NPASS Compound

Structure

CID293286 OpenBabel06191716102D 35 37 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 -3.4641 -2.0000 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 -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 -1.7321 -2.0000 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 -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 -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 -0.0000 -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 -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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 13 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 23 1 0 0 0 0 14 25 2 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 23 26 2 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 30 2 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 0 0 0 0 27 33 2 0 0 0 0 28 29 1 0 0 0 0 28 34 1 1 0 0 0 29 22 1 6 0 0 0 29 35 1 0 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.26
Volume:	519.353
LogP:	7.424
LogD:	4.441
LogS:	-2.768
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.408
Synthetic Accessibility Score:	4.033
Fsp3:	0.367
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:	-4.867
MDCK Permeability:	1.6034351574489847e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.227
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.97
30% Bioavailability (F30%):	0.336

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	86.08329772949219%
Volume Distribution (VD):	1.687
Pgp-substrate:	13.926011085510254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.79
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.886
CYP2C9-substrate:	0.934
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.308
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	11.75
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.359
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.701
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.146

Download Data

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

Natural Product: NPC293286

Natural Product ID:	NPC293286
*Common Name:**	Lespeflorin B3
IUPAC Name:	(2R,3R)-3,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]-6,8-bis(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms:	Lespeflorin B3
Standard InCHIKey:	IKKCPYPLJMVWMP-URLMMPGGSA-N
Standard InCHI:	InChI=1S/C30H36O5/c1-17(2)7-10-20-15-22(12-14-25(20)31)29-28(34)27(33)24-16-21(11-8-18(3)4)26(32)23(30(24)35-29)13-9-19(5)6/h7-9,12,14-16,28-29,31-32,34H,10-11,13H2,1-6H3/t28-,29+/m0/s1
SMILES:	CC(=CCc1c2O[C@H](c3ccc(c(c3)CC=C(C)C)O)[C@H](C(=O)c2cc(c1O)CC=C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL549408
PubChem CID:	25243247
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	=	680.0	nM	PMID[555588]

☑ 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 NPC293286 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	387
0.1-0.2	1396
0.2-0.3	3394
0.3-0.4	8342
0.4-0.5	10138
0.5-0.6	3771
0.6-0.7	5179
0.7-0.8	5285
0.8-0.85	2804
0.85-0.9	1441
0.9-0.95	498
0.95-1	62

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC138288
0.9932	High Similarity	NPC171651
0.9932	High Similarity	NPC35567
0.9932	High Similarity	NPC243171
0.9863	High Similarity	NPC262038
0.9863	High Similarity	NPC254412
0.9863	High Similarity	NPC319910
0.9863	High Similarity	NPC262039
0.9863	High Similarity	NPC278476
0.9796	High Similarity	NPC216035
0.9796	High Similarity	NPC217149
0.9795	High Similarity	NPC105136
0.9732	High Similarity	NPC215917
0.9732	High Similarity	NPC10754
0.9732	High Similarity	NPC20530
0.9728	High Similarity	NPC471677
0.9728	High Similarity	NPC263384
0.9728	High Similarity	NPC472420
0.9728	High Similarity	NPC472422
0.9728	High Similarity	NPC471676
0.9728	High Similarity	NPC244577
0.9664	High Similarity	NPC304207
0.9664	High Similarity	NPC259710
0.9664	High Similarity	NPC111341
0.9664	High Similarity	NPC304745
0.9664	High Similarity	NPC217706
0.9664	High Similarity	NPC477958
0.9664	High Similarity	NPC48579
0.9664	High Similarity	NPC207809
0.9597	High Similarity	NPC223701
0.9597	High Similarity	NPC248793
0.9597	High Similarity	NPC100134
0.9597	High Similarity	NPC20907
0.9597	High Similarity	NPC209760
0.9597	High Similarity	NPC268193
0.9597	High Similarity	NPC180301
0.9597	High Similarity	NPC472583
0.9597	High Similarity	NPC7989
0.9597	High Similarity	NPC244250
0.9592	High Similarity	NPC472628
0.9592	High Similarity	NPC89442
0.9589	High Similarity	NPC211466
0.9589	High Similarity	NPC44721
0.9589	High Similarity	NPC122828
0.9589	High Similarity	NPC40086
0.9589	High Similarity	NPC176869
0.9589	High Similarity	NPC3779
0.9589	High Similarity	NPC476182
0.953	High Similarity	NPC56232
0.953	High Similarity	NPC150123
0.953	High Similarity	NPC477957
0.953	High Similarity	NPC10807
0.953	High Similarity	NPC244583
0.953	High Similarity	NPC475790
0.953	High Similarity	NPC473996
0.953	High Similarity	NPC210597
0.953	High Similarity	NPC161881
0.9527	High Similarity	NPC61258
0.9521	High Similarity	NPC1940
0.9521	High Similarity	NPC472629
0.9521	High Similarity	NPC148011
0.9474	High Similarity	NPC22192
0.947	High Similarity	NPC78492
0.947	High Similarity	NPC208152
0.9467	High Similarity	NPC311579
0.9467	High Similarity	NPC469405
0.9467	High Similarity	NPC236756
0.9463	High Similarity	NPC471229
0.9463	High Similarity	NPC289774
0.9463	High Similarity	NPC474021
0.9463	High Similarity	NPC474023
0.9463	High Similarity	NPC477897
0.9463	High Similarity	NPC209846
0.9463	High Similarity	NPC474744
0.9463	High Similarity	NPC472423
0.9463	High Similarity	NPC474772
0.9463	High Similarity	NPC328740
0.9463	High Similarity	NPC472580
0.9463	High Similarity	NPC472636
0.9456	High Similarity	NPC472918
0.9456	High Similarity	NPC472627
0.9456	High Similarity	NPC91902
0.9452	High Similarity	NPC87486
0.9452	High Similarity	NPC62290
0.9452	High Similarity	NPC279417
0.9452	High Similarity	NPC326506
0.9452	High Similarity	NPC208176
0.9452	High Similarity	NPC124780
0.9452	High Similarity	NPC142731
0.9452	High Similarity	NPC306607
0.9452	High Similarity	NPC470890
0.9452	High Similarity	NPC4152
0.9452	High Similarity	NPC236766
0.9452	High Similarity	NPC197252
0.9452	High Similarity	NPC49130
0.9412	High Similarity	NPC306978
0.9412	High Similarity	NPC282009
0.9412	High Similarity	NPC287328
0.9404	High Similarity	NPC470681
0.9404	High Similarity	NPC471116
0.9404	High Similarity	NPC476169
0.94	High Similarity	NPC285623
0.94	High Similarity	NPC327269
0.94	High Similarity	NPC31627
0.94	High Similarity	NPC476238
0.9396	High Similarity	NPC267117
0.9396	High Similarity	NPC124478
0.9396	High Similarity	NPC177308
0.9396	High Similarity	NPC472421
0.9392	High Similarity	NPC10097
0.9392	High Similarity	NPC218569
0.9388	High Similarity	NPC316769
0.9388	High Similarity	NPC229190
0.9384	High Similarity	NPC175504
0.9384	High Similarity	NPC91560
0.9384	High Similarity	NPC221432
0.9384	High Similarity	NPC310130
0.9384	High Similarity	NPC143896
0.9384	High Similarity	NPC245482
0.9384	High Similarity	NPC164980
0.9384	High Similarity	NPC149026
0.9384	High Similarity	NPC169591
0.9384	High Similarity	NPC75049
0.9384	High Similarity	NPC257097
0.9384	High Similarity	NPC39329
0.9384	High Similarity	NPC301751
0.9384	High Similarity	NPC185276
0.9384	High Similarity	NPC150408
0.9384	High Similarity	NPC68104
0.9351	High Similarity	NPC471499
0.9351	High Similarity	NPC3629
0.9346	High Similarity	NPC123544
0.9338	High Similarity	NPC88983
0.9338	High Similarity	NPC203080
0.9338	High Similarity	NPC109594
0.9338	High Similarity	NPC326592
0.9338	High Similarity	NPC193200
0.9338	High Similarity	NPC112701
0.9333	High Similarity	NPC471675
0.9329	High Similarity	NPC277032
0.9329	High Similarity	NPC470461
0.9329	High Similarity	NPC307052
0.9329	High Similarity	NPC139966
0.9324	High Similarity	NPC85773
0.9324	High Similarity	NPC470670
0.9324	High Similarity	NPC47388
0.9324	High Similarity	NPC222298
0.9324	High Similarity	NPC51070
0.9324	High Similarity	NPC21835
0.9324	High Similarity	NPC473133
0.932	High Similarity	NPC235217
0.932	High Similarity	NPC224714
0.932	High Similarity	NPC473013
0.932	High Similarity	NPC473015
0.932	High Similarity	NPC216538
0.932	High Similarity	NPC209040
0.932	High Similarity	NPC473014
0.932	High Similarity	NPC273538
0.9315	High Similarity	NPC76372
0.9315	High Similarity	NPC228504
0.9315	High Similarity	NPC10937
0.9315	High Similarity	NPC220998
0.9315	High Similarity	NPC182852
0.9315	High Similarity	NPC167624
0.9315	High Similarity	NPC107572
0.9315	High Similarity	NPC37496
0.9315	High Similarity	NPC227579
0.9315	High Similarity	NPC265040
0.9315	High Similarity	NPC76338
0.9315	High Similarity	NPC223500
0.9315	High Similarity	NPC1089
0.9315	High Similarity	NPC161506
0.9315	High Similarity	NPC40833
0.9315	High Similarity	NPC148545
0.9315	High Similarity	NPC78
0.9315	High Similarity	NPC66515
0.9315	High Similarity	NPC166482
0.9315	High Similarity	NPC32739
0.9315	High Similarity	NPC324436
0.9315	High Similarity	NPC64915
0.9315	High Similarity	NPC328164
0.9315	High Similarity	NPC177354
0.9315	High Similarity	NPC306829
0.9315	High Similarity	NPC125855
0.9315	High Similarity	NPC194432
0.9315	High Similarity	NPC296917
0.9315	High Similarity	NPC166934
0.9315	High Similarity	NPC148757
0.9315	High Similarity	NPC324134
0.929	High Similarity	NPC259834
0.929	High Similarity	NPC211107
0.929	High Similarity	NPC131745
0.9286	High Similarity	NPC471976
0.9286	High Similarity	NPC470326
0.9286	High Similarity	NPC470183
0.9281	High Similarity	NPC281137
0.9281	High Similarity	NPC282390
0.9281	High Similarity	NPC472598
0.9281	High Similarity	NPC23817
0.9281	High Similarity	NPC291508

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 NPC293286 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	868
0.2-0.3	1667
0.3-0.4	2558
0.4-0.5	1926
0.5-0.6	1100
0.6-0.7	469
0.7-0.8	168
0.8-0.85	37
0.85-0.9	18
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9536	High Similarity	NPD7075	Discontinued
0.9467	High Similarity	NPD7096	Clinical (unspecified phase)
0.9396	High Similarity	NPD4380	Phase 2
0.932	High Similarity	NPD4378	Clinical (unspecified phase)
0.9211	High Similarity	NPD2393	Clinical (unspecified phase)
0.9145	High Similarity	NPD6801	Discontinued
0.9119	High Similarity	NPD7804	Clinical (unspecified phase)
0.9041	High Similarity	NPD1549	Phase 2
0.9032	High Similarity	NPD4381	Clinical (unspecified phase)
0.902	High Similarity	NPD1934	Approved
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8931	High Similarity	NPD6166	Phase 2
0.8931	High Similarity	NPD6167	Clinical (unspecified phase)
0.8931	High Similarity	NPD6168	Clinical (unspecified phase)
0.8903	High Similarity	NPD8443	Clinical (unspecified phase)
0.8867	High Similarity	NPD6799	Approved
0.8776	High Similarity	NPD2796	Approved
0.8726	High Similarity	NPD3882	Suspended
0.8718	High Similarity	NPD7819	Suspended
0.871	High Similarity	NPD7411	Suspended
0.8707	High Similarity	NPD1510	Phase 2
0.8684	High Similarity	NPD7410	Clinical (unspecified phase)
0.8645	High Similarity	NPD6599	Discontinued
0.8627	High Similarity	NPD1512	Approved
0.8606	High Similarity	NPD7251	Discontinued
0.8599	High Similarity	NPD2801	Approved
0.8598	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD5403	Approved
0.8562	High Similarity	NPD1240	Approved
0.8554	High Similarity	NPD7808	Phase 3
0.8545	High Similarity	NPD6797	Phase 2
0.8544	High Similarity	NPD3817	Phase 2
0.8537	High Similarity	NPD7054	Approved
0.8497	Intermediate Similarity	NPD1511	Approved
0.8494	Intermediate Similarity	NPD6559	Discontinued
0.8485	Intermediate Similarity	NPD7472	Approved
0.8476	Intermediate Similarity	NPD3818	Discontinued
0.8447	Intermediate Similarity	NPD5494	Approved
0.8446	Intermediate Similarity	NPD1607	Approved
0.8442	Intermediate Similarity	NPD5401	Approved
0.8428	Intermediate Similarity	NPD5402	Approved
0.8395	Intermediate Similarity	NPD6959	Discontinued
0.8375	Intermediate Similarity	NPD7768	Phase 2
0.8375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD5844	Phase 1
0.8182	Intermediate Similarity	NPD4628	Phase 3
0.8117	Intermediate Similarity	NPD2800	Approved
0.8084	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD3750	Approved
0.8057	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD1551	Phase 2
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD3749	Approved
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7987	Intermediate Similarity	NPD920	Approved
0.7961	Intermediate Similarity	NPD6651	Approved
0.7952	Intermediate Similarity	NPD1247	Approved
0.7939	Intermediate Similarity	NPD919	Approved
0.7907	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5953	Discontinued
0.7885	Intermediate Similarity	NPD1243	Approved
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7848	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3751	Discontinued
0.7821	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2313	Discontinued
0.7815	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7584	Approved
0.7765	Intermediate Similarity	NPD4360	Phase 2
0.7765	Intermediate Similarity	NPD4363	Phase 3
0.7759	Intermediate Similarity	NPD8313	Approved
0.7759	Intermediate Similarity	NPD8312	Approved
0.7756	Intermediate Similarity	NPD2344	Approved
0.7751	Intermediate Similarity	NPD3926	Phase 2
0.7742	Intermediate Similarity	NPD3748	Approved
0.7727	Intermediate Similarity	NPD8434	Phase 2
0.7712	Intermediate Similarity	NPD943	Approved
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7697	Intermediate Similarity	NPD6798	Discontinued
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7683	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4908	Phase 1
0.7682	Intermediate Similarity	NPD6832	Phase 2
0.7669	Intermediate Similarity	NPD3226	Approved
0.7662	Intermediate Similarity	NPD6355	Discontinued
0.765	Intermediate Similarity	NPD6781	Approved
0.765	Intermediate Similarity	NPD6776	Approved
0.765	Intermediate Similarity	NPD6778	Approved
0.765	Intermediate Similarity	NPD6780	Approved
0.765	Intermediate Similarity	NPD6779	Approved
0.765	Intermediate Similarity	NPD6777	Approved
0.765	Intermediate Similarity	NPD6782	Approved
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD7033	Discontinued
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8150	Discontinued
0.7622	Intermediate Similarity	NPD7435	Discontinued
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.7595	Intermediate Similarity	NPD2424	Discontinued
0.759	Intermediate Similarity	NPD8455	Phase 2
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7566	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2309	Approved
0.7561	Intermediate Similarity	NPD7458	Discontinued
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5124	Phase 1
0.7548	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6233	Phase 2
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7698	Approved
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.75	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7486	Intermediate Similarity	NPD3823	Discontinued
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7390	Discontinued
0.746	Intermediate Similarity	NPD7701	Phase 2
0.7455	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6190	Approved
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1652	Phase 2
0.7436	Intermediate Similarity	NPD230	Phase 1
0.7436	Intermediate Similarity	NPD1933	Approved
0.7434	Intermediate Similarity	NPD2798	Approved
0.7432	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4361	Phase 2
0.7425	Intermediate Similarity	NPD6844	Discontinued
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4661	Approved
0.7423	Intermediate Similarity	NPD4662	Approved
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7405	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD9717	Approved
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7382	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7874	Approved
0.7378	Intermediate Similarity	NPD5049	Phase 3
0.7377	Intermediate Similarity	NPD6534	Approved
0.7377	Intermediate Similarity	NPD6535	Approved
0.7372	Intermediate Similarity	NPD4060	Phase 1
0.7368	Intermediate Similarity	NPD7585	Approved
0.7355	Intermediate Similarity	NPD3268	Approved
0.7351	Intermediate Similarity	NPD7700	Phase 2
0.7351	Intermediate Similarity	NPD7699	Phase 2
0.7346	Intermediate Similarity	NPD3887	Approved
0.7346	Intermediate Similarity	NPD2354	Approved
0.7344	Intermediate Similarity	NPD7801	Approved
0.7341	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1729	Discontinued
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD447	Suspended
0.7316	Intermediate Similarity	NPD7583	Approved
0.7299	Intermediate Similarity	NPD2403	Approved
0.7299	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.729	Intermediate Similarity	NPD4625	Phase 3
0.7289	Intermediate Similarity	NPD1653	Approved
0.7287	Intermediate Similarity	NPD6823	Phase 2
0.7283	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD5761	Phase 2
0.7278	Intermediate Similarity	NPD5760	Phase 2
0.7255	Intermediate Similarity	NPD2797	Approved
0.7254	Intermediate Similarity	NPD7783	Phase 2
0.7254	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6104	Discontinued
0.7244	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4536	Approved
0.7233	Intermediate Similarity	NPD4538	Approved
0.7233	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7219	Intermediate Similarity	NPD37	Approved
0.7216	Intermediate Similarity	NPD7893	Clinical (unspecified phase)

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