NPASS Compound

Structure

NPC257173 OpenBabel07101718232D 21 23 0 0 0 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 6 1 0 0 0 0 2 5 2 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 3 9 2 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 12 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.01
Volume:	256.965
LogP:	1.185
LogD:	0.271
LogS:	-3.338
# Rotatable Bonds:	1
TPSA:	138.18
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	2.764
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:	-5.049
MDCK Permeability:	1.732492273731623e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.766
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	80.51049041748047%
Volume Distribution (VD):	0.63
Pgp-substrate:	20.341291427612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.226
CYP1A2-substrate:	0.091
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.151
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.089
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.99
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.272
Skin Sensitization:	0.748
Carcinogencity:	0.035
Eye Corrosion:	0.022
Eye Irritation:	0.761
Respiratory Toxicity:	0.183

Download Data

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

Natural Product: NPC257173

Natural Product ID:	NPC257173
*Common Name:**	Phelligridin J
IUPAC Name:	8,9-dihydroxy-1,6-dioxopyrano[4,3-c]isochromene-3-carboxylic acid
Synonyms:	Phelligridin J
Standard InCHIKey:	HRPMTHJYSWKEDI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H6O8/c14-6-1-4-5(2-7(6)15)12(18)20-8-3-9(11(16)17)21-13(19)10(4)8/h1-3,14-15H,(H,16,17)
SMILES:	OC(=O)c1oc(=O)c2c(c1)oc(=O)c1c2cc(O)c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL373529
PubChem CID:	16109845
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	2
Individual Protein	1
Others	2
Subcellular	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4200.0	nM	PMID[526723]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	8400.0	nM	PMID[526723]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	10000.0	nM	PMID[526723]
NPT27	Others	Unspecified		IC50	=	7200.0	nM	PMID[526723]
NPT27	Others	Unspecified		IC50	=	9200.0	nM	PMID[526723]
NPT1084	Subcellular	Liver microsomes	Rattus norvegicus	IC50	=	6500.0	nM	PMID[526723]

☑ 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 NPC257173 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	529
0.1-0.2	2337
0.2-0.3	5680
0.3-0.4	11135
0.4-0.5	5896
0.5-0.6	4734
0.6-0.7	5789
0.7-0.8	5243
0.8-0.85	1106
0.85-0.9	229
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9403	High Similarity	NPC156307
0.9203	High Similarity	NPC91546
0.913	High Similarity	NPC290664
0.8819	High Similarity	NPC17042
0.8819	High Similarity	NPC155910
0.8725	High Similarity	NPC123208
0.8699	High Similarity	NPC9099
0.8652	High Similarity	NPC191280
0.8603	High Similarity	NPC94810
0.8581	High Similarity	NPC92747
0.8581	High Similarity	NPC265862
0.8571	High Similarity	NPC326847
0.8523	High Similarity	NPC161159
0.8493	Intermediate Similarity	NPC268366
0.8467	Intermediate Similarity	NPC226855
0.8456	Intermediate Similarity	NPC158654
0.8442	Intermediate Similarity	NPC322982
0.8431	Intermediate Similarity	NPC155101
0.8414	Intermediate Similarity	NPC470130
0.8392	Intermediate Similarity	NPC134969
0.8367	Intermediate Similarity	NPC229264
0.8357	Intermediate Similarity	NPC283823
0.8357	Intermediate Similarity	NPC159418
0.8356	Intermediate Similarity	NPC257025
0.8322	Intermediate Similarity	NPC239943
0.8288	Intermediate Similarity	NPC50221
0.8288	Intermediate Similarity	NPC114242
0.8286	Intermediate Similarity	NPC111888
0.8264	Intermediate Similarity	NPC105525
0.8264	Intermediate Similarity	NPC12218
0.8264	Intermediate Similarity	NPC75763
0.8264	Intermediate Similarity	NPC225036
0.8227	Intermediate Similarity	NPC1321
0.8227	Intermediate Similarity	NPC304929
0.8227	Intermediate Similarity	NPC156124
0.8227	Intermediate Similarity	NPC239855
0.8224	Intermediate Similarity	NPC291510
0.8224	Intermediate Similarity	NPC197188
0.8224	Intermediate Similarity	NPC43872
0.8224	Intermediate Similarity	NPC116850
0.8224	Intermediate Similarity	NPC281703
0.8224	Intermediate Similarity	NPC144801
0.8224	Intermediate Similarity	NPC238672
0.8224	Intermediate Similarity	NPC178134
0.8224	Intermediate Similarity	NPC125487
0.8219	Intermediate Similarity	NPC314271
0.8214	Intermediate Similarity	NPC264145
0.8207	Intermediate Similarity	NPC326065
0.8207	Intermediate Similarity	NPC477279
0.8207	Intermediate Similarity	NPC38473
0.8207	Intermediate Similarity	NPC327187
0.8195	Intermediate Similarity	NPC156654
0.8188	Intermediate Similarity	NPC324209
0.8188	Intermediate Similarity	NPC43123
0.8182	Intermediate Similarity	NPC156892
0.817	Intermediate Similarity	NPC80489
0.8163	Intermediate Similarity	NPC121573
0.8163	Intermediate Similarity	NPC134975
0.8163	Intermediate Similarity	NPC22176
0.8163	Intermediate Similarity	NPC226738
0.8163	Intermediate Similarity	NPC190587
0.8156	Intermediate Similarity	NPC18074
0.8156	Intermediate Similarity	NPC5419
0.8156	Intermediate Similarity	NPC61
0.8156	Intermediate Similarity	NPC25581
0.8151	Intermediate Similarity	NPC477277
0.8151	Intermediate Similarity	NPC477278
0.8143	Intermediate Similarity	NPC285776
0.8138	Intermediate Similarity	NPC471819
0.8133	Intermediate Similarity	NPC42464
0.8125	Intermediate Similarity	NPC110899
0.8125	Intermediate Similarity	NPC95679
0.8125	Intermediate Similarity	NPC112068
0.8125	Intermediate Similarity	NPC25305
0.8125	Intermediate Similarity	NPC125417
0.8117	Intermediate Similarity	NPC471968
0.8112	Intermediate Similarity	NPC18646
0.8112	Intermediate Similarity	NPC139519
0.8108	Intermediate Similarity	NPC113397
0.8099	Intermediate Similarity	NPC155209
0.8099	Intermediate Similarity	NPC168799
0.8095	Intermediate Similarity	NPC284948
0.8095	Intermediate Similarity	NPC220664
0.8095	Intermediate Similarity	NPC37331
0.8095	Intermediate Similarity	NPC319628
0.8095	Intermediate Similarity	NPC303090
0.8092	Intermediate Similarity	NPC270268
0.8085	Intermediate Similarity	NPC198388
0.8079	Intermediate Similarity	NPC306343
0.8069	Intermediate Similarity	NPC112135
0.8069	Intermediate Similarity	NPC302857
0.8069	Intermediate Similarity	NPC142703
0.8069	Intermediate Similarity	NPC152942
0.8069	Intermediate Similarity	NPC219428
0.8069	Intermediate Similarity	NPC37250
0.8069	Intermediate Similarity	NPC278068
0.8067	Intermediate Similarity	NPC471076
0.8067	Intermediate Similarity	NPC98009
0.8067	Intermediate Similarity	NPC192568
0.8067	Intermediate Similarity	NPC472969
0.8065	Intermediate Similarity	NPC247713
0.8065	Intermediate Similarity	NPC167098
0.8065	Intermediate Similarity	NPC296044
0.8056	Intermediate Similarity	NPC475111
0.8054	Intermediate Similarity	NPC75295
0.8054	Intermediate Similarity	NPC262282
0.8054	Intermediate Similarity	NPC258856
0.8052	Intermediate Similarity	NPC478221
0.8052	Intermediate Similarity	NPC317585
0.805	Intermediate Similarity	NPC20237
0.8041	Intermediate Similarity	NPC474692
0.8041	Intermediate Similarity	NPC469615
0.8041	Intermediate Similarity	NPC229036
0.8041	Intermediate Similarity	NPC258307
0.8038	Intermediate Similarity	NPC249181
0.8027	Intermediate Similarity	NPC471027
0.8027	Intermediate Similarity	NPC224389
0.8027	Intermediate Similarity	NPC297517
0.8027	Intermediate Similarity	NPC477335
0.8027	Intermediate Similarity	NPC35702
0.8027	Intermediate Similarity	NPC206095
0.8027	Intermediate Similarity	NPC13818
0.8026	Intermediate Similarity	NPC252979
0.8014	Intermediate Similarity	NPC476820
0.8014	Intermediate Similarity	NPC289690
0.8014	Intermediate Similarity	NPC274891
0.8014	Intermediate Similarity	NPC26241
0.8014	Intermediate Similarity	NPC303683
0.8014	Intermediate Similarity	NPC476819
0.8014	Intermediate Similarity	NPC474875
0.8014	Intermediate Similarity	NPC288452
0.8014	Intermediate Similarity	NPC295492
0.8014	Intermediate Similarity	NPC247409
0.8014	Intermediate Similarity	NPC205751
0.8013	Intermediate Similarity	NPC267627
0.8013	Intermediate Similarity	NPC471750
0.8013	Intermediate Similarity	NPC37502
0.8013	Intermediate Similarity	NPC476394
0.8013	Intermediate Similarity	NPC40702
0.8013	Intermediate Similarity	NPC98809
0.8	Intermediate Similarity	NPC167463
0.8	Intermediate Similarity	NPC62907
0.8	Intermediate Similarity	NPC283041
0.7987	Intermediate Similarity	NPC108455
0.7987	Intermediate Similarity	NPC191930
0.7987	Intermediate Similarity	NPC469683
0.7987	Intermediate Similarity	NPC478231
0.7975	Intermediate Similarity	NPC144557
0.7974	Intermediate Similarity	NPC228662
0.7974	Intermediate Similarity	NPC267091
0.7974	Intermediate Similarity	NPC124842
0.7973	Intermediate Similarity	NPC277315
0.7973	Intermediate Similarity	NPC43158
0.7973	Intermediate Similarity	NPC472016
0.7973	Intermediate Similarity	NPC322112
0.7973	Intermediate Similarity	NPC258469
0.7973	Intermediate Similarity	NPC192831
0.7972	Intermediate Similarity	NPC4170
0.7972	Intermediate Similarity	NPC307006
0.7972	Intermediate Similarity	NPC129889
0.7962	Intermediate Similarity	NPC24627
0.7962	Intermediate Similarity	NPC243701
0.7961	Intermediate Similarity	NPC142654
0.7959	Intermediate Similarity	NPC9218
0.7958	Intermediate Similarity	NPC318799
0.7956	Intermediate Similarity	NPC46634
0.7956	Intermediate Similarity	NPC225710
0.795	Intermediate Similarity	NPC328321
0.7949	Intermediate Similarity	NPC135222
0.7949	Intermediate Similarity	NPC472889
0.7949	Intermediate Similarity	NPC474010
0.7947	Intermediate Similarity	NPC142528
0.7947	Intermediate Similarity	NPC120621
0.7947	Intermediate Similarity	NPC248257
0.7947	Intermediate Similarity	NPC476463
0.7945	Intermediate Similarity	NPC325625
0.7945	Intermediate Similarity	NPC207516
0.7945	Intermediate Similarity	NPC284409
0.7943	Intermediate Similarity	NPC208536
0.7943	Intermediate Similarity	NPC64111
0.7935	Intermediate Similarity	NPC472890
0.7935	Intermediate Similarity	NPC16286
0.7935	Intermediate Similarity	NPC145425
0.7933	Intermediate Similarity	NPC473867
0.7933	Intermediate Similarity	NPC98356
0.7929	Intermediate Similarity	NPC281020
0.7925	Intermediate Similarity	NPC134047
0.7925	Intermediate Similarity	NPC173729
0.7925	Intermediate Similarity	NPC223006
0.7925	Intermediate Similarity	NPC272750
0.7922	Intermediate Similarity	NPC44730
0.7922	Intermediate Similarity	NPC295646
0.7919	Intermediate Similarity	NPC160378
0.7919	Intermediate Similarity	NPC473090
0.7917	Intermediate Similarity	NPC45404
0.7917	Intermediate Similarity	NPC175943
0.7917	Intermediate Similarity	NPC155098
0.7917	Intermediate Similarity	NPC474895
0.7908	Intermediate Similarity	NPC243891
0.7908	Intermediate Similarity	NPC96501

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 NPC257173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	466
0.1-0.2	1128
0.2-0.3	2164
0.3-0.4	2652
0.4-0.5	1587
0.5-0.6	785
0.6-0.7	252
0.7-0.8	99
0.8-0.85	12
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8227	Intermediate Similarity	NPD230	Phase 1
0.8224	Intermediate Similarity	NPD1465	Phase 2
0.8095	Intermediate Similarity	NPD6190	Approved
0.7956	Intermediate Similarity	NPD9269	Phase 2
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD1512	Approved
0.7762	Intermediate Similarity	NPD3764	Approved
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD9268	Approved
0.7651	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1511	Approved
0.7595	Intermediate Similarity	NPD3817	Phase 2
0.7591	Intermediate Similarity	NPD9545	Approved
0.7552	Intermediate Similarity	NPD9494	Approved
0.744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3882	Suspended
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6232	Discontinued
0.7421	Intermediate Similarity	NPD2801	Approved
0.732	Intermediate Similarity	NPD3750	Approved
0.732	Intermediate Similarity	NPD4628	Phase 3
0.7297	Intermediate Similarity	NPD943	Approved
0.7293	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7473	Discontinued
0.7278	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD7685	Pre-registration
0.7267	Intermediate Similarity	NPD5402	Approved
0.725	Intermediate Similarity	NPD1934	Approved
0.7248	Intermediate Similarity	NPD447	Suspended
0.7246	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7209	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7075	Discontinued
0.7176	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD6801	Discontinued
0.7134	Intermediate Similarity	NPD6234	Discontinued
0.7126	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6166	Phase 2
0.7124	Intermediate Similarity	NPD7266	Discontinued
0.7101	Intermediate Similarity	NPD5844	Phase 1
0.7099	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8166	Discontinued
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD6799	Approved
0.7044	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5403	Approved
0.7035	Intermediate Similarity	NPD7808	Phase 3
0.7032	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5401	Approved
0.7025	Intermediate Similarity	NPD2532	Approved
0.7025	Intermediate Similarity	NPD2533	Approved
0.7025	Intermediate Similarity	NPD2534	Approved
0.7019	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD7054	Approved
0.6994	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7819	Suspended
0.6993	Remote Similarity	NPD1510	Phase 2
0.6993	Remote Similarity	NPD3748	Approved
0.6975	Remote Similarity	NPD6386	Approved
0.6975	Remote Similarity	NPD6385	Approved
0.6964	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7472	Approved
0.6957	Remote Similarity	NPD3455	Phase 2
0.695	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2354	Approved
0.6939	Remote Similarity	NPD1470	Approved
0.6933	Remote Similarity	NPD37	Approved
0.6929	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD919	Approved
0.6918	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6599	Discontinued
0.691	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4967	Phase 2
0.6909	Remote Similarity	NPD4965	Approved
0.6909	Remote Similarity	NPD4966	Approved
0.6903	Remote Similarity	NPD2346	Discontinued
0.6894	Remote Similarity	NPD1653	Approved
0.6883	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD3749	Approved
0.6867	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7095	Approved
0.686	Remote Similarity	NPD7074	Phase 3
0.6846	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1247	Approved
0.6842	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD7228	Approved
0.6842	Remote Similarity	NPD3751	Discontinued
0.6839	Remote Similarity	NPD2935	Discontinued
0.6821	Remote Similarity	NPD2313	Discontinued
0.68	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1201	Approved
0.678	Remote Similarity	NPD8434	Phase 2
0.6776	Remote Similarity	NPD6233	Phase 2
0.6757	Remote Similarity	NPD1283	Approved
0.6757	Remote Similarity	NPD3225	Approved
0.6752	Remote Similarity	NPD1549	Phase 2
0.6747	Remote Similarity	NPD5353	Approved
0.6746	Remote Similarity	NPD7199	Phase 2
0.6735	Remote Similarity	NPD1481	Phase 2
0.6732	Remote Similarity	NPD1240	Approved
0.6731	Remote Similarity	NPD5405	Approved
0.6731	Remote Similarity	NPD5406	Approved
0.6731	Remote Similarity	NPD5404	Approved
0.6731	Remote Similarity	NPD5408	Approved
0.6714	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD228	Approved
0.6713	Remote Similarity	NPD9493	Approved
0.6711	Remote Similarity	NPD1203	Approved
0.6711	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3146	Approved
0.6705	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6355	Discontinued
0.6688	Remote Similarity	NPD4340	Discontinued
0.6688	Remote Similarity	NPD2353	Approved
0.6688	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1471	Phase 3
0.6688	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD1535	Discovery
0.6667	Remote Similarity	NPD5242	Approved
0.6647	Remote Similarity	NPD8127	Discontinued
0.6647	Remote Similarity	NPD6959	Discontinued
0.6645	Remote Similarity	NPD1607	Approved
0.6624	Remote Similarity	NPD1551	Phase 2
0.6623	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1613	Approved
0.6622	Remote Similarity	NPD9717	Approved
0.661	Remote Similarity	NPD8312	Approved
0.661	Remote Similarity	NPD8313	Approved
0.6608	Remote Similarity	NPD3787	Discontinued
0.6605	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2800	Approved
0.6601	Remote Similarity	NPD3268	Approved
0.6601	Remote Similarity	NPD411	Approved
0.6588	Remote Similarity	NPD5494	Approved
0.6584	Remote Similarity	NPD3300	Phase 2
0.6582	Remote Similarity	NPD2344	Approved
0.657	Remote Similarity	NPD3926	Phase 2
0.6569	Remote Similarity	NPD164	Approved
0.6564	Remote Similarity	NPD6273	Approved
0.6562	Remote Similarity	NPD7003	Approved
0.6561	Remote Similarity	NPD4308	Phase 3
0.6558	Remote Similarity	NPD4062	Phase 3
0.6556	Remote Similarity	NPD257	Approved
0.6556	Remote Similarity	NPD258	Approved
0.6554	Remote Similarity	NPD422	Phase 1
0.6554	Remote Similarity	NPD1281	Approved
0.6554	Remote Similarity	NPD3705	Approved
0.6548	Remote Similarity	NPD4288	Approved
0.6545	Remote Similarity	NPD7458	Discontinued
0.6545	Remote Similarity	NPD824	Approved
0.6543	Remote Similarity	NPD7435	Discontinued
0.6543	Remote Similarity	NPD7390	Discontinued
0.6536	Remote Similarity	NPD3027	Phase 3
0.6532	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD920	Approved
0.6522	Remote Similarity	NPD3887	Approved
0.6516	Remote Similarity	NPD825	Approved
0.6516	Remote Similarity	NPD826	Approved
0.6513	Remote Similarity	NPD9569	Approved
0.6512	Remote Similarity	NPD5710	Approved
0.6512	Remote Similarity	NPD5711	Approved
0.6503	Remote Similarity	NPD642	Clinical (unspecified phase)
0.65	Remote Similarity	NPD1243	Approved
0.65	Remote Similarity	NPD74	Approved
0.65	Remote Similarity	NPD2182	Approved
0.65	Remote Similarity	NPD9266	Approved
0.6497	Remote Similarity	NPD7039	Approved
0.6497	Remote Similarity	NPD7038	Approved
0.6494	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1164	Approved
0.649	Remote Similarity	NPD2797	Approved
0.6488	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD555	Phase 2
0.6474	Remote Similarity	NPD1933	Approved
0.6463	Remote Similarity	NPD5049	Phase 3
0.646	Remote Similarity	NPD4110	Phase 3
0.646	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD3022	Approved
0.6454	Remote Similarity	NPD3021	Approved
0.6452	Remote Similarity	NPD259	Phase 1
0.645	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2798	Approved
0.6446	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5536	Phase 2
0.6433	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD9263	Approved
0.6429	Remote Similarity	NPD9267	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