NPASS Compound

Structure

CID49242 OpenBabel06191715382D 22 24 0 0 0 0 0 0 0 0999 V2000 -4.3301 4.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 -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 0.8660 1.5000 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 -0.8660 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 -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 -3.4641 3.0000 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -4.3301 3.5000 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 6 15 2 0 0 0 0 7 11 2 0 0 0 0 7 22 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 18 2 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.05
Volume:	288.636
LogP:	1.747
LogD:	1.812
LogS:	-3.881
# Rotatable Bonds:	2
TPSA:	93.81
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.846
Synthetic Accessibility Score:	2.763
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	1.7086576917790808e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.212

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	90.34695434570312%
Volume Distribution (VD):	0.433
Pgp-substrate:	4.6645002365112305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.774
CYP2C19-inhibitor:	0.911
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.294
CYP3A4-inhibitor:	0.674
CYP3A4-substrate:	0.116

ADMET: Excretion

Clearance (CL):	3.662
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.463
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.761
Carcinogencity:	0.857
Eye Corrosion:	0.009
Eye Irritation:	0.641
Respiratory Toxicity:	0.668

Download Data

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

Natural Product: NPC49242

Natural Product ID:	NPC49242
*Common Name:**	Bowdichione
IUPAC Name:	2-(7-hydroxy-4-oxochromen-3-yl)-5-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:	Bowdichione
Standard InCHIKey:	GCAIEHBYLQNGAF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H10O6/c1-21-15-6-12(18)10(5-13(15)19)11-7-22-14-4-8(17)2-3-9(14)16(11)20/h2-7,17H,1H3
SMILES:	COC1=CC(=O)C(=CC1=O)c1coc2cc(ccc2c1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087008
PubChem CID:	5281705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[23743282]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9525107]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22420	Lignum dalbergiae odoriferae rosewood	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18117	Dalbergia odorifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	>	100.0	uM	PMID[502071]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.9	uM	PMID[502071]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.7	uM	PMID[502071]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	1.4	uM	PMID[502071]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	0.01	uM	PMID[502071]

☑ 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 NPC49242 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	386
0.1-0.2	1756
0.2-0.3	4810
0.3-0.4	10905
0.4-0.5	7121
0.5-0.6	4491
0.6-0.7	5661
0.7-0.8	4298
0.8-0.85	2141
0.85-0.9	1011
0.9-0.95	115
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC25427
0.9412	High Similarity	NPC181124
0.9412	High Similarity	NPC162680
0.9412	High Similarity	NPC209560
0.9412	High Similarity	NPC294409
0.9412	High Similarity	NPC7013
0.9412	High Similarity	NPC303644
0.9412	High Similarity	NPC116632
0.9343	High Similarity	NPC278323
0.9343	High Similarity	NPC90665
0.9343	High Similarity	NPC12175
0.9343	High Similarity	NPC55162
0.9343	High Similarity	NPC309154
0.9343	High Similarity	NPC279668
0.9281	High Similarity	NPC136840
0.9275	High Similarity	NPC295384
0.9265	High Similarity	NPC234560
0.9265	High Similarity	NPC39426
0.9254	High Similarity	NPC65060
0.9248	High Similarity	NPC185497
0.9209	High Similarity	NPC144118
0.9209	High Similarity	NPC80962
0.9209	High Similarity	NPC230285
0.9209	High Similarity	NPC259166
0.9209	High Similarity	NPC281207
0.9209	High Similarity	NPC146679
0.9209	High Similarity	NPC59951
0.9209	High Similarity	NPC48624
0.9209	High Similarity	NPC101366
0.9209	High Similarity	NPC184536
0.9209	High Similarity	NPC172250
0.9209	High Similarity	NPC215311
0.9209	High Similarity	NPC103342
0.9209	High Similarity	NPC204985
0.9209	High Similarity	NPC326109
0.9209	High Similarity	NPC103904
0.9209	High Similarity	NPC219917
0.9209	High Similarity	NPC269652
0.9209	High Similarity	NPC213659
0.9197	High Similarity	NPC87545
0.9197	High Similarity	NPC235428
0.9191	High Similarity	NPC286336
0.9185	High Similarity	NPC129132
0.9185	High Similarity	NPC87231
0.9185	High Similarity	NPC212631
0.9185	High Similarity	NPC257756
0.9185	High Similarity	NPC205468
0.9173	High Similarity	NPC60558
0.9149	High Similarity	NPC473813
0.9149	High Similarity	NPC473812
0.9143	High Similarity	NPC90582
0.9143	High Similarity	NPC26051
0.9143	High Similarity	NPC262094
0.9143	High Similarity	NPC55832
0.9143	High Similarity	NPC469404
0.9143	High Similarity	NPC268204
0.9143	High Similarity	NPC52789
0.9137	High Similarity	NPC283429
0.9137	High Similarity	NPC241838
0.9137	High Similarity	NPC143799
0.9137	High Similarity	NPC152042
0.913	High Similarity	NPC250266
0.913	High Similarity	NPC212767
0.913	High Similarity	NPC266597
0.9118	High Similarity	NPC144051
0.9118	High Similarity	NPC472365
0.9118	High Similarity	NPC263670
0.9118	High Similarity	NPC188646
0.9118	High Similarity	NPC242294
0.9118	High Similarity	NPC159623
0.9118	High Similarity	NPC82225
0.9118	High Similarity	NPC56031
0.9118	High Similarity	NPC294593
0.9118	High Similarity	NPC204960
0.9118	High Similarity	NPC175098
0.9118	High Similarity	NPC192304
0.9118	High Similarity	NPC312318
0.9118	High Similarity	NPC139813
0.9118	High Similarity	NPC28753
0.9118	High Similarity	NPC20560
0.9118	High Similarity	NPC337373
0.9118	High Similarity	NPC18877
0.9111	High Similarity	NPC308037
0.9111	High Similarity	NPC262359
0.9111	High Similarity	NPC313618
0.9111	High Similarity	NPC64359
0.9098	High Similarity	NPC80694
0.9098	High Similarity	NPC186098
0.9085	High Similarity	NPC472446
0.9085	High Similarity	NPC472447
0.9071	High Similarity	NPC253822
0.9065	High Similarity	NPC188947
0.9065	High Similarity	NPC124269
0.9065	High Similarity	NPC280284
0.9065	High Similarity	NPC99333
0.9058	High Similarity	NPC150399
0.9058	High Similarity	NPC47815
0.9058	High Similarity	NPC98115
0.9058	High Similarity	NPC1486
0.9058	High Similarity	NPC41461
0.9058	High Similarity	NPC29353
0.9058	High Similarity	NPC477243
0.9058	High Similarity	NPC25287
0.9058	High Similarity	NPC124784
0.9058	High Similarity	NPC477244
0.9058	High Similarity	NPC193792
0.9058	High Similarity	NPC234133
0.9058	High Similarity	NPC477242
0.9058	High Similarity	NPC186838
0.9058	High Similarity	NPC249606
0.9058	High Similarity	NPC231772
0.9058	High Similarity	NPC12165
0.9058	High Similarity	NPC168105
0.9058	High Similarity	NPC66349
0.9058	High Similarity	NPC473887
0.9058	High Similarity	NPC274109
0.9058	High Similarity	NPC127447
0.9058	High Similarity	NPC194281
0.9051	High Similarity	NPC164136
0.9044	High Similarity	NPC182428
0.9037	High Similarity	NPC250057
0.903	High Similarity	NPC212379
0.903	High Similarity	NPC69235
0.9023	High Similarity	NPC128428
0.9023	High Similarity	NPC305518
0.9021	High Similarity	NPC5820
0.9021	High Similarity	NPC329678
0.9021	High Similarity	NPC306488
0.9021	High Similarity	NPC470458
0.9021	High Similarity	NPC178343
0.9014	High Similarity	NPC117836
0.9014	High Similarity	NPC475705
0.9014	High Similarity	NPC158874
0.9014	High Similarity	NPC470216
0.9014	High Similarity	NPC51887
0.9014	High Similarity	NPC245482
0.9014	High Similarity	NPC476178
0.9014	High Similarity	NPC301751
0.9014	High Similarity	NPC475201
0.9007	High Similarity	NPC110969
0.9007	High Similarity	NPC3188
0.9	High Similarity	NPC78913
0.9	High Similarity	NPC265871
0.9	High Similarity	NPC23257
0.9	High Similarity	NPC329203
0.9	High Similarity	NPC225153
0.9	High Similarity	NPC20709
0.9	High Similarity	NPC150648
0.9	High Similarity	NPC473076
0.9	High Similarity	NPC469523
0.9	High Similarity	NPC18260
0.9	High Similarity	NPC470211
0.9	High Similarity	NPC261234
0.9	High Similarity	NPC222342
0.9	High Similarity	NPC310135
0.9	High Similarity	NPC274784
0.8993	High Similarity	NPC472419
0.8993	High Similarity	NPC188879
0.8993	High Similarity	NPC275055
0.8993	High Similarity	NPC228661
0.8993	High Similarity	NPC153979
0.8993	High Similarity	NPC299379
0.8993	High Similarity	NPC317119
0.8993	High Similarity	NPC290291
0.8986	High Similarity	NPC60667
0.8986	High Similarity	NPC131039
0.8986	High Similarity	NPC13575
0.8986	High Similarity	NPC156092
0.8978	High Similarity	NPC223354
0.8978	High Similarity	NPC223457
0.8971	High Similarity	NPC475008
0.8971	High Similarity	NPC189106
0.8971	High Similarity	NPC112192
0.8971	High Similarity	NPC31872
0.8971	High Similarity	NPC186097
0.8971	High Similarity	NPC473584
0.8971	High Similarity	NPC475009
0.8971	High Similarity	NPC475589
0.8971	High Similarity	NPC164236
0.8971	High Similarity	NPC66384
0.8971	High Similarity	NPC309717
0.8971	High Similarity	NPC128348
0.8966	High Similarity	NPC470461
0.8963	High Similarity	NPC247779
0.8951	High Similarity	NPC476055
0.8951	High Similarity	NPC273538
0.8951	High Similarity	NPC216538
0.8944	High Similarity	NPC226636
0.8944	High Similarity	NPC473042
0.8944	High Similarity	NPC162476
0.8944	High Similarity	NPC148545
0.8944	High Similarity	NPC11561
0.8944	High Similarity	NPC200694
0.8944	High Similarity	NPC204469
0.8944	High Similarity	NPC202981
0.8936	High Similarity	NPC129853
0.8936	High Similarity	NPC6407
0.8936	High Similarity	NPC261227
0.8936	High Similarity	NPC471587
0.8936	High Similarity	NPC159275

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 NPC49242 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	993
0.2-0.3	1661
0.3-0.4	2699
0.4-0.5	1909
0.5-0.6	1051
0.6-0.7	317
0.7-0.8	105
0.8-0.85	37
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9265	High Similarity	NPD1510	Phase 2
0.9111	High Similarity	NPD1240	Approved
0.8978	High Similarity	NPD1607	Approved
0.8951	High Similarity	NPD4378	Clinical (unspecified phase)
0.8929	High Similarity	NPD1549	Phase 2
0.8857	High Similarity	NPD1552	Clinical (unspecified phase)
0.8857	High Similarity	NPD1550	Clinical (unspecified phase)
0.8652	High Similarity	NPD2796	Approved
0.8621	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD7410	Clinical (unspecified phase)
0.8553	High Similarity	NPD7075	Discontinued
0.8542	High Similarity	NPD1878	Clinical (unspecified phase)
0.8533	High Similarity	NPD6801	Discontinued
0.8523	High Similarity	NPD4380	Phase 2
0.8477	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6599	Discontinued
0.8378	Intermediate Similarity	NPD1512	Approved
0.8366	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD7411	Suspended
0.831	Intermediate Similarity	NPD6651	Approved
0.8289	Intermediate Similarity	NPD1934	Approved
0.8288	Intermediate Similarity	NPD3750	Approved
0.8243	Intermediate Similarity	NPD1511	Approved
0.8235	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD5403	Approved
0.8194	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD5401	Approved
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD7819	Suspended
0.8117	Intermediate Similarity	NPD2801	Approved
0.8095	Intermediate Similarity	NPD2800	Approved
0.8075	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1551	Phase 2
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD3748	Approved
0.7902	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7768	Phase 2
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7888	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6797	Phase 2
0.7852	Intermediate Similarity	NPD1243	Approved
0.7848	Intermediate Similarity	NPD3749	Approved
0.7843	Intermediate Similarity	NPD920	Approved
0.7838	Intermediate Similarity	NPD2344	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7829	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD2532	Approved
0.7829	Intermediate Similarity	NPD2534	Approved
0.7823	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7251	Discontinued
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD919	Approved
0.7793	Intermediate Similarity	NPD943	Approved
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD2798	Approved
0.7737	Intermediate Similarity	NPD9545	Approved
0.7733	Intermediate Similarity	NPD2654	Approved
0.773	Intermediate Similarity	NPD7473	Discontinued
0.7721	Intermediate Similarity	NPD9493	Approved
0.7714	Intermediate Similarity	NPD9717	Approved
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6959	Discontinued
0.7702	Intermediate Similarity	NPD1247	Approved
0.7676	Intermediate Similarity	NPD1203	Approved
0.7665	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5953	Discontinued
0.7643	Intermediate Similarity	NPD422	Phase 1
0.7643	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7054	Approved
0.7632	Intermediate Similarity	NPD2309	Approved
0.7609	Intermediate Similarity	NPD1548	Phase 1
0.759	Intermediate Similarity	NPD7472	Approved
0.759	Intermediate Similarity	NPD7074	Phase 3
0.7584	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2313	Discontinued
0.7531	Intermediate Similarity	NPD5494	Approved
0.753	Intermediate Similarity	NPD7286	Phase 2
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.7467	Intermediate Similarity	NPD2799	Discontinued
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7465	Intermediate Similarity	NPD3972	Approved
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6100	Approved
0.7417	Intermediate Similarity	NPD6099	Approved
0.7415	Intermediate Similarity	NPD3268	Approved
0.7405	Intermediate Similarity	NPD3226	Approved
0.7397	Intermediate Similarity	NPD4908	Phase 1
0.7396	Intermediate Similarity	NPD6559	Discontinued
0.7394	Intermediate Similarity	NPD1610	Phase 2
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD4308	Phase 3
0.7337	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2797	Approved
0.731	Intermediate Similarity	NPD1470	Approved
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7297	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1296	Phase 2
0.7284	Intermediate Similarity	NPD4288	Approved
0.7267	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5124	Phase 1
0.726	Intermediate Similarity	NPD1019	Discontinued
0.7255	Intermediate Similarity	NPD1471	Phase 3
0.7246	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2403	Approved
0.7241	Intermediate Similarity	NPD1876	Approved
0.7241	Intermediate Similarity	NPD3225	Approved
0.7229	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD5711	Approved
0.7219	Intermediate Similarity	NPD5844	Phase 1
0.7214	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9494	Approved
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7192	Intermediate Similarity	NPD3267	Approved
0.7192	Intermediate Similarity	NPD3266	Approved
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7181	Intermediate Similarity	NPD411	Approved
0.7181	Intermediate Similarity	NPD3764	Approved
0.7179	Intermediate Similarity	NPD2354	Approved
0.7176	Intermediate Similarity	NPD1729	Discontinued
0.7153	Intermediate Similarity	NPD1201	Approved
0.7152	Intermediate Similarity	NPD1933	Approved
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7132	Intermediate Similarity	NPD9266	Approved
0.7132	Intermediate Similarity	NPD74	Approved
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7095	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4361	Phase 2
0.7086	Intermediate Similarity	NPD4307	Phase 2
0.7075	Intermediate Similarity	NPD1164	Approved
0.7073	Intermediate Similarity	NPD2296	Approved
0.707	Intermediate Similarity	NPD3887	Approved
0.7063	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9267	Approved
0.7059	Intermediate Similarity	NPD9264	Approved
0.7059	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9263	Approved
0.7055	Intermediate Similarity	NPD4749	Approved
0.7039	Intermediate Similarity	NPD6355	Discontinued
0.7032	Intermediate Similarity	NPD2353	Approved
0.7032	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD3027	Phase 3
0.6994	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8434	Phase 2
0.6986	Remote Similarity	NPD1608	Approved
0.6982	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3142	Approved
0.6974	Remote Similarity	NPD3140	Approved
0.6974	Remote Similarity	NPD1613	Approved
0.6968	Remote Similarity	NPD5408	Approved
0.6968	Remote Similarity	NPD5406	Approved
0.6968	Remote Similarity	NPD5404	Approved
0.6968	Remote Similarity	NPD5405	Approved
0.6962	Remote Similarity	NPD6190	Approved
0.6954	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1652	Phase 2
0.694	Remote Similarity	NPD6780	Approved
0.694	Remote Similarity	NPD6779	Approved
0.694	Remote Similarity	NPD6777	Approved
0.694	Remote Similarity	NPD6778	Approved
0.694	Remote Similarity	NPD940	Approved
0.694	Remote Similarity	NPD846	Approved
0.694	Remote Similarity	NPD6781	Approved
0.694	Remote Similarity	NPD6776	Approved
0.694	Remote Similarity	NPD6782	Approved
0.6937	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3787	Discontinued
0.6919	Remote Similarity	NPD7435	Discontinued
0.6913	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4287	Approved
0.6894	Remote Similarity	NPD5049	Phase 3
0.689	Remote Similarity	NPD5890	Approved
0.689	Remote Similarity	NPD5889	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