NPASS Compound

Structure

NPC295384 OpenBabel07101718202D 22 24 0 0 0 0 0 0 0 0999 V2000 3.4641 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -2.5981 3.5000 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 1.7321 -0.0000 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 3.0000 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 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 1.7321 2.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 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 1.7321 3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 22 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.212
LogD:	2.223
LogS:	-3.316
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	2.518
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:	-4.889
MDCK Permeability:	9.815918929234613e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.307
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	99.1164779663086%
Volume Distribution (VD):	0.387
Pgp-substrate:	1.5703450441360474%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.514
CYP2C19-inhibitor:	0.408
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.693
CYP2C9-substrate:	0.681
CYP2D6-inhibitor:	0.417
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.179
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	5.955
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.865
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.665
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.911
Carcinogencity:	0.407
Eye Corrosion:	0.004
Eye Irritation:	0.869
Respiratory Toxicity:	0.049

Download Data

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

Natural Product: NPC295384

Natural Product ID:	NPC295384
*Common Name:**	4',5,7-Trihydroxy-6,8-Dimethylisoflavone
IUPAC Name:	5,7-dihydroxy-3-(4-hydroxyphenyl)-6,8-dimethylchromen-4-one
Synonyms:
Standard InCHIKey:	VSEIMGCATUFLSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-8-14(19)9(2)17-13(15(8)20)16(21)12(7-22-17)10-3-5-11(18)6-4-10/h3-7,18-20H,1-2H3
SMILES:	Oc1ccc(cc1)c1coc2c(c1=O)c(O)c(c(c2C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512579
PubChem CID:	637048
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO32723	henriettella fascicularis	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502307]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	IC50	=	880.0	nM	PMID[530475]
NPT2738	Cell Line	Ishikawa	Homo sapiens	IC50	>	20000.0	nM	PMID[530475]
NPT2738	Cell Line	Ishikawa	Homo sapiens	IC50	=	10500.0	nM	PMID[530475]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	=	10200.0	nM	PMID[530475]

☑ 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 NPC295384 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	1805
0.2-0.3	4215
0.3-0.4	11015
0.4-0.5	7144
0.5-0.6	3954
0.6-0.7	5780
0.7-0.8	4457
0.8-0.85	1876
0.85-0.9	1434
0.9-0.95	511
0.95-1	95

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC48624
0.9925	High Similarity	NPC80962
0.9925	High Similarity	NPC219917
0.9925	High Similarity	NPC215311
0.9925	High Similarity	NPC213659
0.9925	High Similarity	NPC259166
0.9925	High Similarity	NPC326109
0.9925	High Similarity	NPC172250
0.9925	High Similarity	NPC101366
0.9925	High Similarity	NPC144118
0.9925	High Similarity	NPC204985
0.9852	High Similarity	NPC55832
0.9852	High Similarity	NPC469404
0.9852	High Similarity	NPC52789
0.9852	High Similarity	NPC26051
0.9852	High Similarity	NPC268204
0.9851	High Similarity	NPC283429
0.985	High Similarity	NPC7013
0.985	High Similarity	NPC116632
0.985	High Similarity	NPC294409
0.985	High Similarity	NPC162680
0.985	High Similarity	NPC303644
0.985	High Similarity	NPC181124
0.985	High Similarity	NPC209560
0.9778	High Similarity	NPC253822
0.9776	High Similarity	NPC12175
0.9776	High Similarity	NPC90665
0.9776	High Similarity	NPC55162
0.9776	High Similarity	NPC309154
0.9776	High Similarity	NPC278323
0.9776	High Similarity	NPC279668
0.9708	High Similarity	NPC476178
0.9708	High Similarity	NPC117836
0.9708	High Similarity	NPC51887
0.9708	High Similarity	NPC475705
0.9699	High Similarity	NPC234560
0.9699	High Similarity	NPC39426
0.9638	High Similarity	NPC476055
0.963	High Similarity	NPC21350
0.9627	High Similarity	NPC66349
0.9627	High Similarity	NPC98115
0.9627	High Similarity	NPC235428
0.9627	High Similarity	NPC477242
0.9627	High Similarity	NPC186838
0.9627	High Similarity	NPC41461
0.9627	High Similarity	NPC1486
0.9627	High Similarity	NPC25287
0.9627	High Similarity	NPC477244
0.9627	High Similarity	NPC274109
0.9627	High Similarity	NPC87545
0.9627	High Similarity	NPC168105
0.9627	High Similarity	NPC150399
0.9627	High Similarity	NPC249606
0.9627	High Similarity	NPC477243
0.9627	High Similarity	NPC12165
0.9562	High Similarity	NPC110969
0.9562	High Similarity	NPC470089
0.9562	High Similarity	NPC3188
0.9562	High Similarity	NPC321980
0.9562	High Similarity	NPC470087
0.9559	High Similarity	NPC470211
0.9559	High Similarity	NPC477956
0.9559	High Similarity	NPC18260
0.9559	High Similarity	NPC78913
0.9556	High Similarity	NPC472419
0.9556	High Similarity	NPC317119
0.9556	High Similarity	NPC212767
0.9556	High Similarity	NPC153979
0.9552	High Similarity	NPC156092
0.9552	High Similarity	NPC13575
0.9552	High Similarity	NPC131039
0.95	High Similarity	NPC79469
0.95	High Similarity	NPC97716
0.95	High Similarity	NPC237635
0.95	High Similarity	NPC24673
0.95	High Similarity	NPC51070
0.95	High Similarity	NPC104406
0.95	High Similarity	NPC201731
0.95	High Similarity	NPC222298
0.9496	High Similarity	NPC234629
0.9496	High Similarity	NPC311741
0.9493	High Similarity	NPC11561
0.9493	High Similarity	NPC226636
0.9489	High Similarity	NPC270883
0.9489	High Similarity	NPC261227
0.9489	High Similarity	NPC241100
0.9489	High Similarity	NPC11056
0.9489	High Similarity	NPC159275
0.9489	High Similarity	NPC172986
0.9485	High Similarity	NPC243528
0.9485	High Similarity	NPC201395
0.9485	High Similarity	NPC471620
0.9485	High Similarity	NPC251681
0.9481	High Similarity	NPC193792
0.9478	High Similarity	NPC286336
0.9478	High Similarity	NPC103842
0.9474	High Similarity	NPC129132
0.9474	High Similarity	NPC257756
0.9474	High Similarity	NPC87231
0.9474	High Similarity	NPC182428
0.9474	High Similarity	NPC205468
0.9474	High Similarity	NPC212631
0.9433	High Similarity	NPC6511
0.9433	High Similarity	NPC266572
0.9433	High Similarity	NPC168085
0.9424	High Similarity	NPC301751
0.9424	High Similarity	NPC175504
0.9424	High Similarity	NPC149026
0.9424	High Similarity	NPC91560
0.9424	High Similarity	NPC245482
0.9424	High Similarity	NPC143896
0.9424	High Similarity	NPC310130
0.9424	High Similarity	NPC166138
0.9424	High Similarity	NPC75049
0.9424	High Similarity	NPC18585
0.9424	High Similarity	NPC39329
0.9424	High Similarity	NPC169591
0.9424	High Similarity	NPC257097
0.9424	High Similarity	NPC68104
0.9424	High Similarity	NPC150408
0.9424	High Similarity	NPC106985
0.9424	High Similarity	NPC164980
0.9424	High Similarity	NPC221432
0.942	High Similarity	NPC213322
0.942	High Similarity	NPC118840
0.942	High Similarity	NPC205006
0.942	High Similarity	NPC4743
0.942	High Similarity	NPC147688
0.942	High Similarity	NPC103362
0.942	High Similarity	NPC282300
0.942	High Similarity	NPC156590
0.942	High Similarity	NPC64908
0.942	High Similarity	NPC312391
0.942	High Similarity	NPC324386
0.9416	High Similarity	NPC303633
0.9416	High Similarity	NPC217186
0.9416	High Similarity	NPC220062
0.9416	High Similarity	NPC53181
0.9416	High Similarity	NPC55018
0.9416	High Similarity	NPC96565
0.9416	High Similarity	NPC216978
0.9416	High Similarity	NPC472366
0.9416	High Similarity	NPC301217
0.9412	High Similarity	NPC228661
0.9412	High Similarity	NPC250266
0.9412	High Similarity	NPC266597
0.9403	High Similarity	NPC312318
0.9403	High Similarity	NPC159623
0.9403	High Similarity	NPC337373
0.9403	High Similarity	NPC144051
0.9403	High Similarity	NPC82225
0.9403	High Similarity	NPC175098
0.9403	High Similarity	NPC18877
0.9403	High Similarity	NPC56031
0.9403	High Similarity	NPC263670
0.9403	High Similarity	NPC28753
0.9403	High Similarity	NPC223354
0.9403	High Similarity	NPC20560
0.9403	High Similarity	NPC188646
0.9403	High Similarity	NPC472365
0.9403	High Similarity	NPC204960
0.9403	High Similarity	NPC27643
0.9403	High Similarity	NPC139813
0.9403	High Similarity	NPC294593
0.9403	High Similarity	NPC192304
0.9403	High Similarity	NPC242294
0.9398	High Similarity	NPC64359
0.9398	High Similarity	NPC313618
0.9398	High Similarity	NPC262359
0.9398	High Similarity	NPC308037
0.9366	High Similarity	NPC38545
0.9366	High Similarity	NPC171916
0.9366	High Similarity	NPC317492
0.9362	High Similarity	NPC473077
0.9362	High Similarity	NPC296998
0.9362	High Similarity	NPC110303
0.9362	High Similarity	NPC23728
0.9357	High Similarity	NPC224714
0.9357	High Similarity	NPC197252
0.9357	High Similarity	NPC273538
0.9357	High Similarity	NPC473013
0.9357	High Similarity	NPC209040
0.9357	High Similarity	NPC216538
0.9357	High Similarity	NPC236766
0.9357	High Similarity	NPC319752
0.9357	High Similarity	NPC473015
0.9357	High Similarity	NPC271288
0.9353	High Similarity	NPC182852
0.9353	High Similarity	NPC37496
0.9353	High Similarity	NPC40833
0.9353	High Similarity	NPC64915
0.9353	High Similarity	NPC167624
0.9353	High Similarity	NPC107572
0.9353	High Similarity	NPC76338
0.9353	High Similarity	NPC297600
0.9353	High Similarity	NPC223500
0.9353	High Similarity	NPC473042
0.9353	High Similarity	NPC1089
0.9353	High Similarity	NPC265040
0.9353	High Similarity	NPC78

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 NPC295384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	992
0.2-0.3	1527
0.3-0.4	2629
0.4-0.5	1911
0.5-0.6	1138
0.6-0.7	365
0.7-0.8	117
0.8-0.85	41
0.85-0.9	25
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9699	High Similarity	NPD1510	Phase 2
0.9398	High Similarity	NPD1240	Approved
0.9357	High Similarity	NPD4378	Clinical (unspecified phase)
0.9259	High Similarity	NPD1607	Approved
0.9203	High Similarity	NPD1549	Phase 2
0.9167	High Similarity	NPD4380	Phase 2
0.913	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1552	Clinical (unspecified phase)
0.9085	High Similarity	NPD7410	Clinical (unspecified phase)
0.9058	High Similarity	NPD2796	Approved
0.8851	High Similarity	NPD2393	Clinical (unspecified phase)
0.8844	High Similarity	NPD7411	Suspended
0.88	High Similarity	NPD7075	Discontinued
0.8792	High Similarity	NPD8443	Clinical (unspecified phase)
0.8725	High Similarity	NPD7819	Suspended
0.8725	High Similarity	NPD7096	Clinical (unspecified phase)
0.8658	High Similarity	NPD6801	Discontinued
0.8658	High Similarity	NPD1934	Approved
0.8621	High Similarity	NPD1511	Approved
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8542	High Similarity	NPD3750	Approved
0.8542	High Similarity	NPD1878	Clinical (unspecified phase)
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.8521	High Similarity	NPD2935	Discontinued
0.8503	High Similarity	NPD1512	Approved
0.8493	Intermediate Similarity	NPD6799	Approved
0.8487	Intermediate Similarity	NPD7768	Phase 2
0.8477	Intermediate Similarity	NPD2801	Approved
0.8472	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD6651	Approved
0.8392	Intermediate Similarity	NPD1551	Phase 2
0.8366	Intermediate Similarity	NPD3882	Suspended
0.8345	Intermediate Similarity	NPD1243	Approved
0.8345	Intermediate Similarity	NPD2800	Approved
0.8322	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD920	Approved
0.8302	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD6599	Discontinued
0.8269	Intermediate Similarity	NPD6959	Discontinued
0.8217	Intermediate Similarity	NPD6232	Discontinued
0.8194	Intermediate Similarity	NPD3748	Approved
0.8194	Intermediate Similarity	NPD3749	Approved
0.8188	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2532	Approved
0.8188	Intermediate Similarity	NPD2534	Approved
0.8188	Intermediate Similarity	NPD2533	Approved
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD7473	Discontinued
0.8169	Intermediate Similarity	NPD943	Approved
0.8156	Intermediate Similarity	NPD2313	Discontinued
0.8156	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2798	Approved
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD6166	Phase 2
0.8113	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5494	Approved
0.8086	Intermediate Similarity	NPD5953	Discontinued
0.8082	Intermediate Similarity	NPD2344	Approved
0.8079	Intermediate Similarity	NPD5403	Approved
0.8069	Intermediate Similarity	NPD2799	Discontinued
0.8067	Intermediate Similarity	NPD5401	Approved
0.7963	Intermediate Similarity	NPD7286	Phase 2
0.7963	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD1203	Approved
0.7927	Intermediate Similarity	NPD6559	Discontinued
0.7914	Intermediate Similarity	NPD7472	Approved
0.7914	Intermediate Similarity	NPD7074	Phase 3
0.7911	Intermediate Similarity	NPD919	Approved
0.7902	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD7390	Discontinued
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7867	Intermediate Similarity	NPD2309	Approved
0.7866	Intermediate Similarity	NPD6797	Phase 2
0.7857	Intermediate Similarity	NPD3226	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7818	Intermediate Similarity	NPD7251	Discontinued
0.7812	Intermediate Similarity	NPD1247	Approved
0.78	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.777	Intermediate Similarity	NPD1610	Phase 2
0.7762	Intermediate Similarity	NPD6832	Phase 2
0.7762	Intermediate Similarity	NPD4908	Phase 1
0.7744	Intermediate Similarity	NPD5844	Phase 1
0.7742	Intermediate Similarity	NPD7458	Discontinued
0.7737	Intermediate Similarity	NPD9545	Approved
0.7733	Intermediate Similarity	NPD2654	Approved
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD9493	Approved
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7714	Intermediate Similarity	NPD9717	Approved
0.7714	Intermediate Similarity	NPD3972	Approved
0.7703	Intermediate Similarity	NPD7033	Discontinued
0.7703	Intermediate Similarity	NPD4308	Phase 3
0.7676	Intermediate Similarity	NPD1470	Approved
0.7676	Intermediate Similarity	NPD1164	Approved
0.7665	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3268	Approved
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD422	Phase 1
0.7643	Intermediate Similarity	NPD1201	Approved
0.763	Intermediate Similarity	NPD4363	Phase 3
0.763	Intermediate Similarity	NPD4360	Phase 2
0.7619	Intermediate Similarity	NPD230	Phase 1
0.7586	Intermediate Similarity	NPD4361	Phase 2
0.7586	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7003	Approved
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2797	Approved
0.7546	Intermediate Similarity	NPD5710	Approved
0.7546	Intermediate Similarity	NPD5711	Approved
0.7543	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD5408	Approved
0.7533	Intermediate Similarity	NPD5404	Approved
0.7533	Intermediate Similarity	NPD5405	Approved
0.7533	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD1729	Discontinued
0.7483	Intermediate Similarity	NPD1876	Approved
0.7483	Intermediate Similarity	NPD3225	Approved
0.7467	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7432	Intermediate Similarity	NPD4307	Phase 2
0.7431	Intermediate Similarity	NPD3267	Approved
0.7431	Intermediate Similarity	NPD3266	Approved
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1933	Approved
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7368	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3027	Phase 3
0.7347	Intermediate Similarity	NPD4625	Phase 3
0.7343	Intermediate Similarity	NPD1608	Approved
0.7329	Intermediate Similarity	NPD9494	Approved
0.7318	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1613	Approved
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5889	Approved
0.7312	Intermediate Similarity	NPD5890	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD411	Approved
0.7297	Intermediate Similarity	NPD1296	Phase 2
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2296	Approved
0.7279	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD447	Suspended
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1019	Discontinued
0.7255	Intermediate Similarity	NPD1471	Phase 3
0.7241	Intermediate Similarity	NPD1283	Approved
0.7229	Intermediate Similarity	NPD7229	Phase 3
0.7211	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4287	Approved
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7183	Intermediate Similarity	NPD1651	Approved
0.7181	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3751	Discontinued
0.716	Intermediate Similarity	NPD6844	Discontinued
0.716	Intermediate Similarity	NPD37	Approved
0.716	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7133	Intermediate Similarity	NPD17	Approved
0.7132	Intermediate Similarity	NPD74	Approved
0.7132	Intermediate Similarity	NPD9266	Approved
0.7127	Intermediate Similarity	NPD6778	Approved
0.7127	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD6780	Approved
0.7127	Intermediate Similarity	NPD6779	Approved
0.7127	Intermediate Similarity	NPD6782	Approved
0.7127	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD6777	Approved
0.711	Intermediate Similarity	NPD8313	Approved
0.711	Intermediate Similarity	NPD8312	Approved
0.7092	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4476	Approved
0.7078	Intermediate Similarity	NPD4477	Approved
0.707	Intermediate Similarity	NPD2354	Approved
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7059	Intermediate Similarity	NPD9267	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9264	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