NPASS Compound

Structure

CID205006 OpenBabel06191715592D 24 26 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 4.3301 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 1.7321 -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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 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 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 9 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.14
Volume:	342.876
LogP:	4.729
LogD:	3.992
LogS:	-3.558
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	2.548
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.79
MDCK Permeability:	1.9144265024806373e-05
Pgp-inhibitor:	0.915
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	99.62396240234375%
Volume Distribution (VD):	0.388
Pgp-substrate:	0.6496615409851074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.947
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	7.53
Half-life (T1/2):	0.678

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.731
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.763
Carcinogencity:	0.891
Eye Corrosion:	0.003
Eye Irritation:	0.181
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC205006

Natural Product ID:	NPC205006
*Common Name:**	1-(5-Hydroxy-2,2-Dimethylchromen-6-Yl)-3-(4-Hydroxyphenyl)Propan-1-One
IUPAC Name:	1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-(4-hydroxyphenyl)propan-1-one
Synonyms:
Standard InCHIKey:	BHFVJSQVKWDKGD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O4/c1-20(2)12-11-16-18(24-20)10-8-15(19(16)23)17(22)9-5-13-3-6-14(21)7-4-13/h3-4,6-8,10-12,21,23H,5,9H2,1-2H3
SMILES:	CC1(C)C=Cc2c(ccc(C(=O)CCc3ccc(cc3)O)c2O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL185018
PubChem CID:	9973521
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19102656]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11451	Lespedeza cyrtobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10080	Teucrium betonicum	Species	Lamiaceae	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	1
MIC	1
Others	1

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	89.0	%	PMID[565801]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[565802]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	MIC	=	30860.0	nM	PMID[565803]

☑ 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 NPC205006 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	382
0.1-0.2	1603
0.2-0.3	4155
0.3-0.4	10898
0.4-0.5	7253
0.5-0.6	3671
0.6-0.7	5792
0.7-0.8	5047
0.8-0.85	1975
0.85-0.9	1154
0.9-0.95	600
0.95-1	167

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC64908
1.0	High Similarity	NPC118840
1.0	High Similarity	NPC147688
1.0	High Similarity	NPC156590
0.9926	High Similarity	NPC226636
0.9926	High Similarity	NPC235239
0.9926	High Similarity	NPC172986
0.9926	High Similarity	NPC270883
0.9926	High Similarity	NPC305355
0.9926	High Similarity	NPC475680
0.9926	High Similarity	NPC11561
0.9926	High Similarity	NPC261227
0.9854	High Similarity	NPC38219
0.9853	High Similarity	NPC110969
0.9853	High Similarity	NPC103362
0.9852	High Similarity	NPC301217
0.9852	High Similarity	NPC303633
0.9852	High Similarity	NPC55018
0.9852	High Similarity	NPC216978
0.9852	High Similarity	NPC220062
0.9852	High Similarity	NPC96565
0.9783	High Similarity	NPC234629
0.9783	High Similarity	NPC311741
0.9781	High Similarity	NPC293852
0.9781	High Similarity	NPC214236
0.9781	High Similarity	NPC299080
0.9781	High Similarity	NPC59739
0.9781	High Similarity	NPC78803
0.9781	High Similarity	NPC217083
0.9781	High Similarity	NPC62840
0.9781	High Similarity	NPC144499
0.9779	High Similarity	NPC150522
0.9779	High Similarity	NPC69769
0.9779	High Similarity	NPC241100
0.9779	High Similarity	NPC159275
0.9778	High Similarity	NPC201395
0.971	High Similarity	NPC18585
0.971	High Similarity	NPC166138
0.971	High Similarity	NPC219915
0.971	High Similarity	NPC106985
0.9708	High Similarity	NPC282300
0.9706	High Similarity	NPC78913
0.9706	High Similarity	NPC18260
0.9706	High Similarity	NPC53181
0.9706	High Similarity	NPC217186
0.9643	High Similarity	NPC104406
0.9643	High Similarity	NPC79469
0.9643	High Similarity	NPC201731
0.9643	High Similarity	NPC97716
0.9643	High Similarity	NPC110303
0.9643	High Similarity	NPC23728
0.9643	High Similarity	NPC237635
0.9643	High Similarity	NPC24673
0.964	High Similarity	NPC278175
0.964	High Similarity	NPC257236
0.964	High Similarity	NPC469953
0.964	High Similarity	NPC209040
0.9638	High Similarity	NPC200694
0.9632	High Similarity	NPC470669
0.9632	High Similarity	NPC470668
0.963	High Similarity	NPC13408
0.9574	High Similarity	NPC6511
0.9574	High Similarity	NPC160821
0.9574	High Similarity	NPC132592
0.9574	High Similarity	NPC266572
0.9571	High Similarity	NPC312973
0.9571	High Similarity	NPC267375
0.9571	High Similarity	NPC88964
0.9571	High Similarity	NPC214774
0.9571	High Similarity	NPC475052
0.9571	High Similarity	NPC83357
0.9571	High Similarity	NPC111786
0.9571	High Similarity	NPC470647
0.9571	High Similarity	NPC195621
0.9571	High Similarity	NPC54577
0.9571	High Similarity	NPC477955
0.9571	High Similarity	NPC124729
0.9571	High Similarity	NPC246948
0.9571	High Similarity	NPC142405
0.9571	High Similarity	NPC301276
0.9571	High Similarity	NPC67805
0.9571	High Similarity	NPC176229
0.9571	High Similarity	NPC20488
0.9568	High Similarity	NPC143896
0.9568	High Similarity	NPC9117
0.9568	High Similarity	NPC221432
0.9568	High Similarity	NPC214166
0.9568	High Similarity	NPC478086
0.9568	High Similarity	NPC316816
0.9568	High Similarity	NPC164980
0.9568	High Similarity	NPC190637
0.9568	High Similarity	NPC75049
0.9568	High Similarity	NPC39329
0.9568	High Similarity	NPC149026
0.9568	High Similarity	NPC310130
0.9568	High Similarity	NPC169591
0.9568	High Similarity	NPC293053
0.9568	High Similarity	NPC68104
0.9568	High Similarity	NPC212932
0.9568	High Similarity	NPC175504
0.9568	High Similarity	NPC91560
0.9568	High Similarity	NPC24821
0.9568	High Similarity	NPC257097
0.9568	High Similarity	NPC150408
0.9568	High Similarity	NPC11700
0.9565	High Similarity	NPC3188
0.9565	High Similarity	NPC14871
0.9562	High Similarity	NPC23257
0.9559	High Similarity	NPC250266
0.9559	High Similarity	NPC317119
0.9559	High Similarity	NPC266597
0.9559	High Similarity	NPC228661
0.9556	High Similarity	NPC151113
0.9507	High Similarity	NPC37208
0.9507	High Similarity	NPC10027
0.9507	High Similarity	NPC65775
0.9507	High Similarity	NPC221868
0.9504	High Similarity	NPC283234
0.9504	High Similarity	NPC14001
0.9504	High Similarity	NPC180477
0.9504	High Similarity	NPC473077
0.9504	High Similarity	NPC296998
0.9504	High Similarity	NPC166757
0.95	High Similarity	NPC473013
0.95	High Similarity	NPC216538
0.95	High Similarity	NPC131579
0.95	High Similarity	NPC273538
0.95	High Similarity	NPC319752
0.95	High Similarity	NPC197252
0.95	High Similarity	NPC326500
0.95	High Similarity	NPC473015
0.95	High Similarity	NPC236766
0.95	High Similarity	NPC131568
0.9496	High Similarity	NPC36181
0.9496	High Similarity	NPC78
0.9496	High Similarity	NPC147145
0.9496	High Similarity	NPC166482
0.9496	High Similarity	NPC194432
0.9496	High Similarity	NPC324436
0.9496	High Similarity	NPC328164
0.9496	High Similarity	NPC265040
0.9496	High Similarity	NPC177354
0.9496	High Similarity	NPC227579
0.9496	High Similarity	NPC10937
0.9496	High Similarity	NPC228504
0.9496	High Similarity	NPC296917
0.9496	High Similarity	NPC66515
0.9496	High Similarity	NPC148757
0.9496	High Similarity	NPC324134
0.9496	High Similarity	NPC40833
0.9496	High Similarity	NPC1089
0.9496	High Similarity	NPC125855
0.9496	High Similarity	NPC182852
0.9496	High Similarity	NPC107572
0.9496	High Similarity	NPC223500
0.9496	High Similarity	NPC306829
0.9496	High Similarity	NPC76372
0.9496	High Similarity	NPC161506
0.9496	High Similarity	NPC32739
0.9496	High Similarity	NPC37496
0.9496	High Similarity	NPC166934
0.9496	High Similarity	NPC473042
0.9496	High Similarity	NPC167624
0.9496	High Similarity	NPC64915
0.9496	High Similarity	NPC76338
0.9496	High Similarity	NPC220998
0.9493	High Similarity	NPC172250
0.9493	High Similarity	NPC471587
0.9493	High Similarity	NPC215311
0.9493	High Similarity	NPC213659
0.9493	High Similarity	NPC80962
0.9493	High Similarity	NPC48624
0.9493	High Similarity	NPC204985
0.9493	High Similarity	NPC259166
0.9493	High Similarity	NPC144118
0.9493	High Similarity	NPC326109
0.9493	High Similarity	NPC219917
0.9489	High Similarity	NPC21350
0.9489	High Similarity	NPC131130
0.9489	High Similarity	NPC124269
0.9489	High Similarity	NPC248995
0.9489	High Similarity	NPC254168
0.9489	High Similarity	NPC272844
0.9485	High Similarity	NPC477244
0.9485	High Similarity	NPC274109
0.9485	High Similarity	NPC127447
0.9485	High Similarity	NPC194281
0.9485	High Similarity	NPC150399
0.9485	High Similarity	NPC98115
0.9485	High Similarity	NPC477243
0.9485	High Similarity	NPC234133
0.9485	High Similarity	NPC29353
0.9485	High Similarity	NPC124784
0.9485	High Similarity	NPC249606
0.9485	High Similarity	NPC174999
0.9485	High Similarity	NPC66349
0.9485	High Similarity	NPC1486
0.9485	High Similarity	NPC473887
0.9485	High Similarity	NPC12165
0.9485	High Similarity	NPC186838

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 NPC205006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	966
0.2-0.3	1481
0.3-0.4	2604
0.4-0.5	1906
0.5-0.6	1190
0.6-0.7	446
0.7-0.8	144
0.8-0.85	40
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.964	High Similarity	NPD7410	Clinical (unspecified phase)
0.95	High Similarity	NPD4378	Clinical (unspecified phase)
0.9209	High Similarity	NPD1549	Phase 2
0.9137	High Similarity	NPD1552	Clinical (unspecified phase)
0.9137	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1510	Phase 2
0.9118	High Similarity	NPD1240	Approved
0.9065	High Similarity	NPD2796	Approved
0.8986	High Similarity	NPD1607	Approved
0.898	High Similarity	NPD7411	Suspended
0.8912	High Similarity	NPD4380	Phase 2
0.8859	High Similarity	NPD2393	Clinical (unspecified phase)
0.8808	High Similarity	NPD7075	Discontinued
0.88	High Similarity	NPD8443	Clinical (unspecified phase)
0.8792	High Similarity	NPD6801	Discontinued
0.8759	High Similarity	NPD1511	Approved
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8733	High Similarity	NPD7819	Suspended
0.8681	High Similarity	NPD3750	Approved
0.8639	High Similarity	NPD1512	Approved
0.863	High Similarity	NPD6799	Approved
0.8611	High Similarity	NPD7421	Clinical (unspecified phase)
0.8609	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD1934	Approved
0.8497	Intermediate Similarity	NPD7768	Phase 2
0.8483	Intermediate Similarity	NPD2800	Approved
0.8483	Intermediate Similarity	NPD1243	Approved
0.8471	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD3749	Approved
0.8411	Intermediate Similarity	NPD6599	Discontinued
0.8377	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD3748	Approved
0.8333	Intermediate Similarity	NPD2799	Discontinued
0.8322	Intermediate Similarity	NPD6651	Approved
0.8313	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD2313	Discontinued
0.8298	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6959	Discontinued
0.8276	Intermediate Similarity	NPD2935	Discontinued
0.8276	Intermediate Similarity	NPD1551	Phase 2
0.8219	Intermediate Similarity	NPD2344	Approved
0.8212	Intermediate Similarity	NPD5403	Approved
0.8212	Intermediate Similarity	NPD920	Approved
0.8201	Intermediate Similarity	NPD1203	Approved
0.8194	Intermediate Similarity	NPD3817	Phase 2
0.8188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD6166	Phase 2
0.8125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5494	Approved
0.8098	Intermediate Similarity	NPD5953	Discontinued
0.8086	Intermediate Similarity	NPD7286	Phase 2
0.8082	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD5401	Approved
0.8054	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD3268	Approved
0.8027	Intermediate Similarity	NPD6099	Approved
0.8027	Intermediate Similarity	NPD6100	Approved
0.8014	Intermediate Similarity	NPD2798	Approved
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD2309	Approved
0.7987	Intermediate Similarity	NPD3226	Approved
0.7986	Intermediate Similarity	NPD9717	Approved
0.7975	Intermediate Similarity	NPD7054	Approved
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7961	Intermediate Similarity	NPD2533	Approved
0.7961	Intermediate Similarity	NPD2532	Approved
0.7961	Intermediate Similarity	NPD2534	Approved
0.7959	Intermediate Similarity	NPD7033	Discontinued
0.7959	Intermediate Similarity	NPD4308	Phase 3
0.7943	Intermediate Similarity	NPD2797	Approved
0.7939	Intermediate Similarity	NPD6559	Discontinued
0.7933	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD943	Approved
0.7927	Intermediate Similarity	NPD7074	Phase 3
0.7927	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD422	Phase 1
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6832	Phase 2
0.7883	Intermediate Similarity	NPD1548	Phase 1
0.7879	Intermediate Similarity	NPD6797	Phase 2
0.7852	Intermediate Similarity	NPD2346	Discontinued
0.7848	Intermediate Similarity	NPD5402	Approved
0.7831	Intermediate Similarity	NPD7251	Discontinued
0.7815	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD919	Approved
0.7784	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD4908	Phase 1
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD5124	Phase 1
0.7755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3225	Approved
0.7724	Intermediate Similarity	NPD4625	Phase 3
0.7716	Intermediate Similarity	NPD1247	Approved
0.7692	Intermediate Similarity	NPD3267	Approved
0.7692	Intermediate Similarity	NPD3266	Approved
0.7687	Intermediate Similarity	NPD4307	Phase 2
0.7679	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1610	Phase 2
0.7657	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4363	Phase 3
0.7644	Intermediate Similarity	NPD4360	Phase 2
0.7632	Intermediate Similarity	NPD2654	Approved
0.7625	Intermediate Similarity	NPD4288	Approved
0.7622	Intermediate Similarity	NPD3926	Phase 2
0.7606	Intermediate Similarity	NPD3972	Approved
0.7605	Intermediate Similarity	NPD1729	Discontinued
0.76	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4361	Phase 2
0.7595	Intermediate Similarity	NPD6585	Discontinued
0.7562	Intermediate Similarity	NPD1465	Phase 2
0.7551	Intermediate Similarity	NPD1296	Phase 2
0.7551	Intermediate Similarity	NPD3764	Approved
0.7547	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9545	Approved
0.7483	Intermediate Similarity	NPD1608	Approved
0.7482	Intermediate Similarity	NPD9493	Approved
0.7456	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5049	Phase 3
0.7448	Intermediate Similarity	NPD1470	Approved
0.7448	Intermediate Similarity	NPD1164	Approved
0.7438	Intermediate Similarity	NPD5890	Approved
0.7438	Intermediate Similarity	NPD5889	Approved
0.7434	Intermediate Similarity	NPD5406	Approved
0.7434	Intermediate Similarity	NPD5405	Approved
0.7434	Intermediate Similarity	NPD5408	Approved
0.7434	Intermediate Similarity	NPD5404	Approved
0.7432	Intermediate Similarity	NPD411	Approved
0.7431	Intermediate Similarity	NPD4749	Approved
0.7421	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD2354	Approved
0.7415	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4287	Approved
0.7413	Intermediate Similarity	NPD1201	Approved
0.7407	Intermediate Similarity	NPD2296	Approved
0.74	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD447	Suspended
0.7391	Intermediate Similarity	NPD1241	Discontinued
0.7386	Intermediate Similarity	NPD1471	Phase 3
0.7381	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7584	Approved
0.7355	Intermediate Similarity	NPD7003	Approved
0.7349	Intermediate Similarity	NPD5711	Approved
0.7349	Intermediate Similarity	NPD5710	Approved
0.7347	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6798	Discontinued
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6104	Discontinued
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD1019	Discontinued
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD17	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2353	Approved
0.7273	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD1481	Phase 2
0.7219	Intermediate Similarity	NPD1613	Approved
0.7219	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3887	Approved
0.7181	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6844	Discontinued
0.7178	Intermediate Similarity	NPD7577	Discontinued
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1535	Discovery
0.717	Intermediate Similarity	NPD4662	Approved
0.717	Intermediate Similarity	NPD4661	Approved
0.716	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD1876	Approved
0.7134	Intermediate Similarity	NPD5761	Phase 2
0.7134	Intermediate Similarity	NPD5760	Phase 2
0.7126	Intermediate Similarity	NPD8312	Approved
0.7126	Intermediate Similarity	NPD8313	Approved
0.7115	Intermediate Similarity	NPD2424	Discontinued
0.7108	Intermediate Similarity	NPD6971	Discontinued
0.7107	Intermediate Similarity	NPD7213	Phase 3
0.7107	Intermediate Similarity	NPD7212	Phase 2
0.7105	Intermediate Similarity	NPD3140	Approved
0.7105	Intermediate Similarity	NPD3142	Approved
0.7102	Intermediate Similarity	NPD8434	Phase 2
0.7097	Intermediate Similarity	NPD4476	Approved
0.7097	Intermediate Similarity	NPD4477	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