NPASS Compound

Structure

NPC171651 OpenBabel07101718292D 30 32 0 0 1 0 0 0 0 0999 V2000 -6.0622 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 4.3301 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -3.4641 -1.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 2 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 23 28 2 0 0 0 0 24 25 1 0 0 0 0 24 29 1 1 0 0 0 25 18 1 6 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.19
Volume:	435.51
LogP:	5.551
LogD:	3.887
LogS:	-3.057
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	3.765
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.827
MDCK Permeability:	1.5340438039856963e-05
Pgp-inhibitor:	0.904
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.506

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	94.20446014404297%
Volume Distribution (VD):	0.813
Pgp-substrate:	5.504602909088135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.778
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.87
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.909
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	11.258
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.705
Drug-inuced Liver Injury (DILI):	0.645
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.285
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.25
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.256
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC171651

Natural Product ID:	NPC171651
*Common Name:**	Lespeflorin B1
IUPAC Name:	(2R,3R)-3,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:	Lespeflorin B1
Standard InCHIKey:	YELBDRXMPXVGQT-LOSJGSFVSA-N
Standard InCHI:	InChI=1S/C25H28O5/c1-14(2)5-7-16-11-18(9-10-20(16)26)25-24(29)23(28)19-12-17(8-6-15(3)4)21(27)13-22(19)30-25/h5-6,9-13,24-27,29H,7-8H2,1-4H3/t24-,25+/m0/s1
SMILES:	CC(=CCc1cc(ccc1O)[C@@H]1[C@H](C(=O)c2cc(CC=C(C)C)c(cc2O1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561905
PubChem CID:	25243246
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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	=	2870.0	nM	PMID[566531]

☑ 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 NPC171651 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	385
0.1-0.2	1424
0.2-0.3	3612
0.3-0.4	8597
0.4-0.5	9763
0.5-0.6	3661
0.6-0.7	5114
0.7-0.8	5159
0.8-0.85	2749
0.85-0.9	1575
0.9-0.95	573
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC35567
1.0	High Similarity	NPC243171
0.9932	High Similarity	NPC293286
0.9931	High Similarity	NPC278476
0.9931	High Similarity	NPC262038
0.9931	High Similarity	NPC262039
0.9931	High Similarity	NPC254412
0.9931	High Similarity	NPC319910
0.9863	High Similarity	NPC138288
0.9863	High Similarity	NPC216035
0.9863	High Similarity	NPC217149
0.9862	High Similarity	NPC105136
0.9795	High Similarity	NPC471676
0.9795	High Similarity	NPC263384
0.9795	High Similarity	NPC472422
0.9795	High Similarity	NPC244577
0.9795	High Similarity	NPC472420
0.973	High Similarity	NPC304745
0.973	High Similarity	NPC207809
0.973	High Similarity	NPC217706
0.973	High Similarity	NPC304207
0.973	High Similarity	NPC111341
0.973	High Similarity	NPC259710
0.973	High Similarity	NPC48579
0.9664	High Similarity	NPC215917
0.9664	High Similarity	NPC20530
0.9664	High Similarity	NPC10754
0.9662	High Similarity	NPC223701
0.9662	High Similarity	NPC244250
0.9662	High Similarity	NPC472583
0.9662	High Similarity	NPC20907
0.9662	High Similarity	NPC7989
0.9662	High Similarity	NPC248793
0.9662	High Similarity	NPC180301
0.9662	High Similarity	NPC268193
0.966	High Similarity	NPC471677
0.9658	High Similarity	NPC89442
0.9655	High Similarity	NPC44721
0.9655	High Similarity	NPC122828
0.9655	High Similarity	NPC3779
0.9655	High Similarity	NPC176869
0.9655	High Similarity	NPC40086
0.9655	High Similarity	NPC211466
0.9655	High Similarity	NPC476182
0.9597	High Similarity	NPC477958
0.9595	High Similarity	NPC475790
0.9595	High Similarity	NPC244583
0.9595	High Similarity	NPC210597
0.9595	High Similarity	NPC56232
0.9595	High Similarity	NPC161881
0.9595	High Similarity	NPC473996
0.9595	High Similarity	NPC10807
0.9595	High Similarity	NPC150123
0.9592	High Similarity	NPC61258
0.9586	High Similarity	NPC472629
0.9586	High Similarity	NPC148011
0.9586	High Similarity	NPC1940
0.9536	High Similarity	NPC22192
0.9533	High Similarity	NPC78492
0.9533	High Similarity	NPC208152
0.953	High Similarity	NPC236756
0.953	High Similarity	NPC469405
0.953	High Similarity	NPC100134
0.953	High Similarity	NPC209760
0.953	High Similarity	NPC311579
0.9527	High Similarity	NPC289774
0.9527	High Similarity	NPC471229
0.9527	High Similarity	NPC472580
0.9527	High Similarity	NPC472636
0.9527	High Similarity	NPC328740
0.9527	High Similarity	NPC474744
0.9527	High Similarity	NPC474772
0.9527	High Similarity	NPC209846
0.9527	High Similarity	NPC477897
0.9527	High Similarity	NPC474021
0.9527	High Similarity	NPC474023
0.9527	High Similarity	NPC472423
0.9524	High Similarity	NPC472628
0.9521	High Similarity	NPC472627
0.9521	High Similarity	NPC472918
0.9517	High Similarity	NPC326506
0.9517	High Similarity	NPC279417
0.9517	High Similarity	NPC470890
0.9517	High Similarity	NPC124780
0.9517	High Similarity	NPC87486
0.9517	High Similarity	NPC49130
0.9517	High Similarity	NPC4152
0.9517	High Similarity	NPC142731
0.9517	High Similarity	NPC306607
0.9517	High Similarity	NPC62290
0.9517	High Similarity	NPC208176
0.9474	High Similarity	NPC306978
0.9474	High Similarity	NPC287328
0.9474	High Similarity	NPC282009
0.9467	High Similarity	NPC471116
0.9467	High Similarity	NPC470681
0.9467	High Similarity	NPC476169
0.9463	High Similarity	NPC477957
0.9463	High Similarity	NPC476238
0.9463	High Similarity	NPC327269
0.9463	High Similarity	NPC285623
0.9463	High Similarity	NPC31627
0.9459	High Similarity	NPC177308
0.9459	High Similarity	NPC267117
0.9459	High Similarity	NPC124478
0.9459	High Similarity	NPC472421
0.9456	High Similarity	NPC10097
0.9456	High Similarity	NPC218569
0.9452	High Similarity	NPC229190
0.9452	High Similarity	NPC316769
0.9448	High Similarity	NPC245482
0.9448	High Similarity	NPC143896
0.9448	High Similarity	NPC149026
0.9448	High Similarity	NPC75049
0.9448	High Similarity	NPC39329
0.9448	High Similarity	NPC310130
0.9448	High Similarity	NPC175504
0.9448	High Similarity	NPC169591
0.9448	High Similarity	NPC68104
0.9448	High Similarity	NPC91560
0.9448	High Similarity	NPC257097
0.9448	High Similarity	NPC150408
0.9448	High Similarity	NPC164980
0.9448	High Similarity	NPC221432
0.9448	High Similarity	NPC301751
0.9412	High Similarity	NPC471499
0.9408	High Similarity	NPC123544
0.94	High Similarity	NPC109594
0.94	High Similarity	NPC326592
0.94	High Similarity	NPC203080
0.94	High Similarity	NPC112701
0.94	High Similarity	NPC88983
0.9396	High Similarity	NPC471675
0.9392	High Similarity	NPC470461
0.9392	High Similarity	NPC307052
0.9392	High Similarity	NPC139966
0.9392	High Similarity	NPC277032
0.9388	High Similarity	NPC85773
0.9388	High Similarity	NPC51070
0.9388	High Similarity	NPC470670
0.9388	High Similarity	NPC473133
0.9388	High Similarity	NPC21835
0.9388	High Similarity	NPC91902
0.9388	High Similarity	NPC222298
0.9388	High Similarity	NPC47388
0.9384	High Similarity	NPC236766
0.9384	High Similarity	NPC473015
0.9384	High Similarity	NPC273538
0.9384	High Similarity	NPC216538
0.9384	High Similarity	NPC224714
0.9384	High Similarity	NPC209040
0.9384	High Similarity	NPC197252
0.9384	High Similarity	NPC473013
0.9379	High Similarity	NPC166934
0.9379	High Similarity	NPC220998
0.9379	High Similarity	NPC37496
0.9379	High Similarity	NPC64915
0.9379	High Similarity	NPC167624
0.9379	High Similarity	NPC107572
0.9379	High Similarity	NPC227579
0.9379	High Similarity	NPC10937
0.9379	High Similarity	NPC40833
0.9379	High Similarity	NPC223500
0.9379	High Similarity	NPC76338
0.9379	High Similarity	NPC1089
0.9379	High Similarity	NPC265040
0.9379	High Similarity	NPC78
0.9379	High Similarity	NPC166482
0.9379	High Similarity	NPC76372
0.9379	High Similarity	NPC324436
0.9379	High Similarity	NPC161506
0.9379	High Similarity	NPC177354
0.9379	High Similarity	NPC32739
0.9379	High Similarity	NPC296917
0.9379	High Similarity	NPC148545
0.9379	High Similarity	NPC66515
0.9379	High Similarity	NPC328164
0.9379	High Similarity	NPC306829
0.9379	High Similarity	NPC194432
0.9379	High Similarity	NPC148757
0.9379	High Similarity	NPC125855
0.9379	High Similarity	NPC228504
0.9379	High Similarity	NPC324134
0.9379	High Similarity	NPC182852
0.9351	High Similarity	NPC259834
0.9351	High Similarity	NPC131745
0.9346	High Similarity	NPC471976
0.9346	High Similarity	NPC470326
0.9342	High Similarity	NPC472598
0.9342	High Similarity	NPC52530
0.9342	High Similarity	NPC23817
0.9342	High Similarity	NPC474055
0.9342	High Similarity	NPC291508
0.9338	High Similarity	NPC477530
0.9338	High Similarity	NPC321779
0.9333	High Similarity	NPC256141
0.9324	High Similarity	NPC168085
0.9324	High Similarity	NPC39195
0.9324	High Similarity	NPC296869
0.9324	High Similarity	NPC470460

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 NPC171651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	866
0.2-0.3	1666
0.3-0.4	2560
0.4-0.5	1891
0.5-0.6	1124
0.6-0.7	480
0.7-0.8	168
0.8-0.85	35
0.85-0.9	17
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD7075	Discontinued
0.9459	High Similarity	NPD4380	Phase 2
0.94	High Similarity	NPD7096	Clinical (unspecified phase)
0.9384	High Similarity	NPD4378	Clinical (unspecified phase)
0.9272	High Similarity	NPD2393	Clinical (unspecified phase)
0.9205	High Similarity	NPD6801	Discontinued
0.9103	High Similarity	NPD1549	Phase 2
0.9091	High Similarity	NPD4381	Clinical (unspecified phase)
0.9079	High Similarity	NPD1934	Approved
0.9057	High Similarity	NPD7804	Clinical (unspecified phase)
0.9034	High Similarity	NPD1552	Clinical (unspecified phase)
0.9034	High Similarity	NPD1550	Clinical (unspecified phase)
0.8987	High Similarity	NPD6168	Clinical (unspecified phase)
0.8987	High Similarity	NPD6167	Clinical (unspecified phase)
0.8987	High Similarity	NPD6166	Phase 2
0.8926	High Similarity	NPD6799	Approved
0.8839	High Similarity	NPD8443	Clinical (unspecified phase)
0.8836	High Similarity	NPD2796	Approved
0.8782	High Similarity	NPD3882	Suspended
0.8767	High Similarity	NPD1510	Phase 2
0.8766	High Similarity	NPD7411	Suspended
0.8742	High Similarity	NPD7410	Clinical (unspecified phase)
0.8701	High Similarity	NPD6599	Discontinued
0.8684	High Similarity	NPD1512	Approved
0.8654	High Similarity	NPD7819	Suspended
0.8654	High Similarity	NPD2801	Approved
0.8627	High Similarity	NPD5403	Approved
0.8621	High Similarity	NPD1240	Approved
0.8599	High Similarity	NPD3817	Phase 2
0.8598	High Similarity	NPD6797	Phase 2
0.8553	High Similarity	NPD1511	Approved
0.8545	High Similarity	NPD6559	Discontinued
0.8545	High Similarity	NPD7251	Discontinued
0.8537	High Similarity	NPD7074	Phase 3
0.8528	High Similarity	NPD3818	Discontinued
0.8503	High Similarity	NPD1607	Approved
0.85	High Similarity	NPD5494	Approved
0.8497	Intermediate Similarity	NPD5401	Approved
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8481	Intermediate Similarity	NPD5402	Approved
0.8476	Intermediate Similarity	NPD7054	Approved
0.8447	Intermediate Similarity	NPD6959	Discontinued
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7472	Approved
0.8405	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5844	Phase 1
0.8235	Intermediate Similarity	NPD4628	Phase 3
0.817	Intermediate Similarity	NPD2800	Approved
0.8117	Intermediate Similarity	NPD3750	Approved
0.8092	Intermediate Similarity	NPD2935	Discontinued
0.8092	Intermediate Similarity	NPD1551	Phase 2
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8038	Intermediate Similarity	NPD920	Approved
0.8037	Intermediate Similarity	NPD3749	Approved
0.8024	Intermediate Similarity	NPD7473	Discontinued
0.8023	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5953	Discontinued
0.7935	Intermediate Similarity	NPD1243	Approved
0.7929	Intermediate Similarity	NPD7286	Phase 2
0.7911	Intermediate Similarity	NPD2533	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD2532	Approved
0.7908	Intermediate Similarity	NPD2799	Discontinued
0.7898	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6651	Approved
0.7885	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7871	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3751	Discontinued
0.7867	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2313	Discontinued
0.7862	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD4363	Phase 3
0.7809	Intermediate Similarity	NPD4360	Phase 2
0.7806	Intermediate Similarity	NPD2344	Approved
0.7798	Intermediate Similarity	NPD3926	Phase 2
0.7792	Intermediate Similarity	NPD3748	Approved
0.7763	Intermediate Similarity	NPD943	Approved
0.7748	Intermediate Similarity	NPD6798	Discontinued
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7738	Intermediate Similarity	NPD3787	Discontinued
0.7733	Intermediate Similarity	NPD4908	Phase 1
0.773	Intermediate Similarity	NPD7584	Approved
0.7716	Intermediate Similarity	NPD3226	Approved
0.7701	Intermediate Similarity	NPD8313	Approved
0.7701	Intermediate Similarity	NPD8312	Approved
0.7692	Intermediate Similarity	NPD6782	Approved
0.7692	Intermediate Similarity	NPD6778	Approved
0.7692	Intermediate Similarity	NPD6779	Approved
0.7692	Intermediate Similarity	NPD6776	Approved
0.7692	Intermediate Similarity	NPD2346	Discontinued
0.7692	Intermediate Similarity	NPD6777	Approved
0.7692	Intermediate Similarity	NPD6780	Approved
0.7692	Intermediate Similarity	NPD6781	Approved
0.7677	Intermediate Similarity	NPD7033	Discontinued
0.7677	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD1203	Approved
0.7643	Intermediate Similarity	NPD2424	Discontinued
0.7628	Intermediate Similarity	NPD6099	Approved
0.7628	Intermediate Similarity	NPD6100	Approved
0.7622	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD6832	Phase 2
0.7616	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2309	Approved
0.7597	Intermediate Similarity	NPD6355	Discontinued
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7582	Intermediate Similarity	NPD6233	Phase 2
0.7571	Intermediate Similarity	NPD8150	Discontinued
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.7566	Intermediate Similarity	NPD3027	Phase 3
0.755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD8455	Phase 2
0.7529	Intermediate Similarity	NPD3823	Discontinued
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1933	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD1652	Phase 2
0.7483	Intermediate Similarity	NPD2798	Approved
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD4361	Phase 2
0.7473	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7698	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4661	Approved
0.7469	Intermediate Similarity	NPD4662	Approved
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7452	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD9717	Approved
0.7442	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7427	Intermediate Similarity	NPD5710	Approved
0.7427	Intermediate Similarity	NPD5711	Approved
0.7423	Intermediate Similarity	NPD5049	Phase 3
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7418	Intermediate Similarity	NPD6535	Approved
0.7418	Intermediate Similarity	NPD6534	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7701	Phase 2
0.7403	Intermediate Similarity	NPD3268	Approved
0.7391	Intermediate Similarity	NPD2354	Approved
0.7391	Intermediate Similarity	NPD3887	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1729	Discontinued
0.7368	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD6844	Discontinued
0.7342	Intermediate Similarity	NPD4308	Phase 3
0.7341	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2403	Approved
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD1653	Approved
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7874	Approved
0.7316	Intermediate Similarity	NPD7585	Approved
0.7303	Intermediate Similarity	NPD2797	Approved
0.7297	Intermediate Similarity	NPD7700	Phase 2
0.7297	Intermediate Similarity	NPD7699	Phase 2
0.7292	Intermediate Similarity	NPD7801	Approved
0.7278	Intermediate Similarity	NPD4538	Approved
0.7278	Intermediate Similarity	NPD4536	Approved
0.7278	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7583	Approved
0.7262	Intermediate Similarity	NPD37	Approved
0.7251	Intermediate Similarity	NPD6234	Discontinued
0.725	Intermediate Similarity	NPD1471	Phase 3
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4062	Phase 3
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4966	Approved
0.7234	Intermediate Similarity	NPD6823	Phase 2
0.723	Intermediate Similarity	NPD9545	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