NPASS Compound

Structure

CID138288 OpenBabel06191715492D 36 38 0 0 1 0 0 0 0 0999 V2000 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 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 -3.4641 0.0000 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 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 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 -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 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 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 0.8660 0.5000 0.0000 C 0 0 0 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 1.7321 3.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 16 2 0 0 0 0 8 12 1 0 0 0 0 8 17 2 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 11 20 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 19 23 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 22 30 2 0 0 0 0 23 31 1 0 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 24 30 1 0 0 0 0 25 32 1 0 0 0 0 26 33 1 0 0 0 0 27 28 1 0 0 0 0 27 34 2 0 0 0 0 28 29 1 0 0 0 0 28 35 1 1 0 0 0 29 20 1 6 0 0 0 29 36 1 0 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.14
Volume:	303.165
LogP:	0.121
LogD:	-0.23
LogS:	-0.847
# Rotatable Bonds:	4
TPSA:	84.22
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.857
Synthetic Accessibility Score:	3.201
Fsp3:	0.438
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:	-5.449
MDCK Permeability:	8.681739018356893e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.513
Human Intestinal Absorption (HIA):	0.851
20% Bioavailability (F20%):	0.167
30% Bioavailability (F30%):	0.632

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.692
Plasma Protein Binding (PPB):	31.303125381469727%
Volume Distribution (VD):	1.857
Pgp-substrate:	77.970703125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.228
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.332
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	8.575
Half-life (T1/2):	0.766

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.72
Drug-inuced Liver Injury (DILI):	0.584
AMES Toxicity:	0.444
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.792
Skin Sensitization:	0.735
Carcinogencity:	0.455
Eye Corrosion:	0.005
Eye Irritation:	0.025
Respiratory Toxicity:	0.786

Download Data

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

Natural Product: NPC138288

Natural Product ID:	NPC138288
*Common Name:**	Lespeflorin B4
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:	Lespeflorin B4
Standard InCHIKey:	HPUMCKZHBQPWBN-URLMMPGGSA-N
Standard InCHI:	InChI=1S/C30H36O6/c1-16(2)7-10-19-15-20(11-14-23(19)31)29-28(35)27(34)24-26(33)21(12-8-17(3)4)25(32)22(30(24)36-29)13-9-18(5)6/h7-9,11,14-15,28-29,31-33,35H,10,12-13H2,1-6H3/t28-,29+/m0/s1
SMILES:	CC(=CCc1cc(ccc1O)[C@@H]1[C@H](C(=O)c2c(c(CC=C(C)C)c(c(CC=C(C)C)c2O1)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562301
PubChem CID:	25243248
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003642] 8-prenylated flavans [CHEMONTID:0003508] 8-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	=	1230.0	nM	PMID[503791]

☑ 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 NPC138288 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	1387
0.2-0.3	3348
0.3-0.4	8387
0.4-0.5	10188
0.5-0.6	3742
0.6-0.7	5179
0.7-0.8	5403
0.8-0.85	2793
0.85-0.9	1321
0.9-0.95	491
0.95-1	73

Similarity Score	Similarity Level	Natural Product ID
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	NPC216035
0.9863	High Similarity	NPC35567
0.9863	High Similarity	NPC171651
0.9863	High Similarity	NPC243171
0.9863	High Similarity	NPC217149
0.9862	High Similarity	NPC105136
0.9797	High Similarity	NPC215917
0.9797	High Similarity	NPC10754
0.9797	High Similarity	NPC20530
0.9795	High Similarity	NPC471677
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
0.9662	High Similarity	NPC244250
0.9662	High Similarity	NPC209760
0.9662	High Similarity	NPC20907
0.9662	High Similarity	NPC248793
0.9662	High Similarity	NPC180301
0.9662	High Similarity	NPC268193
0.9662	High Similarity	NPC100134
0.966	High Similarity	NPC244577
0.966	High Similarity	NPC472422
0.966	High Similarity	NPC472420
0.966	High Similarity	NPC263384
0.966	High Similarity	NPC471676
0.9658	High Similarity	NPC472628
0.9655	High Similarity	NPC44721
0.9655	High Similarity	NPC122828
0.9655	High Similarity	NPC3779
0.9655	High Similarity	NPC176869
0.9655	High Similarity	NPC476182
0.9655	High Similarity	NPC211466
0.9655	High Similarity	NPC40086
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	NPC10807
0.9595	High Similarity	NPC150123
0.9586	High Similarity	NPC472629
0.9536	High Similarity	NPC22192
0.953	High Similarity	NPC236756
0.953	High Similarity	NPC223701
0.953	High Similarity	NPC472583
0.953	High Similarity	NPC7989
0.953	High Similarity	NPC311579
0.9527	High Similarity	NPC289774
0.9527	High Similarity	NPC472636
0.9527	High Similarity	NPC328740
0.9527	High Similarity	NPC209846
0.9527	High Similarity	NPC474021
0.9527	High Similarity	NPC474023
0.9527	High Similarity	NPC477897
0.9524	High Similarity	NPC89442
0.9521	High Similarity	NPC91902
0.9521	High Similarity	NPC472627
0.9521	High Similarity	NPC472918
0.9517	High Similarity	NPC279417
0.9517	High Similarity	NPC326506
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	NPC282009
0.9474	High Similarity	NPC287328
0.9467	High Similarity	NPC471116
0.9467	High Similarity	NPC476169
0.9463	High Similarity	NPC477957
0.9463	High Similarity	NPC473996
0.9459	High Similarity	NPC61258
0.9456	High Similarity	NPC10097
0.9456	High Similarity	NPC218569
0.9452	High Similarity	NPC148011
0.9452	High Similarity	NPC1940
0.9448	High Similarity	NPC185276
0.9412	High Similarity	NPC471499
0.9408	High Similarity	NPC123544
0.9404	High Similarity	NPC78492
0.9404	High Similarity	NPC208152
0.94	High Similarity	NPC109594
0.94	High Similarity	NPC326592
0.94	High Similarity	NPC112701
0.94	High Similarity	NPC88983
0.94	High Similarity	NPC469405
0.94	High Similarity	NPC193200
0.9396	High Similarity	NPC472580
0.9396	High Similarity	NPC472423
0.9396	High Similarity	NPC471229
0.9396	High Similarity	NPC474772
0.9396	High Similarity	NPC471675
0.9396	High Similarity	NPC474744
0.9392	High Similarity	NPC470461
0.9392	High Similarity	NPC139966
0.9392	High Similarity	NPC307052
0.9392	High Similarity	NPC277032
0.9388	High Similarity	NPC85773
0.9388	High Similarity	NPC470670
0.9388	High Similarity	NPC473133
0.9388	High Similarity	NPC21835
0.9388	High Similarity	NPC47388
0.9384	High Similarity	NPC236766
0.9384	High Similarity	NPC235217
0.9384	High Similarity	NPC273538
0.9384	High Similarity	NPC216538
0.9384	High Similarity	NPC224714
0.9384	High Similarity	NPC197252
0.9384	High Similarity	NPC473014
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	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	NPC32739
0.9379	High Similarity	NPC265040
0.9379	High Similarity	NPC177354
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	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	NPC296917
0.9379	High Similarity	NPC227579
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
0.9351	High Similarity	NPC211107
0.9346	High Similarity	NPC470183
0.9346	High Similarity	NPC470326
0.9346	High Similarity	NPC306978
0.9342	High Similarity	NPC281137
0.9342	High Similarity	NPC472598
0.9342	High Similarity	NPC474055
0.9342	High Similarity	NPC282390
0.9338	High Similarity	NPC226025
0.9338	High Similarity	NPC321779
0.9338	High Similarity	NPC470681
0.9333	High Similarity	NPC327269
0.9333	High Similarity	NPC476238
0.9333	High Similarity	NPC31627
0.9333	High Similarity	NPC285623
0.9329	High Similarity	NPC472421
0.9329	High Similarity	NPC124478
0.9329	High Similarity	NPC177308
0.9329	High Similarity	NPC267117
0.9324	High Similarity	NPC145467
0.9324	High Similarity	NPC296869
0.9324	High Similarity	NPC470460
0.932	High Similarity	NPC24136
0.932	High Similarity	NPC470458
0.932	High Similarity	NPC5820
0.932	High Similarity	NPC187282
0.932	High Similarity	NPC285630
0.932	High Similarity	NPC229190
0.932	High Similarity	NPC474302
0.932	High Similarity	NPC127059
0.932	High Similarity	NPC316769
0.932	High Similarity	NPC178343
0.932	High Similarity	NPC124729
0.932	High Similarity	NPC306488
0.932	High Similarity	NPC290133
0.9315	High Similarity	NPC107177
0.9315	High Similarity	NPC223812
0.9315	High Similarity	NPC164980
0.9315	High Similarity	NPC149026
0.9315	High Similarity	NPC77794
0.9315	High Similarity	NPC245482
0.9315	High Similarity	NPC175504
0.9315	High Similarity	NPC169591
0.9315	High Similarity	NPC212932

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 NPC138288 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	863
0.2-0.3	1655
0.3-0.4	2577
0.4-0.5	1907
0.5-0.6	1102
0.6-0.7	491
0.7-0.8	167
0.8-0.85	34
0.85-0.9	15
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.947	High Similarity	NPD7075	Discontinued
0.94	High Similarity	NPD7096	Clinical (unspecified phase)
0.9384	High Similarity	NPD4378	Clinical (unspecified phase)
0.9329	High Similarity	NPD4380	Phase 2
0.9272	High Similarity	NPD2393	Clinical (unspecified phase)
0.9177	High Similarity	NPD7804	Clinical (unspecified phase)
0.9079	High Similarity	NPD1934	Approved
0.9079	High Similarity	NPD6801	Discontinued
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	NPD6166	Phase 2
0.8987	High Similarity	NPD6167	Clinical (unspecified phase)
0.8973	High Similarity	NPD1549	Phase 2
0.8968	High Similarity	NPD4381	Clinical (unspecified phase)
0.8961	High Similarity	NPD8443	Clinical (unspecified phase)
0.88	High Similarity	NPD6799	Approved
0.8707	High Similarity	NPD2796	Approved
0.8684	High Similarity	NPD1512	Approved
0.8662	High Similarity	NPD3882	Suspended
0.8659	High Similarity	NPD7251	Discontinued
0.8654	High Similarity	NPD7819	Suspended
0.8654	High Similarity	NPD2801	Approved
0.865	High Similarity	NPD7074	Phase 3
0.8645	High Similarity	NPD7411	Suspended
0.8639	High Similarity	NPD1510	Phase 2
0.8618	High Similarity	NPD7410	Clinical (unspecified phase)
0.8606	High Similarity	NPD7808	Phase 3
0.8599	High Similarity	NPD3817	Phase 2
0.8598	High Similarity	NPD6797	Phase 2
0.8589	High Similarity	NPD7054	Approved
0.8581	High Similarity	NPD6599	Discontinued
0.8553	High Similarity	NPD1511	Approved
0.8537	High Similarity	NPD7472	Approved
0.8506	High Similarity	NPD5403	Approved
0.8493	Intermediate Similarity	NPD1240	Approved
0.8447	Intermediate Similarity	NPD6959	Discontinued
0.8434	Intermediate Similarity	NPD6559	Discontinued
0.8415	Intermediate Similarity	NPD3818	Discontinued
0.8385	Intermediate Similarity	NPD5494	Approved
0.8383	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1607	Approved
0.8377	Intermediate Similarity	NPD5401	Approved
0.8365	Intermediate Similarity	NPD5402	Approved
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD2800	Approved
0.817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5844	Phase 1
0.8133	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD4628	Phase 3
0.8108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6232	Discontinued
0.8023	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6651	Approved
0.8	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2935	Discontinued
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7953	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7286	Phase 2
0.7927	Intermediate Similarity	NPD3749	Approved
0.7925	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD2533	Approved
0.7911	Intermediate Similarity	NPD2534	Approved
0.7911	Intermediate Similarity	NPD2532	Approved
0.7892	Intermediate Similarity	NPD1247	Approved
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7879	Intermediate Similarity	NPD919	Approved
0.7871	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5953	Discontinued
0.7821	Intermediate Similarity	NPD1243	Approved
0.7809	Intermediate Similarity	NPD4363	Phase 3
0.7809	Intermediate Similarity	NPD4360	Phase 2
0.7799	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7785	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3751	Discontinued
0.7748	Intermediate Similarity	NPD6798	Discontinued
0.7748	Intermediate Similarity	NPD2313	Discontinued
0.7742	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3787	Discontinued
0.7733	Intermediate Similarity	NPD4908	Phase 1
0.773	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7584	Approved
0.7712	Intermediate Similarity	NPD6355	Discontinued
0.7701	Intermediate Similarity	NPD8312	Approved
0.7701	Intermediate Similarity	NPD8313	Approved
0.7692	Intermediate Similarity	NPD2344	Approved
0.7692	Intermediate Similarity	NPD3926	Phase 2
0.7677	Intermediate Similarity	NPD7033	Discontinued
0.7677	Intermediate Similarity	NPD3748	Approved
0.767	Intermediate Similarity	NPD8434	Phase 2
0.7647	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD2424	Discontinued
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7636	Intermediate Similarity	NPD8455	Phase 2
0.7619	Intermediate Similarity	NPD1610	Phase 2
0.7616	Intermediate Similarity	NPD6832	Phase 2
0.7616	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD3226	Approved
0.7597	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5124	Phase 1
0.7596	Intermediate Similarity	NPD6781	Approved
0.7596	Intermediate Similarity	NPD6776	Approved
0.7596	Intermediate Similarity	NPD6778	Approved
0.7596	Intermediate Similarity	NPD6777	Approved
0.7596	Intermediate Similarity	NPD6779	Approved
0.7596	Intermediate Similarity	NPD6782	Approved
0.7596	Intermediate Similarity	NPD6780	Approved
0.7582	Intermediate Similarity	NPD6233	Phase 2
0.758	Intermediate Similarity	NPD2346	Discontinued
0.7571	Intermediate Similarity	NPD8150	Discontinued
0.7568	Intermediate Similarity	NPD7435	Discontinued
0.7566	Intermediate Similarity	NPD3027	Phase 3
0.7564	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1203	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1652	Phase 2
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4361	Phase 2
0.7473	Intermediate Similarity	NPD7698	Approved
0.7469	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.7442	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7871	Phase 2
0.7433	Intermediate Similarity	NPD7870	Phase 2
0.7429	Intermediate Similarity	NPD3823	Discontinued
0.7427	Intermediate Similarity	NPD5710	Approved
0.7427	Intermediate Similarity	NPD5711	Approved
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7701	Phase 2
0.7403	Intermediate Similarity	NPD3268	Approved
0.7394	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6190	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD1933	Approved
0.7372	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD2798	Approved
0.7368	Intermediate Similarity	NPD8151	Discontinued
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD6844	Discontinued
0.7362	Intermediate Similarity	NPD4662	Approved
0.7362	Intermediate Similarity	NPD4661	Approved
0.7342	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2403	Approved
0.7338	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD9717	Approved
0.733	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7874	Approved
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7322	Intermediate Similarity	NPD6534	Approved
0.7322	Intermediate Similarity	NPD6535	Approved
0.7317	Intermediate Similarity	NPD5049	Phase 3
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	NPD7783	Phase 2
0.7292	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7801	Approved
0.729	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3887	Approved
0.7284	Intermediate Similarity	NPD2354	Approved
0.7278	Intermediate Similarity	NPD4538	Approved
0.7278	Intermediate Similarity	NPD4536	Approved
0.7278	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1729	Discontinued
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2654	Approved
0.7263	Intermediate Similarity	NPD7583	Approved
0.7262	Intermediate Similarity	NPD37	Approved
0.7261	Intermediate Similarity	NPD447	Suspended
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7228	Approved
0.7251	Intermediate Similarity	NPD6234	Discontinued
0.7244	Intermediate Similarity	NPD4062	Phase 3
0.7241	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD8651	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4965	Approved
0.7235	Intermediate Similarity	NPD4966	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