NPASS Compound

Structure

NPC278323 OpenBabel07101718282D 23 25 0 0 0 0 0 0 0 0999 V2000 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 -1.5000 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 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 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 0.8660 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 0.5000 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 -3.4641 2.0000 0.0000 O 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 4.3301 -1.5000 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 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 23 1 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	3.08
LogD:	2.77
LogS:	-3.566
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.327
Fsp3:	0.118
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:	-4.785
MDCK Permeability:	1.2895844520244282e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	94.70122528076172%
Volume Distribution (VD):	0.57
Pgp-substrate:	5.799776554107666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.847
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.901
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	7.995
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.223
Rat Oral Acute Toxicity:	0.198
Maximum Recommended Daily Dose:	0.618
Skin Sensitization:	0.672
Carcinogencity:	0.076
Eye Corrosion:	0.018
Eye Irritation:	0.922
Respiratory Toxicity:	0.318

Download Data

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

Natural Product: NPC278323

Natural Product ID:	NPC278323
*Common Name:**	2'-Methoxybiochanin A
IUPAC Name:	3-(2,4-dimethoxyphenyl)-5,7-dihydroxychromen-4-one
Synonyms:	2'-Methoxybiochanin A
Standard InCHIKey:	PBUHDEMRGWYORH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-10-3-4-11(14(7-10)22-2)12-8-23-15-6-9(18)5-13(19)16(15)17(12)20/h3-8,18-19H,1-2H3
SMILES:	COc1ccc(c2coc3cc(cc(c3c2=O)O)O)c(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1088580
PubChem CID:	44257324
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-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
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO14114	Dalbergia parviflora	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
Others	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	3.1	uM	PMID[473676]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	1.8	uM	PMID[473676]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[473676]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[473676]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.4	uM	PMID[473676]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	19.6	uM	PMID[473676]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	3.2	uM	PMID[473676]

☑ 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 NPC278323 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	411
0.1-0.2	1786
0.2-0.3	4221
0.3-0.4	10641
0.4-0.5	7523
0.5-0.6	3890
0.6-0.7	5763
0.7-0.8	4331
0.8-0.85	2078
0.85-0.9	1614
0.9-0.95	361
0.95-1	78

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC279668
1.0	High Similarity	NPC12175
1.0	High Similarity	NPC309154
1.0	High Similarity	NPC90665
1.0	High Similarity	NPC55162
0.9924	High Similarity	NPC162680
0.9924	High Similarity	NPC209560
0.9924	High Similarity	NPC7013
0.9924	High Similarity	NPC294409
0.9924	High Similarity	NPC303644
0.9924	High Similarity	NPC116632
0.9924	High Similarity	NPC181124
0.9851	High Similarity	NPC101366
0.9848	High Similarity	NPC87545
0.9848	High Similarity	NPC235428
0.9778	High Similarity	NPC52789
0.9778	High Similarity	NPC26051
0.9778	High Similarity	NPC55832
0.9778	High Similarity	NPC268204
0.9776	High Similarity	NPC295384
0.9773	High Similarity	NPC234560
0.9773	High Similarity	NPC39426
0.9704	High Similarity	NPC80962
0.9704	High Similarity	NPC326109
0.9704	High Similarity	NPC172250
0.9704	High Similarity	NPC48624
0.9704	High Similarity	NPC213659
0.9704	High Similarity	NPC259166
0.9704	High Similarity	NPC144118
0.9704	High Similarity	NPC204985
0.9704	High Similarity	NPC219917
0.9704	High Similarity	NPC253822
0.9704	High Similarity	NPC215311
0.9632	High Similarity	NPC469404
0.963	High Similarity	NPC283429
0.9627	High Similarity	NPC212767
0.9565	High Similarity	NPC476055
0.9552	High Similarity	NPC193792
0.9549	High Similarity	NPC286336
0.9545	High Similarity	NPC205468
0.9545	High Similarity	NPC129132
0.9545	High Similarity	NPC87231
0.9545	High Similarity	NPC182428
0.9545	High Similarity	NPC212631
0.9545	High Similarity	NPC257756
0.9493	High Similarity	NPC117836
0.9493	High Similarity	NPC51887
0.9493	High Similarity	NPC475705
0.9493	High Similarity	NPC476178
0.9485	High Similarity	NPC477956
0.9481	High Similarity	NPC266597
0.9481	High Similarity	NPC472419
0.9481	High Similarity	NPC228661
0.9481	High Similarity	NPC250266
0.9474	High Similarity	NPC20560
0.9474	High Similarity	NPC472365
0.9474	High Similarity	NPC159623
0.9474	High Similarity	NPC188646
0.9474	High Similarity	NPC139813
0.9474	High Similarity	NPC242294
0.9474	High Similarity	NPC192304
0.9474	High Similarity	NPC144051
0.9474	High Similarity	NPC294593
0.9474	High Similarity	NPC337373
0.9474	High Similarity	NPC28753
0.9474	High Similarity	NPC312318
0.9474	High Similarity	NPC175098
0.9474	High Similarity	NPC223354
0.9474	High Similarity	NPC82225
0.9474	High Similarity	NPC263670
0.9474	High Similarity	NPC56031
0.9474	High Similarity	NPC18877
0.9474	High Similarity	NPC204960
0.947	High Similarity	NPC262359
0.947	High Similarity	NPC64359
0.947	High Similarity	NPC308037
0.947	High Similarity	NPC313618
0.9424	High Similarity	NPC234629
0.9424	High Similarity	NPC303185
0.9424	High Similarity	NPC184649
0.9424	High Similarity	NPC311741
0.942	High Similarity	NPC202981
0.9412	High Similarity	NPC21350
0.9412	High Similarity	NPC99333
0.9412	High Similarity	NPC188947
0.9412	High Similarity	NPC124269
0.9412	High Similarity	NPC280284
0.9407	High Similarity	NPC213603
0.9407	High Similarity	NPC41461
0.9407	High Similarity	NPC477244
0.9407	High Similarity	NPC234133
0.9407	High Similarity	NPC274109
0.9407	High Similarity	NPC150399
0.9407	High Similarity	NPC98115
0.9407	High Similarity	NPC47815
0.9407	High Similarity	NPC477243
0.9407	High Similarity	NPC473887
0.9407	High Similarity	NPC186838
0.9407	High Similarity	NPC29353
0.9407	High Similarity	NPC477242
0.9407	High Similarity	NPC124784
0.9407	High Similarity	NPC168105
0.9407	High Similarity	NPC66349
0.9407	High Similarity	NPC1486
0.9407	High Similarity	NPC25287
0.9407	High Similarity	NPC473391
0.9407	High Similarity	NPC231772
0.9407	High Similarity	NPC249606
0.9407	High Similarity	NPC472364
0.9407	High Similarity	NPC127447
0.9407	High Similarity	NPC12165
0.9407	High Similarity	NPC194281
0.9362	High Similarity	NPC266572
0.9357	High Similarity	NPC12377
0.9357	High Similarity	NPC299011
0.9353	High Similarity	NPC113770
0.9348	High Similarity	NPC3188
0.9348	High Similarity	NPC110969
0.9348	High Similarity	NPC321980
0.9348	High Similarity	NPC49108
0.9348	High Similarity	NPC470089
0.9348	High Similarity	NPC470087
0.9343	High Similarity	NPC78913
0.9343	High Similarity	NPC261234
0.9343	High Similarity	NPC222342
0.9343	High Similarity	NPC49242
0.9343	High Similarity	NPC150648
0.9343	High Similarity	NPC225153
0.9343	High Similarity	NPC470211
0.9343	High Similarity	NPC329203
0.9343	High Similarity	NPC310135
0.9343	High Similarity	NPC274784
0.9343	High Similarity	NPC18260
0.9343	High Similarity	NPC265871
0.9343	High Similarity	NPC20709
0.9338	High Similarity	NPC275055
0.9338	High Similarity	NPC317119
0.9338	High Similarity	NPC153979
0.9338	High Similarity	NPC290291
0.9338	High Similarity	NPC188879
0.9333	High Similarity	NPC156092
0.9333	High Similarity	NPC131039
0.9333	High Similarity	NPC13575
0.9323	High Similarity	NPC128348
0.9323	High Similarity	NPC309717
0.9323	High Similarity	NPC66384
0.9323	High Similarity	NPC164236
0.9323	High Similarity	NPC475008
0.9323	High Similarity	NPC112192
0.9323	High Similarity	NPC186097
0.9323	High Similarity	NPC189106
0.9323	High Similarity	NPC475009
0.9318	High Similarity	NPC185497
0.9318	High Similarity	NPC247779
0.9296	High Similarity	NPC317492
0.9296	High Similarity	NPC264550
0.9296	High Similarity	NPC195763
0.9296	High Similarity	NPC139293
0.9296	High Similarity	NPC69430
0.9296	High Similarity	NPC200060
0.9296	High Similarity	NPC333691
0.9296	High Similarity	NPC142876
0.9296	High Similarity	NPC40290
0.9296	High Similarity	NPC264289
0.9291	High Similarity	NPC104406
0.9291	High Similarity	NPC97716
0.9291	High Similarity	NPC79469
0.9291	High Similarity	NPC201731
0.9291	High Similarity	NPC222298
0.9291	High Similarity	NPC24673
0.9291	High Similarity	NPC237635
0.9291	High Similarity	NPC51070
0.9286	High Similarity	NPC311144
0.9281	High Similarity	NPC11561
0.9281	High Similarity	NPC226636
0.9275	High Similarity	NPC129853
0.9275	High Similarity	NPC188243
0.9275	High Similarity	NPC110228
0.9275	High Similarity	NPC269652
0.9275	High Similarity	NPC6407
0.9275	High Similarity	NPC76445
0.9275	High Similarity	NPC270883
0.9275	High Similarity	NPC159275
0.9275	High Similarity	NPC284550
0.9275	High Similarity	NPC241100
0.9275	High Similarity	NPC281207
0.9275	High Similarity	NPC172986
0.9275	High Similarity	NPC261227
0.9275	High Similarity	NPC265178
0.9275	High Similarity	NPC11056
0.927	High Similarity	NPC118813
0.927	High Similarity	NPC251681
0.927	High Similarity	NPC471620
0.927	High Similarity	NPC25427
0.927	High Similarity	NPC329225
0.927	High Similarity	NPC201395
0.927	High Similarity	NPC243528
0.927	High Similarity	NPC472460
0.927	High Similarity	NPC147686
0.927	High Similarity	NPC472368

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 NPC278323 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	966
0.2-0.3	1579
0.3-0.4	2624
0.4-0.5	1909
0.5-0.6	1130
0.6-0.7	364
0.7-0.8	111
0.8-0.85	42
0.85-0.9	25
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9773	High Similarity	NPD1510	Phase 2
0.947	High Similarity	NPD1240	Approved
0.9328	High Similarity	NPD1607	Approved
0.927	High Similarity	NPD1549	Phase 2
0.9197	High Similarity	NPD1552	Clinical (unspecified phase)
0.9197	High Similarity	NPD1550	Clinical (unspecified phase)
0.9149	High Similarity	NPD4378	Clinical (unspecified phase)
0.9124	High Similarity	NPD2796	Approved
0.8966	High Similarity	NPD4380	Phase 2
0.8881	High Similarity	NPD7410	Clinical (unspecified phase)
0.8732	High Similarity	NPD1878	Clinical (unspecified phase)
0.8716	High Similarity	NPD1934	Approved
0.8681	High Similarity	NPD1511	Approved
0.8658	High Similarity	NPD2393	Clinical (unspecified phase)
0.8658	High Similarity	NPD2801	Approved
0.8649	High Similarity	NPD7411	Suspended
0.8609	High Similarity	NPD7075	Discontinued
0.8609	High Similarity	NPD4381	Clinical (unspecified phase)
0.8601	High Similarity	NPD3750	Approved
0.86	High Similarity	NPD8443	Clinical (unspecified phase)
0.8592	High Similarity	NPD970	Clinical (unspecified phase)
0.8562	High Similarity	NPD1512	Approved
0.8552	High Similarity	NPD6799	Approved
0.8543	High Similarity	NPD3882	Suspended
0.8533	High Similarity	NPD7819	Suspended
0.8533	High Similarity	NPD7096	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6801	Discontinued
0.8451	Intermediate Similarity	NPD1551	Phase 2
0.8366	Intermediate Similarity	NPD3749	Approved
0.8357	Intermediate Similarity	NPD943	Approved
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8301	Intermediate Similarity	NPD7768	Phase 2
0.8291	Intermediate Similarity	NPD3818	Discontinued
0.828	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD2800	Approved
0.8264	Intermediate Similarity	NPD2344	Approved
0.8255	Intermediate Similarity	NPD920	Approved
0.8252	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD3748	Approved
0.8239	Intermediate Similarity	NPD6651	Approved
0.8235	Intermediate Similarity	NPD3817	Phase 2
0.8214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2798	Approved
0.8165	Intermediate Similarity	NPD6166	Phase 2
0.8165	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6232	Discontinued
0.8151	Intermediate Similarity	NPD1243	Approved
0.8133	Intermediate Similarity	NPD5403	Approved
0.8125	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD5401	Approved
0.8121	Intermediate Similarity	NPD2533	Approved
0.8121	Intermediate Similarity	NPD2532	Approved
0.8121	Intermediate Similarity	NPD2534	Approved
0.8121	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7473	Discontinued
0.8108	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6959	Discontinued
0.8085	Intermediate Similarity	NPD2313	Discontinued
0.8065	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2309	Approved
0.8025	Intermediate Similarity	NPD5494	Approved
0.8025	Intermediate Similarity	NPD5953	Discontinued
0.8012	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD2799	Discontinued
0.8	Intermediate Similarity	NPD5402	Approved
0.7986	Intermediate Similarity	NPD1203	Approved
0.7963	Intermediate Similarity	NPD7074	Phase 3
0.7963	Intermediate Similarity	NPD7472	Approved
0.7956	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1548	Phase 1
0.7914	Intermediate Similarity	NPD6797	Phase 2
0.7901	Intermediate Similarity	NPD7286	Phase 2
0.7866	Intermediate Similarity	NPD7251	Discontinued
0.7852	Intermediate Similarity	NPD4628	Phase 3
0.7826	Intermediate Similarity	NPD1610	Phase 2
0.7818	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7808	Phase 3
0.7817	Intermediate Similarity	NPD6832	Phase 2
0.7817	Intermediate Similarity	NPD4908	Phase 1
0.7794	Intermediate Similarity	NPD9545	Approved
0.7793	Intermediate Similarity	NPD230	Phase 1
0.7792	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD2654	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9493	Approved
0.777	Intermediate Similarity	NPD9717	Approved
0.777	Intermediate Similarity	NPD3972	Approved
0.7758	Intermediate Similarity	NPD6559	Discontinued
0.7755	Intermediate Similarity	NPD4308	Phase 3
0.7755	Intermediate Similarity	NPD7033	Discontinued
0.775	Intermediate Similarity	NPD1247	Approved
0.7736	Intermediate Similarity	NPD919	Approved
0.773	Intermediate Similarity	NPD1470	Approved
0.7708	Intermediate Similarity	NPD3764	Approved
0.7708	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3268	Approved
0.7703	Intermediate Similarity	NPD6100	Approved
0.7703	Intermediate Similarity	NPD6099	Approved
0.7698	Intermediate Similarity	NPD422	Phase 1
0.7697	Intermediate Similarity	NPD7390	Discontinued
0.7654	Intermediate Similarity	NPD3926	Phase 2
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.7635	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2797	Approved
0.7595	Intermediate Similarity	NPD1465	Phase 2
0.759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7571	Intermediate Similarity	NPD1201	Approved
0.7564	Intermediate Similarity	NPD7458	Discontinued
0.7551	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4288	Approved
0.7535	Intermediate Similarity	NPD3225	Approved
0.7535	Intermediate Similarity	NPD1876	Approved
0.75	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD5710	Approved
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7483	Intermediate Similarity	NPD3266	Approved
0.7483	Intermediate Similarity	NPD3267	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.7471	Intermediate Similarity	NPD4363	Phase 3
0.7471	Intermediate Similarity	NPD4360	Phase 2
0.7438	Intermediate Similarity	NPD2296	Approved
0.7432	Intermediate Similarity	NPD1933	Approved
0.7432	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD4361	Phase 2
0.7429	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1241	Discontinued
0.7397	Intermediate Similarity	NPD3027	Phase 3
0.7394	Intermediate Similarity	NPD1608	Approved
0.7386	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7003	Approved
0.7365	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1613	Approved
0.7358	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5408	Approved
0.7351	Intermediate Similarity	NPD5404	Approved
0.7351	Intermediate Similarity	NPD5406	Approved
0.7351	Intermediate Similarity	NPD5405	Approved
0.7347	Intermediate Similarity	NPD411	Approved
0.7347	Intermediate Similarity	NPD1296	Phase 2
0.7341	Intermediate Similarity	NPD4287	Approved
0.7329	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1729	Discontinued
0.7315	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5124	Phase 1
0.7312	Intermediate Similarity	NPD6844	Discontinued
0.731	Intermediate Similarity	NPD1019	Discontinued
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD1471	Phase 3
0.7303	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6104	Discontinued
0.723	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6279	Approved
0.7205	Intermediate Similarity	NPD6280	Approved
0.7205	Intermediate Similarity	NPD37	Approved
0.7186	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD9266	Approved
0.7185	Intermediate Similarity	NPD74	Approved
0.7183	Intermediate Similarity	NPD17	Approved
0.7169	Intermediate Similarity	NPD7229	Phase 3
0.7162	Intermediate Similarity	NPD4625	Phase 3
0.7153	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5889	Approved
0.7143	Intermediate Similarity	NPD5890	Approved
0.7126	Intermediate Similarity	NPD5242	Approved
0.7125	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7584	Approved
0.7115	Intermediate Similarity	NPD2354	Approved
0.7115	Intermediate Similarity	NPD6190	Approved
0.7113	Intermediate Similarity	NPD9268	Approved
0.7113	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9267	Approved
0.7111	Intermediate Similarity	NPD9264	Approved
0.7111	Intermediate Similarity	NPD9263	Approved
0.7111	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7103	Intermediate Similarity	NPD4749	Approved
0.7101	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6234	Discontinued
0.7089	Intermediate Similarity	NPD7447	Phase 1
0.7089	Intermediate Similarity	NPD4661	Approved
0.7089	Intermediate Similarity	NPD4662	Approved
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7083	Intermediate Similarity	NPD2403	Approved
0.7073	Intermediate Similarity	NPD4966	Approved
0.7073	Intermediate Similarity	NPD4965	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