NPASS Compound

Structure

NPC42892 OpenBabel07101719512D 22 25 0 0 1 0 0 0 0 0999 V2000 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 8 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 20 1 0 0 0 0 7 21 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 1 0 0 0 15 8 1 6 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.06
Volume:	285.353
LogP:	1.689
LogD:	0.737
LogS:	-2.637
# Rotatable Bonds:	1
TPSA:	85.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.836
Synthetic Accessibility Score:	3.497
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.069
MDCK Permeability:	1.3103628589306027e-05
Pgp-inhibitor:	0.374
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	95.71196746826172%
Volume Distribution (VD):	0.568
Pgp-substrate:	4.4245758056640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.268
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.184
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.427
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.718
CYP2D6-substrate:	0.288
CYP3A4-inhibitor:	0.82
CYP3A4-substrate:	0.587

ADMET: Excretion

Clearance (CL):	4.491
Half-life (T1/2):	0.371

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.219
Skin Sensitization:	0.584
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.339
Respiratory Toxicity:	0.258

Download Data

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

Natural Product: NPC42892

Natural Product ID:	NPC42892
*Common Name:**	(2R,3R)-3-Hydroxy-5-Methoxy-6,7-Methylenedioxyflavanone
IUPAC Name:	(6R,7R)-7,9-dihydroxy-6-phenyl-6,7-dihydro-[1,3]dioxolo[4,5-g]chromen-8-one
Synonyms:
Standard InCHIKey:	WVADKXWSLHLDCL-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C16H12O6/c17-12-11-9(6-10-16(13(11)18)21-7-20-10)22-15(14(12)19)8-4-2-1-3-5-8/h1-6,14-15,18-19H,7H2/t14-,15+/m0/s1
SMILES:	O[C@@H]1[C@H](Oc2c(C1=O)c(O)c1c(c2)OCO1)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1802148
PubChem CID:	56666462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones [CHEMONTID:0001362] Flavanonols

*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
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	root	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	stem	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21542597]
NPO25983	Pisonia aculeata	Species	Nyctaginaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>=	100.0	ug.mL-1	PMID[469458]

☑ 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 NPC42892 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	431
0.1-0.2	1839
0.2-0.3	4608
0.3-0.4	10189
0.4-0.5	7597
0.5-0.6	3886
0.6-0.7	4823
0.7-0.8	5819
0.8-0.85	2148
0.85-0.9	1211
0.9-0.95	143
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC470178
0.9557	High Similarity	NPC162668
0.9506	High Similarity	NPC245014
0.9506	High Similarity	NPC84265
0.9506	High Similarity	NPC282987
0.9506	High Similarity	NPC72249
0.9494	High Similarity	NPC263449
0.9451	High Similarity	NPC472607
0.9448	High Similarity	NPC476405
0.9448	High Similarity	NPC117260
0.9444	High Similarity	NPC112755
0.9444	High Similarity	NPC471457
0.9444	High Similarity	NPC170675
0.9441	High Similarity	NPC113093
0.9441	High Similarity	NPC254306
0.9434	High Similarity	NPC308992
0.9427	High Similarity	NPC201837
0.9394	High Similarity	NPC268533
0.939	High Similarity	NPC169977
0.939	High Similarity	NPC24043
0.939	High Similarity	NPC45522
0.939	High Similarity	NPC21666
0.939	High Similarity	NPC42773
0.939	High Similarity	NPC101026
0.9387	High Similarity	NPC212748
0.9387	High Similarity	NPC22195
0.9387	High Similarity	NPC183357
0.9387	High Similarity	NPC34287
0.9387	High Similarity	NPC471416
0.9387	High Similarity	NPC21190
0.9383	High Similarity	NPC76482
0.9383	High Similarity	NPC48640
0.9383	High Similarity	NPC45618
0.9383	High Similarity	NPC146792
0.9383	High Similarity	NPC149244
0.9383	High Similarity	NPC58716
0.9379	High Similarity	NPC165720
0.9375	High Similarity	NPC469575
0.9371	High Similarity	NPC225624
0.9371	High Similarity	NPC285973
0.9341	High Similarity	NPC473071
0.9341	High Similarity	NPC473073
0.9337	High Similarity	NPC168584
0.9333	High Similarity	NPC43211
0.9333	High Similarity	NPC237435
0.9333	High Similarity	NPC135277
0.9333	High Similarity	NPC477848
0.9333	High Similarity	NPC115760
0.9333	High Similarity	NPC49344
0.9333	High Similarity	NPC101191
0.9333	High Similarity	NPC210094
0.9329	High Similarity	NPC205076
0.9329	High Similarity	NPC307518
0.9329	High Similarity	NPC48773
0.9325	High Similarity	NPC210042
0.9325	High Similarity	NPC226294
0.9325	High Similarity	NPC45638
0.9325	High Similarity	NPC95855
0.9325	High Similarity	NPC472383
0.9325	High Similarity	NPC93337
0.9325	High Similarity	NPC186807
0.9325	High Similarity	NPC475942
0.9325	High Similarity	NPC58053
0.9325	High Similarity	NPC105025
0.9325	High Similarity	NPC472381
0.9325	High Similarity	NPC469931
0.9325	High Similarity	NPC201292
0.9321	High Similarity	NPC67037
0.9321	High Similarity	NPC255615
0.9321	High Similarity	NPC21100
0.9321	High Similarity	NPC197285
0.9317	High Similarity	NPC88043
0.9313	High Similarity	NPC295009
0.9313	High Similarity	NPC260640
0.9304	High Similarity	NPC320825
0.9304	High Similarity	NPC235165
0.9304	High Similarity	NPC13858
0.9304	High Similarity	NPC326037
0.9304	High Similarity	NPC255106
0.9286	High Similarity	NPC473072
0.9277	High Similarity	NPC8573
0.9277	High Similarity	NPC169733
0.9277	High Similarity	NPC156635
0.9277	High Similarity	NPC472380
0.9277	High Similarity	NPC198324
0.9277	High Similarity	NPC211532
0.9277	High Similarity	NPC472382
0.9277	High Similarity	NPC472384
0.9277	High Similarity	NPC233994
0.9277	High Similarity	NPC472385
0.9273	High Similarity	NPC51774
0.9273	High Similarity	NPC239549
0.9273	High Similarity	NPC236191
0.9268	High Similarity	NPC224462
0.9268	High Similarity	NPC44558
0.9268	High Similarity	NPC105511
0.9268	High Similarity	NPC474434
0.9264	High Similarity	NPC160156
0.9264	High Similarity	NPC45400
0.9264	High Similarity	NPC92565
0.9264	High Similarity	NPC93099
0.9259	High Similarity	NPC277205
0.9259	High Similarity	NPC34531
0.9255	High Similarity	NPC127782
0.9255	High Similarity	NPC300537
0.9255	High Similarity	NPC125991
0.9245	High Similarity	NPC162869
0.9245	High Similarity	NPC156057
0.9245	High Similarity	NPC474208
0.9245	High Similarity	NPC99597
0.9245	High Similarity	NPC210084
0.9245	High Similarity	NPC474836
0.9245	High Similarity	NPC475267
0.9245	High Similarity	NPC52530
0.9245	High Similarity	NPC48208
0.9236	High Similarity	NPC9743
0.9236	High Similarity	NPC246162
0.9236	High Similarity	NPC240476
0.9236	High Similarity	NPC36835
0.9236	High Similarity	NPC260491
0.9236	High Similarity	NPC61506
0.9217	High Similarity	NPC264735
0.9212	High Similarity	NPC261254
0.9212	High Similarity	NPC3583
0.9212	High Similarity	NPC245452
0.9212	High Similarity	NPC267254
0.9212	High Similarity	NPC235575
0.9212	High Similarity	NPC301683
0.9212	High Similarity	NPC254540
0.9212	High Similarity	NPC259152
0.9212	High Similarity	NPC172807
0.9212	High Similarity	NPC472386
0.9212	High Similarity	NPC211594
0.9207	High Similarity	NPC203050
0.9207	High Similarity	NPC120099
0.9207	High Similarity	NPC223747
0.9207	High Similarity	NPC476771
0.9207	High Similarity	NPC183036
0.9207	High Similarity	NPC270578
0.9207	High Similarity	NPC225434
0.9207	High Similarity	NPC52382
0.9207	High Similarity	NPC229687
0.9207	High Similarity	NPC219904
0.9202	High Similarity	NPC281131
0.9202	High Similarity	NPC276222
0.9202	High Similarity	NPC274618
0.9202	High Similarity	NPC5778
0.9202	High Similarity	NPC88789
0.9202	High Similarity	NPC253662
0.9202	High Similarity	NPC308404
0.9202	High Similarity	NPC118284
0.9202	High Similarity	NPC179950
0.9202	High Similarity	NPC236934
0.9202	High Similarity	NPC145038
0.9202	High Similarity	NPC56077
0.9198	High Similarity	NPC191306
0.9198	High Similarity	NPC270335
0.9198	High Similarity	NPC29830
0.9198	High Similarity	NPC94777
0.9187	High Similarity	NPC215375
0.9187	High Similarity	NPC152904
0.9187	High Similarity	NPC62518
0.9182	High Similarity	NPC474638
0.9182	High Similarity	NPC250922
0.9177	High Similarity	NPC325028
0.9177	High Similarity	NPC246328
0.9177	High Similarity	NPC27532
0.9177	High Similarity	NPC256346
0.9172	High Similarity	NPC204515
0.9167	High Similarity	NPC473571
0.9167	High Similarity	NPC110941
0.9167	High Similarity	NPC473682
0.9167	High Similarity	NPC470443
0.9167	High Similarity	NPC470444
0.9167	High Similarity	NPC126784
0.9167	High Similarity	NPC241423
0.9162	High Similarity	NPC470949
0.9162	High Similarity	NPC65563
0.9162	High Similarity	NPC257714
0.9157	High Similarity	NPC204693
0.9157	High Similarity	NPC4390
0.9152	High Similarity	NPC235260
0.9152	High Similarity	NPC285197
0.9152	High Similarity	NPC155763
0.9152	High Similarity	NPC20505
0.9152	High Similarity	NPC206123
0.9146	High Similarity	NPC317489
0.9146	High Similarity	NPC127546
0.9146	High Similarity	NPC265530
0.9146	High Similarity	NPC173637
0.9146	High Similarity	NPC226304
0.9146	High Similarity	NPC116745
0.9146	High Similarity	NPC325555
0.9146	High Similarity	NPC84362
0.9146	High Similarity	NPC135345
0.9146	High Similarity	NPC471288
0.9146	High Similarity	NPC223424
0.9146	High Similarity	NPC52550
0.9146	High Similarity	NPC229729
0.9141	High Similarity	NPC19388

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 NPC42892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	954
0.2-0.3	2022
0.3-0.4	2639
0.4-0.5	1709
0.5-0.6	910
0.6-0.7	367
0.7-0.8	120
0.8-0.85	17
0.85-0.9	18
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9383	High Similarity	NPD3818	Discontinued
0.9333	High Similarity	NPD4338	Clinical (unspecified phase)
0.9114	High Similarity	NPD1934	Approved
0.9036	High Similarity	NPD7074	Phase 3
0.8982	High Similarity	NPD6797	Phase 2
0.8976	High Similarity	NPD7054	Approved
0.8944	High Similarity	NPD3882	Suspended
0.8938	High Similarity	NPD2801	Approved
0.8929	High Similarity	NPD7251	Discontinued
0.8922	High Similarity	NPD7472	Approved
0.8909	High Similarity	NPD6168	Clinical (unspecified phase)
0.8909	High Similarity	NPD6167	Clinical (unspecified phase)
0.8909	High Similarity	NPD6166	Phase 2
0.8876	High Similarity	NPD7808	Phase 3
0.882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8773	High Similarity	NPD4381	Clinical (unspecified phase)
0.8734	High Similarity	NPD1512	Approved
0.8608	High Similarity	NPD1511	Approved
0.8554	High Similarity	NPD5494	Approved
0.8537	High Similarity	NPD3817	Phase 2
0.8529	High Similarity	NPD7804	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD5402	Approved
0.8293	Intermediate Similarity	NPD4380	Phase 2
0.8291	Intermediate Similarity	NPD1549	Phase 2
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1247	Approved
0.815	Intermediate Similarity	NPD3751	Discontinued
0.8103	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD6801	Discontinued
0.8061	Intermediate Similarity	NPD1653	Approved
0.8037	Intermediate Similarity	NPD6799	Approved
0.8036	Intermediate Similarity	NPD1465	Phase 2
0.8023	Intermediate Similarity	NPD3787	Discontinued
0.8	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7977	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7199	Phase 2
0.7962	Intermediate Similarity	NPD1613	Approved
0.7962	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD919	Approved
0.7953	Intermediate Similarity	NPD6234	Discontinued
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7892	Intermediate Similarity	NPD5403	Approved
0.7886	Intermediate Similarity	NPD7473	Discontinued
0.7879	Intermediate Similarity	NPD5401	Approved
0.7874	Intermediate Similarity	NPD3926	Phase 2
0.787	Intermediate Similarity	NPD37	Approved
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7848	Intermediate Similarity	NPD943	Approved
0.7841	Intermediate Similarity	NPD7228	Approved
0.7836	Intermediate Similarity	NPD4965	Approved
0.7836	Intermediate Similarity	NPD4967	Phase 2
0.7836	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD2796	Approved
0.7824	Intermediate Similarity	NPD7819	Suspended
0.7818	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1240	Approved
0.7707	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7411	Suspended
0.7697	Intermediate Similarity	NPD6190	Approved
0.7672	Intermediate Similarity	NPD6778	Approved
0.7672	Intermediate Similarity	NPD6776	Approved
0.7672	Intermediate Similarity	NPD6777	Approved
0.7672	Intermediate Similarity	NPD6779	Approved
0.7672	Intermediate Similarity	NPD6780	Approved
0.7672	Intermediate Similarity	NPD6781	Approved
0.7672	Intermediate Similarity	NPD6782	Approved
0.7667	Intermediate Similarity	NPD7685	Pre-registration
0.7657	Intermediate Similarity	NPD6959	Discontinued
0.7643	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1607	Approved
0.7636	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8312	Approved
0.7582	Intermediate Similarity	NPD8313	Approved
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7578	Intermediate Similarity	NPD1933	Approved
0.7576	Intermediate Similarity	NPD2800	Approved
0.756	Intermediate Similarity	NPD2532	Approved
0.756	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2533	Approved
0.756	Intermediate Similarity	NPD2534	Approved
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.7546	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7471	Intermediate Similarity	NPD920	Approved
0.7469	Intermediate Similarity	NPD447	Suspended
0.7461	Intermediate Similarity	NPD7698	Approved
0.7461	Intermediate Similarity	NPD7696	Phase 3
0.7461	Intermediate Similarity	NPD7697	Approved
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7456	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7423	Intermediate Similarity	NPD7870	Phase 2
0.7423	Intermediate Similarity	NPD7871	Phase 2
0.7407	Intermediate Similarity	NPD6534	Approved
0.7407	Intermediate Similarity	NPD6535	Approved
0.7398	Intermediate Similarity	NPD7701	Phase 2
0.7377	Intermediate Similarity	NPD7240	Approved
0.7349	Intermediate Similarity	NPD2344	Approved
0.7337	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7768	Phase 2
0.7323	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7874	Approved
0.7292	Intermediate Similarity	NPD7700	Phase 2
0.7292	Intermediate Similarity	NPD7699	Phase 2
0.7286	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7783	Phase 2
0.7286	Intermediate Similarity	NPD7801	Approved
0.7284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8151	Discontinued
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1243	Approved
0.7259	Intermediate Similarity	NPD7584	Approved
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7266	Discontinued
0.7243	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6823	Phase 2
0.7229	Intermediate Similarity	NPD3748	Approved
0.7216	Intermediate Similarity	NPD8455	Phase 2
0.7216	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD9494	Approved
0.7184	Intermediate Similarity	NPD3226	Approved
0.7181	Intermediate Similarity	NPD8150	Discontinued
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7176	Intermediate Similarity	NPD2309	Approved
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5006	Approved
0.7143	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7135	Intermediate Similarity	NPD5953	Discontinued
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7127	Intermediate Similarity	NPD5710	Approved
0.7127	Intermediate Similarity	NPD5711	Approved
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7099	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD6099	Approved
0.7081	Intermediate Similarity	NPD1203	Approved
0.7077	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6798	Discontinued
0.7062	Intermediate Similarity	NPD6844	Discontinued
0.7049	Intermediate Similarity	NPD2403	Approved
0.7048	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD1610	Phase 2
0.7044	Intermediate Similarity	NPD1091	Approved
0.7039	Intermediate Similarity	NPD4111	Phase 1
0.7039	Intermediate Similarity	NPD4665	Approved
0.7026	Intermediate Similarity	NPD4420	Approved
0.7024	Intermediate Similarity	NPD2799	Discontinued
0.7024	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7680	Approved
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6995	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5242	Approved
0.6995	Remote Similarity	NPD6212	Phase 3
0.6995	Remote Similarity	NPD6213	Phase 3
0.6989	Remote Similarity	NPD7458	Discontinued
0.6986	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8320	Phase 1
0.6985	Remote Similarity	NPD8319	Approved
0.6983	Remote Similarity	NPD5353	Approved
0.6973	Remote Similarity	NPD2163	Approved
0.6971	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4363	Phase 3
0.6959	Remote Similarity	NPD4360	Phase 2
0.6959	Remote Similarity	NPD6674	Discontinued
0.6957	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4908	Phase 1
0.6946	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7229	Phase 3
0.6933	Remote Similarity	NPD2798	Approved
0.6927	Remote Similarity	NPD4287	Approved
0.6919	Remote Similarity	NPD3452	Approved
0.6919	Remote Similarity	NPD2493	Approved
0.6919	Remote Similarity	NPD2494	Approved
0.6919	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3450	Approved
0.691	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6651	Approved
0.6901	Remote Similarity	NPD2424	Discontinued

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