NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.05
Volume:	265.186
LogP:	2.965
LogD:	2.426
LogS:	-3.454
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	2.544
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.096
MDCK Permeability:	2.2467802409664728e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.578

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.182
Plasma Protein Binding (PPB):	98.4681625366211%
Volume Distribution (VD):	0.498
Pgp-substrate:	1.5810297727584839%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.596
CYP2C9-substrate:	0.568
CYP2D6-inhibitor:	0.574
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	12.402
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.52
AMES Toxicity:	0.384
Rat Oral Acute Toxicity:	0.559
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.918
Carcinogencity:	0.476
Eye Corrosion:	0.018
Eye Irritation:	0.957
Respiratory Toxicity:	0.596

Download Data

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

Natural Product: NPC62907

Natural Product ID:	NPC62907
*Common Name:**	Thunberginol F
IUPAC Name:	(3Z)-3-[(3,4-dihydroxyphenyl)methylidene]-7-hydroxy-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	CFXQRFYFWXTZOJ-QPEQYQDCSA-N
Standard InCHI:	InChI=1S/C15H10O5/c16-10-5-4-8(6-12(10)18)7-13-9-2-1-3-11(17)14(9)15(19)20-13/h1-7,16-18H/b13-7-
SMILES:	Oc1cc(ccc1O)/C=C/1OC(=O)c2c1cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL69084
PubChem CID:	6439493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004191] Isocoumarans [CHEMONTID:0003409] Isobenzofuranones

*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
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11549443]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17609121]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO33513	hydrangeae dulcis folium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9871657]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9360.1	Hydrangea macrophylla var. thunbergii	Varieties	Hydrangeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	2.1	%	PMID[476397]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	6.2	%	PMID[476397]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	8.3	%	PMID[476397]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	-54.8	%	PMID[476397]

☑ 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 NPC62907 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	371
0.1-0.2	1712
0.2-0.3	4201
0.3-0.4	10328
0.4-0.5	7640
0.5-0.6	3914
0.6-0.7	7795
0.7-0.8	6432
0.8-0.85	270
0.85-0.9	32
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9407	High Similarity	NPC134969
0.9071	High Similarity	NPC257025
0.9	High Similarity	NPC258307
0.8944	High Similarity	NPC85734
0.8944	High Similarity	NPC32058
0.8832	High Similarity	NPC72918
0.8794	High Similarity	NPC314271
0.8769	High Similarity	NPC198336
0.875	High Similarity	NPC476463
0.8714	High Similarity	NPC471819
0.8712	High Similarity	NPC265910
0.8712	High Similarity	NPC91475
0.8702	High Similarity	NPC283514
0.8686	High Similarity	NPC157478
0.8686	High Similarity	NPC295406
0.8686	High Similarity	NPC289572
0.8686	High Similarity	NPC200422
0.8633	High Similarity	NPC326847
0.8581	High Similarity	NPC295646
0.8571	High Similarity	NPC96501
0.8562	High Similarity	NPC55327
0.8561	High Similarity	NPC204257
0.8561	High Similarity	NPC254832
0.8561	High Similarity	NPC176102
0.8561	High Similarity	NPC229638
0.8561	High Similarity	NPC71108
0.8561	High Similarity	NPC267539
0.8561	High Similarity	NPC29317
0.8552	High Similarity	NPC138978
0.854	High Similarity	NPC7012
0.8529	High Similarity	NPC94810
0.8521	High Similarity	NPC290664
0.8519	High Similarity	NPC181715
0.8514	High Similarity	NPC204350
0.8511	High Similarity	NPC233780
0.85	High Similarity	NPC160425
0.85	High Similarity	NPC223836
0.8497	Intermediate Similarity	NPC22324
0.8487	Intermediate Similarity	NPC200594
0.8473	Intermediate Similarity	NPC260837
0.8467	Intermediate Similarity	NPC199926
0.8462	Intermediate Similarity	NPC130485
0.8462	Intermediate Similarity	NPC91546
0.844	Intermediate Similarity	NPC261292
0.844	Intermediate Similarity	NPC301915
0.8433	Intermediate Similarity	NPC288945
0.8421	Intermediate Similarity	NPC46634
0.8411	Intermediate Similarity	NPC227062
0.8411	Intermediate Similarity	NPC150227
0.8411	Intermediate Similarity	NPC54928
0.8406	Intermediate Similarity	NPC318799
0.838	Intermediate Similarity	NPC126739
0.838	Intermediate Similarity	NPC197666
0.8377	Intermediate Similarity	NPC144843
0.8369	Intermediate Similarity	NPC156307
0.8357	Intermediate Similarity	NPC175943
0.8356	Intermediate Similarity	NPC262282
0.8355	Intermediate Similarity	NPC77679
0.8355	Intermediate Similarity	NPC84935
0.8355	Intermediate Similarity	NPC143328
0.8355	Intermediate Similarity	NPC190020
0.8345	Intermediate Similarity	NPC470130
0.8344	Intermediate Similarity	NPC79998
0.8344	Intermediate Similarity	NPC38898
0.8333	Intermediate Similarity	NPC90411
0.8322	Intermediate Similarity	NPC247409
0.8321	Intermediate Similarity	NPC95537
0.8311	Intermediate Similarity	NPC19545
0.831	Intermediate Similarity	NPC308976
0.8288	Intermediate Similarity	NPC279121
0.8286	Intermediate Similarity	NPC294226
0.8284	Intermediate Similarity	NPC244351
0.8278	Intermediate Similarity	NPC281477
0.8276	Intermediate Similarity	NPC322112
0.8273	Intermediate Similarity	NPC34070
0.8273	Intermediate Similarity	NPC469526
0.8267	Intermediate Similarity	NPC202157
0.8264	Intermediate Similarity	NPC327187
0.8264	Intermediate Similarity	NPC187690
0.8264	Intermediate Similarity	NPC155205
0.8247	Intermediate Similarity	NPC47623
0.8244	Intermediate Similarity	NPC125252
0.8243	Intermediate Similarity	NPC239312
0.8243	Intermediate Similarity	NPC130230
0.8243	Intermediate Similarity	NPC140840
0.8243	Intermediate Similarity	NPC86847
0.8243	Intermediate Similarity	NPC275772
0.8239	Intermediate Similarity	NPC324929
0.8231	Intermediate Similarity	NPC160777
0.8231	Intermediate Similarity	NPC70136
0.8231	Intermediate Similarity	NPC73416
0.8227	Intermediate Similarity	NPC106406
0.8224	Intermediate Similarity	NPC80489
0.8224	Intermediate Similarity	NPC20541
0.8224	Intermediate Similarity	NPC16082
0.8224	Intermediate Similarity	NPC82592
0.8219	Intermediate Similarity	NPC175013
0.8219	Intermediate Similarity	NPC287722
0.8219	Intermediate Similarity	NPC474692
0.8214	Intermediate Similarity	NPC135801
0.8212	Intermediate Similarity	NPC199773
0.8207	Intermediate Similarity	NPC84273
0.8207	Intermediate Similarity	NPC220106
0.8205	Intermediate Similarity	NPC477689
0.8201	Intermediate Similarity	NPC31539
0.8201	Intermediate Similarity	NPC26697
0.8201	Intermediate Similarity	NPC244441
0.8201	Intermediate Similarity	NPC233056
0.8201	Intermediate Similarity	NPC117609
0.82	Intermediate Similarity	NPC119929
0.82	Intermediate Similarity	NPC151473
0.82	Intermediate Similarity	NPC260582
0.8195	Intermediate Similarity	NPC233282
0.8194	Intermediate Similarity	NPC191280
0.8194	Intermediate Similarity	NPC275356
0.8188	Intermediate Similarity	NPC118726
0.8188	Intermediate Similarity	NPC276930
0.8188	Intermediate Similarity	NPC107636
0.8188	Intermediate Similarity	NPC12367
0.8182	Intermediate Similarity	NPC290030
0.8182	Intermediate Similarity	NPC238381
0.8176	Intermediate Similarity	NPC179271
0.8176	Intermediate Similarity	NPC20791
0.8169	Intermediate Similarity	NPC311742
0.8163	Intermediate Similarity	NPC142165
0.8158	Intermediate Similarity	NPC125487
0.8158	Intermediate Similarity	NPC281703
0.8158	Intermediate Similarity	NPC89474
0.8156	Intermediate Similarity	NPC153783
0.8156	Intermediate Similarity	NPC263817
0.8153	Intermediate Similarity	NPC29411
0.8151	Intermediate Similarity	NPC105648
0.8151	Intermediate Similarity	NPC284556
0.8151	Intermediate Similarity	NPC250755
0.8151	Intermediate Similarity	NPC301178
0.8146	Intermediate Similarity	NPC200773
0.8146	Intermediate Similarity	NPC118427
0.8146	Intermediate Similarity	NPC240768
0.8143	Intermediate Similarity	NPC470831
0.8143	Intermediate Similarity	NPC214702
0.8143	Intermediate Similarity	NPC189823
0.8143	Intermediate Similarity	NPC219892
0.8138	Intermediate Similarity	NPC203063
0.8138	Intermediate Similarity	NPC158472
0.8133	Intermediate Similarity	NPC261322
0.8133	Intermediate Similarity	NPC296197
0.8133	Intermediate Similarity	NPC9099
0.8133	Intermediate Similarity	NPC216318
0.8133	Intermediate Similarity	NPC17286
0.8133	Intermediate Similarity	NPC37220
0.8133	Intermediate Similarity	NPC259713
0.8133	Intermediate Similarity	NPC195351
0.8129	Intermediate Similarity	NPC226855
0.8129	Intermediate Similarity	NPC300680
0.8125	Intermediate Similarity	NPC206207
0.8125	Intermediate Similarity	NPC112135
0.8121	Intermediate Similarity	NPC51443
0.8121	Intermediate Similarity	NPC168803
0.8121	Intermediate Similarity	NPC166583
0.8121	Intermediate Similarity	NPC155910
0.8121	Intermediate Similarity	NPC74881
0.8121	Intermediate Similarity	NPC108406
0.8121	Intermediate Similarity	NPC53362
0.8121	Intermediate Similarity	NPC17042
0.812	Intermediate Similarity	NPC184579
0.812	Intermediate Similarity	NPC233165
0.8116	Intermediate Similarity	NPC71525
0.8116	Intermediate Similarity	NPC473787
0.8116	Intermediate Similarity	NPC214620
0.8116	Intermediate Similarity	NPC158654
0.8112	Intermediate Similarity	NPC235115
0.8112	Intermediate Similarity	NPC291454
0.8112	Intermediate Similarity	NPC50455
0.8112	Intermediate Similarity	NPC90431
0.8108	Intermediate Similarity	NPC83272
0.8106	Intermediate Similarity	NPC278652
0.8105	Intermediate Similarity	NPC56786
0.8105	Intermediate Similarity	NPC67396
0.8105	Intermediate Similarity	NPC471456
0.8105	Intermediate Similarity	NPC471800
0.8105	Intermediate Similarity	NPC80534
0.8102	Intermediate Similarity	NPC4164
0.8099	Intermediate Similarity	NPC300776
0.8099	Intermediate Similarity	NPC176814
0.8099	Intermediate Similarity	NPC5310
0.8099	Intermediate Similarity	NPC248150
0.8099	Intermediate Similarity	NPC4982
0.8099	Intermediate Similarity	NPC68779
0.8095	Intermediate Similarity	NPC471417
0.8095	Intermediate Similarity	NPC66593
0.8095	Intermediate Similarity	NPC238629
0.8095	Intermediate Similarity	NPC254659
0.8092	Intermediate Similarity	NPC289968
0.8092	Intermediate Similarity	NPC164912
0.8092	Intermediate Similarity	NPC125300
0.8092	Intermediate Similarity	NPC312338
0.8092	Intermediate Similarity	NPC478220
0.8092	Intermediate Similarity	NPC149889
0.8088	Intermediate Similarity	NPC212541
0.8085	Intermediate Similarity	NPC477406

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 NPC62907 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	944
0.2-0.3	1585
0.3-0.4	2705
0.4-0.5	1831
0.5-0.6	1161
0.6-0.7	460
0.7-0.8	119
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8288	Intermediate Similarity	NPD1511	Approved
0.8286	Intermediate Similarity	NPD447	Suspended
0.8214	Intermediate Similarity	NPD943	Approved
0.8182	Intermediate Similarity	NPD2935	Discontinued
0.8176	Intermediate Similarity	NPD1512	Approved
0.8112	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD1203	Approved
0.8071	Intermediate Similarity	NPD3764	Approved
0.8069	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD3882	Suspended
0.7922	Intermediate Similarity	NPD2801	Approved
0.7922	Intermediate Similarity	NPD1465	Phase 2
0.7911	Intermediate Similarity	NPD6232	Discontinued
0.7895	Intermediate Similarity	NPD9493	Approved
0.7877	Intermediate Similarity	NPD2346	Discontinued
0.7857	Intermediate Similarity	NPD1934	Approved
0.7842	Intermediate Similarity	NPD1164	Approved
0.7806	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7473	Discontinued
0.7761	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD9717	Approved
0.7754	Intermediate Similarity	NPD9269	Phase 2
0.7748	Intermediate Similarity	NPD2533	Approved
0.7748	Intermediate Similarity	NPD2532	Approved
0.7748	Intermediate Similarity	NPD2534	Approved
0.774	Intermediate Similarity	NPD2799	Discontinued
0.7718	Intermediate Similarity	NPD3750	Approved
0.7716	Intermediate Similarity	NPD3818	Discontinued
0.7714	Intermediate Similarity	NPD1470	Approved
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2313	Discontinued
0.7687	Intermediate Similarity	NPD5408	Approved
0.7687	Intermediate Similarity	NPD5406	Approved
0.7687	Intermediate Similarity	NPD5404	Approved
0.7687	Intermediate Similarity	NPD5405	Approved
0.7681	Intermediate Similarity	NPD1201	Approved
0.7658	Intermediate Similarity	NPD3749	Approved
0.7643	Intermediate Similarity	NPD3817	Phase 2
0.7635	Intermediate Similarity	NPD2344	Approved
0.7569	Intermediate Similarity	NPD411	Approved
0.7568	Intermediate Similarity	NPD1551	Phase 2
0.7557	Intermediate Similarity	NPD74	Approved
0.7557	Intermediate Similarity	NPD9266	Approved
0.7548	Intermediate Similarity	NPD3226	Approved
0.7534	Intermediate Similarity	NPD1933	Approved
0.7534	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD9494	Approved
0.7481	Intermediate Similarity	NPD9267	Approved
0.7481	Intermediate Similarity	NPD9264	Approved
0.7481	Intermediate Similarity	NPD9263	Approved
0.7468	Intermediate Similarity	NPD7819	Suspended
0.7466	Intermediate Similarity	NPD1240	Approved
0.7464	Intermediate Similarity	NPD9268	Approved
0.7434	Intermediate Similarity	NPD2309	Approved
0.7434	Intermediate Similarity	NPD6190	Approved
0.7431	Intermediate Similarity	NPD6832	Phase 2
0.74	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1283	Approved
0.7383	Intermediate Similarity	NPD3748	Approved
0.7378	Intermediate Similarity	NPD6166	Phase 2
0.7378	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1481	Phase 2
0.7368	Intermediate Similarity	NPD8166	Discontinued
0.7365	Intermediate Similarity	NPD1607	Approved
0.7351	Intermediate Similarity	NPD1549	Phase 2
0.7349	Intermediate Similarity	NPD7054	Approved
0.7343	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6799	Approved
0.7326	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD3455	Phase 2
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1535	Discovery
0.7305	Intermediate Similarity	NPD7472	Approved
0.7305	Intermediate Similarity	NPD7074	Phase 3
0.7296	Intermediate Similarity	NPD37	Approved
0.7292	Intermediate Similarity	NPD2798	Approved
0.729	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD4965	Approved
0.7267	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD4966	Approved
0.7266	Intermediate Similarity	NPD9545	Approved
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7255	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7241	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD5494	Approved
0.723	Intermediate Similarity	NPD4060	Phase 1
0.7226	Intermediate Similarity	NPD9281	Approved
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3268	Approved
0.719	Intermediate Similarity	NPD2800	Approved
0.7186	Intermediate Similarity	NPD7228	Approved
0.7183	Intermediate Similarity	NPD1281	Approved
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7178	Intermediate Similarity	NPD919	Approved
0.7176	Intermediate Similarity	NPD9261	Approved
0.7172	Intermediate Similarity	NPD1019	Discontinued
0.7171	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1471	Phase 3
0.717	Intermediate Similarity	NPD6599	Discontinued
0.716	Intermediate Similarity	NPD7768	Phase 2
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5710	Approved
0.7152	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD1608	Approved
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7117	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7390	Discontinued
0.7114	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1613	Approved
0.7111	Intermediate Similarity	NPD3022	Approved
0.7111	Intermediate Similarity	NPD3021	Approved
0.7091	Intermediate Similarity	NPD7199	Phase 2
0.7089	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5403	Approved
0.7089	Intermediate Similarity	NPD920	Approved
0.7078	Intermediate Similarity	NPD1243	Approved
0.7076	Intermediate Similarity	NPD7808	Phase 3
0.707	Intermediate Similarity	NPD5401	Approved
0.707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7266	Discontinued
0.7052	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3300	Phase 2
0.7047	Intermediate Similarity	NPD520	Approved
0.7042	Intermediate Similarity	NPD4626	Approved
0.7035	Intermediate Similarity	NPD8312	Approved
0.7035	Intermediate Similarity	NPD8313	Approved
0.7034	Intermediate Similarity	NPD1876	Approved
0.7034	Intermediate Similarity	NPD3225	Approved
0.7025	Intermediate Similarity	NPD6273	Approved
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7018	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7007	Intermediate Similarity	NPD228	Approved
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6988	Remote Similarity	NPD6959	Discontinued
0.6988	Remote Similarity	NPD1247	Approved
0.6986	Remote Similarity	NPD3266	Approved
0.6986	Remote Similarity	NPD3267	Approved
0.698	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6798	Discontinued
0.6975	Remote Similarity	NPD6801	Discontinued
0.6968	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD422	Phase 1
0.6943	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD257	Approved
0.6939	Remote Similarity	NPD258	Approved
0.6933	Remote Similarity	NPD6233	Phase 2
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7095	Approved
0.6913	Remote Similarity	NPD3027	Phase 3
0.6913	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1894	Discontinued
0.6892	Remote Similarity	NPD9569	Approved
0.689	Remote Similarity	NPD4288	Approved
0.689	Remote Similarity	NPD2296	Approved
0.689	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD826	Approved
0.6887	Remote Similarity	NPD825	Approved
0.6883	Remote Similarity	NPD9570	Approved
0.6883	Remote Similarity	NPD2796	Approved
0.6883	Remote Similarity	NPD2438	Suspended
0.6883	Remote Similarity	NPD4476	Approved
0.6883	Remote Similarity	NPD4477	Approved
0.6882	Remote Similarity	NPD3751	Discontinued
0.6866	Remote Similarity	NPD164	Approved
0.6864	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1651	Approved
0.6853	Remote Similarity	NPD5691	Approved
0.6842	Remote Similarity	NPD555	Phase 2
0.6832	Remote Similarity	NPD1653	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