NPASS Compound

Structure

NPC474993 OpenBabel07101719512D 29 31 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -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 1.0000 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 0.8660 -1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -0.8660 -1.5000 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 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 2.5981 2.5000 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 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 23 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 20 2 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 29 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.16
Volume:	409.708
LogP:	4.923
LogD:	3.333
LogS:	-5.395
# Rotatable Bonds:	6
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.611
Synthetic Accessibility Score:	2.794
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.921
MDCK Permeability:	1.4275727153290063e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.133

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	93.07176208496094%
Volume Distribution (VD):	0.74
Pgp-substrate:	9.033818244934082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.761
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.188
CYP2C9-inhibitor:	0.859
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.549

ADMET: Excretion

Clearance (CL):	2.799
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.075
Drug-inuced Liver Injury (DILI):	0.668
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.457
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.684
Carcinogencity:	0.038
Eye Corrosion:	0.007
Eye Irritation:	0.54
Respiratory Toxicity:	0.635

Download Data

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

Natural Product: NPC474993

Natural Product ID:	NPC474993
*Common Name:**	Trimethylfremontin
IUPAC Name:	3-[4,5-dimethoxy-2-(2-methylbut-3-en-2-yl)phenyl]-5-hydroxy-7-methoxychromen-4-one
Synonyms:	trimethylfremontin
Standard InCHIKey:	JVBWQMXKHDHBIZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O6/c1-7-23(2,3)16-11-19(28-6)18(27-5)10-14(16)15-12-29-20-9-13(26-4)8-17(24)21(20)22(15)25/h7-12,24H,1H2,2-6H3
SMILES:	CC(C)(C=C)C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491345
PubChem CID:	11589323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002602] 7-O-methylated isoflavonoids [CHEMONTID:0002689] 7-O-methylisoflavones

*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
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	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
IC50	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	146000.0	nM	PMID[554338]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	250000.0	nM	PMID[554338]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	32300.0	nM	PMID[554338]

☑ 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 NPC474993 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	421
0.1-0.2	1691
0.2-0.3	3929
0.3-0.4	10115
0.4-0.5	8282
0.5-0.6	3446
0.6-0.7	5195
0.7-0.8	5458
0.8-0.85	2664
0.85-0.9	1251
0.9-0.95	235
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9655	High Similarity	NPC474999
0.9592	High Similarity	NPC85131
0.9586	High Similarity	NPC12377
0.9456	High Similarity	NPC194653
0.9456	High Similarity	NPC203747
0.9456	High Similarity	NPC80710
0.9456	High Similarity	NPC139364
0.9456	High Similarity	NPC254702
0.9396	High Similarity	NPC262623
0.9396	High Similarity	NPC256406
0.9392	High Similarity	NPC139293
0.9392	High Similarity	NPC195763
0.9392	High Similarity	NPC333691
0.9392	High Similarity	NPC264550
0.9392	High Similarity	NPC69430
0.9392	High Similarity	NPC200060
0.9392	High Similarity	NPC40290
0.9392	High Similarity	NPC142876
0.9392	High Similarity	NPC264289
0.9379	High Similarity	NPC119663
0.9346	High Similarity	NPC474960
0.9329	High Similarity	NPC156953
0.9329	High Similarity	NPC239363
0.931	High Similarity	NPC185607
0.9272	High Similarity	NPC93552
0.9272	High Similarity	NPC124714
0.9262	High Similarity	NPC38545
0.9262	High Similarity	NPC171916
0.9257	High Similarity	NPC188074
0.9257	High Similarity	NPC125449
0.9216	High Similarity	NPC472963
0.9216	High Similarity	NPC111969
0.9211	High Similarity	NPC255807
0.9211	High Similarity	NPC31018
0.9205	High Similarity	NPC100971
0.9205	High Similarity	NPC100263
0.9205	High Similarity	NPC291802
0.9205	High Similarity	NPC181209
0.9205	High Similarity	NPC209487
0.9205	High Similarity	NPC35763
0.9205	High Similarity	NPC269451
0.9205	High Similarity	NPC245382
0.9205	High Similarity	NPC121522
0.9205	High Similarity	NPC216769
0.9205	High Similarity	NPC131266
0.9195	High Similarity	NPC166036
0.9195	High Similarity	NPC195202
0.9195	High Similarity	NPC238279
0.9195	High Similarity	NPC203077
0.9184	High Similarity	NPC38065
0.9184	High Similarity	NPC242893
0.9178	High Similarity	NPC49108
0.9156	High Similarity	NPC235448
0.915	High Similarity	NPC472907
0.915	High Similarity	NPC474983
0.9145	High Similarity	NPC280937
0.9145	High Similarity	NPC469550
0.9145	High Similarity	NPC472905
0.9145	High Similarity	NPC250557
0.9139	High Similarity	NPC45291
0.9139	High Similarity	NPC19980
0.9139	High Similarity	NPC308451
0.9128	High Similarity	NPC33265
0.9128	High Similarity	NPC12200
0.9128	High Similarity	NPC119660
0.9128	High Similarity	NPC93034
0.9128	High Similarity	NPC62536
0.9122	High Similarity	NPC471590
0.9122	High Similarity	NPC476055
0.9116	High Similarity	NPC476054
0.9116	High Similarity	NPC254659
0.9116	High Similarity	NPC471417
0.9108	High Similarity	NPC303174
0.9103	High Similarity	NPC472964
0.9097	High Similarity	NPC299436
0.9097	High Similarity	NPC472902
0.9097	High Similarity	NPC36217
0.9091	High Similarity	NPC187745
0.9091	High Similarity	NPC178976
0.9091	High Similarity	NPC180011
0.9091	High Similarity	NPC219867
0.9091	High Similarity	NPC161960
0.9091	High Similarity	NPC299520
0.9091	High Similarity	NPC181960
0.9091	High Similarity	NPC304008
0.9091	High Similarity	NPC199463
0.9091	High Similarity	NPC37543
0.9091	High Similarity	NPC129684
0.9085	High Similarity	NPC67396
0.9085	High Similarity	NPC130589
0.9085	High Similarity	NPC134287
0.9085	High Similarity	NPC234255
0.9085	High Similarity	NPC38898
0.9085	High Similarity	NPC39184
0.9079	High Similarity	NPC472912
0.9079	High Similarity	NPC324233
0.9079	High Similarity	NPC35544
0.9079	High Similarity	NPC149889
0.9079	High Similarity	NPC60972
0.9079	High Similarity	NPC257648
0.9079	High Similarity	NPC260979
0.9079	High Similarity	NPC312338
0.9079	High Similarity	NPC323626
0.9079	High Similarity	NPC39732
0.9079	High Similarity	NPC477231
0.9079	High Similarity	NPC104728
0.9073	High Similarity	NPC338131
0.9073	High Similarity	NPC50728
0.9073	High Similarity	NPC10467
0.9073	High Similarity	NPC166753
0.9073	High Similarity	NPC472279
0.9067	High Similarity	NPC474903
0.906	High Similarity	NPC216314
0.906	High Similarity	NPC120924
0.906	High Similarity	NPC195919
0.9054	High Similarity	NPC142165
0.9054	High Similarity	NPC207732
0.9048	High Similarity	NPC284556
0.9048	High Similarity	NPC301178
0.9045	High Similarity	NPC220313
0.9045	High Similarity	NPC186686
0.9038	High Similarity	NPC474187
0.9038	High Similarity	NPC472906
0.9038	High Similarity	NPC234644
0.9038	High Similarity	NPC57715
0.9034	High Similarity	NPC181124
0.9034	High Similarity	NPC7013
0.9034	High Similarity	NPC212767
0.9034	High Similarity	NPC209560
0.9034	High Similarity	NPC294409
0.9034	High Similarity	NPC44573
0.9034	High Similarity	NPC162680
0.9034	High Similarity	NPC116632
0.9034	High Similarity	NPC303644
0.9032	High Similarity	NPC74178
0.9032	High Similarity	NPC184755
0.9026	High Similarity	NPC77807
0.9026	High Similarity	NPC472455
0.9026	High Similarity	NPC5379
0.9026	High Similarity	NPC227062
0.9026	High Similarity	NPC24640
0.9026	High Similarity	NPC14561
0.9026	High Similarity	NPC115853
0.902	High Similarity	NPC18727
0.902	High Similarity	NPC472915
0.9013	High Similarity	NPC78505
0.9013	High Similarity	NPC226973
0.9013	High Similarity	NPC208043
0.9013	High Similarity	NPC31363
0.9013	High Similarity	NPC236769
0.9007	High Similarity	NPC177298
0.9007	High Similarity	NPC92722
0.9007	High Similarity	NPC223579
0.9007	High Similarity	NPC102003
0.9007	High Similarity	NPC328119
0.9007	High Similarity	NPC159103
0.9007	High Similarity	NPC137062
0.9007	High Similarity	NPC287101
0.9007	High Similarity	NPC48479
0.9007	High Similarity	NPC183950
0.9007	High Similarity	NPC52005
0.9	High Similarity	NPC470511
0.8993	High Similarity	NPC157133
0.8987	High Similarity	NPC472277
0.8986	High Similarity	NPC287722
0.8981	High Similarity	NPC201800
0.8981	High Similarity	NPC229632
0.898	High Similarity	NPC259166
0.898	High Similarity	NPC48624
0.898	High Similarity	NPC215311
0.898	High Similarity	NPC172250
0.898	High Similarity	NPC213659
0.898	High Similarity	NPC219917
0.898	High Similarity	NPC204985
0.898	High Similarity	NPC144118
0.898	High Similarity	NPC110419
0.898	High Similarity	NPC80962
0.898	High Similarity	NPC11056
0.898	High Similarity	NPC326109
0.8974	High Similarity	NPC471973
0.8974	High Similarity	NPC297212
0.8974	High Similarity	NPC474287
0.8974	High Similarity	NPC188433
0.8974	High Similarity	NPC476283
0.8974	High Similarity	NPC28241
0.8974	High Similarity	NPC475886
0.8973	High Similarity	NPC279668
0.8973	High Similarity	NPC472368
0.8973	High Similarity	NPC309154
0.8973	High Similarity	NPC12175
0.8973	High Similarity	NPC55162
0.8973	High Similarity	NPC278323
0.8973	High Similarity	NPC90665
0.8968	High Similarity	NPC52889
0.8968	High Similarity	NPC476981
0.8968	High Similarity	NPC67876
0.8968	High Similarity	NPC241904
0.8968	High Similarity	NPC300727
0.8968	High Similarity	NPC165977
0.8968	High Similarity	NPC217677

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 NPC474993 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	987
0.2-0.3	1653
0.3-0.4	2630
0.4-0.5	1880
0.5-0.6	986
0.6-0.7	459
0.7-0.8	121
0.8-0.85	38
0.85-0.9	17
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8954	High Similarity	NPD1934	Approved
0.8897	High Similarity	NPD1510	Phase 2
0.8896	High Similarity	NPD2801	Approved
0.8782	High Similarity	NPD3882	Suspended
0.8774	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD6232	Discontinued
0.8696	High Similarity	NPD7473	Discontinued
0.8675	High Similarity	NPD1511	Approved
0.8621	High Similarity	NPD1240	Approved
0.8599	High Similarity	NPD3817	Phase 2
0.8581	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD1512	Approved
0.8535	High Similarity	NPD7819	Suspended
0.8528	High Similarity	NPD3818	Discontinued
0.8519	High Similarity	NPD6168	Clinical (unspecified phase)
0.8519	High Similarity	NPD6167	Clinical (unspecified phase)
0.8519	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD1607	Approved
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1549	Phase 2
0.8467	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2796	Approved
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD5494	Approved
0.8364	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8313	Intermediate Similarity	NPD7074	Phase 3
0.8313	Intermediate Similarity	NPD7472	Approved
0.8261	Intermediate Similarity	NPD7075	Discontinued
0.8261	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8243	Intermediate Similarity	NPD943	Approved
0.8235	Intermediate Similarity	NPD3750	Approved
0.8199	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6799	Approved
0.8187	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7808	Phase 3
0.8155	Intermediate Similarity	NPD6797	Phase 2
0.8153	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6801	Discontinued
0.811	Intermediate Similarity	NPD6959	Discontinued
0.8107	Intermediate Similarity	NPD7251	Discontinued
0.8075	Intermediate Similarity	NPD1465	Phase 2
0.8063	Intermediate Similarity	NPD7411	Suspended
0.8059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.7988	Intermediate Similarity	NPD919	Approved
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7927	Intermediate Similarity	NPD3749	Approved
0.7908	Intermediate Similarity	NPD3748	Approved
0.7908	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6651	Approved
0.7892	Intermediate Similarity	NPD1247	Approved
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.7866	Intermediate Similarity	NPD7768	Phase 2
0.7857	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6099	Approved
0.7857	Intermediate Similarity	NPD6100	Approved
0.7824	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2800	Approved
0.7812	Intermediate Similarity	NPD5403	Approved
0.7805	Intermediate Similarity	NPD5402	Approved
0.78	Intermediate Similarity	NPD3027	Phase 3
0.7791	Intermediate Similarity	NPD37	Approved
0.779	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7199	Phase 2
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7736	Intermediate Similarity	NPD7390	Discontinued
0.7736	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2798	Approved
0.7712	Intermediate Similarity	NPD230	Phase 1
0.7707	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5401	Approved
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD9494	Approved
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7651	Intermediate Similarity	NPD4965	Approved
0.7651	Intermediate Similarity	NPD4967	Phase 2
0.7651	Intermediate Similarity	NPD4966	Approved
0.7635	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7458	Discontinued
0.7607	Intermediate Similarity	NPD3226	Approved
0.7597	Intermediate Similarity	NPD447	Suspended
0.758	Intermediate Similarity	NPD2344	Approved
0.7568	Intermediate Similarity	NPD3972	Approved
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1470	Approved
0.7532	Intermediate Similarity	NPD1613	Approved
0.7532	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5242	Approved
0.7485	Intermediate Similarity	NPD920	Approved
0.7484	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7457	Intermediate Similarity	NPD3751	Discontinued
0.7453	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2799	Discontinued
0.7438	Intermediate Similarity	NPD7003	Approved
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5405	Approved
0.7405	Intermediate Similarity	NPD5408	Approved
0.7405	Intermediate Similarity	NPD5404	Approved
0.7405	Intermediate Similarity	NPD5406	Approved
0.7397	Intermediate Similarity	NPD5536	Phase 2
0.7391	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD4908	Phase 1
0.7362	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7228	Approved
0.7326	Intermediate Similarity	NPD3787	Discontinued
0.732	Intermediate Similarity	NPD3018	Phase 2
0.7314	Intermediate Similarity	NPD7286	Phase 2
0.7303	Intermediate Similarity	NPD1203	Approved
0.7301	Intermediate Similarity	NPD4357	Discontinued
0.729	Intermediate Similarity	NPD3764	Approved
0.729	Intermediate Similarity	NPD3268	Approved
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2313	Discontinued
0.7288	Intermediate Similarity	NPD7685	Pre-registration
0.7284	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD4288	Approved
0.7278	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7267	Intermediate Similarity	NPD2654	Approved
0.7237	Intermediate Similarity	NPD1876	Approved
0.7233	Intermediate Similarity	NPD7033	Discontinued
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7229	Intermediate Similarity	NPD1653	Approved
0.7226	Intermediate Similarity	NPD4625	Phase 3
0.7222	Intermediate Similarity	NPD8166	Discontinued
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7212	Intermediate Similarity	NPD6273	Approved
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7202	Intermediate Similarity	NPD6385	Approved
0.7202	Intermediate Similarity	NPD6386	Approved
0.7191	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2797	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8150	Discontinued
0.7176	Intermediate Similarity	NPD5978	Approved
0.7176	Intermediate Similarity	NPD5977	Approved
0.7176	Intermediate Similarity	NPD5353	Approved
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.7168	Intermediate Similarity	NPD8127	Discontinued
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD4110	Phase 3
0.7117	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9545	Approved
0.7111	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD7696	Phase 3
0.7105	Intermediate Similarity	NPD7697	Approved
0.7105	Intermediate Similarity	NPD7698	Approved
0.7105	Intermediate Similarity	NPD9269	Phase 2
0.7105	Intermediate Similarity	NPD9717	Approved
0.7105	Intermediate Similarity	NPD2981	Phase 2
0.7105	Intermediate Similarity	NPD7435	Discontinued
0.7101	Intermediate Similarity	NPD5089	Approved
0.7101	Intermediate Similarity	NPD5090	Approved
0.7097	Intermediate Similarity	NPD4362	Clinical (unspecified phase)

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