NPASS Compound

Structure

NPC61258 OpenBabel07101718202D 26 28 0 0 1 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 -0.8660 -3.5000 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 1.0000 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 -6.0622 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 -4.3301 -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 -5.1962 0.0000 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 -6.9282 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 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -1.7321 -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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 25 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 1 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.15
Volume:	368.962
LogP:	3.529
LogD:	3.333
LogS:	-3.825
# Rotatable Bonds:	5
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	3.204
Fsp3:	0.286
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:	-4.76
MDCK Permeability:	1.7590546121937223e-05
Pgp-inhibitor:	0.464
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	98.52814483642578%
Volume Distribution (VD):	0.548
Pgp-substrate:	0.918351411819458%

ADMET: Metabolism

CYP1A2-inhibitor:	0.752
CYP1A2-substrate:	0.719
CYP2C19-inhibitor:	0.548
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.723
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.924
CYP2D6-substrate:	0.809
CYP3A4-inhibitor:	0.611
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	9.281
Half-life (T1/2):	0.507

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.637
Drug-inuced Liver Injury (DILI):	0.158
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.403
Maximum Recommended Daily Dose:	0.877
Skin Sensitization:	0.132
Carcinogencity:	0.824
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.799

Download Data

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

Natural Product: NPC61258

Natural Product ID:	NPC61258
*Common Name:**	Lespeflorin C7
IUPAC Name:	(2S)-2-hydroxy-3-(4-hydroxyphenyl)-1-(7-methoxy-2,2-dimethylchromen-6-yl)propan-1-one
Synonyms:	Lespeflorin C7
Standard InCHIKey:	CSJQGXKXWYTHHQ-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C21H22O5/c1-21(2)9-8-14-11-16(19(25-3)12-18(14)26-21)20(24)17(23)10-13-4-6-15(22)7-5-13/h4-9,11-12,17,22-23H,10H2,1-3H3/t17-/m0/s1
SMILES:	CC1(C)C=Cc2cc(c(cc2O1)OC)C(=O)[C@H](Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560626
PubChem CID:	25243326
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[19132934]
NPO13293	Lespedeza floribunda	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	3780.0	nM	PMID[546260]

☑ 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 NPC61258 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	376
0.1-0.2	1450
0.2-0.3	3635
0.3-0.4	8843
0.4-0.5	9639
0.5-0.6	3639
0.6-0.7	5469
0.7-0.8	5130
0.8-0.85	2531
0.85-0.9	1353
0.9-0.95	546
0.95-1	86

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC124729
0.9655	High Similarity	NPC470461
0.9655	High Similarity	NPC5173
0.965	High Similarity	NPC216538
0.965	High Similarity	NPC224714
0.965	High Similarity	NPC273538
0.9595	High Similarity	NPC259710
0.9595	High Similarity	NPC207809
0.9595	High Similarity	NPC217706
0.9595	High Similarity	NPC304207
0.9595	High Similarity	NPC48579
0.9592	High Similarity	NPC243171
0.9592	High Similarity	NPC171651
0.9592	High Similarity	NPC35567
0.9586	High Similarity	NPC296869
0.9586	High Similarity	NPC168085
0.9586	High Similarity	NPC244407
0.9586	High Similarity	NPC6511
0.9586	High Similarity	NPC470460
0.9583	High Similarity	NPC470458
0.9583	High Similarity	NPC472629
0.9583	High Similarity	NPC306488
0.9583	High Similarity	NPC5820
0.9583	High Similarity	NPC178343
0.958	High Similarity	NPC245482
0.958	High Similarity	NPC190637
0.958	High Similarity	NPC476178
0.958	High Similarity	NPC301751
0.958	High Similarity	NPC51887
0.958	High Similarity	NPC212932
0.958	High Similarity	NPC293053
0.958	High Similarity	NPC9117
0.958	High Similarity	NPC117836
0.958	High Similarity	NPC475705
0.958	High Similarity	NPC24821
0.9527	High Similarity	NPC311579
0.9527	High Similarity	NPC248793
0.9527	High Similarity	NPC223701
0.9527	High Similarity	NPC472583
0.9527	High Similarity	NPC293286
0.9527	High Similarity	NPC180301
0.9527	High Similarity	NPC7989
0.9527	High Similarity	NPC236756
0.9527	High Similarity	NPC193200
0.9524	High Similarity	NPC263384
0.9524	High Similarity	NPC319910
0.9524	High Similarity	NPC262039
0.9524	High Similarity	NPC471676
0.9524	High Similarity	NPC278476
0.9524	High Similarity	NPC472422
0.9524	High Similarity	NPC472420
0.9524	High Similarity	NPC254412
0.9524	High Similarity	NPC262038
0.9524	High Similarity	NPC244577
0.9521	High Similarity	NPC317492
0.9517	High Similarity	NPC97716
0.9517	High Similarity	NPC79469
0.9517	High Similarity	NPC14001
0.9517	High Similarity	NPC166757
0.9517	High Similarity	NPC237635
0.9517	High Similarity	NPC201731
0.9517	High Similarity	NPC222298
0.9517	High Similarity	NPC51070
0.9517	High Similarity	NPC23728
0.9517	High Similarity	NPC110303
0.9517	High Similarity	NPC296998
0.9517	High Similarity	NPC104406
0.9517	High Similarity	NPC473077
0.9517	High Similarity	NPC24673
0.9514	High Similarity	NPC209040
0.9514	High Similarity	NPC326500
0.9514	High Similarity	NPC470890
0.9514	High Similarity	NPC124780
0.9514	High Similarity	NPC311741
0.9514	High Similarity	NPC87486
0.9514	High Similarity	NPC234629
0.951	High Similarity	NPC473042
0.951	High Similarity	NPC200694
0.951	High Similarity	NPC11561
0.951	High Similarity	NPC162476
0.951	High Similarity	NPC148545
0.951	High Similarity	NPC226636
0.9467	High Similarity	NPC282390
0.9467	High Similarity	NPC281137
0.9463	High Similarity	NPC111341
0.9463	High Similarity	NPC470681
0.9463	High Similarity	NPC304745
0.9459	High Similarity	NPC216035
0.9459	High Similarity	NPC217149
0.9459	High Similarity	NPC476238
0.9459	High Similarity	NPC327269
0.9459	High Similarity	NPC138288
0.9459	High Similarity	NPC285623
0.9459	High Similarity	NPC31627
0.9456	High Similarity	NPC105136
0.9456	High Similarity	NPC472633
0.9456	High Similarity	NPC37348
0.9452	High Similarity	NPC132592
0.9452	High Similarity	NPC160821
0.9452	High Similarity	NPC266572
0.9448	High Similarity	NPC470647
0.9448	High Similarity	NPC312973
0.9448	High Similarity	NPC142405
0.9448	High Similarity	NPC220418
0.9448	High Similarity	NPC20488
0.9448	High Similarity	NPC267375
0.9448	High Similarity	NPC176229
0.9448	High Similarity	NPC214774
0.9448	High Similarity	NPC301276
0.9448	High Similarity	NPC67805
0.9448	High Similarity	NPC88964
0.9448	High Similarity	NPC111786
0.9448	High Similarity	NPC246948
0.9448	High Similarity	NPC54577
0.9448	High Similarity	NPC195621
0.9448	High Similarity	NPC475052
0.9448	High Similarity	NPC83357
0.9444	High Similarity	NPC310130
0.9444	High Similarity	NPC143896
0.9444	High Similarity	NPC18585
0.9444	High Similarity	NPC91560
0.9444	High Similarity	NPC175504
0.9444	High Similarity	NPC316816
0.9444	High Similarity	NPC75049
0.9444	High Similarity	NPC39329
0.9444	High Similarity	NPC149026
0.9444	High Similarity	NPC68104
0.9444	High Similarity	NPC169591
0.9444	High Similarity	NPC257097
0.9444	High Similarity	NPC166138
0.9444	High Similarity	NPC150408
0.9444	High Similarity	NPC164980
0.9444	High Similarity	NPC106985
0.9444	High Similarity	NPC214166
0.9444	High Similarity	NPC158874
0.9444	High Similarity	NPC221432
0.9444	High Similarity	NPC478086
0.9441	High Similarity	NPC110969
0.9441	High Similarity	NPC103362
0.9441	High Similarity	NPC64908
0.9441	High Similarity	NPC469404
0.9441	High Similarity	NPC470087
0.9441	High Similarity	NPC321980
0.9441	High Similarity	NPC156590
0.9441	High Similarity	NPC118840
0.9441	High Similarity	NPC205006
0.9441	High Similarity	NPC147688
0.94	High Similarity	NPC215917
0.94	High Similarity	NPC20530
0.94	High Similarity	NPC10754
0.9396	High Similarity	NPC469405
0.9396	High Similarity	NPC268193
0.9392	High Similarity	NPC472423
0.9392	High Similarity	NPC471677
0.9392	High Similarity	NPC474772
0.9392	High Similarity	NPC474744
0.9392	High Similarity	NPC471675
0.9384	High Similarity	NPC283234
0.9384	High Similarity	NPC472627
0.9379	High Similarity	NPC197252
0.9379	High Similarity	NPC473013
0.9379	High Similarity	NPC131579
0.9379	High Similarity	NPC236766
0.9379	High Similarity	NPC131568
0.9379	High Similarity	NPC319752
0.9379	High Similarity	NPC473015
0.9375	High Similarity	NPC166934
0.9375	High Similarity	NPC220998
0.9375	High Similarity	NPC306829
0.9375	High Similarity	NPC37496
0.9375	High Similarity	NPC167624
0.9375	High Similarity	NPC107572
0.9375	High Similarity	NPC227579
0.9375	High Similarity	NPC10937
0.9375	High Similarity	NPC40833
0.9375	High Similarity	NPC223500
0.9375	High Similarity	NPC76338
0.9375	High Similarity	NPC1089
0.9375	High Similarity	NPC265040
0.9375	High Similarity	NPC144499
0.9375	High Similarity	NPC78
0.9375	High Similarity	NPC166482
0.9375	High Similarity	NPC76372
0.9375	High Similarity	NPC324436
0.9375	High Similarity	NPC161506
0.9375	High Similarity	NPC177354
0.9375	High Similarity	NPC32739
0.9375	High Similarity	NPC66515
0.9375	High Similarity	NPC328164
0.9375	High Similarity	NPC147145
0.9375	High Similarity	NPC324134
0.9375	High Similarity	NPC194432
0.9375	High Similarity	NPC148757
0.9375	High Similarity	NPC125855
0.9375	High Similarity	NPC64915
0.9375	High Similarity	NPC296917
0.9375	High Similarity	NPC228504
0.9375	High Similarity	NPC182852
0.9371	High Similarity	NPC261227
0.9371	High Similarity	NPC48624

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 NPC61258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	908
0.2-0.3	1584
0.3-0.4	2547
0.4-0.5	1928
0.5-0.6	1158
0.6-0.7	452
0.7-0.8	178
0.8-0.85	33
0.85-0.9	19
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.965	High Similarity	NPD4378	Clinical (unspecified phase)
0.9195	High Similarity	NPD4380	Phase 2
0.9116	High Similarity	NPD7410	Clinical (unspecified phase)
0.9097	High Similarity	NPD1549	Phase 2
0.9091	High Similarity	NPD2796	Approved
0.9085	High Similarity	NPD7075	Discontinued
0.9073	High Similarity	NPD6801	Discontinued
0.9028	High Similarity	NPD1552	Clinical (unspecified phase)
0.9028	High Similarity	NPD1550	Clinical (unspecified phase)
0.9021	High Similarity	NPD1510	Phase 2
0.9013	High Similarity	NPD2393	Clinical (unspecified phase)
0.9013	High Similarity	NPD7096	Clinical (unspecified phase)
0.8839	High Similarity	NPD4381	Clinical (unspecified phase)
0.8831	High Similarity	NPD8443	Clinical (unspecified phase)
0.8812	High Similarity	NPD7804	Clinical (unspecified phase)
0.8758	High Similarity	NPD7411	Suspended
0.8741	High Similarity	NPD1240	Approved
0.8701	High Similarity	NPD1934	Approved
0.8675	High Similarity	NPD1512	Approved
0.8667	High Similarity	NPD6799	Approved
0.8645	High Similarity	NPD7819	Suspended
0.8625	High Similarity	NPD6168	Clinical (unspecified phase)
0.8625	High Similarity	NPD6167	Clinical (unspecified phase)
0.8625	High Similarity	NPD6166	Phase 2
0.8621	High Similarity	NPD1607	Approved
0.8543	High Similarity	NPD1511	Approved
0.8535	High Similarity	NPD3882	Suspended
0.8526	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD5403	Approved
0.8471	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD6599	Discontinued
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8418	Intermediate Similarity	NPD7768	Phase 2
0.8405	Intermediate Similarity	NPD3818	Discontinued
0.84	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD5401	Approved
0.8364	Intermediate Similarity	NPD6797	Phase 2
0.8354	Intermediate Similarity	NPD5402	Approved
0.8344	Intermediate Similarity	NPD3750	Approved
0.8313	Intermediate Similarity	NPD7251	Discontinued
0.8278	Intermediate Similarity	NPD2800	Approved
0.8263	Intermediate Similarity	NPD7808	Phase 3
0.8261	Intermediate Similarity	NPD5494	Approved
0.8258	Intermediate Similarity	NPD920	Approved
0.8242	Intermediate Similarity	NPD7054	Approved
0.8204	Intermediate Similarity	NPD6559	Discontinued
0.82	Intermediate Similarity	NPD2935	Discontinued
0.82	Intermediate Similarity	NPD1551	Phase 2
0.8193	Intermediate Similarity	NPD7472	Approved
0.8193	Intermediate Similarity	NPD7074	Phase 3
0.8158	Intermediate Similarity	NPD1243	Approved
0.8155	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD3749	Approved
0.8129	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2313	Discontinued
0.8092	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5953	Discontinued
0.8024	Intermediate Similarity	NPD7286	Phase 2
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD7033	Discontinued
0.8013	Intermediate Similarity	NPD2799	Discontinued
0.8013	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD6651	Approved
0.7988	Intermediate Similarity	NPD1247	Approved
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7975	Intermediate Similarity	NPD919	Approved
0.7939	Intermediate Similarity	NPD6232	Discontinued
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD2344	Approved
0.7904	Intermediate Similarity	NPD7473	Discontinued
0.7898	Intermediate Similarity	NPD4360	Phase 2
0.7898	Intermediate Similarity	NPD4363	Phase 3
0.7852	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD5124	Phase 1
0.7812	Intermediate Similarity	NPD3226	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1203	Approved
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7718	Intermediate Similarity	NPD4908	Phase 1
0.7718	Intermediate Similarity	NPD6832	Phase 2
0.7707	Intermediate Similarity	NPD2309	Approved
0.7703	Intermediate Similarity	NPD2798	Approved
0.7692	Intermediate Similarity	NPD1548	Phase 1
0.7679	Intermediate Similarity	NPD3926	Phase 2
0.7677	Intermediate Similarity	NPD2346	Discontinued
0.7662	Intermediate Similarity	NPD4308	Phase 3
0.7654	Intermediate Similarity	NPD4361	Phase 2
0.7654	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD943	Approved
0.7622	Intermediate Similarity	NPD7584	Approved
0.7616	Intermediate Similarity	NPD3268	Approved
0.761	Intermediate Similarity	NPD7390	Discontinued
0.7607	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1610	Phase 2
0.7557	Intermediate Similarity	NPD8434	Phase 2
0.7551	Intermediate Similarity	NPD9717	Approved
0.7517	Intermediate Similarity	NPD2797	Approved
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7486	Intermediate Similarity	NPD6777	Approved
0.7486	Intermediate Similarity	NPD6779	Approved
0.7486	Intermediate Similarity	NPD6778	Approved
0.7486	Intermediate Similarity	NPD6782	Approved
0.7486	Intermediate Similarity	NPD6780	Approved
0.7486	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD6776	Approved
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD1729	Discontinued
0.7455	Intermediate Similarity	NPD6844	Discontinued
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7427	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.741	Intermediate Similarity	NPD1465	Phase 2
0.741	Intermediate Similarity	NPD5760	Phase 2
0.741	Intermediate Similarity	NPD5761	Phase 2
0.7405	Intermediate Similarity	NPD2424	Discontinued
0.7403	Intermediate Similarity	NPD4307	Phase 2
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7378	Intermediate Similarity	NPD7458	Discontinued
0.7375	Intermediate Similarity	NPD3887	Approved
0.7375	Intermediate Similarity	NPD6190	Approved
0.7366	Intermediate Similarity	NPD7698	Approved
0.7366	Intermediate Similarity	NPD7697	Approved
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7366	Intermediate Similarity	NPD7696	Phase 3
0.7365	Intermediate Similarity	NPD4288	Approved
0.7362	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8150	Discontinued
0.7358	Intermediate Similarity	NPD2654	Approved
0.7355	Intermediate Similarity	NPD230	Phase 1
0.7355	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD1471	Phase 3
0.7342	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7333	Intermediate Similarity	NPD3225	Approved
0.7329	Intermediate Similarity	NPD9545	Approved
0.7326	Intermediate Similarity	NPD2403	Approved
0.7326	Intermediate Similarity	NPD7871	Phase 2
0.7326	Intermediate Similarity	NPD7870	Phase 2
0.7325	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3027	Phase 3
0.7315	Intermediate Similarity	NPD3972	Approved
0.7314	Intermediate Similarity	NPD3823	Discontinued
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7301	Intermediate Similarity	NPD5049	Phase 3
0.7297	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5890	Approved
0.7289	Intermediate Similarity	NPD5889	Approved
0.7285	Intermediate Similarity	NPD3266	Approved
0.7285	Intermediate Similarity	NPD3267	Approved
0.7273	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3764	Approved
0.7267	Intermediate Similarity	NPD2354	Approved
0.7255	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1652	Phase 2
0.7244	Intermediate Similarity	NPD1933	Approved
0.7244	Intermediate Similarity	NPD447	Suspended
0.7241	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4661	Approved
0.7239	Intermediate Similarity	NPD4662	Approved
0.7237	Intermediate Similarity	NPD1019	Discontinued
0.7233	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6004	Phase 3
0.7233	Intermediate Similarity	NPD6005	Phase 3
0.7233	Intermediate Similarity	NPD6002	Phase 3
0.7229	Intermediate Similarity	NPD6585	Discontinued
0.7222	Intermediate Similarity	NPD1241	Discontinued
0.7213	Intermediate Similarity	NPD6535	Approved
0.7213	Intermediate Similarity	NPD6534	Approved
0.7211	Intermediate Similarity	NPD7701	Phase 2
0.7211	Intermediate Similarity	NPD7585	Approved
0.7207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD8455	Phase 2
0.72	Intermediate Similarity	NPD1608	Approved
0.7195	Intermediate Similarity	NPD6273	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