NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.03
Volume:	242.021
LogP:	1.432
LogD:	1.138
LogS:	-3.219
# Rotatable Bonds:	0
TPSA:	100.88
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.47
Synthetic Accessibility Score:	2.677
Fsp3:	0.077
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:	-4.846
MDCK Permeability:	1.3322921404324006e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.455
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	84.76329803466797%
Volume Distribution (VD):	0.609
Pgp-substrate:	15.394632339477539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.802
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.326
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.465
CYP2D6-substrate:	0.356
CYP3A4-inhibitor:	0.147
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	3.231
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.907
Carcinogencity:	0.035
Eye Corrosion:	0.187
Eye Irritation:	0.946
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC156307

Natural Product ID:	NPC156307
*Common Name:**	Phelligridin A
IUPAC Name:	8,9-dihydroxy-3-methylpyrano[4,3-c]isochromene-1,6-dione
Synonyms:
Standard InCHIKey:	AQXTXYPAJZSNIZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O6/c1-5-2-10-11(13(17)18-5)6-3-8(14)9(15)4-7(6)12(16)19-10/h2-4,14-15H,1H3
SMILES:	Cc1cc2c(c3cc(c(cc3c(=O)o2)O)O)c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446850
PubChem CID:	44559563
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

*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
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165144]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844878]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16209522]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17279797]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20583752]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24588	Phellinus igniarius	Species	Hymenochaetaceae	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	192.0	nM	PMID[498366]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	181.0	nM	PMID[498366]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	109.0	nM	PMID[498366]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	110.0	nM	PMID[498366]
NPT1085	Cell Line	KETR3	Homo sapiens	IC50	>	192.0	nM	PMID[498366]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	192.0	nM	PMID[498366]

☑ 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 NPC156307 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	461
0.1-0.2	2111
0.2-0.3	4859
0.3-0.4	10746
0.4-0.5	6857
0.5-0.6	4310
0.6-0.7	5866
0.7-0.8	5540
0.8-0.85	1542
0.85-0.9	379
0.9-0.95	20
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC290664
0.9481	High Similarity	NPC91546
0.9403	High Similarity	NPC257173
0.9078	High Similarity	NPC155910
0.9078	High Similarity	NPC17042
0.9051	High Similarity	NPC191280
0.9015	High Similarity	NPC226855
0.9015	High Similarity	NPC94810
0.9008	High Similarity	NPC158654
0.8971	High Similarity	NPC326847
0.8777	High Similarity	NPC134969
0.875	High Similarity	NPC156124
0.875	High Similarity	NPC1321
0.875	High Similarity	NPC304929
0.875	High Similarity	NPC239855
0.875	High Similarity	NPC283823
0.875	High Similarity	NPC159418
0.8741	High Similarity	NPC264145
0.8732	High Similarity	NPC257025
0.8723	High Similarity	NPC314271
0.8716	High Similarity	NPC123208
0.8696	High Similarity	NPC156892
0.8676	High Similarity	NPC111888
0.8662	High Similarity	NPC470130
0.8643	High Similarity	NPC471819
0.8623	High Similarity	NPC18646
0.8582	High Similarity	NPC327187
0.8582	High Similarity	NPC326065
0.8571	High Similarity	NPC112135
0.8561	High Similarity	NPC475111
0.8542	High Similarity	NPC258856
0.8542	High Similarity	NPC75295
0.8529	High Similarity	NPC285776
0.85	High Similarity	NPC110899
0.85	High Similarity	NPC25305
0.85	High Similarity	NPC95679
0.85	High Similarity	NPC112068
0.85	High Similarity	NPC125417
0.8485	Intermediate Similarity	NPC46634
0.8483	Intermediate Similarity	NPC268366
0.8472	Intermediate Similarity	NPC113397
0.8462	Intermediate Similarity	NPC156654
0.8446	Intermediate Similarity	NPC265862
0.8446	Intermediate Similarity	NPC92747
0.844	Intermediate Similarity	NPC239943
0.8435	Intermediate Similarity	NPC9099
0.8417	Intermediate Similarity	NPC175943
0.8411	Intermediate Similarity	NPC167098
0.8411	Intermediate Similarity	NPC296044
0.8403	Intermediate Similarity	NPC469615
0.8389	Intermediate Similarity	NPC161159
0.838	Intermediate Similarity	NPC75763
0.838	Intermediate Similarity	NPC225036
0.838	Intermediate Similarity	NPC105525
0.838	Intermediate Similarity	NPC12218
0.8369	Intermediate Similarity	NPC62907
0.8367	Intermediate Similarity	NPC476394
0.8367	Intermediate Similarity	NPC98809
0.8345	Intermediate Similarity	NPC469683
0.8333	Intermediate Similarity	NPC144801
0.8333	Intermediate Similarity	NPC238672
0.8333	Intermediate Similarity	NPC281703
0.8333	Intermediate Similarity	NPC43872
0.8333	Intermediate Similarity	NPC291510
0.8333	Intermediate Similarity	NPC197188
0.8333	Intermediate Similarity	NPC116850
0.8333	Intermediate Similarity	NPC318799
0.8333	Intermediate Similarity	NPC125487
0.8322	Intermediate Similarity	NPC124842
0.8322	Intermediate Similarity	NPC270268
0.8321	Intermediate Similarity	NPC64111
0.8321	Intermediate Similarity	NPC208536
0.8312	Intermediate Similarity	NPC322982
0.8311	Intermediate Similarity	NPC142654
0.8309	Intermediate Similarity	NPC281020
0.8309	Intermediate Similarity	NPC324209
0.8299	Intermediate Similarity	NPC472969
0.8299	Intermediate Similarity	NPC476463
0.8288	Intermediate Similarity	NPC262282
0.8286	Intermediate Similarity	NPC155098
0.8276	Intermediate Similarity	NPC190587
0.8276	Intermediate Similarity	NPC121573
0.8276	Intermediate Similarity	NPC134975
0.8276	Intermediate Similarity	NPC258307
0.8276	Intermediate Similarity	NPC226738
0.8276	Intermediate Similarity	NPC473090
0.8276	Intermediate Similarity	NPC22176
0.8273	Intermediate Similarity	NPC477407
0.8267	Intermediate Similarity	NPC295646
0.8261	Intermediate Similarity	NPC285361
0.8255	Intermediate Similarity	NPC96501
0.8252	Intermediate Similarity	NPC92655
0.8252	Intermediate Similarity	NPC247409
0.8248	Intermediate Similarity	NPC167463
0.8248	Intermediate Similarity	NPC46192
0.8243	Intermediate Similarity	NPC107636
0.8235	Intermediate Similarity	NPC154275
0.8231	Intermediate Similarity	NPC32058
0.8231	Intermediate Similarity	NPC138978
0.8231	Intermediate Similarity	NPC85734
0.8227	Intermediate Similarity	NPC139519
0.8227	Intermediate Similarity	NPC208760
0.8224	Intermediate Similarity	NPC471968
0.8212	Intermediate Similarity	NPC62051
0.8212	Intermediate Similarity	NPC281477
0.8209	Intermediate Similarity	NPC225710
0.8207	Intermediate Similarity	NPC322112
0.8207	Intermediate Similarity	NPC285550
0.82	Intermediate Similarity	NPC221249
0.82	Intermediate Similarity	NPC267091
0.82	Intermediate Similarity	NPC204350
0.8194	Intermediate Similarity	NPC9218
0.8182	Intermediate Similarity	NPC24627
0.8182	Intermediate Similarity	NPC207516
0.8182	Intermediate Similarity	NPC155101
0.8182	Intermediate Similarity	NPC126739
0.8182	Intermediate Similarity	NPC197666
0.8175	Intermediate Similarity	NPC32163
0.8175	Intermediate Similarity	NPC16651
0.817	Intermediate Similarity	NPC247713
0.8169	Intermediate Similarity	NPC50455
0.8168	Intermediate Similarity	NPC150919
0.8158	Intermediate Similarity	NPC38898
0.8158	Intermediate Similarity	NPC80489
0.8158	Intermediate Similarity	NPC199926
0.8158	Intermediate Similarity	NPC82592
0.8158	Intermediate Similarity	NPC16082
0.8158	Intermediate Similarity	NPC472835
0.8158	Intermediate Similarity	NPC16286
0.8156	Intermediate Similarity	NPC311339
0.8156	Intermediate Similarity	NPC106406
0.8154	Intermediate Similarity	NPC4665
0.8151	Intermediate Similarity	NPC50221
0.8151	Intermediate Similarity	NPC50954
0.8151	Intermediate Similarity	NPC183824
0.8151	Intermediate Similarity	NPC114242
0.8151	Intermediate Similarity	NPC229036
0.8148	Intermediate Similarity	NPC212541
0.8141	Intermediate Similarity	NPC327809
0.8133	Intermediate Similarity	NPC243891
0.8125	Intermediate Similarity	NPC268052
0.8125	Intermediate Similarity	NPC32360
0.8117	Intermediate Similarity	NPC267627
0.8117	Intermediate Similarity	NPC40702
0.8117	Intermediate Similarity	NPC37502
0.8116	Intermediate Similarity	NPC234175
0.8108	Intermediate Similarity	NPC229264
0.8106	Intermediate Similarity	NPC27633
0.8106	Intermediate Similarity	NPC94298
0.8105	Intermediate Similarity	NPC54928
0.8105	Intermediate Similarity	NPC227062
0.8105	Intermediate Similarity	NPC150227
0.8105	Intermediate Similarity	NPC197751
0.8099	Intermediate Similarity	NPC72918
0.8095	Intermediate Similarity	NPC108455
0.8095	Intermediate Similarity	NPC275278
0.8092	Intermediate Similarity	NPC178134
0.8092	Intermediate Similarity	NPC131192
0.8088	Intermediate Similarity	NPC85565
0.8085	Intermediate Similarity	NPC4170
0.8085	Intermediate Similarity	NPC153783
0.8085	Intermediate Similarity	NPC129889
0.8085	Intermediate Similarity	NPC307006
0.8082	Intermediate Similarity	NPC169214
0.8082	Intermediate Similarity	NPC229218
0.8082	Intermediate Similarity	NPC176030
0.8082	Intermediate Similarity	NPC141817
0.8082	Intermediate Similarity	NPC192597
0.8082	Intermediate Similarity	NPC82913
0.8079	Intermediate Similarity	NPC202157
0.8079	Intermediate Similarity	NPC228662
0.8079	Intermediate Similarity	NPC75695
0.8071	Intermediate Similarity	NPC219892
0.8071	Intermediate Similarity	NPC189823
0.8069	Intermediate Similarity	NPC477279
0.8067	Intermediate Similarity	NPC306343
0.8065	Intermediate Similarity	NPC300680
0.8056	Intermediate Similarity	NPC221104
0.8056	Intermediate Similarity	NPC325625
0.8054	Intermediate Similarity	NPC142528
0.8054	Intermediate Similarity	NPC248257
0.8054	Intermediate Similarity	NPC120621
0.8054	Intermediate Similarity	NPC81835
0.8054	Intermediate Similarity	NPC43123
0.8052	Intermediate Similarity	NPC190020
0.8052	Intermediate Similarity	NPC84935
0.8052	Intermediate Similarity	NPC77679
0.8042	Intermediate Similarity	NPC223836
0.8042	Intermediate Similarity	NPC235115
0.8041	Intermediate Similarity	NPC287495
0.8041	Intermediate Similarity	NPC84786
0.8041	Intermediate Similarity	NPC131766
0.8041	Intermediate Similarity	NPC70136
0.8041	Intermediate Similarity	NPC473867
0.8041	Intermediate Similarity	NPC9370
0.8039	Intermediate Similarity	NPC20541
0.8039	Intermediate Similarity	NPC79998
0.8029	Intermediate Similarity	NPC197832
0.8029	Intermediate Similarity	NPC67951
0.8028	Intermediate Similarity	NPC204582

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 NPC156307 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	1045
0.2-0.3	1916
0.3-0.4	2679
0.4-0.5	1737
0.5-0.6	920
0.6-0.7	299
0.7-0.8	102
0.8-0.85	15
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD230	Phase 1
0.8209	Intermediate Similarity	NPD9269	Phase 2
0.8129	Intermediate Similarity	NPD3764	Approved
0.8125	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD9545	Approved
0.8092	Intermediate Similarity	NPD1465	Phase 2
0.7973	Intermediate Similarity	NPD1511	Approved
0.7914	Intermediate Similarity	NPD9494	Approved
0.791	Intermediate Similarity	NPD9268	Approved
0.7871	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1512	Approved
0.7838	Intermediate Similarity	NPD6190	Approved
0.7793	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2801	Approved
0.7651	Intermediate Similarity	NPD3750	Approved
0.7651	Intermediate Similarity	NPD4628	Phase 3
0.7639	Intermediate Similarity	NPD943	Approved
0.7625	Intermediate Similarity	NPD6232	Discontinued
0.7616	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3226	Approved
0.7586	Intermediate Similarity	NPD447	Suspended
0.7564	Intermediate Similarity	NPD1934	Approved
0.7554	Intermediate Similarity	NPD1608	Approved
0.7538	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD8166	Discontinued
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.747	Intermediate Similarity	NPD7685	Pre-registration
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7467	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2533	Approved
0.7451	Intermediate Similarity	NPD2534	Approved
0.7451	Intermediate Similarity	NPD2532	Approved
0.7421	Intermediate Similarity	NPD3882	Suspended
0.7394	Intermediate Similarity	NPD5844	Phase 1
0.7338	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.7333	Intermediate Similarity	NPD3818	Discontinued
0.7333	Intermediate Similarity	NPD7266	Discontinued
0.7329	Intermediate Similarity	NPD6234	Discontinued
0.7315	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3748	Approved
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7278	Intermediate Similarity	NPD6386	Approved
0.7278	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7267	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7261	Intermediate Similarity	NPD3455	Phase 2
0.7254	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1283	Approved
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7054	Approved
0.7185	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9493	Approved
0.7174	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1240	Approved
0.716	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7125	Intermediate Similarity	NPD37	Approved
0.7115	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1201	Approved
0.7108	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6166	Phase 2
0.7108	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4380	Phase 2
0.7101	Intermediate Similarity	NPD6797	Phase 2
0.7099	Intermediate Similarity	NPD4965	Approved
0.7099	Intermediate Similarity	NPD4966	Approved
0.7099	Intermediate Similarity	NPD4967	Phase 2
0.7086	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD3225	Approved
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD1481	Phase 2
0.7063	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD7251	Discontinued
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7059	Intermediate Similarity	NPD228	Approved
0.7055	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7075	Discontinued
0.7051	Intermediate Similarity	NPD6799	Approved
0.7045	Intermediate Similarity	NPD164	Approved
0.7041	Intermediate Similarity	NPD7074	Phase 3
0.7039	Intermediate Similarity	NPD5408	Approved
0.7039	Intermediate Similarity	NPD5405	Approved
0.7039	Intermediate Similarity	NPD5404	Approved
0.7039	Intermediate Similarity	NPD5406	Approved
0.7037	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD5402	Approved
0.7034	Intermediate Similarity	NPD1203	Approved
0.7027	Intermediate Similarity	NPD3268	Approved
0.7024	Intermediate Similarity	NPD7228	Approved
0.7007	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD2344	Approved
0.6993	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1281	Approved
0.6993	Remote Similarity	NPD422	Phase 1
0.6993	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD257	Approved
0.6986	Remote Similarity	NPD258	Approved
0.6981	Remote Similarity	NPD1653	Approved
0.6975	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4308	Phase 3
0.6968	Remote Similarity	NPD7003	Approved
0.6963	Remote Similarity	NPD2182	Approved
0.6962	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD7411	Suspended
0.6951	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5242	Approved
0.6933	Remote Similarity	NPD825	Approved
0.6933	Remote Similarity	NPD826	Approved
0.6928	Remote Similarity	NPD7199	Phase 2
0.6928	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD2354	Approved
0.6919	Remote Similarity	NPD7808	Phase 3
0.6918	Remote Similarity	NPD2797	Approved
0.6914	Remote Similarity	NPD6801	Discontinued
0.6913	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD411	Approved
0.6912	Remote Similarity	NPD3022	Approved
0.6912	Remote Similarity	NPD3021	Approved
0.6909	Remote Similarity	NPD919	Approved
0.6906	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1243	Approved
0.6903	Remote Similarity	NPD2800	Approved
0.6899	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6599	Discontinued
0.6887	Remote Similarity	NPD555	Phase 2
0.6886	Remote Similarity	NPD5710	Approved
0.6886	Remote Similarity	NPD5711	Approved
0.6875	Remote Similarity	NPD3705	Approved
0.6871	Remote Similarity	NPD2798	Approved
0.6867	Remote Similarity	NPD5494	Approved
0.6867	Remote Similarity	NPD259	Phase 1
0.6857	Remote Similarity	NPD8150	Discontinued
0.6853	Remote Similarity	NPD4626	Approved
0.6849	Remote Similarity	NPD1876	Approved
0.6846	Remote Similarity	NPD3027	Phase 3
0.6846	Remote Similarity	NPD7095	Approved
0.6845	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7390	Discontinued
0.6835	Remote Similarity	NPD1241	Discontinued
0.6832	Remote Similarity	NPD7458	Discontinued
0.6832	Remote Similarity	NPD824	Approved
0.6829	Remote Similarity	NPD4288	Approved
0.6828	Remote Similarity	NPD3972	Approved
0.6826	Remote Similarity	NPD8127	Discontinued
0.6826	Remote Similarity	NPD1247	Approved
0.6826	Remote Similarity	NPD6959	Discontinued
0.6824	Remote Similarity	NPD9569	Approved
0.6821	Remote Similarity	NPD2979	Phase 3
0.6821	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1613	Approved
0.6821	Remote Similarity	NPD4060	Phase 1
0.6818	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD6100	Approved
0.6815	Remote Similarity	NPD2309	Approved
0.6813	Remote Similarity	NPD920	Approved
0.6813	Remote Similarity	NPD5403	Approved
0.6805	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1164	Approved
0.6803	Remote Similarity	NPD3267	Approved
0.6803	Remote Similarity	NPD3266	Approved
0.6798	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5401	Approved
0.6788	Remote Similarity	NPD7768	Phase 2
0.6783	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1933	Approved
0.6774	Remote Similarity	NPD1471	Phase 3
0.6768	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7039	Approved
0.6763	Remote Similarity	NPD7038	Approved
0.6761	Remote Similarity	NPD5536	Phase 2
0.6761	Remote Similarity	NPD8434	Phase 2
0.6755	Remote Similarity	NPD6663	Approved
0.6755	Remote Similarity	NPD6233	Phase 2
0.6752	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4110	Phase 3
0.6739	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2932	Approved
0.6736	Remote Similarity	NPD3019	Approved
0.6736	Remote Similarity	NPD1778	Approved
0.6733	Remote Similarity	NPD9536	Phase 1
0.6733	Remote Similarity	NPD9537	Phase 1
0.6733	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD3751	Discontinued
0.6725	Remote Similarity	NPD7177	Discontinued
0.6715	Remote Similarity	NPD74	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