NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	438.2
Volume:	461.596
LogP:	6.224
LogD:	4.046
LogS:	-3.094
# Rotatable Bonds:	6
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	3.609
Fsp3:	0.346
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	1.619881186343264e-05
Pgp-inhibitor:	0.419
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.244
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	101.18733215332031%
Volume Distribution (VD):	0.782
Pgp-substrate:	0.946164608001709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.768
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.83
CYP3A4-inhibitor:	0.541
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	9.869
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.249
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.607
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.845
Carcinogencity:	0.631
Eye Corrosion:	0.003
Eye Irritation:	0.655
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC477955

Natural Product ID:	NPC477955
*Common Name:**	Cyclokuraridin
IUPAC Name:	(E)-3-(2,4-dihydroxyphenyl)-1-[5-hydroxy-7-methoxy-2,2-dimethyl-3-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]prop-2-en-1-one
Synonyms:	cyclokuraridin
Standard InCHIKey:	JJMWPCIGAITBBF-DHZHZOJOSA-N
Standard InCHI:	InChI=1S/C26H30O6/c1-15(2)6-9-17-12-19-22(32-26(17,3)4)14-23(31-5)24(25(19)30)20(28)11-8-16-7-10-18(27)13-21(16)29/h6-8,10-11,13-14,17,27,29-30H,9,12H2,1-5H3/b11-8+
SMILES:	CC(=CCC1CC2=C(C(=C(C=C2OC1(C)C)OC)C(=O)/C=C/C3=C(C=C(C=C3)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16083181
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	15.1	ug/ml	PMID[16933887]

☑ 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 NPC477955 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	383
0.1-0.2	1519
0.2-0.3	3558
0.3-0.4	9244
0.4-0.5	9256
0.5-0.6	3510
0.6-0.7	5508
0.7-0.8	5386
0.8-0.85	2202
0.85-0.9	1339
0.9-0.95	693
0.95-1	99

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC106985
0.9856	High Similarity	NPC18585
0.9856	High Similarity	NPC166138
0.9786	High Similarity	NPC271288
0.9784	High Similarity	NPC144499
0.9718	High Similarity	NPC39195
0.965	High Similarity	NPC473016
0.9648	High Similarity	NPC308200
0.9645	High Similarity	NPC473013
0.9645	High Similarity	NPC209040
0.9645	High Similarity	NPC473015
0.9645	High Similarity	NPC131579
0.9645	High Similarity	NPC234629
0.9645	High Similarity	NPC131568
0.9645	High Similarity	NPC311741
0.9643	High Similarity	NPC226636
0.9643	High Similarity	NPC202981
0.9643	High Similarity	NPC11561
0.964	High Similarity	NPC69769
0.9583	High Similarity	NPC471115
0.9583	High Similarity	NPC29777
0.958	High Similarity	NPC145467
0.9577	High Similarity	NPC285630
0.9577	High Similarity	NPC127059
0.9577	High Similarity	NPC299011
0.9574	High Similarity	NPC68104
0.9574	High Similarity	NPC125894
0.9574	High Similarity	NPC107177
0.9574	High Similarity	NPC175504
0.9574	High Similarity	NPC38219
0.9574	High Similarity	NPC143896
0.9574	High Similarity	NPC257097
0.9574	High Similarity	NPC278249
0.9574	High Similarity	NPC85162
0.9574	High Similarity	NPC150408
0.9574	High Similarity	NPC221432
0.9574	High Similarity	NPC91560
0.9574	High Similarity	NPC223812
0.9574	High Similarity	NPC164980
0.9574	High Similarity	NPC316816
0.9574	High Similarity	NPC75049
0.9574	High Similarity	NPC39329
0.9574	High Similarity	NPC149026
0.9574	High Similarity	NPC214166
0.9574	High Similarity	NPC310130
0.9574	High Similarity	NPC478086
0.9574	High Similarity	NPC81697
0.9574	High Similarity	NPC169591
0.9574	High Similarity	NPC77794
0.9574	High Similarity	NPC219915
0.9571	High Similarity	NPC103362
0.9571	High Similarity	NPC156590
0.9571	High Similarity	NPC118840
0.9571	High Similarity	NPC110969
0.9571	High Similarity	NPC64908
0.9571	High Similarity	NPC282300
0.9571	High Similarity	NPC3188
0.9571	High Similarity	NPC147688
0.9571	High Similarity	NPC205006
0.9517	High Similarity	NPC305965
0.9514	High Similarity	NPC471114
0.951	High Similarity	NPC10990
0.951	High Similarity	NPC104406
0.951	High Similarity	NPC97716
0.951	High Similarity	NPC237635
0.951	High Similarity	NPC79469
0.951	High Similarity	NPC24673
0.951	High Similarity	NPC23728
0.951	High Similarity	NPC201731
0.951	High Similarity	NPC473077
0.951	High Similarity	NPC300988
0.951	High Similarity	NPC110303
0.951	High Similarity	NPC296998
0.9507	High Similarity	NPC197252
0.9507	High Similarity	NPC184649
0.9507	High Similarity	NPC473014
0.9507	High Similarity	NPC311144
0.9507	High Similarity	NPC303185
0.9507	High Similarity	NPC236766
0.9507	High Similarity	NPC235217
0.9504	High Similarity	NPC324134
0.9504	High Similarity	NPC10937
0.9504	High Similarity	NPC40833
0.9504	High Similarity	NPC125855
0.9504	High Similarity	NPC161506
0.9504	High Similarity	NPC296917
0.9504	High Similarity	NPC37496
0.9504	High Similarity	NPC166934
0.9504	High Similarity	NPC194432
0.9504	High Similarity	NPC306829
0.9504	High Similarity	NPC32739
0.9504	High Similarity	NPC76338
0.9504	High Similarity	NPC223500
0.9504	High Similarity	NPC228504
0.9504	High Similarity	NPC107572
0.9504	High Similarity	NPC78
0.9504	High Similarity	NPC166482
0.9504	High Similarity	NPC147145
0.9504	High Similarity	NPC265040
0.9504	High Similarity	NPC177354
0.9504	High Similarity	NPC64915
0.9504	High Similarity	NPC324436
0.9504	High Similarity	NPC1089
0.9504	High Similarity	NPC167624
0.9504	High Similarity	NPC220998
0.9504	High Similarity	NPC182852
0.9504	High Similarity	NPC66515
0.9504	High Similarity	NPC76372
0.9504	High Similarity	NPC227579
0.9504	High Similarity	NPC328164
0.9504	High Similarity	NPC148757
0.95	High Similarity	NPC129853
0.95	High Similarity	NPC475680
0.95	High Similarity	NPC284550
0.95	High Similarity	NPC270883
0.95	High Similarity	NPC172986
0.95	High Similarity	NPC477272
0.95	High Similarity	NPC159275
0.95	High Similarity	NPC235239
0.95	High Similarity	NPC241100
0.95	High Similarity	NPC305355
0.95	High Similarity	NPC261227
0.95	High Similarity	NPC76445
0.95	High Similarity	NPC150522
0.9496	High Similarity	NPC470672
0.9496	High Similarity	NPC21350
0.9496	High Similarity	NPC474504
0.9496	High Similarity	NPC470671
0.9496	High Similarity	NPC474487
0.9444	High Similarity	NPC160821
0.9444	High Similarity	NPC296869
0.9444	High Similarity	NPC266572
0.9444	High Similarity	NPC132592
0.9444	High Similarity	NPC6511
0.9441	High Similarity	NPC214774
0.9441	High Similarity	NPC142405
0.9441	High Similarity	NPC20488
0.9441	High Similarity	NPC124729
0.9441	High Similarity	NPC267375
0.9441	High Similarity	NPC176229
0.9441	High Similarity	NPC301276
0.9441	High Similarity	NPC196114
0.9441	High Similarity	NPC67805
0.9441	High Similarity	NPC470647
0.9441	High Similarity	NPC88964
0.9441	High Similarity	NPC111786
0.9441	High Similarity	NPC312973
0.9441	High Similarity	NPC246948
0.9441	High Similarity	NPC54577
0.9441	High Similarity	NPC195621
0.9441	High Similarity	NPC472629
0.9441	High Similarity	NPC475052
0.9441	High Similarity	NPC83357
0.9437	High Similarity	NPC113770
0.9437	High Similarity	NPC11700
0.9437	High Similarity	NPC185276
0.9433	High Similarity	NPC324386
0.9433	High Similarity	NPC96408
0.9433	High Similarity	NPC279650
0.9433	High Similarity	NPC248372
0.9433	High Similarity	NPC166689
0.9433	High Similarity	NPC213322
0.9433	High Similarity	NPC110038
0.9433	High Similarity	NPC17170
0.9433	High Similarity	NPC258630
0.9433	High Similarity	NPC312391
0.9433	High Similarity	NPC4743
0.9433	High Similarity	NPC156190
0.9429	High Similarity	NPC220062
0.9429	High Similarity	NPC53181
0.9429	High Similarity	NPC55018
0.9429	High Similarity	NPC216978
0.9429	High Similarity	NPC477956
0.9429	High Similarity	NPC301217
0.9429	High Similarity	NPC303633
0.9429	High Similarity	NPC217186
0.9429	High Similarity	NPC316480
0.9429	High Similarity	NPC18260
0.9429	High Similarity	NPC261234
0.9429	High Similarity	NPC96565
0.9429	High Similarity	NPC78913
0.9424	High Similarity	NPC153979
0.9424	High Similarity	NPC317119
0.9384	High Similarity	NPC472420
0.9384	High Similarity	NPC472422
0.9384	High Similarity	NPC471676
0.9384	High Similarity	NPC263384
0.9384	High Similarity	NPC472580
0.9384	High Similarity	NPC244577
0.9384	High Similarity	NPC178484
0.9379	High Similarity	NPC10027
0.9379	High Similarity	NPC65775
0.9379	High Similarity	NPC266499
0.9375	High Similarity	NPC472627
0.9375	High Similarity	NPC283234
0.9371	High Similarity	NPC470673
0.9371	High Similarity	NPC87486
0.9371	High Similarity	NPC216538
0.9371	High Similarity	NPC470674
0.9371	High Similarity	NPC326500

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 NPC477955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	938
0.2-0.3	1461
0.3-0.4	2507
0.4-0.5	1990
0.5-0.6	1180
0.6-0.7	497
0.7-0.8	150
0.8-0.85	48
0.85-0.9	21
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9371	High Similarity	NPD4378	Clinical (unspecified phase)
0.9236	High Similarity	NPD7410	Clinical (unspecified phase)
0.922	High Similarity	NPD1549	Phase 2
0.9195	High Similarity	NPD8443	Clinical (unspecified phase)
0.9149	High Similarity	NPD1552	Clinical (unspecified phase)
0.9149	High Similarity	NPD1550	Clinical (unspecified phase)
0.9007	High Similarity	NPD1510	Phase 2
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD7819	Suspended
0.8993	High Similarity	NPD7411	Suspended
0.8993	High Similarity	NPD1240	Approved
0.8947	High Similarity	NPD7075	Discontinued
0.8944	High Similarity	NPD2796	Approved
0.8926	High Similarity	NPD4380	Phase 2
0.8874	High Similarity	NPD7096	Clinical (unspecified phase)
0.8865	High Similarity	NPD1607	Approved
0.8726	High Similarity	NPD7852	Clinical (unspecified phase)
0.8684	High Similarity	NPD1934	Approved
0.8636	High Similarity	NPD7768	Phase 2
0.8581	High Similarity	NPD4381	Clinical (unspecified phase)
0.8581	High Similarity	NPD3749	Approved
0.8571	High Similarity	NPD3750	Approved
0.8562	High Similarity	NPD6801	Discontinued
0.8535	High Similarity	NPD6959	Discontinued
0.8523	High Similarity	NPD1511	Approved
0.8523	High Similarity	NPD6799	Approved
0.8506	High Similarity	NPD2801	Approved
0.8503	High Similarity	NPD7421	Clinical (unspecified phase)
0.8503	High Similarity	NPD2800	Approved
0.8483	Intermediate Similarity	NPD2799	Discontinued
0.8471	Intermediate Similarity	NPD5494	Approved
0.8435	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD6599	Discontinued
0.8411	Intermediate Similarity	NPD1512	Approved
0.8397	Intermediate Similarity	NPD3882	Suspended
0.8345	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD2935	Discontinued
0.8299	Intermediate Similarity	NPD1551	Phase 2
0.8299	Intermediate Similarity	NPD6099	Approved
0.8299	Intermediate Similarity	NPD6100	Approved
0.8261	Intermediate Similarity	NPD6166	Phase 2
0.8261	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1243	Approved
0.8243	Intermediate Similarity	NPD2344	Approved
0.8242	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD3748	Approved
0.821	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4908	Phase 1
0.8137	Intermediate Similarity	NPD6232	Discontinued
0.8121	Intermediate Similarity	NPD5953	Discontinued
0.8117	Intermediate Similarity	NPD920	Approved
0.8108	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2533	Approved
0.8105	Intermediate Similarity	NPD2532	Approved
0.8105	Intermediate Similarity	NPD2534	Approved
0.8101	Intermediate Similarity	NPD3817	Phase 2
0.8092	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6559	Discontinued
0.8071	Intermediate Similarity	NPD1610	Phase 2
0.8069	Intermediate Similarity	NPD2313	Discontinued
0.8061	Intermediate Similarity	NPD7074	Phase 3
0.805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.8042	Intermediate Similarity	NPD2798	Approved
0.8026	Intermediate Similarity	NPD2309	Approved
0.8013	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD5403	Approved
0.8	Intermediate Similarity	NPD2346	Discontinued
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7286	Phase 2
0.7987	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1203	Approved
0.7961	Intermediate Similarity	NPD4628	Phase 3
0.7961	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7472	Approved
0.7945	Intermediate Similarity	NPD3268	Approved
0.7943	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6797	Phase 2
0.7877	Intermediate Similarity	NPD4625	Phase 3
0.7874	Intermediate Similarity	NPD4360	Phase 2
0.7874	Intermediate Similarity	NPD4363	Phase 3
0.7871	Intermediate Similarity	NPD5401	Approved
0.7857	Intermediate Similarity	NPD7251	Discontinued
0.7847	Intermediate Similarity	NPD2797	Approved
0.7838	Intermediate Similarity	NPD943	Approved
0.7811	Intermediate Similarity	NPD7808	Phase 3
0.7808	Intermediate Similarity	NPD6832	Phase 2
0.7806	Intermediate Similarity	NPD7390	Discontinued
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7764	Intermediate Similarity	NPD5402	Approved
0.7762	Intermediate Similarity	NPD9717	Approved
0.7758	Intermediate Similarity	NPD3926	Phase 2
0.7748	Intermediate Similarity	NPD4308	Phase 3
0.7748	Intermediate Similarity	NPD7033	Discontinued
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD4361	Phase 2
0.7727	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4749	Approved
0.7706	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1465	Phase 2
0.7688	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD7458	Discontinued
0.766	Intermediate Similarity	NPD1548	Phase 1
0.7643	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3972	Approved
0.7639	Intermediate Similarity	NPD1608	Approved
0.7636	Intermediate Similarity	NPD1247	Approved
0.7613	Intermediate Similarity	NPD7003	Approved
0.7603	Intermediate Similarity	NPD3266	Approved
0.7603	Intermediate Similarity	NPD3267	Approved
0.759	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD5710	Approved
0.7588	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3764	Approved
0.7584	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD422	Phase 1
0.7557	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1933	Approved
0.7548	Intermediate Similarity	NPD2654	Approved
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD4288	Approved
0.7543	Intermediate Similarity	NPD4287	Approved
0.7532	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1729	Discontinued
0.7486	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7483	Intermediate Similarity	NPD4307	Phase 2
0.7483	Intermediate Similarity	NPD1470	Approved
0.7483	Intermediate Similarity	NPD1164	Approved
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.745	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1201	Approved
0.7439	Intermediate Similarity	NPD2296	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD17	Approved
0.7423	Intermediate Similarity	NPD7577	Discontinued
0.7419	Intermediate Similarity	NPD1471	Phase 3
0.7415	Intermediate Similarity	NPD3225	Approved
0.7415	Intermediate Similarity	NPD1876	Approved
0.7413	Intermediate Similarity	NPD9545	Approved
0.7412	Intermediate Similarity	NPD3751	Discontinued
0.7407	Intermediate Similarity	NPD6585	Discontinued
0.7405	Intermediate Similarity	NPD7584	Approved
0.7396	Intermediate Similarity	NPD2403	Approved
0.7394	Intermediate Similarity	NPD9493	Approved
0.7383	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2861	Phase 2
0.7378	Intermediate Similarity	NPD5761	Phase 2
0.7378	Intermediate Similarity	NPD5760	Phase 2
0.7368	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1613	Approved
0.7362	Intermediate Similarity	NPD5889	Approved
0.7362	Intermediate Similarity	NPD5890	Approved
0.7351	Intermediate Similarity	NPD411	Approved
0.7341	Intermediate Similarity	NPD6104	Discontinued
0.733	Intermediate Similarity	NPD8434	Phase 2
0.7321	Intermediate Similarity	NPD7199	Phase 2
0.732	Intermediate Similarity	NPD230	Phase 1
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD447	Suspended
0.731	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1241	Discontinued
0.729	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3787	Discontinued
0.7268	Intermediate Similarity	NPD6777	Approved
0.7268	Intermediate Similarity	NPD6781	Approved
0.7268	Intermediate Similarity	NPD6779	Approved
0.7268	Intermediate Similarity	NPD6776	Approved
0.7268	Intermediate Similarity	NPD6778	Approved
0.7268	Intermediate Similarity	NPD6780	Approved
0.7268	Intermediate Similarity	NPD6782	Approved
0.7267	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD5049	Phase 3
0.7261	Intermediate Similarity	NPD2424	Discontinued
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7251	Intermediate Similarity	NPD3446	Phase 1
0.725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4476	Approved
0.7244	Intermediate Similarity	NPD4477	Approved
0.7241	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7235	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2354	Approved
0.7232	Intermediate Similarity	NPD8150	Discontinued
0.7212	Intermediate Similarity	NPD6280	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