0.843	Intermediate Similarity	NPC329980
0.8425	Intermediate Similarity	NPC40377
0.8425	Intermediate Similarity	NPC63179
0.8421	Intermediate Similarity	NPC254759
0.8421	Intermediate Similarity	NPC160283
0.8417	Intermediate Similarity	NPC69539
0.8387	Intermediate Similarity	NPC150026
0.8372	Intermediate Similarity	NPC162801
0.8362	Intermediate Similarity	NPC241549
0.8361	Intermediate Similarity	NPC320987
0.8361	Intermediate Similarity	NPC51341
0.8361	Intermediate Similarity	NPC181969
0.8361	Intermediate Similarity	NPC471449
0.8359	Intermediate Similarity	NPC158477
0.8347	Intermediate Similarity	NPC187993
0.8347	Intermediate Similarity	NPC238176
0.8333	Intermediate Similarity	NPC177160
0.8333	Intermediate Similarity	NPC472334
0.8333	Intermediate Similarity	NPC209985
0.8333	Intermediate Similarity	NPC301321
0.8333	Intermediate Similarity	NPC156502
0.8333	Intermediate Similarity	NPC10737
0.8333	Intermediate Similarity	NPC475628
0.8333	Intermediate Similarity	NPC263367
0.8333	Intermediate Similarity	NPC477939
0.8333	Intermediate Similarity	NPC81641
0.8333	Intermediate Similarity	NPC472336
0.8333	Intermediate Similarity	NPC29799
0.8333	Intermediate Similarity	NPC54743
0.8333	Intermediate Similarity	NPC327735
0.8321	Intermediate Similarity	NPC124085
0.8321	Intermediate Similarity	NPC106215
0.8321	Intermediate Similarity	NPC16485
0.8321	Intermediate Similarity	NPC117048
0.8308	Intermediate Similarity	NPC18842
0.8308	Intermediate Similarity	NPC2190
0.8306	Intermediate Similarity	NPC470804
0.8306	Intermediate Similarity	NPC285289
0.8305	Intermediate Similarity	NPC195873
0.8296	Intermediate Similarity	NPC107161
0.8293	Intermediate Similarity	NPC177475
0.8293	Intermediate Similarity	NPC148615
0.8293	Intermediate Similarity	NPC35071
0.8284	Intermediate Similarity	NPC27495
0.8281	Intermediate Similarity	NPC45774
0.8281	Intermediate Similarity	NPC282703
0.8281	Intermediate Similarity	NPC129570
0.8281	Intermediate Similarity	NPC87224
0.8281	Intermediate Similarity	NPC11258
0.8281	Intermediate Similarity	NPC184733
0.8281	Intermediate Similarity	NPC128208
0.8281	Intermediate Similarity	NPC222572
0.8281	Intermediate Similarity	NPC21867
0.8279	Intermediate Similarity	NPC255675
0.8276	Intermediate Similarity	NPC251306
0.8271	Intermediate Similarity	NPC326797
0.8271	Intermediate Similarity	NPC176051
0.8271	Intermediate Similarity	NPC103976
0.8271	Intermediate Similarity	NPC474282
0.8271	Intermediate Similarity	NPC102904
0.8271	Intermediate Similarity	NPC107551
0.8268	Intermediate Similarity	NPC112596
0.8268	Intermediate Similarity	NPC58607
0.8268	Intermediate Similarity	NPC178284
0.8268	Intermediate Similarity	NPC476006
0.8268	Intermediate Similarity	NPC191037
0.8264	Intermediate Similarity	NPC221049
0.8258	Intermediate Similarity	NPC475029
0.8258	Intermediate Similarity	NPC472337
0.8258	Intermediate Similarity	NPC151224
0.8258	Intermediate Similarity	NPC476018
0.8254	Intermediate Similarity	NPC109822
0.8254	Intermediate Similarity	NPC94276
0.825	Intermediate Similarity	NPC161696
0.8244	Intermediate Similarity	NPC26394
0.8244	Intermediate Similarity	NPC85435
0.824	Intermediate Similarity	NPC209567
0.824	Intermediate Similarity	NPC474864
0.824	Intermediate Similarity	NPC135414
0.824	Intermediate Similarity	NPC120638
0.8235	Intermediate Similarity	NPC477616
0.8235	Intermediate Similarity	NPC98372
0.8231	Intermediate Similarity	NPC82503
0.8231	Intermediate Similarity	NPC277804
0.8226	Intermediate Similarity	NPC218753
0.8222	Intermediate Similarity	NPC247291
0.8222	Intermediate Similarity	NPC311530
0.8217	Intermediate Similarity	NPC266868
0.8211	Intermediate Similarity	NPC135961
0.8209	Intermediate Similarity	NPC232164
0.8209	Intermediate Similarity	NPC236306
0.8209	Intermediate Similarity	NPC473739
0.8203	Intermediate Similarity	NPC50368
0.8203	Intermediate Similarity	NPC41706
0.8203	Intermediate Similarity	NPC216836
0.8203	Intermediate Similarity	NPC163332
0.8203	Intermediate Similarity	NPC183181
0.8203	Intermediate Similarity	NPC292056
0.8203	Intermediate Similarity	NPC319625
0.8203	Intermediate Similarity	NPC118787
0.8203	Intermediate Similarity	NPC147821
0.8203	Intermediate Similarity	NPC111247
0.8195	Intermediate Similarity	NPC476698
0.8195	Intermediate Similarity	NPC230734
0.8195	Intermediate Similarity	NPC227503
0.8195	Intermediate Similarity	NPC3049
0.8195	Intermediate Similarity	NPC262585
0.8195	Intermediate Similarity	NPC474639
0.8195	Intermediate Similarity	NPC20829
0.8195	Intermediate Similarity	NPC18189
0.8189	Intermediate Similarity	NPC470510
0.8189	Intermediate Similarity	NPC167571
0.8189	Intermediate Similarity	NPC207179
0.8189	Intermediate Similarity	NPC194519
0.8189	Intermediate Similarity	NPC278552
0.8175	Intermediate Similarity	NPC12641
0.8175	Intermediate Similarity	NPC280092
0.8175	Intermediate Similarity	NPC93323
0.8175	Intermediate Similarity	NPC45257
0.8174	Intermediate Similarity	NPC130817
0.8168	Intermediate Similarity	NPC61477
0.8168	Intermediate Similarity	NPC261619
0.8168	Intermediate Similarity	NPC207400
0.8168	Intermediate Similarity	NPC230219
0.8168	Intermediate Similarity	NPC4940
0.8168	Intermediate Similarity	NPC126029
0.8168	Intermediate Similarity	NPC15658
0.8168	Intermediate Similarity	NPC219876
0.8168	Intermediate Similarity	NPC78770
0.8168	Intermediate Similarity	NPC181049
0.8168	Intermediate Similarity	NPC185604
0.8167	Intermediate Similarity	NPC301735
0.816	Intermediate Similarity	NPC476343
0.816	Intermediate Similarity	NPC476165
0.816	Intermediate Similarity	NPC212965
0.8154	Intermediate Similarity	NPC42300
0.8154	Intermediate Similarity	NPC187998
0.8154	Intermediate Similarity	NPC77040
0.8154	Intermediate Similarity	NPC64201
0.8154	Intermediate Similarity	NPC153739
0.8154	Intermediate Similarity	NPC174495
0.8154	Intermediate Similarity	NPC257582
0.8154	Intermediate Similarity	NPC92164
0.8154	Intermediate Similarity	NPC145305
0.8154	Intermediate Similarity	NPC242807
0.8154	Intermediate Similarity	NPC241522
0.8148	Intermediate Similarity	NPC309124
0.8148	Intermediate Similarity	NPC184797
0.814	Intermediate Similarity	NPC47283
0.814	Intermediate Similarity	NPC266691
0.814	Intermediate Similarity	NPC39064
0.814	Intermediate Similarity	NPC470084
0.814	Intermediate Similarity	NPC38604
0.814	Intermediate Similarity	NPC211179
0.8134	Intermediate Similarity	NPC276490
0.8134	Intermediate Similarity	NPC474687
0.8129	Intermediate Similarity	NPC16269
0.8129	Intermediate Similarity	NPC21776
0.8125	Intermediate Similarity	NPC245060
0.8125	Intermediate Similarity	NPC471215
0.8125	Intermediate Similarity	NPC262573
0.812	Intermediate Similarity	NPC112939
0.812	Intermediate Similarity	NPC474206
0.812	Intermediate Similarity	NPC255147
0.812	Intermediate Similarity	NPC121812
0.812	Intermediate Similarity	NPC61946
0.812	Intermediate Similarity	NPC201357

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 NPC475529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	918
0.2-0.3	1838
0.3-0.4	2728
0.4-0.5	1617
0.5-0.6	1005
0.6-0.7	629
0.7-0.8	104
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8644	High Similarity	NPD6671	Approved
0.8492	Intermediate Similarity	NPD2861	Phase 2
0.8435	Intermediate Similarity	NPD290	Approved
0.84	Intermediate Similarity	NPD6696	Suspended
0.819	Intermediate Similarity	NPD968	Approved
0.8168	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8168	Intermediate Similarity	NPD1613	Approved
0.8051	Intermediate Similarity	NPD2684	Approved
0.8016	Intermediate Similarity	NPD1091	Approved
0.8	Intermediate Similarity	NPD228	Approved
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3496	Discontinued
0.7923	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD4749	Approved
0.7874	Intermediate Similarity	NPD1610	Phase 2
0.784	Intermediate Similarity	NPD1548	Phase 1
0.7803	Intermediate Similarity	NPD3027	Phase 3
0.7787	Intermediate Similarity	NPD7843	Approved
0.7759	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7157	Approved
0.7724	Intermediate Similarity	NPD1398	Phase 1
0.7717	Intermediate Similarity	NPD1778	Approved
0.7669	Intermediate Similarity	NPD4625	Phase 3
0.763	Intermediate Similarity	NPD4060	Phase 1
0.7594	Intermediate Similarity	NPD4908	Phase 1
0.7557	Intermediate Similarity	NPD8651	Approved
0.7554	Intermediate Similarity	NPD5763	Approved
0.7554	Intermediate Similarity	NPD5762	Approved
0.754	Intermediate Similarity	NPD7340	Approved
0.7519	Intermediate Similarity	NPD1712	Approved
0.75	Intermediate Similarity	NPD1357	Approved
0.7481	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3705	Approved
0.7462	Intermediate Similarity	NPD422	Phase 1
0.7447	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD844	Approved
0.7405	Intermediate Similarity	NPD2231	Phase 2
0.7405	Intermediate Similarity	NPD1608	Approved
0.7405	Intermediate Similarity	NPD2235	Phase 2
0.7391	Intermediate Similarity	NPD6653	Approved
0.7372	Intermediate Similarity	NPD1558	Phase 1
0.7368	Intermediate Similarity	NPD9365	Approved
0.736	Intermediate Similarity	NPD821	Approved
0.7353	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD288	Approved
0.7345	Intermediate Similarity	NPD9295	Approved
0.7343	Intermediate Similarity	NPD2677	Approved
0.7333	Intermediate Similarity	NPD596	Approved
0.7333	Intermediate Similarity	NPD600	Approved
0.7328	Intermediate Similarity	NPD776	Approved
0.7328	Intermediate Similarity	NPD1611	Approved
0.7319	Intermediate Similarity	NPD5735	Approved
0.7319	Intermediate Similarity	NPD6355	Discontinued
0.7313	Intermediate Similarity	NPD6584	Phase 3
0.7313	Intermediate Similarity	NPD558	Phase 2
0.7313	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6002	Phase 3
0.7305	Intermediate Similarity	NPD1375	Discontinued
0.7305	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6004	Phase 3
0.7305	Intermediate Similarity	NPD6005	Phase 3
0.7305	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5058	Phase 3
0.7287	Intermediate Similarity	NPD1182	Approved
0.7286	Intermediate Similarity	NPD5588	Approved
0.7286	Intermediate Similarity	NPD7033	Discontinued
0.7279	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD2232	Approved
0.7273	Intermediate Similarity	NPD2233	Approved
0.7273	Intermediate Similarity	NPD2230	Approved
0.7254	Intermediate Similarity	NPD2424	Discontinued
0.725	Intermediate Similarity	NPD291	Approved
0.7246	Intermediate Similarity	NPD2238	Phase 2
0.7239	Intermediate Similarity	NPD1794	Approved
0.7234	Intermediate Similarity	NPD6032	Approved
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7218	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD4536	Approved
0.7214	Intermediate Similarity	NPD4538	Approved
0.72	Intermediate Similarity	NPD1934	Approved
0.7176	Intermediate Similarity	NPD17	Approved
0.7176	Intermediate Similarity	NPD6516	Phase 2
0.7176	Intermediate Similarity	NPD5846	Approved
0.7176	Intermediate Similarity	NPD4626	Approved
0.7174	Intermediate Similarity	NPD840	Approved
0.7174	Intermediate Similarity	NPD6233	Phase 2
0.7174	Intermediate Similarity	NPD3162	Approved
0.7174	Intermediate Similarity	NPD839	Approved
0.7174	Intermediate Similarity	NPD3163	Approved
0.7165	Intermediate Similarity	NPD5283	Phase 1
0.7153	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD2157	Approved
0.7143	Intermediate Similarity	NPD1840	Phase 2
0.7132	Intermediate Similarity	NPD2237	Approved
0.7123	Intermediate Similarity	NPD1774	Approved
0.7122	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD3620	Phase 2
0.7113	Intermediate Similarity	NPD6100	Approved
0.7113	Intermediate Similarity	NPD6099	Approved
0.7111	Intermediate Similarity	NPD987	Approved
0.7107	Intermediate Similarity	NPD940	Approved
0.7107	Intermediate Similarity	NPD846	Approved
0.7099	Intermediate Similarity	NPD5691	Approved
0.709	Intermediate Similarity	NPD6582	Phase 2
0.709	Intermediate Similarity	NPD6583	Phase 3
0.709	Intermediate Similarity	NPD5327	Phase 3
0.7083	Intermediate Similarity	NPD1652	Phase 2
0.7068	Intermediate Similarity	NPD1535	Discovery
0.7059	Intermediate Similarity	NPD3691	Phase 2
0.7059	Intermediate Similarity	NPD3690	Phase 2
0.7055	Intermediate Similarity	NPD3122	Phase 3
0.7054	Intermediate Similarity	NPD709	Approved
0.7054	Intermediate Similarity	NPD2557	Approved
0.705	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2156	Approved
0.7042	Intermediate Similarity	NPD2155	Approved
0.7042	Intermediate Similarity	NPD5960	Phase 3
0.7042	Intermediate Similarity	NPD2154	Approved
0.7039	Intermediate Similarity	NPD5929	Approved
0.7039	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2801	Approved
0.7034	Intermediate Similarity	NPD9296	Approved
0.7034	Intermediate Similarity	NPD4628	Phase 3
0.7029	Intermediate Similarity	NPD3179	Approved
0.7029	Intermediate Similarity	NPD3180	Approved
0.7021	Intermediate Similarity	NPD6353	Approved
0.7015	Intermediate Similarity	NPD1481	Phase 2
0.7	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2560	Approved
0.6993	Remote Similarity	NPD2161	Phase 2
0.6993	Remote Similarity	NPD2563	Approved
0.6985	Remote Similarity	NPD1818	Approved
0.6985	Remote Similarity	NPD1820	Approved
0.6985	Remote Similarity	NPD1819	Approved
0.6985	Remote Similarity	NPD1817	Approved
0.6984	Remote Similarity	NPD4750	Phase 3
0.6978	Remote Similarity	NPD7985	Registered
0.6978	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1048	Approved
0.6978	Remote Similarity	NPD1336	Approved
0.6972	Remote Similarity	NPD7097	Phase 1
0.697	Remote Similarity	NPD3444	Approved
0.697	Remote Similarity	NPD3443	Approved
0.697	Remote Similarity	NPD3445	Approved
0.697	Remote Similarity	NPD5585	Approved
0.6966	Remote Similarity	NPD4237	Approved
0.6966	Remote Similarity	NPD6674	Discontinued
0.6966	Remote Similarity	NPD4236	Phase 3
0.6963	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3685	Discontinued
0.696	Remote Similarity	NPD1358	Approved
0.6959	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7635	Approved
0.695	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.695	Remote Similarity	NPD447	Suspended
0.695	Remote Similarity	NPD5124	Phase 1
0.6949	Remote Similarity	NPD845	Approved
0.6948	Remote Similarity	NPD3882	Suspended
0.6944	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD9697	Approved
0.6934	Remote Similarity	NPD5647	Approved
0.6918	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3892	Phase 2
0.6913	Remote Similarity	NPD2675	Approved
0.6913	Remote Similarity	NPD2676	Approved
0.6899	Remote Similarity	NPD594	Approved
0.6899	Remote Similarity	NPD592	Approved
0.6899	Remote Similarity	NPD1241	Discontinued
0.6897	Remote Similarity	NPD1549	Phase 2
0.6892	Remote Similarity	NPD1511	Approved
0.6891	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9494	Approved
0.6884	Remote Similarity	NPD3018	Phase 2
0.6883	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD2935	Discontinued
0.6867	Remote Similarity	NPD5976	Discontinued
0.6861	Remote Similarity	NPD2797	Approved
0.6853	Remote Similarity	NPD696	Discontinued
0.685	Remote Similarity	NPD3022	Approved
0.685	Remote Similarity	NPD3021	Approved
0.6849	Remote Similarity	NPD5177	Phase 3
0.6846	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3049	Approved
0.6839	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD2859	Approved
0.6833	Remote Similarity	NPD2860	Approved
0.6831	Remote Similarity	NPD4340	Discontinued
0.6825	Remote Similarity	NPD9552	Approved
0.6822	Remote Similarity	NPD5535	Approved
0.6822	Remote Similarity	NPD1138	Approved
0.6821	Remote Similarity	NPD3686	Approved
0.6821	Remote Similarity	NPD3687	Approved
0.6818	Remote Similarity	NPD5772	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