NPASS Compound

Structure

NPC136750 OpenBabel07101719512D 28 31 0 0 1 0 0 0 0 0999 V2000 6.1559 -1.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0279 -2.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8474 1.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8474 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2245 -1.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3833 1.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2493 1.7138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2493 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5334 0.3955 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 5.4128 -1.2807 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4346 -1.4886 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3833 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 -0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1154 1.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1154 0.2138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -1.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5173 -0.2862 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9346 -0.6226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9814 1.7138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9814 -0.2862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 -2.0316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 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 4.6038 0.1205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 15 2 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 2 0 0 0 0 11 26 1 0 0 0 0 11 27 1 0 0 0 0 12 1 1 1 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 2 1 1 0 0 0 13 21 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 22 2 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 14 1 6 0 0 0 20 28 1 0 0 0 0 21 15 1 6 0 0 0 21 28 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.17
Volume:	391.765
LogP:	4.638
LogD:	4.077
LogS:	-5.7
# Rotatable Bonds:	5
TPSA:	55.38
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	3.527
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.764
MDCK Permeability:	6.479614967247471e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	88.60665130615234%
Volume Distribution (VD):	1.236
Pgp-substrate:	4.241413116455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.948
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.889
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.878

ADMET: Excretion

Clearance (CL):	12.694
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.13
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.156
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.702
Carcinogencity:	0.539
Eye Corrosion:	0.004
Eye Irritation:	0.032
Respiratory Toxicity:	0.155

Download Data

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

Natural Product: NPC136750

Natural Product ID:	NPC136750
*Common Name:**	Rel-Saurufurin B
IUPAC Name:	6-[(2R,3R,4S,5S)-5-(3,4-dimethoxyphenyl)-3,4-dimethyloxolan-2-yl]-4-methoxy-1,3-benzodioxole
Synonyms:
Standard InCHIKey:	YCVPIUIGBBJALE-WVGOSAFVSA-N
Standard InCHI:	InChI=1S/C22H26O6/c1-12-13(2)21(15-9-18(25-5)22-19(10-15)26-11-27-22)28-20(12)14-6-7-16(23-3)17(8-14)24-4/h6-10,12-13,20-21H,11H2,1-5H3/t12-,13+,20-,21+/m0/s1
SMILES:	C[C@H]1[C@@H](C)[C@H](c2cc(c3c(c2)OCO3)OC)O[C@@H]1c1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104950
PubChem CID:	76310172
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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	3
Others	3

Activity Type	# Activity
NON-MOLECULAR	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	85000.0	nM	PMID[458797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56000.0	nM	PMID[458797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37200.0	nM	PMID[458797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	98.9	%	PMID[458797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	80.3	%	PMID[458797]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	75.6	%	PMID[458797]

☑ 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 NPC136750 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	473
0.1-0.2	1512
0.2-0.3	4195
0.3-0.4	11398
0.4-0.5	7377
0.5-0.6	5530
0.6-0.7	8928
0.7-0.8	2439
0.8-0.85	542
0.85-0.9	214
0.9-0.95	75
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC266848
0.9921	High Similarity	NPC261812
0.9921	High Similarity	NPC72046
0.9921	High Similarity	NPC65183
0.9844	High Similarity	NPC189474
0.9841	High Similarity	NPC192255
0.9766	High Similarity	NPC31530
0.969	High Similarity	NPC25333
0.969	High Similarity	NPC148893
0.969	High Similarity	NPC49235
0.9615	High Similarity	NPC121651
0.9609	High Similarity	NPC7744
0.9603	High Similarity	NPC226862
0.9603	High Similarity	NPC165128
0.9603	High Similarity	NPC82862
0.9603	High Similarity	NPC158471
0.9603	High Similarity	NPC57119
0.9603	High Similarity	NPC222127
0.9542	High Similarity	NPC185908
0.9531	High Similarity	NPC82111
0.9531	High Similarity	NPC227160
0.9524	High Similarity	NPC8050
0.9524	High Similarity	NPC473093
0.9524	High Similarity	NPC473092
0.9474	High Similarity	NPC312199
0.947	High Similarity	NPC113550
0.9466	High Similarity	NPC11453
0.9453	High Similarity	NPC233224
0.9453	High Similarity	NPC271208
0.9449	High Similarity	NPC328682
0.9449	High Similarity	NPC281864
0.9449	High Similarity	NPC54321
0.9444	High Similarity	NPC112571
0.9444	High Similarity	NPC50683
0.9444	High Similarity	NPC285725
0.9403	High Similarity	NPC472562
0.9403	High Similarity	NPC80326
0.9398	High Similarity	NPC216434
0.9398	High Similarity	NPC46591
0.9398	High Similarity	NPC103448
0.9398	High Similarity	NPC177868
0.9394	High Similarity	NPC283949
0.9389	High Similarity	NPC150534
0.9385	High Similarity	NPC1474
0.9385	High Similarity	NPC196937
0.9333	High Similarity	NPC298317
0.9333	High Similarity	NPC255566
0.9328	High Similarity	NPC300798
0.9328	High Similarity	NPC58137
0.9318	High Similarity	NPC143895
0.9308	High Similarity	NPC100223
0.9308	High Similarity	NPC158526
0.9308	High Similarity	NPC129687
0.9308	High Similarity	NPC171928
0.9308	High Similarity	NPC33611
0.9308	High Similarity	NPC16830
0.9291	High Similarity	NPC9891
0.9291	High Similarity	NPC88297
0.9291	High Similarity	NPC186845
0.9286	High Similarity	NPC18449
0.9286	High Similarity	NPC121783
0.9286	High Similarity	NPC34902
0.9259	High Similarity	NPC311057
0.9259	High Similarity	NPC174522
0.9259	High Similarity	NPC287124
0.9259	High Similarity	NPC474295
0.9254	High Similarity	NPC226547
0.9254	High Similarity	NPC56091
0.9242	High Similarity	NPC474139
0.9197	High Similarity	NPC180953
0.9191	High Similarity	NPC185071
0.9191	High Similarity	NPC12728
0.9191	High Similarity	NPC474808
0.9173	High Similarity	NPC32189
0.9167	High Similarity	NPC90083
0.9167	High Similarity	NPC170779
0.9167	High Similarity	NPC47181
0.916	High Similarity	NPC219671
0.916	High Similarity	NPC259742
0.916	High Similarity	NPC104077
0.916	High Similarity	NPC147616
0.9124	High Similarity	NPC166884
0.9124	High Similarity	NPC141569
0.9124	High Similarity	NPC477701
0.9118	High Similarity	NPC176586
0.9118	High Similarity	NPC210354
0.9104	High Similarity	NPC196420
0.9104	High Similarity	NPC474039
0.9098	High Similarity	NPC236522
0.9098	High Similarity	NPC18576
0.9098	High Similarity	NPC142547
0.9098	High Similarity	NPC126409
0.9098	High Similarity	NPC99572
0.9098	High Similarity	NPC135777
0.907	High Similarity	NPC158737
0.9058	High Similarity	NPC205316
0.9058	High Similarity	NPC477702
0.9048	High Similarity	NPC80241
0.9048	High Similarity	NPC301641
0.9048	High Similarity	NPC57268
0.9048	High Similarity	NPC172676
0.9048	High Similarity	NPC126935
0.9048	High Similarity	NPC312713
0.9048	High Similarity	NPC65933
0.9048	High Similarity	NPC216929
0.9037	High Similarity	NPC9068
0.9037	High Similarity	NPC88640
0.9037	High Similarity	NPC193666
0.9037	High Similarity	NPC123526
0.903	High Similarity	NPC25695
0.903	High Similarity	NPC78047
0.903	High Similarity	NPC172818
0.9023	High Similarity	NPC185680
0.9023	High Similarity	NPC145722
0.9023	High Similarity	NPC256776
0.9008	High Similarity	NPC237169
0.9008	High Similarity	NPC470624
0.9008	High Similarity	NPC63574
0.8993	High Similarity	NPC212890
0.8986	High Similarity	NPC239254
0.8986	High Similarity	NPC191158
0.8986	High Similarity	NPC50696
0.8986	High Similarity	NPC177644
0.8986	High Similarity	NPC172171
0.8978	High Similarity	NPC151423
0.8978	High Similarity	NPC40237
0.8963	High Similarity	NPC469981
0.8963	High Similarity	NPC101807
0.8955	High Similarity	NPC24490
0.8955	High Similarity	NPC174191
0.8955	High Similarity	NPC165155
0.8955	High Similarity	NPC141765
0.8955	High Similarity	NPC34103
0.8947	High Similarity	NPC58585
0.8947	High Similarity	NPC158331
0.8936	High Similarity	NPC51328
0.8936	High Similarity	NPC55158
0.8936	High Similarity	NPC286235
0.8931	High Similarity	NPC476748
0.8921	High Similarity	NPC178014
0.8921	High Similarity	NPC11422
0.8921	High Similarity	NPC474749
0.8921	High Similarity	NPC42716
0.8921	High Similarity	NPC475868
0.8913	High Similarity	NPC474288
0.8913	High Similarity	NPC218510
0.8913	High Similarity	NPC76415
0.8898	High Similarity	NPC477886
0.8897	High Similarity	NPC156376
0.8889	High Similarity	NPC344161
0.8889	High Similarity	NPC197166
0.8881	High Similarity	NPC474478
0.8881	High Similarity	NPC287745
0.8872	High Similarity	NPC175067
0.8872	High Similarity	NPC471505
0.8872	High Similarity	NPC204215
0.8872	High Similarity	NPC475856
0.8865	High Similarity	NPC301961
0.8865	High Similarity	NPC248132
0.8865	High Similarity	NPC166584
0.8865	High Similarity	NPC130449
0.8865	High Similarity	NPC71726
0.8857	High Similarity	NPC162193
0.8857	High Similarity	NPC154971
0.8857	High Similarity	NPC252286
0.8849	High Similarity	NPC92693
0.8849	High Similarity	NPC187774
0.8849	High Similarity	NPC326144
0.8849	High Similarity	NPC472713
0.8849	High Similarity	NPC118385
0.8849	High Similarity	NPC218841
0.8849	High Similarity	NPC475000
0.8849	High Similarity	NPC473046
0.8849	High Similarity	NPC472712
0.8846	High Similarity	NPC213711
0.8846	High Similarity	NPC40352
0.8846	High Similarity	NPC206882
0.8841	High Similarity	NPC230538
0.8841	High Similarity	NPC103637
0.8841	High Similarity	NPC41782
0.8841	High Similarity	NPC246947
0.8841	High Similarity	NPC229172
0.8841	High Similarity	NPC36531
0.8832	High Similarity	NPC284464
0.8828	High Similarity	NPC261661
0.8824	High Similarity	NPC166184
0.8815	High Similarity	NPC101624
0.8815	High Similarity	NPC184938
0.881	High Similarity	NPC254625
0.881	High Similarity	NPC475961
0.881	High Similarity	NPC119949
0.8806	High Similarity	NPC112237
0.8803	High Similarity	NPC85141
0.8803	High Similarity	NPC35877
0.8803	High Similarity	NPC95392
0.8803	High Similarity	NPC55715
0.8797	High Similarity	NPC158079
0.8797	High Similarity	NPC40432
0.8797	High Similarity	NPC115207
0.8797	High Similarity	NPC469698

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 NPC136750 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	369
0.1-0.2	865
0.2-0.3	1774
0.3-0.4	2854
0.4-0.5	1726
0.5-0.6	1034
0.6-0.7	454
0.7-0.8	67
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD3705	Approved
0.8507	High Similarity	NPD3027	Phase 3
0.8389	Intermediate Similarity	NPD4967	Phase 2
0.8389	Intermediate Similarity	NPD4965	Approved
0.8389	Intermediate Similarity	NPD4966	Approved
0.8333	Intermediate Similarity	NPD5283	Phase 1
0.8278	Intermediate Similarity	NPD6234	Discontinued
0.8188	Intermediate Similarity	NPD37	Approved
0.812	Intermediate Similarity	NPD2981	Phase 2
0.806	Intermediate Similarity	NPD2983	Phase 2
0.806	Intermediate Similarity	NPD2982	Phase 2
0.7973	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD3018	Phase 2
0.7935	Intermediate Similarity	NPD7199	Phase 2
0.7929	Intermediate Similarity	NPD1613	Approved
0.7929	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7228	Approved
0.7877	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1357	Approved
0.777	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7240	Approved
0.7698	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4908	Phase 1
0.7632	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6674	Discontinued
0.7584	Intermediate Similarity	NPD7124	Phase 2
0.7535	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5494	Approved
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7517	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3384	Approved
0.7484	Intermediate Similarity	NPD3383	Approved
0.7484	Intermediate Similarity	NPD3382	Approved
0.7483	Intermediate Similarity	NPD1375	Discontinued
0.7469	Intermediate Similarity	NPD3818	Discontinued
0.7451	Intermediate Similarity	NPD1653	Approved
0.7447	Intermediate Similarity	NPD2861	Phase 2
0.7415	Intermediate Similarity	NPD3539	Phase 1
0.7407	Intermediate Similarity	NPD5536	Phase 2
0.7397	Intermediate Similarity	NPD6111	Discontinued
0.7391	Intermediate Similarity	NPD1091	Approved
0.7389	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3540	Phase 1
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7365	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5058	Phase 3
0.732	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5111	Phase 2
0.7292	Intermediate Similarity	NPD5110	Phase 2
0.7292	Intermediate Similarity	NPD5109	Approved
0.7273	Intermediate Similarity	NPD7074	Phase 3
0.7267	Intermediate Similarity	NPD4237	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7261	Intermediate Similarity	NPD1934	Approved
0.726	Intermediate Similarity	NPD3657	Discovery
0.723	Intermediate Similarity	NPD4108	Discontinued
0.7226	Intermediate Similarity	NPD4210	Discontinued
0.7226	Intermediate Similarity	NPD1548	Phase 1
0.7219	Intermediate Similarity	NPD4110	Phase 3
0.7219	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD228	Approved
0.7215	Intermediate Similarity	NPD2978	Approved
0.7215	Intermediate Similarity	NPD2977	Approved
0.7212	Intermediate Similarity	NPD7054	Approved
0.7192	Intermediate Similarity	NPD3620	Phase 2
0.7192	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4005	Discontinued
0.7172	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3817	Phase 2
0.7169	Intermediate Similarity	NPD7472	Approved
0.7163	Intermediate Similarity	NPD4749	Approved
0.7163	Intermediate Similarity	NPD5327	Phase 3
0.7153	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4675	Approved
0.7134	Intermediate Similarity	NPD7028	Phase 2
0.7134	Intermediate Similarity	NPD4678	Approved
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7157	Approved
0.7125	Intermediate Similarity	NPD3882	Suspended
0.7122	Intermediate Similarity	NPD5125	Phase 3
0.7122	Intermediate Similarity	NPD5126	Approved
0.7121	Intermediate Similarity	NPD2684	Approved
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7466	Approved
0.7105	Intermediate Similarity	NPD6331	Phase 2
0.7103	Intermediate Similarity	NPD4625	Phase 3
0.7097	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4357	Discontinued
0.7075	Intermediate Similarity	NPD4060	Phase 1
0.7073	Intermediate Similarity	NPD5242	Approved
0.707	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3022	Approved
0.7068	Intermediate Similarity	NPD3021	Approved
0.7067	Intermediate Similarity	NPD2161	Phase 2
0.7067	Intermediate Similarity	NPD3454	Phase 3
0.7067	Intermediate Similarity	NPD2438	Suspended
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5585	Approved
0.7047	Intermediate Similarity	NPD6896	Approved
0.7047	Intermediate Similarity	NPD6895	Approved
0.7042	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7808	Phase 3
0.7039	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5535	Approved
0.7037	Intermediate Similarity	NPD7843	Approved
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7027	Intermediate Similarity	NPD5735	Approved
0.7024	Intermediate Similarity	NPD6797	Phase 2
0.7019	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD2801	Approved
0.7	Intermediate Similarity	NPD5588	Approved
0.7	Intermediate Similarity	NPD7680	Approved
0.6993	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3892	Phase 2
0.6982	Remote Similarity	NPD7251	Discontinued
0.6982	Remote Similarity	NPD6559	Discontinued
0.6975	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3926	Phase 2
0.6968	Remote Similarity	NPD5297	Approved
0.6959	Remote Similarity	NPD2979	Phase 3
0.6959	Remote Similarity	NPD2238	Phase 2
0.6957	Remote Similarity	NPD5353	Approved
0.6954	Remote Similarity	NPD2796	Approved
0.6944	Remote Similarity	NPD5005	Approved
0.6944	Remote Similarity	NPD5006	Approved
0.6941	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5451	Approved
0.6936	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD919	Approved
0.6933	Remote Similarity	NPD4536	Approved
0.6933	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4538	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6928	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6166	Phase 2
0.6928	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3060	Approved
0.6928	Remote Similarity	NPD5177	Phase 3
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1358	Approved
0.6909	Remote Similarity	NPD6232	Discontinued
0.6908	Remote Similarity	NPD5762	Approved
0.6908	Remote Similarity	NPD5763	Approved
0.6886	Remote Similarity	NPD7473	Discontinued
0.6884	Remote Similarity	NPD6387	Discontinued
0.6882	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2922	Phase 1
0.6875	Remote Similarity	NPD8651	Approved
0.6871	Remote Similarity	NPD7095	Approved
0.6871	Remote Similarity	NPD4055	Discovery
0.6867	Remote Similarity	NPD2492	Phase 1
0.6857	Remote Similarity	NPD1182	Approved
0.6853	Remote Similarity	NPD1840	Phase 2
0.6853	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD1247	Approved
0.6846	Remote Similarity	NPD4140	Approved
0.6846	Remote Similarity	NPD1558	Phase 1
0.6842	Remote Similarity	NPD3134	Approved
0.6842	Remote Similarity	NPD7549	Discontinued
0.6839	Remote Similarity	NPD2219	Phase 1
0.6838	Remote Similarity	NPD1137	Approved
0.6838	Remote Similarity	NPD1139	Approved
0.6835	Remote Similarity	NPD5976	Discontinued
0.6832	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5718	Phase 2
0.6821	Remote Similarity	NPD7097	Phase 1
0.6818	Remote Similarity	NPD1652	Phase 2
0.6818	Remote Similarity	NPD4162	Approved
0.6816	Remote Similarity	NPD4420	Approved
0.6815	Remote Similarity	NPD4123	Phase 3
0.6809	Remote Similarity	NPD1651	Approved
0.6807	Remote Similarity	NPD3787	Discontinued
0.6807	Remote Similarity	NPD7229	Phase 3
0.6806	Remote Similarity	NPD3685	Discontinued
0.6806	Remote Similarity	NPD4359	Approved
0.68	Remote Similarity	NPD5124	Phase 1
0.68	Remote Similarity	NPD1933	Approved
0.68	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8455	Phase 2
0.6788	Remote Similarity	NPD1138	Approved
0.6783	Remote Similarity	NPD422	Phase 1
0.6783	Remote Similarity	NPD1281	Approved
0.6779	Remote Similarity	NPD6233	Phase 2
0.6776	Remote Similarity	NPD5960	Phase 3
0.6776	Remote Similarity	NPD3748	Approved
0.6774	Remote Similarity	NPD4628	Phase 3

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