NPASS Compound

Structure

CID186316 OpenBabel06191715562D 38 43 0 0 1 0 0 0 0 0999 V2000 0.6022 2.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7578 -2.3101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0976 -0.6114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6714 -2.7168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0112 -0.2046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3931 0.9709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0533 -3.8924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0654 3.9992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2341 -0.5994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2759 -5.2502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9488 -2.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2886 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8274 -1.5130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7759 -3.7113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1157 0.7899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3067 1.3777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9669 -4.2991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1519 3.5924 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8328 -1.4085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3428 4.1802 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4293 3.7735 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3248 2.7789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0353 -2.4911 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6249 -0.4303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4261 -2.3220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1338 2.1912 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1699 4.9937 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4474 5.1747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6203 4.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4112 2.3722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5520 -2.5299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4112 2.3722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4910 0.0697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5849 -4.2991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2759 -5.2502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0293 1.1966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0473 2.5979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1692 -2.9911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 17 1 0 0 0 0 8 27 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 10 35 1 0 0 0 0 13 9 1 6 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 34 1 0 0 0 0 15 16 2 0 0 0 0 15 36 1 0 0 0 0 16 32 1 0 0 0 0 17 35 1 0 0 0 0 18 8 1 1 0 0 0 18 20 1 0 0 0 0 18 37 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 26 1 0 0 0 0 22 30 1 6 0 0 0 23 11 1 1 0 0 0 23 38 1 0 0 0 0 24 12 1 1 0 0 0 24 33 1 0 0 0 0 25 31 2 0 0 0 0 25 38 1 0 0 0 0 26 36 1 1 0 0 0 26 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	532.16
Volume:	493.941
LogP:	0.927
LogD:	1.187
LogS:	-3.97
# Rotatable Bonds:	6
TPSA:	162.6
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	4.533
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.888
MDCK Permeability:	4.972657188773155e-05
Pgp-inhibitor:	0.165
Pgp-substrate:	0.277
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.063
Plasma Protein Binding (PPB):	79.90541076660156%
Volume Distribution (VD):	0.485
Pgp-substrate:	11.031232833862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.264
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.193
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.872
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	3.12
Half-life (T1/2):	0.185

ADMET: Toxicity

hERG Blockers:	0.352
Human Hepatotoxicity (H-HT):	0.212
Drug-inuced Liver Injury (DILI):	0.709
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.09
Carcinogencity:	0.594
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC186316

Natural Product ID:	NPC186316
*Common Name:**	Styraxlignolide B
IUPAC Name:	(3R,3aR,6R,6aS)-6-(1,3-benzodioxol-5-yl)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3,3a,6,6a-tetrahydro-1H-furo[3,4-c]furan-4-one
Synonyms:	Styraxlignolide B
Standard InCHIKey:	HMBAEDHCQQWOCW-KVDZAEMRSA-N
Standard InCHI:	InChI=1S/C26H28O12/c1-32-16-6-12(3-5-15(16)36-26-22(30)21(29)20(28)18(8-27)37-26)24-19-13(9-33-24)23(38-25(19)31)11-2-4-14-17(7-11)35-10-34-14/h2-7,13,18-24,26-30H,8-10H2,1H3/t13-,18-,19-,20-,21+,22-,23+,24+,26-/m1/s1
SMILES:	COc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@H]1[C@H]2[C@@H](CO1)[C@H](c1ccc3c(c1)OCO3)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519719
PubChem CID:	11752938
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001511] Lignan glycosides

*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
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[15577246]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[15620237]
NPO30866	Styrax japonica	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17951	Styrax japonicus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17951	Styrax japonicus	Species	Styracaceae	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
NPT1	Others	Radical scavenging activity		IC50	>	500000.0	nM	PMID[537939]

☑ 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 NPC186316 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	327
0.1-0.2	1222
0.2-0.3	2905
0.3-0.4	6226
0.4-0.5	10756
0.5-0.6	7241
0.6-0.7	8762
0.7-0.8	4741
0.8-0.85	421
0.85-0.9	78
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC478055
0.9527	High Similarity	NPC158635
0.9527	High Similarity	NPC229882
0.9338	High Similarity	NPC299706
0.9338	High Similarity	NPC61604
0.9338	High Similarity	NPC115466
0.9338	High Similarity	NPC245615
0.9257	High Similarity	NPC3982
0.9205	High Similarity	NPC164082
0.9156	High Similarity	NPC163635
0.9145	High Similarity	NPC56184
0.9073	High Similarity	NPC477698
0.9045	High Similarity	NPC115624
0.9026	High Similarity	NPC136757
0.8986	High Similarity	NPC246947
0.8968	High Similarity	NPC38699
0.8961	High Similarity	NPC473236
0.8933	High Similarity	NPC223185
0.8919	High Similarity	NPC471908
0.8896	High Similarity	NPC477699
0.8875	High Similarity	NPC222531
0.8861	High Similarity	NPC218471
0.8861	High Similarity	NPC96593
0.8861	High Similarity	NPC239818
0.8854	High Similarity	NPC223335
0.8854	High Similarity	NPC40920
0.8844	High Similarity	NPC14022
0.8808	High Similarity	NPC279298
0.8808	High Similarity	NPC38041
0.8808	High Similarity	NPC469586
0.8808	High Similarity	NPC22150
0.8805	High Similarity	NPC152424
0.8805	High Similarity	NPC100465
0.8805	High Similarity	NPC288149
0.8797	High Similarity	NPC76211
0.8797	High Similarity	NPC469654
0.879	High Similarity	NPC228357
0.8784	High Similarity	NPC156376
0.875	High Similarity	NPC205796
0.875	High Similarity	NPC276753
0.875	High Similarity	NPC112861
0.8742	High Similarity	NPC166884
0.8742	High Similarity	NPC179521
0.8742	High Similarity	NPC141569
0.8742	High Similarity	NPC92693
0.8742	High Similarity	NPC191158
0.8742	High Similarity	NPC119910
0.8742	High Similarity	NPC477701
0.8742	High Similarity	NPC218841
0.8742	High Similarity	NPC44507
0.8742	High Similarity	NPC177644
0.8733	High Similarity	NPC52664
0.8727	High Similarity	NPC107739
0.8726	High Similarity	NPC254163
0.8718	High Similarity	NPC137813
0.8701	High Similarity	NPC474965
0.8701	High Similarity	NPC125570
0.8701	High Similarity	NPC668
0.8701	High Similarity	NPC293757
0.8701	High Similarity	NPC145569
0.8701	High Similarity	NPC216223
0.8701	High Similarity	NPC174512
0.8701	High Similarity	NPC477695
0.8701	High Similarity	NPC111785
0.8696	High Similarity	NPC14294
0.8696	High Similarity	NPC116759
0.8684	High Similarity	NPC18979
0.8679	High Similarity	NPC173726
0.8679	High Similarity	NPC241600
0.8675	High Similarity	NPC185307
0.8675	High Similarity	NPC470950
0.8675	High Similarity	NPC477898
0.8675	High Similarity	NPC23593
0.8671	High Similarity	NPC237946
0.8671	High Similarity	NPC32373
0.8671	High Similarity	NPC11411
0.8667	High Similarity	NPC100675
0.8667	High Similarity	NPC105137
0.8667	High Similarity	NPC166137
0.8667	High Similarity	NPC282291
0.8667	High Similarity	NPC184624
0.8654	High Similarity	NPC302610
0.8654	High Similarity	NPC36130
0.8654	High Similarity	NPC134905
0.8639	High Similarity	NPC19890
0.8639	High Similarity	NPC110958
0.8639	High Similarity	NPC47181
0.8636	High Similarity	NPC116229
0.8634	High Similarity	NPC22324
0.8627	High Similarity	NPC193779
0.8625	High Similarity	NPC150943
0.8625	High Similarity	NPC91634
0.8625	High Similarity	NPC268718
0.8623	High Similarity	NPC35266
0.8618	High Similarity	NPC283995
0.8618	High Similarity	NPC217635
0.8618	High Similarity	NPC471063
0.8618	High Similarity	NPC129417
0.8618	High Similarity	NPC79429
0.8618	High Similarity	NPC470235
0.8618	High Similarity	NPC471667
0.8618	High Similarity	NPC84181
0.8616	High Similarity	NPC19947
0.8616	High Similarity	NPC286919
0.8616	High Similarity	NPC207584
0.8616	High Similarity	NPC475663
0.8614	High Similarity	NPC475244
0.8609	High Similarity	NPC476356
0.8609	High Similarity	NPC151423
0.8609	High Similarity	NPC210354
0.8609	High Similarity	NPC40237
0.8609	High Similarity	NPC176586
0.8609	High Similarity	NPC287124
0.8609	High Similarity	NPC302506
0.8608	High Similarity	NPC10205
0.8606	High Similarity	NPC292712
0.8606	High Similarity	NPC114550
0.8606	High Similarity	NPC20114
0.8606	High Similarity	NPC312006
0.8606	High Similarity	NPC474075
0.8606	High Similarity	NPC471922
0.8606	High Similarity	NPC129930
0.8606	High Similarity	NPC471920
0.8606	High Similarity	NPC471921
0.8599	High Similarity	NPC308555
0.8591	High Similarity	NPC469981
0.859	High Similarity	NPC477700
0.8589	High Similarity	NPC306475
0.8581	High Similarity	NPC51328
0.8581	High Similarity	NPC55158
0.8581	High Similarity	NPC18576
0.8581	High Similarity	NPC286235
0.8571	High Similarity	NPC236089
0.8571	High Similarity	NPC205915
0.8563	High Similarity	NPC263955
0.8562	High Similarity	NPC469384
0.8562	High Similarity	NPC43508
0.8562	High Similarity	NPC476301
0.8553	High Similarity	NPC471405
0.8553	High Similarity	NPC474288
0.8553	High Similarity	NPC46092
0.8544	High Similarity	NPC327032
0.8544	High Similarity	NPC191046
0.8544	High Similarity	NPC194095
0.8543	High Similarity	NPC472711
0.8537	High Similarity	NPC185498
0.8533	High Similarity	NPC123526
0.8533	High Similarity	NPC88640
0.8533	High Similarity	NPC193666
0.8526	High Similarity	NPC475224
0.8526	High Similarity	NPC98624
0.8519	High Similarity	NPC61594
0.8519	High Similarity	NPC56735
0.8516	High Similarity	NPC130449
0.8516	High Similarity	NPC248132
0.8514	High Similarity	NPC476411
0.8514	High Similarity	NPC187194
0.8512	High Similarity	NPC29587
0.8506	High Similarity	NPC212890
0.85	High Similarity	NPC226759
0.8497	Intermediate Similarity	NPC475000
0.8497	Intermediate Similarity	NPC15743
0.8491	Intermediate Similarity	NPC131532
0.8481	Intermediate Similarity	NPC245948
0.8481	Intermediate Similarity	NPC44730
0.8477	Intermediate Similarity	NPC226547
0.8477	Intermediate Similarity	NPC56091
0.8477	Intermediate Similarity	NPC46591
0.8471	Intermediate Similarity	NPC13985
0.8471	Intermediate Similarity	NPC210642
0.8471	Intermediate Similarity	NPC32079
0.8467	Intermediate Similarity	NPC308976
0.8467	Intermediate Similarity	NPC101807
0.8466	Intermediate Similarity	NPC147596
0.8462	Intermediate Similarity	NPC35877
0.8462	Intermediate Similarity	NPC177476
0.8462	Intermediate Similarity	NPC262455
0.8462	Intermediate Similarity	NPC95392
0.8462	Intermediate Similarity	NPC55715
0.8462	Intermediate Similarity	NPC478242
0.8457	Intermediate Similarity	NPC7191
0.8457	Intermediate Similarity	NPC149873
0.8452	Intermediate Similarity	NPC193473
0.8452	Intermediate Similarity	NPC213074
0.8452	Intermediate Similarity	NPC224674
0.8452	Intermediate Similarity	NPC31325
0.8452	Intermediate Similarity	NPC39657
0.8452	Intermediate Similarity	NPC114505
0.8452	Intermediate Similarity	NPC275284
0.8452	Intermediate Similarity	NPC15956
0.8443	Intermediate Similarity	NPC316539
0.8442	Intermediate Similarity	NPC477702
0.8435	Intermediate Similarity	NPC227160
0.8435	Intermediate Similarity	NPC82111
0.8434	Intermediate Similarity	NPC179240
0.8431	Intermediate Similarity	NPC478239
0.8428	Intermediate Similarity	NPC103197
0.8428	Intermediate Similarity	NPC30009
0.8424	Intermediate Similarity	NPC298847
0.8421	Intermediate Similarity	NPC246474

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 NPC186316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	735
0.2-0.3	1696
0.3-0.4	2596
0.4-0.5	2123
0.5-0.6	1120
0.6-0.7	514
0.7-0.8	90
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD4965	Approved
0.8671	High Similarity	NPD4967	Phase 2
0.8671	High Similarity	NPD4966	Approved
0.8562	High Similarity	NPD6234	Discontinued
0.8537	High Similarity	NPD7228	Approved
0.8481	Intermediate Similarity	NPD37	Approved
0.8457	Intermediate Similarity	NPD7199	Phase 2
0.8333	Intermediate Similarity	NPD7240	Approved
0.8242	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7975	Intermediate Similarity	NPD8455	Phase 2
0.7965	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7054	Approved
0.7907	Intermediate Similarity	NPD7685	Pre-registration
0.7895	Intermediate Similarity	NPD7472	Approved
0.7829	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7266	Discontinued
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7785	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4110	Phase 3
0.7772	Intermediate Similarity	NPD7680	Approved
0.7759	Intermediate Similarity	NPD7808	Phase 3
0.7746	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD6355	Discontinued
0.7725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6674	Discontinued
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3817	Phase 2
0.7701	Intermediate Similarity	NPD7251	Discontinued
0.7697	Intermediate Similarity	NPD1934	Approved
0.7669	Intermediate Similarity	NPD1653	Approved
0.7665	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5494	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7614	Intermediate Similarity	NPD8312	Approved
0.7597	Intermediate Similarity	NPD6233	Phase 2
0.7588	Intermediate Similarity	NPD8127	Discontinued
0.7571	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD6166	Phase 2
0.7558	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD6798	Discontinued
0.7517	Intermediate Similarity	NPD3705	Approved
0.7516	Intermediate Similarity	NPD7097	Phase 1
0.7514	Intermediate Similarity	NPD7296	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7467	Intermediate Similarity	NPD1608	Approved
0.7456	Intermediate Similarity	NPD3882	Suspended
0.744	Intermediate Similarity	NPD2801	Approved
0.7436	Intermediate Similarity	NPD1613	Approved
0.7436	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD6190	Approved
0.7389	Intermediate Similarity	NPD1933	Approved
0.7386	Intermediate Similarity	NPD5647	Approved
0.7375	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6005	Phase 3
0.7375	Intermediate Similarity	NPD6002	Phase 3
0.7375	Intermediate Similarity	NPD6004	Phase 3
0.7375	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7028	Phase 2
0.7362	Intermediate Similarity	NPD5058	Phase 3
0.7355	Intermediate Similarity	NPD7095	Approved
0.7342	Intermediate Similarity	NPD6653	Approved
0.7341	Intermediate Similarity	NPD6232	Discontinued
0.7337	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7819	Suspended
0.7314	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD7075	Discontinued
0.7308	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5402	Approved
0.7285	Intermediate Similarity	NPD1091	Approved
0.7273	Intermediate Similarity	NPD3751	Discontinued
0.7267	Intermediate Similarity	NPD17	Approved
0.7261	Intermediate Similarity	NPD4062	Phase 3
0.7247	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1465	Phase 2
0.7228	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2861	Phase 2
0.7222	Intermediate Similarity	NPD5958	Discontinued
0.7219	Intermediate Similarity	NPD4420	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7205	Intermediate Similarity	NPD2438	Suspended
0.72	Intermediate Similarity	NPD1357	Approved
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6801	Discontinued
0.717	Intermediate Similarity	NPD447	Suspended
0.716	Intermediate Similarity	NPD5762	Approved
0.716	Intermediate Similarity	NPD4380	Phase 2
0.716	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7126	Intermediate Similarity	NPD6273	Approved
0.7118	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4534	Discontinued
0.7115	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1511	Approved
0.7108	Intermediate Similarity	NPD6799	Approved
0.7107	Intermediate Similarity	NPD4140	Approved
0.7097	Intermediate Similarity	NPD2797	Approved
0.7089	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5585	Approved
0.7083	Intermediate Similarity	NPD5403	Approved
0.7073	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5005	Approved
0.7068	Intermediate Similarity	NPD5006	Approved
0.7066	Intermediate Similarity	NPD5401	Approved
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD2346	Discontinued
0.7045	Intermediate Similarity	NPD7315	Approved
0.7037	Intermediate Similarity	NPD5588	Approved
0.7035	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1283	Approved
0.7024	Intermediate Similarity	NPD1512	Approved
0.702	Intermediate Similarity	NPD1894	Discontinued
0.7018	Intermediate Similarity	NPD7411	Suspended
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6032	Approved
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2935	Discontinued
0.6981	Remote Similarity	NPD3268	Approved
0.6975	Remote Similarity	NPD4538	Approved
0.6975	Remote Similarity	NPD4536	Approved
0.6975	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD919	Approved
0.697	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD5735	Approved
0.6951	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1375	Discontinued
0.6951	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3687	Approved
0.6941	Remote Similarity	NPD3686	Approved
0.6937	Remote Similarity	NPD8032	Phase 2
0.6933	Remote Similarity	NPD7157	Approved
0.6928	Remote Similarity	NPD5125	Phase 3
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5126	Approved
0.6923	Remote Similarity	NPD7039	Approved
0.6923	Remote Similarity	NPD7038	Approved
0.6919	Remote Similarity	NPD6385	Approved
0.6919	Remote Similarity	NPD6386	Approved
0.6909	Remote Similarity	NPD2424	Discontinued
0.6909	Remote Similarity	NPD1549	Phase 2
0.6901	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3620	Phase 2
0.689	Remote Similarity	NPD2796	Approved
0.6879	Remote Similarity	NPD6362	Approved
0.6875	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3764	Approved
0.6875	Remote Similarity	NPD2313	Discontinued
0.6872	Remote Similarity	NPD7999	Approved
0.6871	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7783	Phase 2
0.6869	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1652	Phase 2
0.6864	Remote Similarity	NPD3146	Approved
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6859	Remote Similarity	NPD4359	Approved
0.6857	Remote Similarity	NPD7768	Phase 2
0.6856	Remote Similarity	NPD7435	Discontinued
0.6855	Remote Similarity	NPD6832	Phase 2
0.6852	Remote Similarity	NPD4622	Approved
0.6852	Remote Similarity	NPD4618	Approved
0.6852	Remote Similarity	NPD230	Phase 1
0.685	Remote Similarity	NPD7930	Approved
0.6848	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7281	Phase 3
0.6848	Remote Similarity	NPD7280	Phase 3
0.6846	Remote Similarity	NPD7843	Approved
0.6846	Remote Similarity	NPD5535	Approved
0.6842	Remote Similarity	NPD5536	Phase 2
0.6839	Remote Similarity	NPD1610	Phase 2
0.6839	Remote Similarity	NPD2977	Approved
0.6839	Remote Similarity	NPD2978	Approved
0.6839	Remote Similarity	NPD1535	Discovery
0.6839	Remote Similarity	NPD1281	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