NPASS Compound

Structure

NPC131866 OpenBabel07101718202D 24 27 0 0 1 0 0 0 0 0999 V2000 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 0.8660 2.5000 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 -0.0000 3.0000 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 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 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 0.8660 -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 1.7321 -0.0000 0.0000 C 0 0 1 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 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 2.5981 -1.5000 0.0000 C 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 5.1962 -2.0000 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 -1.8171 2.8090 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 22 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 18 2 0 0 0 0 12 13 1 6 0 0 0 13 19 2 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.12
Volume:	328.45
LogP:	4.073
LogD:	3.494
LogS:	-4.766
# Rotatable Bonds:	3
TPSA:	61.06
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.791
Synthetic Accessibility Score:	3.167
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851
MDCK Permeability:	2.3646267436561175e-05
Pgp-inhibitor:	0.072
Pgp-substrate:	0.716
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	98.3832778930664%
Volume Distribution (VD):	0.647
Pgp-substrate:	3.6394131183624268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.95
CYP2C19-substrate:	0.636
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.637
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.783

ADMET: Excretion

Clearance (CL):	8.327
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.373
AMES Toxicity:	0.369
Rat Oral Acute Toxicity:	0.559
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.853
Carcinogencity:	0.594
Eye Corrosion:	0.003
Eye Irritation:	0.639
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC131866

Natural Product ID:	NPC131866
*Common Name:**	Smiranicin
IUPAC Name:	3-[(3R)-3,4-dihydro-2H-furo[2,3-h]chromen-3-yl]-2,6-dimethoxyphenol
Synonyms:	smiranicin
Standard InCHIKey:	DGWRIGGEKQHRTA-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C19H18O5/c1-21-16-6-4-13(19(22-2)17(16)20)12-9-11-3-5-15-14(7-8-23-15)18(11)24-10-12/h3-8,12,20H,9-10H2,1-2H3/t12-/m0/s1
SMILES:	COc1ccc([C@H]2Cc3ccc4c(cco4)c3OC2)c(c1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498724
PubChem CID:	11099439
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO6580	Smirnowia iranica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502308]
NPO6580	Smirnowia iranica	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	7

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	193000.0	nM	PMID[485084]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	=	11300.0	nM	PMID[485084]
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	17400.0	nM	PMID[485084]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	22900.0	nM	PMID[485084]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	57600.0	nM	PMID[485084]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	=	81000.0	nM	PMID[485084]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	112000.0	nM	PMID[485084]

☑ 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 NPC131866 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	423
0.1-0.2	1756
0.2-0.3	4038
0.3-0.4	10199
0.4-0.5	8027
0.5-0.6	3561
0.6-0.7	4843
0.7-0.8	5473
0.8-0.85	2457
0.85-0.9	1416
0.9-0.95	500
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC277480
0.9512	High Similarity	NPC310794
0.9506	High Similarity	NPC247973
0.9503	High Similarity	NPC37183
0.9444	High Similarity	NPC235610
0.9383	High Similarity	NPC38914
0.9383	High Similarity	NPC472277
0.9379	High Similarity	NPC312056
0.9379	High Similarity	NPC84515
0.9371	High Similarity	NPC299520
0.9371	High Similarity	NPC129684
0.9321	High Similarity	NPC18100
0.9321	High Similarity	NPC205265
0.9321	High Similarity	NPC472281
0.9321	High Similarity	NPC124038
0.9317	High Similarity	NPC188486
0.9268	High Similarity	NPC241820
0.9268	High Similarity	NPC50394
0.9264	High Similarity	NPC300053
0.9264	High Similarity	NPC108433
0.9264	High Similarity	NPC291110
0.9259	High Similarity	NPC474150
0.9259	High Similarity	NPC474162
0.9259	High Similarity	NPC272722
0.9255	High Similarity	NPC472624
0.925	High Similarity	NPC291508
0.9245	High Similarity	NPC255807
0.9245	High Similarity	NPC152951
0.9245	High Similarity	NPC230149
0.9245	High Similarity	NPC57674
0.9245	High Similarity	NPC168247
0.9245	High Similarity	NPC31018
0.9245	High Similarity	NPC117992
0.9217	High Similarity	NPC174700
0.9212	High Similarity	NPC288813
0.9207	High Similarity	NPC43065
0.9202	High Similarity	NPC133065
0.9198	High Similarity	NPC30655
0.9198	High Similarity	NPC45124
0.9198	High Similarity	NPC266314
0.9198	High Similarity	NPC74854
0.9193	High Similarity	NPC196879
0.9193	High Similarity	NPC16935
0.9187	High Similarity	NPC278778
0.9187	High Similarity	NPC291878
0.9187	High Similarity	NPC195796
0.9187	High Similarity	NPC35038
0.9182	High Similarity	NPC1477
0.9182	High Similarity	NPC227337
0.9182	High Similarity	NPC70433
0.9182	High Similarity	NPC273462
0.9182	High Similarity	NPC49402
0.9182	High Similarity	NPC213608
0.9182	High Similarity	NPC33051
0.9182	High Similarity	NPC469550
0.9172	High Similarity	NPC104682
0.9167	High Similarity	NPC8127
0.9167	High Similarity	NPC49667
0.9162	High Similarity	NPC261471
0.9162	High Similarity	NPC277510
0.9157	High Similarity	NPC279209
0.9157	High Similarity	NPC190351
0.9157	High Similarity	NPC102277
0.9152	High Similarity	NPC186392
0.9146	High Similarity	NPC326520
0.9146	High Similarity	NPC39306
0.9146	High Similarity	NPC36320
0.9146	High Similarity	NPC45449
0.9141	High Similarity	NPC476247
0.9141	High Similarity	NPC81679
0.9141	High Similarity	NPC472635
0.9136	High Similarity	NPC328102
0.9136	High Similarity	NPC36217
0.913	High Similarity	NPC161960
0.913	High Similarity	NPC96167
0.913	High Similarity	NPC245758
0.913	High Similarity	NPC78225
0.913	High Similarity	NPC304008
0.913	High Similarity	NPC181960
0.913	High Similarity	NPC262286
0.913	High Similarity	NPC472598
0.913	High Similarity	NPC472910
0.913	High Similarity	NPC219867
0.913	High Similarity	NPC187745
0.913	High Similarity	NPC180011
0.913	High Similarity	NPC472911
0.913	High Similarity	NPC27337
0.913	High Similarity	NPC474055
0.913	High Similarity	NPC222814
0.913	High Similarity	NPC36852
0.913	High Similarity	NPC472914
0.913	High Similarity	NPC469584
0.913	High Similarity	NPC472913
0.9125	High Similarity	NPC45849
0.9125	High Similarity	NPC200761
0.9125	High Similarity	NPC470327
0.9125	High Similarity	NPC256925
0.9125	High Similarity	NPC477503
0.9119	High Similarity	NPC477231
0.9119	High Similarity	NPC260979
0.9119	High Similarity	NPC257648
0.9119	High Similarity	NPC5871
0.9119	High Similarity	NPC472912
0.9107	High Similarity	NPC287243
0.9102	High Similarity	NPC248593
0.9102	High Similarity	NPC307286
0.9102	High Similarity	NPC28589
0.9091	High Similarity	NPC173292
0.9091	High Similarity	NPC128293
0.9091	High Similarity	NPC170245
0.9091	High Similarity	NPC119589
0.9085	High Similarity	NPC59295
0.9085	High Similarity	NPC273959
0.9085	High Similarity	NPC472278
0.9085	High Similarity	NPC263092
0.9085	High Similarity	NPC473313
0.9085	High Similarity	NPC1755
0.9085	High Similarity	NPC329669
0.9085	High Similarity	NPC319200
0.9085	High Similarity	NPC65846
0.9085	High Similarity	NPC39305
0.9085	High Similarity	NPC1706
0.9085	High Similarity	NPC187491
0.908	High Similarity	NPC134783
0.908	High Similarity	NPC472275
0.9074	High Similarity	NPC55738
0.9074	High Similarity	NPC204879
0.9074	High Similarity	NPC250214
0.9074	High Similarity	NPC40583
0.9074	High Similarity	NPC95936
0.9068	High Similarity	NPC68093
0.9068	High Similarity	NPC115853
0.9068	High Similarity	NPC472626
0.9068	High Similarity	NPC160015
0.9068	High Similarity	NPC470328
0.9068	High Similarity	NPC472916
0.9068	High Similarity	NPC247677
0.9068	High Similarity	NPC45131
0.9068	High Similarity	NPC472461
0.9068	High Similarity	NPC191146
0.9068	High Similarity	NPC472455
0.9068	High Similarity	NPC138243
0.9068	High Similarity	NPC209614
0.9062	High Similarity	NPC18727
0.9062	High Similarity	NPC213896
0.9062	High Similarity	NPC122365
0.9062	High Similarity	NPC192083
0.9059	High Similarity	NPC183843
0.9057	High Similarity	NPC170169
0.9057	High Similarity	NPC31363
0.9048	High Similarity	NPC216842
0.9048	High Similarity	NPC82217
0.9048	High Similarity	NPC476640
0.9048	High Similarity	NPC473834
0.9048	High Similarity	NPC233956
0.9048	High Similarity	NPC65885
0.9042	High Similarity	NPC78830
0.9042	High Similarity	NPC218533
0.9042	High Similarity	NPC472276
0.9036	High Similarity	NPC476459
0.903	High Similarity	NPC62261
0.9024	High Similarity	NPC474033
0.9024	High Similarity	NPC238995
0.9024	High Similarity	NPC472448
0.9024	High Similarity	NPC474034
0.9024	High Similarity	NPC201800
0.9024	High Similarity	NPC83922
0.9018	High Similarity	NPC14353
0.9018	High Similarity	NPC220582
0.9018	High Similarity	NPC282009
0.9018	High Similarity	NPC304839
0.9018	High Similarity	NPC118256
0.9018	High Similarity	NPC476980
0.9018	High Similarity	NPC119209
0.9018	High Similarity	NPC476283
0.9018	High Similarity	NPC56085
0.9018	High Similarity	NPC287328
0.9018	High Similarity	NPC192686
0.9018	High Similarity	NPC228785
0.9012	High Similarity	NPC48208
0.9012	High Similarity	NPC210084
0.9012	High Similarity	NPC162869
0.9012	High Similarity	NPC52889
0.9012	High Similarity	NPC223787
0.9012	High Similarity	NPC260902
0.9012	High Similarity	NPC218313
0.9012	High Similarity	NPC475267
0.9012	High Similarity	NPC474681
0.9012	High Similarity	NPC296957
0.9012	High Similarity	NPC67876
0.9012	High Similarity	NPC474836
0.9012	High Similarity	NPC65504
0.9012	High Similarity	NPC136674
0.9012	High Similarity	NPC156057
0.9012	High Similarity	NPC99597
0.9012	High Similarity	NPC474208
0.9006	High Similarity	NPC321779
0.9006	High Similarity	NPC300757
0.9006	High Similarity	NPC472280
0.9006	High Similarity	NPC113906

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 NPC131866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	950
0.2-0.3	1728
0.3-0.4	2658
0.4-0.5	1851
0.5-0.6	993
0.6-0.7	414
0.7-0.8	117
0.8-0.85	32
0.85-0.9	15
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD2393	Clinical (unspecified phase)
0.9	High Similarity	NPD1934	Approved
0.8951	High Similarity	NPD3882	Suspended
0.8902	High Similarity	NPD5494	Approved
0.8827	High Similarity	NPD2801	Approved
0.8713	High Similarity	NPD6559	Discontinued
0.8698	High Similarity	NPD3818	Discontinued
0.869	High Similarity	NPD6166	Phase 2
0.869	High Similarity	NPD6167	Clinical (unspecified phase)
0.869	High Similarity	NPD6168	Clinical (unspecified phase)
0.8623	High Similarity	NPD1247	Approved
0.8529	High Similarity	NPD7473	Discontinued
0.8503	High Similarity	NPD919	Approved
0.85	High Similarity	NPD1511	Approved
0.8494	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6232	Discontinued
0.8415	Intermediate Similarity	NPD4380	Phase 2
0.8412	Intermediate Similarity	NPD3926	Phase 2
0.8395	Intermediate Similarity	NPD1512	Approved
0.8382	Intermediate Similarity	NPD7074	Phase 3
0.8333	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD5844	Phase 1
0.8324	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8276	Intermediate Similarity	NPD7472	Approved
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD920	Approved
0.8225	Intermediate Similarity	NPD3749	Approved
0.8187	Intermediate Similarity	NPD1549	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8155	Intermediate Similarity	NPD1465	Phase 2
0.8144	Intermediate Similarity	NPD7411	Suspended
0.8136	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6797	Phase 2
0.8125	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD7251	Discontinued
0.8046	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2344	Approved
0.8	Intermediate Similarity	NPD1510	Phase 2
0.7988	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6801	Discontinued
0.7953	Intermediate Similarity	NPD7768	Phase 2
0.795	Intermediate Similarity	NPD2796	Approved
0.7939	Intermediate Similarity	NPD6799	Approved
0.7914	Intermediate Similarity	NPD2800	Approved
0.791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD2532	Approved
0.7892	Intermediate Similarity	NPD2533	Approved
0.7892	Intermediate Similarity	NPD2534	Approved
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7862	Intermediate Similarity	NPD943	Approved
0.7862	Intermediate Similarity	NPD1240	Approved
0.7818	Intermediate Similarity	NPD2309	Approved
0.7805	Intermediate Similarity	NPD1243	Approved
0.7798	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7764	Intermediate Similarity	NPD1607	Approved
0.776	Intermediate Similarity	NPD8434	Phase 2
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7705	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5402	Approved
0.7684	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1613	Approved
0.764	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7622	Intermediate Similarity	NPD1551	Phase 2
0.761	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD230	Phase 1
0.7572	Intermediate Similarity	NPD37	Approved
0.7561	Intermediate Similarity	NPD2799	Discontinued
0.7556	Intermediate Similarity	NPD7228	Approved
0.7547	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD9494	Approved
0.7545	Intermediate Similarity	NPD3750	Approved
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7543	Intermediate Similarity	NPD4965	Approved
0.7528	Intermediate Similarity	NPD7229	Phase 3
0.7516	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.7485	Intermediate Similarity	NPD447	Suspended
0.7485	Intermediate Similarity	NPD5403	Approved
0.747	Intermediate Similarity	NPD2346	Discontinued
0.7459	Intermediate Similarity	NPD3751	Discontinued
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3027	Phase 3
0.744	Intermediate Similarity	NPD4628	Phase 3
0.7432	Intermediate Similarity	NPD5953	Discontinued
0.743	Intermediate Similarity	NPD5710	Approved
0.743	Intermediate Similarity	NPD5711	Approved
0.7429	Intermediate Similarity	NPD5761	Phase 2
0.7429	Intermediate Similarity	NPD5760	Phase 2
0.7418	Intermediate Similarity	NPD7286	Phase 2
0.7412	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD6100	Approved
0.741	Intermediate Similarity	NPD6099	Approved
0.7407	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7685	Pre-registration
0.7391	Intermediate Similarity	NPD4908	Phase 1
0.7368	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7333	Intermediate Similarity	NPD6651	Approved
0.7304	Intermediate Similarity	NPD4665	Approved
0.7304	Intermediate Similarity	NPD4111	Phase 1
0.7302	Intermediate Similarity	NPD4287	Approved
0.7301	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7299	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2296	Approved
0.7286	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD1933	Approved
0.7268	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3748	Approved
0.7241	Intermediate Similarity	NPD1653	Approved
0.724	Intermediate Similarity	NPD4363	Phase 3
0.724	Intermediate Similarity	NPD4360	Phase 2
0.7235	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7907	Approved
0.7202	Intermediate Similarity	NPD4361	Phase 2
0.7202	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5242	Approved
0.7196	Intermediate Similarity	NPD8150	Discontinued
0.7193	Intermediate Similarity	NPD6190	Approved
0.7188	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6279	Approved
0.7175	Intermediate Similarity	NPD6280	Approved
0.717	Intermediate Similarity	NPD1610	Phase 2
0.7167	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1471	Phase 3
0.7158	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7143	Intermediate Similarity	NPD6776	Approved
0.7134	Intermediate Similarity	NPD4625	Phase 3
0.7119	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7240	Approved
0.7102	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD1729	Discontinued
0.7095	Intermediate Similarity	NPD5353	Approved
0.7081	Intermediate Similarity	NPD2163	Approved
0.7071	Intermediate Similarity	NPD3057	Approved
0.7071	Intermediate Similarity	NPD2491	Approved
0.7065	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2798	Approved
0.7049	Intermediate Similarity	NPD6808	Phase 2
0.7044	Intermediate Similarity	NPD7783	Phase 2
0.7044	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD8455	Phase 2
0.7035	Intermediate Similarity	NPD7435	Discontinued
0.7018	Intermediate Similarity	NPD2424	Discontinued
0.7015	Intermediate Similarity	NPD7584	Approved
0.7012	Intermediate Similarity	NPD2861	Phase 2
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7870	Phase 2
0.7	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6995	Remote Similarity	NPD8127	Discontinued
0.6994	Remote Similarity	NPD1203	Approved
0.6988	Remote Similarity	NPD3764	Approved
0.6988	Remote Similarity	NPD3268	Approved
0.6985	Remote Similarity	NPD3448	Approved
0.6985	Remote Similarity	NPD3533	Approved
0.6985	Remote Similarity	NPD2972	Approved
0.6984	Remote Similarity	NPD7549	Discontinued
0.697	Remote Similarity	NPD6832	Phase 2

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