NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	708.49
Volume:	737.38
LogP:	5.192
LogD:	3.137
LogS:	-5.714
# Rotatable Bonds:	23
TPSA:	187.99
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.045
Synthetic Accessibility Score:	5.51
Fsp3:	0.737
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.358
MDCK Permeability:	6.276610656641424e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.93
Plasma Protein Binding (PPB):	52.78490447998047%
Volume Distribution (VD):	0.728
Pgp-substrate:	53.2728385925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.748
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.888

ADMET: Excretion

Clearance (CL):	3.68
Half-life (T1/2):	0.018

ADMET: Toxicity

hERG Blockers:	0.611
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.67
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.948
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC469386

Natural Product ID:	NPC469386
*Common Name:**	Ustusorane E
IUPAC Name:	1-[7-(hydroxymethyl)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzofuran-6-yl]propan-2-ol
Synonyms:
Standard InCHIKey:	VRJXHZFMWFCEBQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-9(17)6-10-4-5-11-7-13(15(2,3)18)19-14(11)12(10)8-16/h4-5,9,13,16-18H,6-8H2,1-3H3
SMILES:	CC(CC1=C(C2=C(CC(O2)C(C)(C)O)C=C1)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077463
PubChem CID:	44557648
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
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[452135]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	130.0	nM	PMID[452135]

☑ 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 NPC469386 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	354
0.1-0.2	1356
0.2-0.3	3670
0.3-0.4	10197
0.4-0.5	8994
0.5-0.6	4564
0.6-0.7	10062
0.7-0.8	3223
0.8-0.85	247
0.85-0.9	27
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9134	High Similarity	NPC11089
0.9008	High Similarity	NPC329980
0.8864	High Similarity	NPC126101
0.8864	High Similarity	NPC327735
0.8759	High Similarity	NPC221318
0.864	High Similarity	NPC475529
0.8613	High Similarity	NPC258083
0.8594	High Similarity	NPC470726
0.8561	High Similarity	NPC18842
0.855	High Similarity	NPC196193
0.855	High Similarity	NPC325003
0.855	High Similarity	NPC470727
0.8527	High Similarity	NPC470724
0.8496	Intermediate Similarity	NPC26394
0.8492	Intermediate Similarity	NPC96423
0.8456	Intermediate Similarity	NPC183781
0.845	Intermediate Similarity	NPC476254
0.845	Intermediate Similarity	NPC131397
0.845	Intermediate Similarity	NPC293801
0.8444	Intermediate Similarity	NPC477939
0.8444	Intermediate Similarity	NPC54743
0.8444	Intermediate Similarity	NPC177160
0.8444	Intermediate Similarity	NPC10737
0.8444	Intermediate Similarity	NPC472800
0.8444	Intermediate Similarity	NPC263367
0.8444	Intermediate Similarity	NPC29799
0.8444	Intermediate Similarity	NPC156502
0.8444	Intermediate Similarity	NPC209985
0.844	Intermediate Similarity	NPC469425
0.8433	Intermediate Similarity	NPC16485
0.8433	Intermediate Similarity	NPC117048
0.8433	Intermediate Similarity	NPC124085
0.8421	Intermediate Similarity	NPC230219
0.8382	Intermediate Similarity	NPC477938
0.8369	Intermediate Similarity	NPC474397
0.8359	Intermediate Similarity	NPC188997
0.8359	Intermediate Similarity	NPC120638
0.8358	Intermediate Similarity	NPC85435
0.8346	Intermediate Similarity	NPC473875
0.8345	Intermediate Similarity	NPC474104
0.8333	Intermediate Similarity	NPC472797
0.8333	Intermediate Similarity	NPC472796
0.8333	Intermediate Similarity	NPC472795
0.8333	Intermediate Similarity	NPC265075
0.8333	Intermediate Similarity	NPC263261
0.8333	Intermediate Similarity	NPC87725
0.8333	Intermediate Similarity	NPC16577
0.8321	Intermediate Similarity	NPC475836
0.8309	Intermediate Similarity	NPC18189
0.8309	Intermediate Similarity	NPC3049
0.8309	Intermediate Similarity	NPC262585
0.8309	Intermediate Similarity	NPC20829
0.8308	Intermediate Similarity	NPC81641
0.8298	Intermediate Similarity	NPC233980
0.8296	Intermediate Similarity	NPC187616
0.8296	Intermediate Similarity	NPC193026
0.8296	Intermediate Similarity	NPC49603
0.8296	Intermediate Similarity	NPC264956
0.8295	Intermediate Similarity	NPC261992
0.8295	Intermediate Similarity	NPC474130
0.8284	Intermediate Similarity	NPC2190
0.8281	Intermediate Similarity	NPC212965
0.8258	Intermediate Similarity	NPC38604
0.8258	Intermediate Similarity	NPC211179
0.8254	Intermediate Similarity	NPC283616
0.8248	Intermediate Similarity	NPC474687
0.8227	Intermediate Similarity	NPC469385
0.8227	Intermediate Similarity	NPC469557
0.8217	Intermediate Similarity	NPC57199
0.8217	Intermediate Similarity	NPC150026
0.8217	Intermediate Similarity	NPC46586
0.8217	Intermediate Similarity	NPC204535
0.8214	Intermediate Similarity	NPC477616
0.8209	Intermediate Similarity	NPC162801
0.8209	Intermediate Similarity	NPC103799
0.8207	Intermediate Similarity	NPC474442
0.8207	Intermediate Similarity	NPC160196
0.8203	Intermediate Similarity	NPC218753
0.8201	Intermediate Similarity	NPC471414
0.8188	Intermediate Similarity	NPC32630
0.8175	Intermediate Similarity	NPC475628
0.8168	Intermediate Similarity	NPC4286
0.8168	Intermediate Similarity	NPC76119
0.8168	Intermediate Similarity	NPC105031
0.8162	Intermediate Similarity	NPC473107
0.8162	Intermediate Similarity	NPC478085
0.8162	Intermediate Similarity	NPC211164
0.8156	Intermediate Similarity	NPC473845
0.8156	Intermediate Similarity	NPC469795
0.8148	Intermediate Similarity	NPC472798
0.8148	Intermediate Similarity	NPC13005
0.8143	Intermediate Similarity	NPC253878
0.8143	Intermediate Similarity	NPC186033
0.812	Intermediate Similarity	NPC19694
0.812	Intermediate Similarity	NPC470084
0.8116	Intermediate Similarity	NPC134260
0.811	Intermediate Similarity	NPC63010
0.8102	Intermediate Similarity	NPC134968
0.8099	Intermediate Similarity	NPC181615
0.8099	Intermediate Similarity	NPC194034
0.8095	Intermediate Similarity	NPC80918
0.8095	Intermediate Similarity	NPC188578
0.8088	Intermediate Similarity	NPC92805
0.8088	Intermediate Similarity	NPC105554
0.8088	Intermediate Similarity	NPC475840
0.8088	Intermediate Similarity	NPC469610
0.808	Intermediate Similarity	NPC161696
0.808	Intermediate Similarity	NPC470837
0.8077	Intermediate Similarity	NPC77789
0.8077	Intermediate Similarity	NPC74137
0.8077	Intermediate Similarity	NPC18128
0.8074	Intermediate Similarity	NPC277804
0.8074	Intermediate Similarity	NPC118114
0.8074	Intermediate Similarity	NPC129784
0.8074	Intermediate Similarity	NPC300875
0.8074	Intermediate Similarity	NPC17343
0.8074	Intermediate Similarity	NPC196765
0.8074	Intermediate Similarity	NPC150011
0.8074	Intermediate Similarity	NPC236014
0.8074	Intermediate Similarity	NPC164574
0.8074	Intermediate Similarity	NPC129106
0.8074	Intermediate Similarity	NPC472590
0.8074	Intermediate Similarity	NPC268917
0.8074	Intermediate Similarity	NPC12875
0.8074	Intermediate Similarity	NPC280653
0.8074	Intermediate Similarity	NPC228369
0.8074	Intermediate Similarity	NPC160623
0.8074	Intermediate Similarity	NPC476166
0.8074	Intermediate Similarity	NPC206224
0.8074	Intermediate Similarity	NPC207892
0.8071	Intermediate Similarity	NPC71046
0.8069	Intermediate Similarity	NPC158784
0.8062	Intermediate Similarity	NPC45663
0.806	Intermediate Similarity	NPC97326
0.806	Intermediate Similarity	NPC222108
0.806	Intermediate Similarity	NPC96719
0.8056	Intermediate Similarity	NPC473876
0.8049	Intermediate Similarity	NPC46844
0.8047	Intermediate Similarity	NPC135961
0.8047	Intermediate Similarity	NPC137294
0.8047	Intermediate Similarity	NPC85895
0.8045	Intermediate Similarity	NPC98745
0.8045	Intermediate Similarity	NPC186889
0.8043	Intermediate Similarity	NPC234952
0.8043	Intermediate Similarity	NPC476698
0.8043	Intermediate Similarity	NPC68292
0.8043	Intermediate Similarity	NPC470802
0.8042	Intermediate Similarity	NPC260397
0.803	Intermediate Similarity	NPC124030
0.803	Intermediate Similarity	NPC470510
0.8029	Intermediate Similarity	NPC225696
0.8029	Intermediate Similarity	NPC115335
0.8029	Intermediate Similarity	NPC471942
0.8029	Intermediate Similarity	NPC223008
0.8029	Intermediate Similarity	NPC253574
0.8029	Intermediate Similarity	NPC311256
0.8029	Intermediate Similarity	NPC97834
0.8029	Intermediate Similarity	NPC198154
0.8029	Intermediate Similarity	NPC296915
0.8029	Intermediate Similarity	NPC98179
0.8028	Intermediate Similarity	NPC164183
0.8028	Intermediate Similarity	NPC45257
0.8028	Intermediate Similarity	NPC93323
0.8028	Intermediate Similarity	NPC284881
0.8028	Intermediate Similarity	NPC280092
0.8028	Intermediate Similarity	NPC474444
0.8028	Intermediate Similarity	NPC264706
0.8028	Intermediate Similarity	NPC12641
0.8028	Intermediate Similarity	NPC473108
0.8028	Intermediate Similarity	NPC50250
0.8028	Intermediate Similarity	NPC93433
0.8016	Intermediate Similarity	NPC474486
0.8015	Intermediate Similarity	NPC96940
0.8015	Intermediate Similarity	NPC469611
0.8014	Intermediate Similarity	NPC131971
0.8014	Intermediate Similarity	NPC302915
0.8014	Intermediate Similarity	NPC2745
0.8	Intermediate Similarity	NPC42300
0.8	Intermediate Similarity	NPC257582
0.8	Intermediate Similarity	NPC242807
0.8	Intermediate Similarity	NPC184797
0.8	Intermediate Similarity	NPC153739
0.8	Intermediate Similarity	NPC160283
0.8	Intermediate Similarity	NPC48623
0.8	Intermediate Similarity	NPC145305
0.8	Intermediate Similarity	NPC470804
0.8	Intermediate Similarity	NPC143483
0.8	Intermediate Similarity	NPC77040
0.8	Intermediate Similarity	NPC220935
0.8	Intermediate Similarity	NPC241522
0.8	Intermediate Similarity	NPC168707
0.8	Intermediate Similarity	NPC309124
0.8	Intermediate Similarity	NPC64201
0.8	Intermediate Similarity	NPC226712
0.8	Intermediate Similarity	NPC254759
0.8	Intermediate Similarity	NPC27187
0.8	Intermediate Similarity	NPC187998
0.8	Intermediate Similarity	NPC174495
0.8	Intermediate Similarity	NPC92164
0.8	Intermediate Similarity	NPC470225

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 NPC469386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	848
0.2-0.3	1822
0.3-0.4	2725
0.4-0.5	1713
0.5-0.6	1027
0.6-0.7	607
0.7-0.8	103
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8372	Intermediate Similarity	NPD6696	Suspended
0.8333	Intermediate Similarity	NPD4625	Phase 3
0.8201	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD290	Approved
0.8058	Intermediate Similarity	NPD5762	Approved
0.8058	Intermediate Similarity	NPD5763	Approved
0.8015	Intermediate Similarity	NPD4749	Approved
0.8	Intermediate Similarity	NPD1091	Approved
0.797	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD1613	Approved
0.7883	Intermediate Similarity	NPD4060	Phase 1
0.7868	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1398	Phase 1
0.782	Intermediate Similarity	NPD8651	Approved
0.7817	Intermediate Similarity	NPD6674	Discontinued
0.7742	Intermediate Similarity	NPD2684	Approved
0.7737	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD7157	Approved
0.771	Intermediate Similarity	NPD5125	Phase 3
0.771	Intermediate Similarity	NPD4626	Approved
0.771	Intermediate Similarity	NPD5126	Approved
0.7698	Intermediate Similarity	NPD5735	Approved
0.7676	Intermediate Similarity	NPD6005	Phase 3
0.7676	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6004	Phase 3
0.7676	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6002	Phase 3
0.7674	Intermediate Similarity	NPD7340	Approved
0.7664	Intermediate Similarity	NPD3027	Phase 3
0.7647	Intermediate Similarity	NPD2861	Phase 2
0.7638	Intermediate Similarity	NPD7843	Approved
0.7634	Intermediate Similarity	NPD5691	Approved
0.7597	Intermediate Similarity	NPD6671	Approved
0.7594	Intermediate Similarity	NPD1610	Phase 2
0.7591	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4908	Phase 1
0.7576	Intermediate Similarity	NPD1778	Approved
0.7518	Intermediate Similarity	NPD1712	Approved
0.7518	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2424	Discontinued
0.7482	Intermediate Similarity	NPD7985	Registered
0.7481	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2677	Approved
0.7463	Intermediate Similarity	NPD3705	Approved
0.7463	Intermediate Similarity	NPD1611	Approved
0.7447	Intermediate Similarity	NPD5124	Phase 1
0.7447	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1548	Phase 1
0.7415	Intermediate Similarity	NPD5058	Phase 3
0.7413	Intermediate Similarity	NPD5588	Approved
0.7397	Intermediate Similarity	NPD3892	Phase 2
0.7397	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4097	Suspended
0.7394	Intermediate Similarity	NPD6653	Approved
0.7394	Intermediate Similarity	NPD2157	Approved
0.7376	Intermediate Similarity	NPD4140	Approved
0.7376	Intermediate Similarity	NPD3620	Phase 2
0.7376	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6099	Approved
0.7361	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD5327	Phase 3
0.7343	Intermediate Similarity	NPD4536	Approved
0.7343	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4538	Approved
0.7315	Intermediate Similarity	NPD2533	Approved
0.7315	Intermediate Similarity	NPD2534	Approved
0.7315	Intermediate Similarity	NPD2532	Approved
0.7292	Intermediate Similarity	NPD7033	Discontinued
0.7287	Intermediate Similarity	NPD228	Approved
0.7279	Intermediate Similarity	NPD4628	Phase 3
0.7279	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6353	Approved
0.7267	Intermediate Similarity	NPD2676	Approved
0.7267	Intermediate Similarity	NPD2675	Approved
0.7261	Intermediate Similarity	NPD4666	Phase 3
0.7259	Intermediate Similarity	NPD3496	Discontinued
0.7254	Intermediate Similarity	NPD2238	Phase 2
0.7239	Intermediate Similarity	NPD1357	Approved
0.7237	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2560	Approved
0.7226	Intermediate Similarity	NPD2563	Approved
0.7208	Intermediate Similarity	NPD37	Approved
0.7203	Intermediate Similarity	NPD6355	Discontinued
0.7197	Intermediate Similarity	NPD5709	Phase 3
0.7194	Intermediate Similarity	NPD558	Phase 2
0.7194	Intermediate Similarity	NPD3691	Phase 2
0.7194	Intermediate Similarity	NPD3690	Phase 2
0.7179	Intermediate Similarity	NPD4966	Approved
0.7179	Intermediate Similarity	NPD4967	Phase 2
0.7179	Intermediate Similarity	NPD4965	Approved
0.7172	Intermediate Similarity	NPD2156	Approved
0.7172	Intermediate Similarity	NPD5960	Phase 3
0.7172	Intermediate Similarity	NPD2154	Approved
0.7172	Intermediate Similarity	NPD2155	Approved
0.7164	Intermediate Similarity	NPD7741	Discontinued
0.7161	Intermediate Similarity	NPD5929	Approved
0.716	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6072	Discontinued
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7131	Intermediate Similarity	NPD844	Approved
0.7125	Intermediate Similarity	NPD2969	Approved
0.7125	Intermediate Similarity	NPD2970	Approved
0.7122	Intermediate Similarity	NPD3094	Phase 2
0.712	Intermediate Similarity	NPD291	Approved
0.7111	Intermediate Similarity	NPD1651	Approved
0.7107	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD1138	Approved
0.7099	Intermediate Similarity	NPD7635	Approved
0.7095	Intermediate Similarity	NPD1652	Phase 2
0.709	Intermediate Similarity	NPD7644	Approved
0.7089	Intermediate Similarity	NPD6234	Discontinued
0.7086	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD776	Approved
0.708	Intermediate Similarity	NPD422	Phase 1
0.708	Intermediate Similarity	NPD3092	Approved
0.7075	Intermediate Similarity	NPD1375	Discontinued
0.7073	Intermediate Similarity	NPD288	Approved
0.7071	Intermediate Similarity	NPD4624	Approved
0.707	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3162	Approved
0.7063	Intermediate Similarity	NPD3163	Approved
0.7063	Intermediate Similarity	NPD3051	Approved
0.7051	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1283	Approved
0.7045	Intermediate Similarity	NPD5283	Phase 1
0.7042	Intermediate Similarity	NPD7095	Approved
0.7031	Intermediate Similarity	NPD968	Approved
0.703	Intermediate Similarity	NPD6559	Discontinued
0.7029	Intermediate Similarity	NPD2232	Approved
0.7029	Intermediate Similarity	NPD1608	Approved
0.7029	Intermediate Similarity	NPD2235	Phase 2
0.7029	Intermediate Similarity	NPD2233	Approved
0.7029	Intermediate Similarity	NPD2230	Approved
0.7029	Intermediate Similarity	NPD2231	Phase 2
0.7023	Intermediate Similarity	NPD1137	Approved
0.7023	Intermediate Similarity	NPD1139	Approved
0.7007	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD1794	Approved
0.6993	Remote Similarity	NPD1336	Approved
0.6993	Remote Similarity	NPD6798	Discontinued
0.6993	Remote Similarity	NPD1048	Approved
0.6993	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3443	Approved
0.6985	Remote Similarity	NPD3445	Approved
0.6985	Remote Similarity	NPD3444	Approved
0.6977	Remote Similarity	NPD2342	Discontinued
0.6975	Remote Similarity	NPD2489	Approved
0.6975	Remote Similarity	NPD27	Approved
0.6972	Remote Similarity	NPD600	Approved
0.6972	Remote Similarity	NPD596	Approved
0.697	Remote Similarity	NPD821	Approved
0.6967	Remote Similarity	NPD845	Approved
0.6959	Remote Similarity	NPD2346	Discontinued
0.6957	Remote Similarity	NPD6071	Discontinued
0.695	Remote Similarity	NPD5647	Approved
0.6948	Remote Similarity	NPD1653	Approved
0.6944	Remote Similarity	NPD840	Approved
0.6944	Remote Similarity	NPD839	Approved
0.6943	Remote Similarity	NPD7819	Suspended
0.6942	Remote Similarity	NPD9365	Approved
0.694	Remote Similarity	NPD709	Approved
0.6934	Remote Similarity	NPD5846	Approved
0.6934	Remote Similarity	NPD6516	Phase 2
0.6928	Remote Similarity	NPD6090	Discontinued
0.6923	Remote Similarity	NPD3179	Approved
0.6923	Remote Similarity	NPD3180	Approved
0.6917	Remote Similarity	NPD592	Approved
0.6917	Remote Similarity	NPD594	Approved
0.6914	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7037	Approved
0.6912	Remote Similarity	NPD3091	Approved
0.6908	Remote Similarity	NPD1774	Approved
0.6906	Remote Similarity	NPD1840	Phase 2
0.6903	Remote Similarity	NPD3226	Approved
0.6901	Remote Similarity	NPD3018	Phase 2
0.6897	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6959	Discontinued
0.6892	Remote Similarity	NPD6032	Approved
0.689	Remote Similarity	NPD7228	Approved
0.6879	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD2797	Approved
0.6867	Remote Similarity	NPD4237	Approved
0.6867	Remote Similarity	NPD4236	Phase 3
0.6859	Remote Similarity	NPD4380	Phase 2
0.6857	Remote Similarity	NPD3685	Discontinued
0.6857	Remote Similarity	NPD1669	Approved
0.6855	Remote Similarity	NPD3882	Suspended
0.6852	Remote Similarity	NPD7229	Phase 3
0.6852	Remote Similarity	NPD3787	Discontinued
0.685	Remote Similarity	NPD846	Approved
0.685	Remote Similarity	NPD940	Approved
0.6845	Remote Similarity	NPD8312	Approved
0.6845	Remote Similarity	NPD7312	Approved
0.6845	Remote Similarity	NPD7311	Approved
0.6845	Remote Similarity	NPD8313	Approved
0.6845	Remote Similarity	NPD7313	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