NPASS Compound

Structure

NPC308992 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -0.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -2.5981 1.5000 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 9 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 12 2 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 6 0 0 0 16 9 1 1 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	1.695
LogD:	0.786
LogS:	-2.669
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.884
Synthetic Accessibility Score:	3.181
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:	-4.92
MDCK Permeability:	7.170395747380098e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.073
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.209
Plasma Protein Binding (PPB):	87.35469818115234%
Volume Distribution (VD):	0.952
Pgp-substrate:	7.34892463684082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.418
CYP2C19-inhibitor:	0.121
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.255
CYP2C9-substrate:	0.868
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.623

ADMET: Excretion

Clearance (CL):	5.334
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.334
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.745
Skin Sensitization:	0.606
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.354
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC308992

Natural Product ID:	NPC308992
*Common Name:**	(2R,3R)-3,7-Dihydroxy-6-Methoxyflavanone
IUPAC Name:	(2R,3R)-3,7-dihydroxy-6-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	GUMFPOIJOXLCLA-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-13-7-10-12(8-11(13)17)21-16(15(19)14(10)18)9-5-3-2-4-6-9/h2-8,15-17,19H,1H3/t15-,16+/m0/s1
SMILES:	COc1cc2c(cc1O)O[C@@H]([C@H](C2=O)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254729
PubChem CID:	44446832
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-O-methylated flavonoids

*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
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[17950610]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	Brazilian	n.a.	PMID[18440233]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26938776]
NPO33288	Brazilian Red Propolis	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[32525315]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	>	100.0	uM	PMID[540287]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[540288]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[540288]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[540288]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[540288]

☑ 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 NPC308992 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	420
0.1-0.2	1693
0.2-0.3	4465
0.3-0.4	10172
0.4-0.5	7558
0.5-0.6	3618
0.6-0.7	4813
0.7-0.8	5305
0.8-0.85	2437
0.85-0.9	1493
0.9-0.95	646
0.95-1	77

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC263449
0.9803	High Similarity	NPC99597
0.9803	High Similarity	NPC210084
0.9803	High Similarity	NPC52530
0.9737	High Similarity	NPC255106
0.9737	High Similarity	NPC320825
0.9737	High Similarity	NPC326037
0.9737	High Similarity	NPC201837
0.9737	High Similarity	NPC235165
0.9737	High Similarity	NPC13858
0.9673	High Similarity	NPC474836
0.9673	High Similarity	NPC162869
0.9673	High Similarity	NPC474208
0.9673	High Similarity	NPC48208
0.9673	High Similarity	NPC475267
0.9673	High Similarity	NPC156057
0.9671	High Similarity	NPC2928
0.961	High Similarity	NPC55738
0.961	High Similarity	NPC152904
0.9608	High Similarity	NPC250922
0.9608	High Similarity	NPC472916
0.9608	High Similarity	NPC474638
0.9605	High Similarity	NPC88645
0.9605	High Similarity	NPC325028
0.9605	High Similarity	NPC292214
0.9605	High Similarity	NPC206238
0.9605	High Similarity	NPC27532
0.9605	High Similarity	NPC271779
0.9605	High Similarity	NPC246328
0.9605	High Similarity	NPC167091
0.9605	High Similarity	NPC256346
0.9554	High Similarity	NPC224280
0.9554	High Similarity	NPC234052
0.9548	High Similarity	NPC287328
0.9548	High Similarity	NPC282009
0.9545	High Similarity	NPC470402
0.9545	High Similarity	NPC472913
0.9545	High Similarity	NPC472914
0.9545	High Similarity	NPC471479
0.9545	High Similarity	NPC472911
0.9545	High Similarity	NPC472910
0.9545	High Similarity	NPC222814
0.9545	High Similarity	NPC96167
0.9545	High Similarity	NPC471515
0.9545	High Similarity	NPC67876
0.9545	High Similarity	NPC245758
0.9542	High Similarity	NPC37392
0.9542	High Similarity	NPC201451
0.9542	High Similarity	NPC44079
0.9542	High Similarity	NPC26227
0.9539	High Similarity	NPC240476
0.9539	High Similarity	NPC9743
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC61506
0.9539	High Similarity	NPC260491
0.9539	High Similarity	NPC120537
0.9539	High Similarity	NPC39007
0.9539	High Similarity	NPC302950
0.9539	High Similarity	NPC161277
0.9539	High Similarity	NPC36835
0.9539	High Similarity	NPC180234
0.9539	High Similarity	NPC236637
0.9539	High Similarity	NPC101996
0.9539	High Similarity	NPC246162
0.9539	High Similarity	NPC199100
0.9487	High Similarity	NPC471499
0.9487	High Similarity	NPC173137
0.9484	High Similarity	NPC250214
0.9484	High Similarity	NPC95936
0.9484	High Similarity	NPC22192
0.9481	High Similarity	NPC49824
0.9481	High Similarity	NPC471500
0.9481	High Similarity	NPC247017
0.9481	High Similarity	NPC266960
0.9481	High Similarity	NPC303255
0.9481	High Similarity	NPC98661
0.9481	High Similarity	NPC43243
0.9481	High Similarity	NPC245546
0.9477	High Similarity	NPC472915
0.9477	High Similarity	NPC18727
0.9477	High Similarity	NPC141212
0.9474	High Similarity	NPC149614
0.9474	High Similarity	NPC204515
0.9474	High Similarity	NPC251110
0.9474	High Similarity	NPC31363
0.9474	High Similarity	NPC171010
0.9474	High Similarity	NPC117579
0.9434	High Similarity	NPC295082
0.9434	High Similarity	NPC243877
0.9434	High Similarity	NPC14662
0.9434	High Similarity	NPC42892
0.943	High Similarity	NPC470457
0.9423	High Similarity	NPC470326
0.9423	High Similarity	NPC470183
0.9419	High Similarity	NPC110070
0.9419	High Similarity	NPC181960
0.9419	High Similarity	NPC474055
0.9419	High Similarity	NPC469584
0.9419	High Similarity	NPC129684
0.9419	High Similarity	NPC287979
0.9419	High Similarity	NPC262286
0.9419	High Similarity	NPC224137
0.9419	High Similarity	NPC291508
0.9419	High Similarity	NPC227192
0.9419	High Similarity	NPC203891
0.9419	High Similarity	NPC299520
0.9419	High Similarity	NPC101830
0.9419	High Similarity	NPC176665
0.9419	High Similarity	NPC223787
0.9419	High Similarity	NPC93376
0.9419	High Similarity	NPC472598
0.9419	High Similarity	NPC78225
0.9419	High Similarity	NPC189179
0.9419	High Similarity	NPC75215
0.9419	High Similarity	NPC163524
0.9419	High Similarity	NPC305663
0.9419	High Similarity	NPC36852
0.9416	High Similarity	NPC256612
0.9416	High Similarity	NPC472909
0.9416	High Similarity	NPC213622
0.9416	High Similarity	NPC20830
0.9412	High Similarity	NPC83508
0.9412	High Similarity	NPC198826
0.9412	High Similarity	NPC275836
0.9412	High Similarity	NPC212678
0.9412	High Similarity	NPC162313
0.9412	High Similarity	NPC477231
0.9412	High Similarity	NPC100971
0.9412	High Similarity	NPC301123
0.9412	High Similarity	NPC25270
0.9412	High Similarity	NPC293183
0.9412	High Similarity	NPC55205
0.9412	High Similarity	NPC222830
0.9412	High Similarity	NPC156222
0.9412	High Similarity	NPC35763
0.9412	High Similarity	NPC256283
0.9412	High Similarity	NPC187498
0.9412	High Similarity	NPC275722
0.9412	High Similarity	NPC131266
0.9412	High Similarity	NPC57030
0.9412	High Similarity	NPC131624
0.9412	High Similarity	NPC100263
0.9412	High Similarity	NPC71334
0.9412	High Similarity	NPC245382
0.9412	High Similarity	NPC301323
0.9412	High Similarity	NPC239128
0.9412	High Similarity	NPC188203
0.9412	High Similarity	NPC216769
0.9412	High Similarity	NPC241498
0.9412	High Similarity	NPC100887
0.9412	High Similarity	NPC181209
0.9412	High Similarity	NPC120163
0.9412	High Similarity	NPC291802
0.9412	High Similarity	NPC19721
0.9412	High Similarity	NPC121522
0.9412	High Similarity	NPC257648
0.9412	High Similarity	NPC269451
0.9412	High Similarity	NPC209487
0.9408	High Similarity	NPC61620
0.9408	High Similarity	NPC248102
0.9408	High Similarity	NPC62042
0.9408	High Similarity	NPC179183
0.9408	High Similarity	NPC29231
0.9371	High Similarity	NPC477517
0.9367	High Similarity	NPC470459
0.9367	High Similarity	NPC124038
0.9367	High Similarity	NPC41301
0.9367	High Similarity	NPC472625
0.9363	High Similarity	NPC266314
0.9359	High Similarity	NPC22472
0.9359	High Similarity	NPC105242
0.9359	High Similarity	NPC4481
0.9359	High Similarity	NPC9609
0.9359	High Similarity	NPC253634
0.9359	High Similarity	NPC195832
0.9359	High Similarity	NPC143828
0.9359	High Similarity	NPC130894
0.9359	High Similarity	NPC18772
0.9359	High Similarity	NPC176300
0.9359	High Similarity	NPC7846
0.9359	High Similarity	NPC300943
0.9359	High Similarity	NPC191459
0.9359	High Similarity	NPC193842
0.9359	High Similarity	NPC288669
0.9359	High Similarity	NPC152166
0.9359	High Similarity	NPC329091
0.9359	High Similarity	NPC18607
0.9359	High Similarity	NPC115798
0.9359	High Similarity	NPC25495
0.9359	High Similarity	NPC261004
0.9359	High Similarity	NPC19687
0.9359	High Similarity	NPC204854
0.9355	High Similarity	NPC278778
0.9355	High Similarity	NPC191146
0.9355	High Similarity	NPC291878
0.9355	High Similarity	NPC474520
0.9355	High Similarity	NPC138243
0.9355	High Similarity	NPC195796
0.9355	High Similarity	NPC68093
0.9355	High Similarity	NPC35038

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 NPC308992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	949
0.2-0.3	1868
0.3-0.4	2600
0.4-0.5	1762
0.5-0.6	952
0.6-0.7	439
0.7-0.8	142
0.8-0.85	29
0.85-0.9	16
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9539	High Similarity	NPD1934	Approved
0.9351	High Similarity	NPD2801	Approved
0.9308	High Similarity	NPD6166	Phase 2
0.9308	High Similarity	NPD6167	Clinical (unspecified phase)
0.9308	High Similarity	NPD6168	Clinical (unspecified phase)
0.9231	High Similarity	NPD3882	Suspended
0.9226	High Similarity	NPD2393	Clinical (unspecified phase)
0.903	High Similarity	NPD4338	Clinical (unspecified phase)
0.902	High Similarity	NPD1512	Approved
0.8957	High Similarity	NPD3818	Discontinued
0.8889	High Similarity	NPD1511	Approved
0.8848	High Similarity	NPD7074	Phase 3
0.882	High Similarity	NPD5494	Approved
0.8805	High Similarity	NPD3817	Phase 2
0.8795	High Similarity	NPD6797	Phase 2
0.8788	High Similarity	NPD7054	Approved
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8743	High Similarity	NPD7251	Discontinued
0.8735	High Similarity	NPD7472	Approved
0.8696	High Similarity	NPD7075	Discontinued
0.869	High Similarity	NPD7808	Phase 3
0.8684	High Similarity	NPD1549	Phase 2
0.8671	High Similarity	NPD4380	Phase 2
0.8625	High Similarity	NPD7096	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.859	High Similarity	NPD4378	Clinical (unspecified phase)
0.858	High Similarity	NPD4381	Clinical (unspecified phase)
0.8571	High Similarity	NPD5402	Approved
0.8571	High Similarity	NPD7993	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5844	Phase 1
0.8447	Intermediate Similarity	NPD6801	Discontinued
0.8424	Intermediate Similarity	NPD1247	Approved
0.8408	Intermediate Similarity	NPD6799	Approved
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8343	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD2796	Approved
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.8224	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8224	Intermediate Similarity	NPD943	Approved
0.821	Intermediate Similarity	NPD6599	Discontinued
0.8171	Intermediate Similarity	NPD7819	Suspended
0.8155	Intermediate Similarity	NPD6232	Discontinued
0.8137	Intermediate Similarity	NPD5403	Approved
0.8125	Intermediate Similarity	NPD5401	Approved
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD1607	Approved
0.8107	Intermediate Similarity	NPD3926	Phase 2
0.8092	Intermediate Similarity	NPD6559	Discontinued
0.8084	Intermediate Similarity	NPD919	Approved
0.807	Intermediate Similarity	NPD3751	Discontinued
0.8049	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6959	Discontinued
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6190	Approved
0.7935	Intermediate Similarity	NPD230	Phase 1
0.7908	Intermediate Similarity	NPD3027	Phase 3
0.7898	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD1653	Approved
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7836	Intermediate Similarity	NPD3787	Discontinued
0.7821	Intermediate Similarity	NPD447	Suspended
0.7811	Intermediate Similarity	NPD3749	Approved
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD2800	Approved
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD9494	Approved
0.7654	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.7595	Intermediate Similarity	NPD1933	Approved
0.7594	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6781	Approved
0.7594	Intermediate Similarity	NPD6776	Approved
0.7594	Intermediate Similarity	NPD6777	Approved
0.7594	Intermediate Similarity	NPD6778	Approved
0.7594	Intermediate Similarity	NPD6782	Approved
0.7594	Intermediate Similarity	NPD6779	Approved
0.7594	Intermediate Similarity	NPD6780	Approved
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2344	Approved
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD2532	Approved
0.7572	Intermediate Similarity	NPD7199	Phase 2
0.7569	Intermediate Similarity	NPD8434	Phase 2
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD6844	Discontinued
0.7471	Intermediate Similarity	NPD37	Approved
0.747	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7458	Intermediate Similarity	NPD7228	Approved
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3748	Approved
0.7442	Intermediate Similarity	NPD4966	Approved
0.7442	Intermediate Similarity	NPD4967	Phase 2
0.7442	Intermediate Similarity	NPD4965	Approved
0.7433	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD5953	Discontinued
0.7416	Intermediate Similarity	NPD7286	Phase 2
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6100	Approved
0.7407	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD2313	Discontinued
0.7403	Intermediate Similarity	NPD8312	Approved
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8313	Approved
0.7394	Intermediate Similarity	NPD2309	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7378	Intermediate Similarity	NPD1243	Approved
0.7358	Intermediate Similarity	NPD6233	Phase 2
0.7349	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2799	Discontinued
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7326	Intermediate Similarity	NPD6534	Approved
0.7326	Intermediate Similarity	NPD6535	Approved
0.732	Intermediate Similarity	NPD7701	Phase 2
0.7308	Intermediate Similarity	NPD1203	Approved
0.7296	Intermediate Similarity	NPD6798	Discontinued
0.7288	Intermediate Similarity	NPD5242	Approved
0.7283	Intermediate Similarity	NPD5353	Approved
0.7278	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7239	Intermediate Similarity	NPD7033	Discontinued
0.7234	Intermediate Similarity	NPD4360	Phase 2
0.7234	Intermediate Similarity	NPD4363	Phase 3
0.7229	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD9269	Phase 2
0.7222	Intermediate Similarity	NPD6651	Approved
0.7215	Intermediate Similarity	NPD2861	Phase 2
0.7211	Intermediate Similarity	NPD7700	Phase 2
0.7211	Intermediate Similarity	NPD7699	Phase 2
0.7208	Intermediate Similarity	NPD7801	Approved
0.7194	Intermediate Similarity	NPD8151	Discontinued
0.7188	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7584	Approved
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7167	Intermediate Similarity	NPD2163	Approved
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7151	Intermediate Similarity	NPD2403	Approved
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7135	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD5711	Approved
0.7129	Intermediate Similarity	NPD4665	Approved
0.7129	Intermediate Similarity	NPD4111	Phase 1
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.7115	Intermediate Similarity	NPD9717	Approved
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6385	Approved
0.7108	Intermediate Similarity	NPD2424	Discontinued
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2354	Approved
0.7066	Intermediate Similarity	NPD1652	Phase 2
0.7065	Intermediate Similarity	NPD7549	Discontinued
0.7059	Intermediate Similarity	NPD4661	Approved
0.7059	Intermediate Similarity	NPD7907	Approved
0.7059	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4662	Approved
0.7056	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1471	Phase 3
0.7044	Intermediate Similarity	NPD2899	Discontinued
0.7044	Intermediate Similarity	NPD2798	Approved
0.703	Intermediate Similarity	NPD4308	Phase 3
0.7011	Intermediate Similarity	NPD7038	Approved
0.7011	Intermediate Similarity	NPD7039	Approved
0.7011	Intermediate Similarity	NPD7240	Approved
0.701	Intermediate Similarity	NPD2493	Approved
0.701	Intermediate Similarity	NPD2494	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