NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	346.031
LogP:	1.71
LogD:	1.992
LogS:	-3.998
# Rotatable Bonds:	3
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.903
Synthetic Accessibility Score:	3.588
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	3.100850517512299e-05
Pgp-inhibitor:	0.354
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	89.1103744506836%
Volume Distribution (VD):	0.493
Pgp-substrate:	11.973481178283691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.302
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.43
CYP2C9-substrate:	0.67
CYP2D6-inhibitor:	0.156
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.752

ADMET: Excretion

Clearance (CL):	2.42
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.192
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.56
Rat Oral Acute Toxicity:	0.551
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.679
Carcinogencity:	0.203
Eye Corrosion:	0.003
Eye Irritation:	0.069
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC477517

Natural Product ID:	NPC477517
*Common Name:**	4-hydroxy-3,10,11-trimethoxy-6a,12a-dihydro-5H-isochromeno[4,3-b]chromen-7-one
IUPAC Name:	4-hydroxy-3,10,11-trimethoxy-6a,12a-dihydro-5H-isochromeno[4,3-b]chromen-7-one
Synonyms:	Diplotasin
Standard InCHIKey:	NPLRFSWZYOARFO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-22-12-6-4-9-11(14(12)20)8-25-19-15(21)10-5-7-13(23-2)18(24-3)17(10)26-16(9)19/h4-7,16,19-20H,8H2,1-3H3
SMILES:	COC1=C(C2=C(C=C1)C3C(C(=O)C4=C(O3)C(=C(C=C4)OC)OC)OC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57397368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21875046]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	whole plant	Taitung County, Taiwan	2009-MAY	PMID[21875046]
NPO17263	Mimosa diplotricha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27715048]
NPO17263	Mimosa diplotricha	Species	Fabaceae	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
GI50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	>	10000	nM	PMID[21875046]
NPT196	Cell Line	AGS	Homo sapiens	GI50	>	10000	nM	PMID[21875046]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	>	10000	nM	PMID[21875046]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	>	10000	nM	PMID[21875046]

☑ 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 NPC477517 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	427
0.1-0.2	1784
0.2-0.3	4379
0.3-0.4	10313
0.4-0.5	7498
0.5-0.6	3436
0.6-0.7	4889
0.7-0.8	5502
0.8-0.85	2657
0.85-0.9	1524
0.9-0.95	283
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC173137
0.956	High Similarity	NPC62261
0.956	High Similarity	NPC224280
0.956	High Similarity	NPC234052
0.9551	High Similarity	NPC471479
0.9551	High Similarity	NPC471515
0.949	High Similarity	NPC55738
0.9487	High Similarity	NPC471500
0.9437	High Similarity	NPC293319
0.9434	High Similarity	NPC472964
0.943	High Similarity	NPC474960
0.943	High Similarity	NPC472902
0.943	High Similarity	NPC36217
0.9427	High Similarity	NPC299520
0.9427	High Similarity	NPC67876
0.9427	High Similarity	NPC52530
0.9427	High Similarity	NPC129684
0.9423	High Similarity	NPC67396
0.9375	High Similarity	NPC186686
0.9371	High Similarity	NPC308992
0.9371	High Similarity	NPC134783
0.9363	High Similarity	NPC320825
0.9363	High Similarity	NPC13858
0.9363	High Similarity	NPC265511
0.9363	High Similarity	NPC24640
0.9363	High Similarity	NPC474638
0.9363	High Similarity	NPC326037
0.9359	High Similarity	NPC18727
0.9321	High Similarity	NPC477154
0.9321	High Similarity	NPC117854
0.9321	High Similarity	NPC6588
0.9321	High Similarity	NPC150131
0.9317	High Similarity	NPC7688
0.9317	High Similarity	NPC72787
0.9317	High Similarity	NPC7154
0.9317	High Similarity	NPC36916
0.9317	High Similarity	NPC58223
0.9317	High Similarity	NPC36
0.9317	High Similarity	NPC125039
0.9317	High Similarity	NPC475888
0.9313	High Similarity	NPC474034
0.9313	High Similarity	NPC474033
0.9313	High Similarity	NPC201800
0.9313	High Similarity	NPC211107
0.9308	High Similarity	NPC470183
0.9308	High Similarity	NPC287328
0.9308	High Similarity	NPC282009
0.9308	High Similarity	NPC200746
0.9308	High Similarity	NPC263449
0.9304	High Similarity	NPC472963
0.9304	High Similarity	NPC99597
0.9304	High Similarity	NPC156057
0.9304	High Similarity	NPC210084
0.9304	High Similarity	NPC241904
0.9304	High Similarity	NPC162869
0.9304	High Similarity	NPC475267
0.9304	High Similarity	NPC291508
0.9304	High Similarity	NPC48208
0.9304	High Similarity	NPC474208
0.9304	High Similarity	NPC300727
0.9304	High Similarity	NPC474836
0.9299	High Similarity	NPC56786
0.9299	High Similarity	NPC255807
0.9299	High Similarity	NPC31018
0.9299	High Similarity	NPC80534
0.9295	High Similarity	NPC219582
0.9295	High Similarity	NPC477231
0.9295	High Similarity	NPC302950
0.9295	High Similarity	NPC236637
0.9295	High Similarity	NPC257648
0.9264	High Similarity	NPC152477
0.9259	High Similarity	NPC43319
0.9259	High Similarity	NPC471213
0.9255	High Similarity	NPC236521
0.9255	High Similarity	NPC472625
0.9255	High Similarity	NPC474240
0.9255	High Similarity	NPC475985
0.9255	High Similarity	NPC248638
0.9255	High Similarity	NPC152659
0.925	High Similarity	NPC471499
0.925	High Similarity	NPC112418
0.925	High Similarity	NPC471210
0.925	High Similarity	NPC472632
0.9245	High Similarity	NPC476242
0.9245	High Similarity	NPC329091
0.9245	High Similarity	NPC210459
0.9245	High Similarity	NPC280680
0.9245	High Similarity	NPC152904
0.9245	High Similarity	NPC22192
0.9241	High Similarity	NPC35038
0.9241	High Similarity	NPC195796
0.9241	High Similarity	NPC255106
0.9241	High Similarity	NPC153512
0.9241	High Similarity	NPC274730
0.9241	High Similarity	NPC472916
0.9241	High Similarity	NPC472907
0.9241	High Similarity	NPC291878
0.9241	High Similarity	NPC278778
0.9241	High Similarity	NPC235165
0.9241	High Similarity	NPC250922
0.9236	High Similarity	NPC141212
0.9236	High Similarity	NPC325028
0.9236	High Similarity	NPC179126
0.9236	High Similarity	NPC27532
0.9236	High Similarity	NPC203080
0.9236	High Similarity	NPC270620
0.9236	High Similarity	NPC236223
0.9236	High Similarity	NPC78326
0.9236	High Similarity	NPC469550
0.9236	High Similarity	NPC246328
0.9236	High Similarity	NPC472905
0.9236	High Similarity	NPC256346
0.9231	High Similarity	NPC31363
0.9202	High Similarity	NPC14662
0.9202	High Similarity	NPC474024
0.9202	High Similarity	NPC218226
0.9202	High Similarity	NPC8965
0.9198	High Similarity	NPC326520
0.9198	High Similarity	NPC239752
0.9198	High Similarity	NPC472277
0.9198	High Similarity	NPC275780
0.9198	High Similarity	NPC472450
0.9193	High Similarity	NPC471745
0.9193	High Similarity	NPC476247
0.9193	High Similarity	NPC474150
0.9193	High Similarity	NPC25152
0.9193	High Similarity	NPC474162
0.9187	High Similarity	NPC471744
0.9187	High Similarity	NPC139036
0.9187	High Similarity	NPC228785
0.9187	High Similarity	NPC192686
0.9187	High Similarity	NPC119209
0.9187	High Similarity	NPC321399
0.9187	High Similarity	NPC56085
0.9187	High Similarity	NPC118256
0.9187	High Similarity	NPC14353
0.9187	High Similarity	NPC174953
0.9187	High Similarity	NPC470326
0.9187	High Similarity	NPC299436
0.9187	High Similarity	NPC471973
0.9182	High Similarity	NPC222814
0.9182	High Similarity	NPC181960
0.9182	High Similarity	NPC110070
0.9182	High Similarity	NPC469584
0.9182	High Similarity	NPC471209
0.9182	High Similarity	NPC96167
0.9182	High Similarity	NPC472913
0.9182	High Similarity	NPC472598
0.9182	High Similarity	NPC472914
0.9182	High Similarity	NPC203891
0.9182	High Similarity	NPC245758
0.9182	High Similarity	NPC474055
0.9182	High Similarity	NPC101830
0.9182	High Similarity	NPC27337
0.9182	High Similarity	NPC472910
0.9182	High Similarity	NPC472911
0.9182	High Similarity	NPC136674
0.9177	High Similarity	NPC117992
0.9177	High Similarity	NPC57674
0.9177	High Similarity	NPC37392
0.9177	High Similarity	NPC2928
0.9177	High Similarity	NPC152951
0.9177	High Similarity	NPC168247
0.9177	High Similarity	NPC470327
0.9177	High Similarity	NPC230149
0.9177	High Similarity	NPC45849
0.9177	High Similarity	NPC200761
0.9177	High Similarity	NPC477503
0.9172	High Similarity	NPC60972
0.9172	High Similarity	NPC61506
0.9172	High Similarity	NPC9743
0.9172	High Similarity	NPC260979
0.9172	High Similarity	NPC260491
0.9172	High Similarity	NPC39732
0.9172	High Similarity	NPC82325
0.9172	High Similarity	NPC279989
0.9172	High Similarity	NPC472912
0.9172	High Similarity	NPC36835
0.9172	High Similarity	NPC240476
0.9172	High Similarity	NPC246162
0.9172	High Similarity	NPC55205
0.9167	High Similarity	NPC338131
0.9167	High Similarity	NPC29231
0.9167	High Similarity	NPC151473
0.9157	High Similarity	NPC108202
0.9152	High Similarity	NPC121333
0.9146	High Similarity	NPC177480
0.9146	High Similarity	NPC242395
0.9146	High Similarity	NPC52382
0.9146	High Similarity	NPC229687
0.9146	High Similarity	NPC270578
0.9146	High Similarity	NPC288813
0.9141	High Similarity	NPC39091
0.9141	High Similarity	NPC170245
0.9141	High Similarity	NPC472449
0.9136	High Similarity	NPC41301
0.9136	High Similarity	NPC205265
0.9136	High Similarity	NPC124038
0.9136	High Similarity	NPC472281
0.9136	High Similarity	NPC18100

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 NPC477517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	963
0.2-0.3	1807
0.3-0.4	2631
0.4-0.5	1750
0.5-0.6	969
0.6-0.7	439
0.7-0.8	140
0.8-0.85	32
0.85-0.9	13
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9317	High Similarity	NPD6167	Clinical (unspecified phase)
0.9317	High Similarity	NPD6166	Phase 2
0.9317	High Similarity	NPD6168	Clinical (unspecified phase)
0.9295	High Similarity	NPD1934	Approved
0.9241	High Similarity	NPD3882	Suspended
0.9114	High Similarity	NPD2393	Clinical (unspecified phase)
0.8994	High Similarity	NPD2801	Approved
0.8922	High Similarity	NPD6797	Phase 2
0.8869	High Similarity	NPD7251	Discontinued
0.8862	High Similarity	NPD7074	Phase 3
0.8834	High Similarity	NPD5494	Approved
0.882	High Similarity	NPD3817	Phase 2
0.8817	High Similarity	NPD7808	Phase 3
0.8817	High Similarity	NPD4338	Clinical (unspecified phase)
0.8802	High Similarity	NPD7054	Approved
0.879	High Similarity	NPD1512	Approved
0.8765	High Similarity	NPD4868	Clinical (unspecified phase)
0.875	High Similarity	NPD7472	Approved
0.8743	High Similarity	NPD3818	Discontinued
0.8712	High Similarity	NPD7075	Discontinued
0.8662	High Similarity	NPD1511	Approved
0.8642	High Similarity	NPD1465	Phase 2
0.8642	High Similarity	NPD7096	Clinical (unspecified phase)
0.8588	High Similarity	NPD7993	Clinical (unspecified phase)
0.8571	High Similarity	NPD4380	Phase 2
0.8491	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD5844	Phase 1
0.8471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1549	Phase 2
0.8443	Intermediate Similarity	NPD6959	Discontinued
0.8428	Intermediate Similarity	NPD6799	Approved
0.8415	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8393	Intermediate Similarity	NPD6232	Discontinued
0.8364	Intermediate Similarity	NPD5402	Approved
0.8354	Intermediate Similarity	NPD6801	Discontinued
0.8353	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8253	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD2796	Approved
0.8198	Intermediate Similarity	NPD3751	Discontinued
0.816	Intermediate Similarity	NPD5403	Approved
0.8153	Intermediate Similarity	NPD1510	Phase 2
0.8129	Intermediate Similarity	NPD3926	Phase 2
0.8118	Intermediate Similarity	NPD1247	Approved
0.8072	Intermediate Similarity	NPD7411	Suspended
0.807	Intermediate Similarity	NPD3787	Discontinued
0.8047	Intermediate Similarity	NPD3749	Approved
0.8038	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD1240	Approved
0.8012	Intermediate Similarity	NPD3750	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1607	Approved
0.791	Intermediate Similarity	NPD6559	Discontinued
0.7901	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD1613	Approved
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2533	Approved
0.7818	Intermediate Similarity	NPD2532	Approved
0.7818	Intermediate Similarity	NPD2534	Approved
0.7807	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6234	Discontinued
0.7784	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD7768	Phase 2
0.7756	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6190	Approved
0.7736	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD8312	Approved
0.7707	Intermediate Similarity	NPD3027	Phase 3
0.7702	Intermediate Similarity	NPD3748	Approved
0.7701	Intermediate Similarity	NPD7199	Phase 2
0.7692	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD3226	Approved
0.7625	Intermediate Similarity	NPD447	Suspended
0.7622	Intermediate Similarity	NPD2800	Approved
0.7619	Intermediate Similarity	NPD6776	Approved
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD6780	Approved
0.7619	Intermediate Similarity	NPD6782	Approved
0.7619	Intermediate Similarity	NPD6779	Approved
0.7619	Intermediate Similarity	NPD6777	Approved
0.7619	Intermediate Similarity	NPD6778	Approved
0.7607	Intermediate Similarity	NPD2346	Discontinued
0.7602	Intermediate Similarity	NPD37	Approved
0.7596	Intermediate Similarity	NPD8150	Discontinued
0.7593	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7546	Intermediate Similarity	NPD2935	Discontinued
0.7546	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD6099	Approved
0.7546	Intermediate Similarity	NPD1551	Phase 2
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD7697	Approved
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7471	Intermediate Similarity	NPD1653	Approved
0.7468	Intermediate Similarity	NPD9494	Approved
0.746	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7390	Discontinued
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD4908	Phase 1
0.7412	Intermediate Similarity	NPD920	Approved
0.7407	Intermediate Similarity	NPD1933	Approved
0.7396	Intermediate Similarity	NPD2494	Approved
0.7396	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD2493	Approved
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.7371	Intermediate Similarity	NPD7871	Phase 2
0.7371	Intermediate Similarity	NPD7870	Phase 2
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5953	Discontinued
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.736	Intermediate Similarity	NPD5710	Approved
0.736	Intermediate Similarity	NPD5711	Approved
0.7354	Intermediate Similarity	NPD6535	Approved
0.7354	Intermediate Similarity	NPD6534	Approved
0.7348	Intermediate Similarity	NPD7286	Phase 2
0.7346	Intermediate Similarity	NPD4060	Phase 1
0.734	Intermediate Similarity	NPD7907	Approved
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7240	Approved
0.7321	Intermediate Similarity	NPD2309	Approved
0.7318	Intermediate Similarity	NPD5242	Approved
0.7308	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD3450	Approved
0.7306	Intermediate Similarity	NPD3452	Approved
0.7301	Intermediate Similarity	NPD6355	Discontinued
0.7294	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD1471	Phase 3
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD4582	Approved
0.7282	Intermediate Similarity	NPD8319	Approved
0.7282	Intermediate Similarity	NPD4583	Approved
0.7278	Intermediate Similarity	NPD2403	Approved
0.7263	Intermediate Similarity	NPD4360	Phase 2
0.7263	Intermediate Similarity	NPD4363	Phase 3
0.7262	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4665	Approved
0.7241	Intermediate Similarity	NPD4111	Phase 1
0.7236	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7801	Approved
0.7236	Intermediate Similarity	NPD7783	Phase 2
0.7231	Intermediate Similarity	NPD4002	Approved
0.7231	Intermediate Similarity	NPD4004	Approved
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7216	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD1243	Approved
0.72	Intermediate Similarity	NPD6844	Discontinued
0.7197	Intermediate Similarity	NPD1610	Phase 2
0.7196	Intermediate Similarity	NPD2490	Approved
0.7196	Intermediate Similarity	NPD2488	Approved
0.7188	Intermediate Similarity	NPD2975	Approved
0.7188	Intermediate Similarity	NPD2973	Approved
0.7188	Intermediate Similarity	NPD2974	Approved
0.7186	Intermediate Similarity	NPD7266	Discontinued
0.7182	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7178	Intermediate Similarity	NPD6233	Phase 2
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD6651	Approved
0.7151	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4287	Approved
0.7125	Intermediate Similarity	NPD1203	Approved
0.7125	Intermediate Similarity	NPD1470	Approved
0.7121	Intermediate Similarity	NPD7584	Approved
0.7119	Intermediate Similarity	NPD4288	Approved
0.7111	Intermediate Similarity	NPD8127	Discontinued
0.7104	Intermediate Similarity	NPD2163	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