NPASS Compound

Structure

NPC303255 OpenBabel07101718272D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.5355 3.5355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 -2.6390 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 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 -0.9659 -0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 1.8625 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 3.4641 -1.0000 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 3.4641 0.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7944 2.5696 0.0000 O 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 11 27 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	371.883
LogP:	2.299
LogD:	2.768
LogS:	-4.565
# Rotatable Bonds:	6
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	3.067
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.671
MDCK Permeability:	2.9142202038201503e-05
Pgp-inhibitor:	0.856
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	89.65821075439453%
Volume Distribution (VD):	0.58
Pgp-substrate:	11.273601531982422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.374
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.822
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.654
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.163
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.906
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	5.153
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.306
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.464
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.15
Carcinogencity:	0.073
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC303255

Natural Product ID:	NPC303255
*Common Name:**	(3R)-3-Hydroxy-3-(4'-Methoxybenzyl)-5,6,7-Trimethoxychroman-4-One
IUPAC Name:	(3R)-3-hydroxy-5,6,7-trimethoxy-3-[(4-methoxyphenyl)methyl]-2H-chromen-4-one
Synonyms:
Standard InCHIKey:	XPJYOBQMHUPHPG-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-23-13-7-5-12(6-8-13)10-20(22)11-27-14-9-15(24-2)17(25-3)18(26-4)16(14)19(20)21/h5-9,22H,10-11H2,1-4H3/t20-/m1/s1
SMILES:	COc1ccc(cc1)C[C@]1(COc2cc(c(c(c2C1=O)OC)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375664
PubChem CID:	71712960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO27354	Urginea depressa	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23659371]
NPO27354	Urginea depressa	Species	Hyacinthaceae	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	3
Others	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	320.0	nM	PMID[548961]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	68.0	nM	PMID[548961]
NPT1383	Cell Line	A2058	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[548961]
NPT179	Cell Line	A2780	Homo sapiens	Ratio IC50	=	5.0	n.a.	PMID[548961]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	71.0	nM	PMID[548961]

☑ 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 NPC303255 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	410
0.1-0.2	1600
0.2-0.3	4242
0.3-0.4	10327
0.4-0.5	7724
0.5-0.6	3606
0.6-0.7	5071
0.7-0.8	5619
0.8-0.85	2415
0.85-0.9	1258
0.9-0.95	419
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC152904
0.9548	High Similarity	NPC224280
0.9548	High Similarity	NPC234052
0.9542	High Similarity	NPC263449
0.9539	High Similarity	NPC48208
0.9539	High Similarity	NPC222814
0.9539	High Similarity	NPC96167
0.9539	High Similarity	NPC474836
0.9539	High Similarity	NPC475267
0.9539	High Similarity	NPC162869
0.9539	High Similarity	NPC67876
0.9539	High Similarity	NPC472913
0.9539	High Similarity	NPC245758
0.9539	High Similarity	NPC472914
0.9539	High Similarity	NPC474208
0.9539	High Similarity	NPC156057
0.9539	High Similarity	NPC472910
0.9539	High Similarity	NPC472911
0.9536	High Similarity	NPC472909
0.9536	High Similarity	NPC37392
0.9533	High Similarity	NPC134677
0.9487	High Similarity	NPC113093
0.9484	High Similarity	NPC41301
0.9481	High Similarity	NPC308992
0.9477	High Similarity	NPC55738
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC472916
0.9474	High Similarity	NPC474638
0.9474	High Similarity	NPC49824
0.9474	High Similarity	NPC255106
0.947	High Similarity	NPC86485
0.947	High Similarity	NPC472915
0.9467	High Similarity	NPC117579
0.9463	High Similarity	NPC238366
0.9412	High Similarity	NPC471479
0.9412	High Similarity	NPC78225
0.9412	High Similarity	NPC181960
0.9412	High Similarity	NPC110070
0.9412	High Similarity	NPC471515
0.9412	High Similarity	NPC469584
0.9412	High Similarity	NPC224137
0.9412	High Similarity	NPC227192
0.9412	High Similarity	NPC99597
0.9412	High Similarity	NPC203891
0.9412	High Similarity	NPC101830
0.9412	High Similarity	NPC93376
0.9412	High Similarity	NPC189179
0.9412	High Similarity	NPC210084
0.9412	High Similarity	NPC75215
0.9408	High Similarity	NPC201451
0.9408	High Similarity	NPC213622
0.9408	High Similarity	NPC32557
0.9408	High Similarity	NPC189960
0.9408	High Similarity	NPC44079
0.9408	High Similarity	NPC26227
0.9408	High Similarity	NPC2928
0.9404	High Similarity	NPC301123
0.9404	High Similarity	NPC199100
0.9404	High Similarity	NPC180234
0.9404	High Similarity	NPC120537
0.9396	High Similarity	NPC63256
0.9396	High Similarity	NPC10304
0.9396	High Similarity	NPC261548
0.9367	High Similarity	NPC152477
0.9355	High Similarity	NPC266314
0.9355	High Similarity	NPC173137
0.9351	High Similarity	NPC105242
0.9351	High Similarity	NPC4481
0.9351	High Similarity	NPC9609
0.9351	High Similarity	NPC22472
0.9351	High Similarity	NPC18607
0.9351	High Similarity	NPC143828
0.9351	High Similarity	NPC130894
0.9351	High Similarity	NPC18772
0.9351	High Similarity	NPC476242
0.9351	High Similarity	NPC176300
0.9351	High Similarity	NPC253634
0.9351	High Similarity	NPC250214
0.9351	High Similarity	NPC95936
0.9351	High Similarity	NPC7846
0.9351	High Similarity	NPC300943
0.9351	High Similarity	NPC152166
0.9351	High Similarity	NPC288669
0.9351	High Similarity	NPC191459
0.9351	High Similarity	NPC115798
0.9351	High Similarity	NPC25495
0.9351	High Similarity	NPC261004
0.9351	High Similarity	NPC19687
0.9351	High Similarity	NPC204854
0.9346	High Similarity	NPC474520
0.9346	High Similarity	NPC201837
0.9346	High Similarity	NPC43243
0.9346	High Similarity	NPC191146
0.9346	High Similarity	NPC68093
0.9346	High Similarity	NPC245546
0.9346	High Similarity	NPC13858
0.9346	High Similarity	NPC266960
0.9346	High Similarity	NPC292107
0.9346	High Similarity	NPC98661
0.9346	High Similarity	NPC247017
0.9346	High Similarity	NPC178854
0.9346	High Similarity	NPC326037
0.9346	High Similarity	NPC471500
0.9346	High Similarity	NPC320825
0.9342	High Similarity	NPC274327
0.9342	High Similarity	NPC206238
0.9342	High Similarity	NPC176775
0.9342	High Similarity	NPC292214
0.9342	High Similarity	NPC69394
0.9342	High Similarity	NPC47781
0.9342	High Similarity	NPC22519
0.9342	High Similarity	NPC160951
0.9342	High Similarity	NPC18727
0.9342	High Similarity	NPC255350
0.9342	High Similarity	NPC145379
0.9342	High Similarity	NPC271779
0.9342	High Similarity	NPC141212
0.9342	High Similarity	NPC167091
0.9342	High Similarity	NPC88645
0.9342	High Similarity	NPC183878
0.9342	High Similarity	NPC231018
0.9342	High Similarity	NPC280937
0.9338	High Similarity	NPC149614
0.9338	High Similarity	NPC208043
0.9338	High Similarity	NPC226973
0.9333	High Similarity	NPC69752
0.9304	High Similarity	NPC8965
0.9299	High Similarity	NPC62261
0.9295	High Similarity	NPC472448
0.9295	High Similarity	NPC83922
0.929	High Similarity	NPC470183
0.929	High Similarity	NPC282009
0.929	High Similarity	NPC287328
0.929	High Similarity	NPC204290
0.929	High Similarity	NPC476980
0.929	High Similarity	NPC246478
0.9286	High Similarity	NPC129684
0.9286	High Similarity	NPC36852
0.9286	High Similarity	NPC27337
0.9286	High Similarity	NPC78302
0.9286	High Similarity	NPC29841
0.9286	High Similarity	NPC305663
0.9286	High Similarity	NPC241904
0.9286	High Similarity	NPC235215
0.9286	High Similarity	NPC176665
0.9286	High Similarity	NPC287979
0.9286	High Similarity	NPC472438
0.9286	High Similarity	NPC470402
0.9286	High Similarity	NPC7973
0.9286	High Similarity	NPC476981
0.9286	High Similarity	NPC262286
0.9286	High Similarity	NPC223787
0.9286	High Similarity	NPC299520
0.9286	High Similarity	NPC300727
0.9286	High Similarity	NPC52530
0.9286	High Similarity	NPC163524
0.9281	High Similarity	NPC163780
0.9281	High Similarity	NPC138360
0.9281	High Similarity	NPC31018
0.9281	High Similarity	NPC201136
0.9281	High Similarity	NPC256612
0.9281	High Similarity	NPC146165
0.9281	High Similarity	NPC196439
0.9281	High Similarity	NPC2476
0.9281	High Similarity	NPC92659
0.9281	High Similarity	NPC167815
0.9281	High Similarity	NPC128863
0.9281	High Similarity	NPC4455
0.9281	High Similarity	NPC50715
0.9281	High Similarity	NPC280339
0.9281	High Similarity	NPC255807
0.9281	High Similarity	NPC20830
0.9281	High Similarity	NPC227325
0.9281	High Similarity	NPC183597
0.9276	High Similarity	NPC71334
0.9276	High Similarity	NPC83508
0.9276	High Similarity	NPC100887
0.9276	High Similarity	NPC275836
0.9276	High Similarity	NPC301323
0.9276	High Similarity	NPC25270
0.9276	High Similarity	NPC236637
0.9276	High Similarity	NPC239128
0.9276	High Similarity	NPC156222
0.9276	High Similarity	NPC57030
0.9276	High Similarity	NPC477231
0.9276	High Similarity	NPC293183
0.9276	High Similarity	NPC256283
0.9276	High Similarity	NPC187498
0.9276	High Similarity	NPC39007
0.9276	High Similarity	NPC472912
0.9276	High Similarity	NPC188203
0.9276	High Similarity	NPC131624
0.9276	High Similarity	NPC161277
0.9276	High Similarity	NPC222830
0.9276	High Similarity	NPC275722
0.9276	High Similarity	NPC241498
0.9276	High Similarity	NPC302950
0.9276	High Similarity	NPC120163
0.9276	High Similarity	NPC162313
0.9276	High Similarity	NPC257648

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 NPC303255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	942
0.2-0.3	1785
0.3-0.4	2618
0.4-0.5	1791
0.5-0.6	985
0.6-0.7	469
0.7-0.8	157
0.8-0.85	26
0.85-0.9	9
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9342	High Similarity	NPD2801	Approved
0.9276	High Similarity	NPD1934	Approved
0.9156	High Similarity	NPD3817	Phase 2
0.9097	High Similarity	NPD3882	Suspended
0.9091	High Similarity	NPD2393	Clinical (unspecified phase)
0.9057	High Similarity	NPD6166	Phase 2
0.9057	High Similarity	NPD6167	Clinical (unspecified phase)
0.9057	High Similarity	NPD6168	Clinical (unspecified phase)
0.8924	High Similarity	NPD5494	Approved
0.8882	High Similarity	NPD1512	Approved
0.8788	High Similarity	NPD4338	Clinical (unspecified phase)
0.875	High Similarity	NPD1511	Approved
0.8726	High Similarity	NPD7096	Clinical (unspecified phase)
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8627	High Similarity	NPD6799	Approved
0.8606	High Similarity	NPD7074	Phase 3
0.8598	High Similarity	NPD3818	Discontinued
0.8563	High Similarity	NPD7808	Phase 3
0.8562	High Similarity	NPD7075	Discontinued
0.8554	High Similarity	NPD6797	Phase 2
0.8545	High Similarity	NPD7054	Approved
0.8519	High Similarity	NPD1247	Approved
0.8503	High Similarity	NPD7251	Discontinued
0.85	High Similarity	NPD4868	Clinical (unspecified phase)
0.8494	Intermediate Similarity	NPD7472	Approved
0.8477	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5402	Approved
0.8421	Intermediate Similarity	NPD1549	Phase 2
0.8418	Intermediate Similarity	NPD6599	Discontinued
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8411	Intermediate Similarity	NPD2796	Approved
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5844	Phase 1
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8303	Intermediate Similarity	NPD3926	Phase 2
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.8171	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1240	Approved
0.8037	Intermediate Similarity	NPD1465	Phase 2
0.8024	Intermediate Similarity	NPD3787	Discontinued
0.8	Intermediate Similarity	NPD5403	Approved
0.7987	Intermediate Similarity	NPD5401	Approved
0.7974	Intermediate Similarity	NPD1607	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7961	Intermediate Similarity	NPD943	Approved
0.7941	Intermediate Similarity	NPD3751	Discontinued
0.7888	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6559	Discontinued
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7815	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD447	Suspended
0.7784	Intermediate Similarity	NPD3749	Approved
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7199	Phase 2
0.7748	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6190	Approved
0.7684	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7677	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2800	Approved
0.7669	Intermediate Similarity	NPD920	Approved
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7643	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4628	Phase 3
0.7625	Intermediate Similarity	NPD3750	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7595	Intermediate Similarity	NPD6100	Approved
0.7595	Intermediate Similarity	NPD6099	Approved
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6233	Phase 2
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8434	Phase 2
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD2403	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD6798	Discontinued
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.747	Intermediate Similarity	NPD3226	Approved
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5242	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.744	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD6844	Discontinued
0.7438	Intermediate Similarity	NPD2344	Approved
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4966	Approved
0.7412	Intermediate Similarity	NPD4965	Approved
0.7407	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD9494	Approved
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7353	Intermediate Similarity	NPD5353	Approved
0.7348	Intermediate Similarity	NPD8150	Discontinued
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7301	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6651	Approved
0.7284	Intermediate Similarity	NPD2424	Discontinued
0.7278	Intermediate Similarity	NPD6386	Approved
0.7278	Intermediate Similarity	NPD6385	Approved
0.7263	Intermediate Similarity	NPD7697	Approved
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD7698	Approved
0.7263	Intermediate Similarity	NPD7696	Phase 3
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2309	Approved
0.7256	Intermediate Similarity	NPD2354	Approved
0.7255	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7232	Intermediate Similarity	NPD7228	Approved
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7225	Intermediate Similarity	NPD7871	Phase 2
0.7225	Intermediate Similarity	NPD7870	Phase 2
0.7222	Intermediate Similarity	NPD7549	Discontinued
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6534	Approved
0.7204	Intermediate Similarity	NPD6535	Approved
0.7202	Intermediate Similarity	NPD7701	Phase 2
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD7229	Phase 3
0.72	Intermediate Similarity	NPD5711	Approved
0.7197	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD1608	Approved
0.7182	Intermediate Similarity	NPD8313	Approved
0.7182	Intermediate Similarity	NPD8312	Approved
0.7179	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7390	Discontinued
0.7161	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD3887	Approved
0.7135	Intermediate Similarity	NPD2163	Approved
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.711	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7801	Approved
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7089	Intermediate Similarity	NPD4625	Phase 3
0.7086	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD5049	Phase 3
0.7078	Intermediate Similarity	NPD9717	Approved
0.7072	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7062	Intermediate Similarity	NPD7584	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD2974	Approved
0.7037	Intermediate Similarity	NPD2975	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