NPASS Compound

Structure

CID193722 OpenBabel06191715582D 29 31 0 0 1 0 0 0 0 0999 V2000 -1.7321 -5.0000 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 2.5981 1.5000 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 5.1962 -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 -2.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 -0.8660 -0.5000 0.0000 C 0 0 1 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 -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 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 12 1 0 0 0 0 6 22 2 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 17 2 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 23 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 26 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 11 1 6 0 0 0 18 20 1 0 0 0 0 18 29 1 0 0 0 0 19 24 1 0 0 0 0 20 13 1 1 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	395.333
LogP:	1.751
LogD:	2.067
LogS:	-4.289
# Rotatable Bonds:	7
TPSA:	103.68
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	3.54
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.747
MDCK Permeability:	2.8704225769615732e-05
Pgp-inhibitor:	0.874
Pgp-substrate:	0.106
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.539
Plasma Protein Binding (PPB):	72.75230407714844%
Volume Distribution (VD):	0.577
Pgp-substrate:	21.352582931518555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.49
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.797
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.823
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.781

ADMET: Excretion

Clearance (CL):	7.741
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.29
Human Hepatotoxicity (H-HT):	0.352
Drug-inuced Liver Injury (DILI):	0.124
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.184
Skin Sensitization:	0.939
Carcinogencity:	0.409
Eye Corrosion:	0.003
Eye Irritation:	0.099
Respiratory Toxicity:	0.442

Download Data

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

Natural Product: NPC193722

Natural Product ID:	NPC193722
*Common Name:**	(7's,8's)-Bilagrewin
IUPAC Name:	(E)-3-[(2S,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydro-1,4-benzodioxin-7-yl]prop-2-enal
Synonyms:	(7'S,8'S)-Bilagrewin
Standard InCHIKey:	NEVUVMGBMOQVHU-BJUCQYRTSA-N
Standard InCHI:	InChI=1S/C21H22O8/c1-25-14-9-13(10-15(26-2)19(14)24)20-18(11-23)29-21-16(27-3)7-12(5-4-6-22)8-17(21)28-20/h4-10,18,20,23-24H,11H2,1-3H3/b5-4+/t18-,20-/m0/s1
SMILES:	O=C/C=C/c1cc2O[C@H]([C@@H](Oc2c(c1)OC)CO)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL274512
PubChem CID:	11567569
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002699] Benzodioxanes [CHEMONTID:0002704] Phenylbenzodioxanes [CHEMONTID:0002707] Phenylbenzo-1,4-dioxanes

*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
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	stem wood	Pakuashan, Changhua County, Taiwan	2006-Jun	PMID[18211005]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4154	Cortinarius violaceus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10592	Phascolosoma elongatum	Species	Phascolosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7348	Streptomyces gannmycicus	Species	Streptomycetaceae	Bacteria	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	48650.0	nM	PMID[517704]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[517704]

☑ 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 NPC193722 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	359
0.1-0.2	1476
0.2-0.3	4465
0.3-0.4	11289
0.4-0.5	6849
0.5-0.6	3698
0.6-0.7	6287
0.7-0.8	6566
0.8-0.85	1287
0.85-0.9	344
0.9-0.95	68
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC278469
0.9925	High Similarity	NPC83375
0.9925	High Similarity	NPC224876
0.9851	High Similarity	NPC267291
0.9552	High Similarity	NPC214729
0.9478	High Similarity	NPC170694
0.9478	High Similarity	NPC476387
0.9478	High Similarity	NPC237594
0.9478	High Similarity	NPC249791
0.9478	High Similarity	NPC119060
0.9403	High Similarity	NPC36490
0.9328	High Similarity	NPC160991
0.9328	High Similarity	NPC7903
0.9328	High Similarity	NPC16208
0.9328	High Similarity	NPC184447
0.9328	High Similarity	NPC35932
0.9296	High Similarity	NPC476348
0.9296	High Similarity	NPC187398
0.927	High Similarity	NPC126206
0.9254	High Similarity	NPC472597
0.9231	High Similarity	NPC106138
0.9225	High Similarity	NPC476347
0.9197	High Similarity	NPC471664
0.9197	High Similarity	NPC306441
0.9197	High Similarity	NPC471665
0.9197	High Similarity	NPC16435
0.9191	High Similarity	NPC310854
0.9185	High Similarity	NPC201587
0.9185	High Similarity	NPC253105
0.9179	High Similarity	NPC472338
0.9167	High Similarity	NPC294522
0.9167	High Similarity	NPC21184
0.9167	High Similarity	NPC205727
0.9167	High Similarity	NPC120426
0.9161	High Similarity	NPC473408
0.9124	High Similarity	NPC470356
0.9124	High Similarity	NPC94750
0.9124	High Similarity	NPC112939
0.9124	High Similarity	NPC61946
0.9124	High Similarity	NPC234333
0.9124	High Similarity	NPC121812
0.9124	High Similarity	NPC260898
0.9124	High Similarity	NPC47398
0.9124	High Similarity	NPC112246
0.9124	High Similarity	NPC474206
0.9111	High Similarity	NPC470095
0.9111	High Similarity	NPC469625
0.9111	High Similarity	NPC470096
0.9111	High Similarity	NPC469613
0.9111	High Similarity	NPC30043
0.911	High Similarity	NPC470769
0.9104	High Similarity	NPC86030
0.9104	High Similarity	NPC3439
0.9104	High Similarity	NPC218856
0.9104	High Similarity	NPC226788
0.9104	High Similarity	NPC210623
0.9104	High Similarity	NPC273295
0.9104	High Similarity	NPC190629
0.9104	High Similarity	NPC222004
0.9104	High Similarity	NPC285339
0.9104	High Similarity	NPC202582
0.9104	High Similarity	NPC5851
0.9104	High Similarity	NPC470258
0.9097	High Similarity	NPC176903
0.9097	High Similarity	NPC30688
0.9097	High Similarity	NPC475250
0.9065	High Similarity	NPC22517
0.9058	High Similarity	NPC471719
0.9058	High Similarity	NPC227503
0.9058	High Similarity	NPC474639
0.9058	High Similarity	NPC302701
0.9058	High Similarity	NPC269091
0.9058	High Similarity	NPC230734
0.9051	High Similarity	NPC135127
0.9044	High Similarity	NPC470752
0.9037	High Similarity	NPC469612
0.9037	High Similarity	NPC469614
0.903	High Similarity	NPC72529
0.9028	High Similarity	NPC478237
0.9021	High Similarity	NPC268515
0.9021	High Similarity	NPC40222
0.9007	High Similarity	NPC469559
0.9007	High Similarity	NPC189115
0.9	High Similarity	NPC266197
0.9	High Similarity	NPC291101
0.9	High Similarity	NPC210478
0.8993	High Similarity	NPC326797
0.8993	High Similarity	NPC102904
0.8993	High Similarity	NPC176051
0.8993	High Similarity	NPC107551
0.8993	High Similarity	NPC211549
0.8993	High Similarity	NPC103976
0.8993	High Similarity	NPC474282
0.8986	High Similarity	NPC164787
0.8986	High Similarity	NPC472337
0.8986	High Similarity	NPC151224
0.8978	High Similarity	NPC229442
0.8978	High Similarity	NPC475840
0.8978	High Similarity	NPC263064
0.8978	High Similarity	NPC11060
0.8978	High Similarity	NPC168059
0.8971	High Similarity	NPC309787
0.8963	High Similarity	NPC476968
0.8963	High Similarity	NPC170844
0.8958	High Similarity	NPC15577
0.8955	High Similarity	NPC319625
0.8955	High Similarity	NPC118787
0.8955	High Similarity	NPC163332
0.8955	High Similarity	NPC41706
0.8955	High Similarity	NPC111247
0.8955	High Similarity	NPC147821
0.8955	High Similarity	NPC292056
0.8955	High Similarity	NPC210355
0.8955	High Similarity	NPC474119
0.8955	High Similarity	NPC183181
0.8944	High Similarity	NPC478239
0.8936	High Similarity	NPC469661
0.8936	High Similarity	NPC471389
0.8929	High Similarity	NPC98777
0.8929	High Similarity	NPC212770
0.8921	High Similarity	NPC265433
0.8921	High Similarity	NPC270456
0.8921	High Similarity	NPC472334
0.8921	High Similarity	NPC472336
0.8921	High Similarity	NPC162659
0.8921	High Similarity	NPC248727
0.8921	High Similarity	NPC470802
0.8913	High Similarity	NPC317380
0.8913	High Similarity	NPC111635
0.8913	High Similarity	NPC309744
0.8912	High Similarity	NPC163598
0.8912	High Similarity	NPC264875
0.8912	High Similarity	NPC120774
0.8905	High Similarity	NPC15658
0.8905	High Similarity	NPC78770
0.8905	High Similarity	NPC127624
0.8905	High Similarity	NPC185604
0.8905	High Similarity	NPC126029
0.8905	High Similarity	NPC86655
0.8905	High Similarity	NPC261619
0.8905	High Similarity	NPC61477
0.8905	High Similarity	NPC219876
0.8905	High Similarity	NPC202762
0.8897	High Similarity	NPC93924
0.8889	High Similarity	NPC245826
0.8889	High Similarity	NPC470213
0.8889	High Similarity	NPC199928
0.8889	High Similarity	NPC474178
0.8889	High Similarity	NPC98631
0.8889	High Similarity	NPC206615
0.8889	High Similarity	NPC252307
0.8889	High Similarity	NPC186843
0.8881	High Similarity	NPC25292
0.8881	High Similarity	NPC93433
0.8881	High Similarity	NPC58607
0.8881	High Similarity	NPC178284
0.8881	High Similarity	NPC264706
0.8881	High Similarity	NPC284881
0.8881	High Similarity	NPC474444
0.8881	High Similarity	NPC473045
0.8881	High Similarity	NPC191037
0.8873	High Similarity	NPC475084
0.8873	High Similarity	NPC157816
0.8873	High Similarity	NPC140502
0.8867	High Similarity	NPC470827
0.8865	High Similarity	NPC309124
0.8865	High Similarity	NPC262189
0.8865	High Similarity	NPC184797
0.8857	High Similarity	NPC474390
0.8857	High Similarity	NPC65530
0.8857	High Similarity	NPC59324
0.8857	High Similarity	NPC276490
0.8851	High Similarity	NPC150442
0.8849	High Similarity	NPC473413
0.8832	High Similarity	NPC268266
0.8832	High Similarity	NPC220825
0.8832	High Similarity	NPC268342
0.8832	High Similarity	NPC474017
0.8832	High Similarity	NPC42760
0.8819	High Similarity	NPC475096
0.8819	High Similarity	NPC274960
0.8819	High Similarity	NPC143120
0.8819	High Similarity	NPC473909
0.8811	High Similarity	NPC473044
0.8808	High Similarity	NPC470828
0.8806	High Similarity	NPC194519
0.8806	High Similarity	NPC87113
0.8806	High Similarity	NPC271985
0.8803	High Similarity	NPC186406
0.8803	High Similarity	NPC178054
0.8794	High Similarity	NPC236306
0.8794	High Similarity	NPC127218
0.8794	High Similarity	NPC471388
0.8794	High Similarity	NPC245207
0.8794	High Similarity	NPC319647
0.8794	High Similarity	NPC232164
0.8794	High Similarity	NPC25966
0.8794	High Similarity	NPC473739
0.8794	High Similarity	NPC260741
0.8794	High Similarity	NPC70682

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 NPC193722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	897
0.2-0.3	1835
0.3-0.4	2742
0.4-0.5	1706
0.5-0.6	898
0.6-0.7	621
0.7-0.8	127
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8963	High Similarity	NPD3027	Phase 3
0.8905	High Similarity	NPD1612	Clinical (unspecified phase)
0.8905	High Similarity	NPD1613	Approved
0.8613	High Similarity	NPD1529	Clinical (unspecified phase)
0.8581	High Similarity	NPD1653	Approved
0.854	High Similarity	NPD1530	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1934	Approved
0.8312	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD6166	Phase 2
0.8291	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7266	Discontinued
0.8182	Intermediate Similarity	NPD2801	Approved
0.8137	Intermediate Similarity	NPD7054	Approved
0.8116	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD7472	Approved
0.8086	Intermediate Similarity	NPD7074	Phase 3
0.8077	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD3818	Discontinued
0.7958	Intermediate Similarity	NPD4908	Phase 1
0.7947	Intermediate Similarity	NPD1511	Approved
0.7927	Intermediate Similarity	NPD6797	Phase 2
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7879	Intermediate Similarity	NPD7251	Discontinued
0.7871	Intermediate Similarity	NPD4380	Phase 2
0.7857	Intermediate Similarity	NPD2982	Phase 2
0.7857	Intermediate Similarity	NPD2983	Phase 2
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1512	Approved
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7831	Intermediate Similarity	NPD7808	Phase 3
0.7831	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6190	Approved
0.781	Intermediate Similarity	NPD1548	Phase 1
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.78	Intermediate Similarity	NPD1652	Phase 2
0.7799	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2981	Phase 2
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7762	Intermediate Similarity	NPD3018	Phase 2
0.775	Intermediate Similarity	NPD6234	Discontinued
0.7722	Intermediate Similarity	NPD1465	Phase 2
0.7688	Intermediate Similarity	NPD7075	Discontinued
0.7687	Intermediate Similarity	NPD228	Approved
0.7658	Intermediate Similarity	NPD37	Approved
0.7639	Intermediate Similarity	NPD2861	Phase 2
0.7636	Intermediate Similarity	NPD7228	Approved
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD1549	Phase 2
0.7609	Intermediate Similarity	NPD5536	Phase 2
0.7597	Intermediate Similarity	NPD4357	Discontinued
0.7593	Intermediate Similarity	NPD5494	Approved
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7568	Intermediate Similarity	NPD5124	Phase 1
0.7568	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD230	Phase 1
0.7562	Intermediate Similarity	NPD5402	Approved
0.755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7199	Phase 2
0.7534	Intermediate Similarity	NPD4625	Phase 3
0.7517	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1558	Phase 1
0.7483	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4536	Approved
0.7467	Intermediate Similarity	NPD4538	Approved
0.7465	Intermediate Similarity	NPD1091	Approved
0.7452	Intermediate Similarity	NPD5403	Approved
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5283	Phase 1
0.7438	Intermediate Similarity	NPD6801	Discontinued
0.7436	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4678	Approved
0.7421	Intermediate Similarity	NPD4675	Approved
0.7412	Intermediate Similarity	NPD7549	Discontinued
0.7394	Intermediate Similarity	NPD6232	Discontinued
0.7391	Intermediate Similarity	NPD7819	Suspended
0.7383	Intermediate Similarity	NPD3620	Phase 2
0.7383	Intermediate Similarity	NPD4060	Phase 1
0.7383	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6799	Approved
0.7372	Intermediate Similarity	NPD7843	Approved
0.7368	Intermediate Similarity	NPD2796	Approved
0.7368	Intermediate Similarity	NPD1551	Phase 2
0.7353	Intermediate Similarity	NPD7685	Pre-registration
0.7349	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6674	Discontinued
0.7338	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD4340	Discontinued
0.7333	Intermediate Similarity	NPD2684	Approved
0.7325	Intermediate Similarity	NPD5401	Approved
0.7315	Intermediate Similarity	NPD6233	Phase 2
0.7303	Intermediate Similarity	NPD1510	Phase 2
0.7303	Intermediate Similarity	NPD5588	Approved
0.7303	Intermediate Similarity	NPD5960	Phase 3
0.729	Intermediate Similarity	NPD3750	Approved
0.729	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7262	Intermediate Similarity	NPD7473	Discontinued
0.725	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6959	Discontinued
0.7229	Intermediate Similarity	NPD8127	Discontinued
0.7226	Intermediate Similarity	NPD3060	Approved
0.7222	Intermediate Similarity	NPD3705	Approved
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7215	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3540	Phase 1
0.7197	Intermediate Similarity	NPD5058	Phase 3
0.7188	Intermediate Similarity	NPD3687	Approved
0.7188	Intermediate Similarity	NPD3686	Approved
0.7181	Intermediate Similarity	NPD7095	Approved
0.717	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3022	Approved
0.7153	Intermediate Similarity	NPD3496	Discontinued
0.7153	Intermediate Similarity	NPD3021	Approved
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7152	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7151	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD3539	Phase 1
0.7143	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD2219	Phase 1
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD1357	Approved
0.7132	Intermediate Similarity	NPD290	Approved
0.7126	Intermediate Similarity	NPD1247	Approved
0.7115	Intermediate Similarity	NPD5177	Phase 3
0.7115	Intermediate Similarity	NPD4237	Approved
0.7115	Intermediate Similarity	NPD4236	Phase 3
0.7115	Intermediate Similarity	NPD4162	Approved
0.7108	Intermediate Similarity	NPD919	Approved
0.7107	Intermediate Similarity	NPD7447	Phase 1
0.7107	Intermediate Similarity	NPD4123	Phase 3
0.7105	Intermediate Similarity	NPD447	Suspended
0.7102	Intermediate Similarity	NPD6842	Approved
0.7102	Intermediate Similarity	NPD6841	Approved
0.7102	Intermediate Similarity	NPD6843	Phase 3
0.7099	Intermediate Similarity	NPD6599	Discontinued
0.7097	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6584	Phase 3
0.7092	Intermediate Similarity	NPD6671	Approved
0.7091	Intermediate Similarity	NPD7768	Phase 2
0.7083	Intermediate Similarity	NPD3787	Discontinued
0.7083	Intermediate Similarity	NPD5846	Approved
0.7083	Intermediate Similarity	NPD6516	Phase 2
0.7075	Intermediate Similarity	NPD8651	Approved
0.707	Intermediate Similarity	NPD4110	Phase 3
0.707	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD968	Approved
0.7055	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7039	Approved
0.7052	Intermediate Similarity	NPD7038	Approved
0.7044	Intermediate Similarity	NPD5297	Approved
0.7041	Intermediate Similarity	NPD3926	Phase 2
0.7039	Intermediate Similarity	NPD943	Approved
0.7037	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2935	Discontinued
0.703	Intermediate Similarity	NPD5353	Approved
0.7025	Intermediate Similarity	NPD2677	Approved
0.7015	Intermediate Similarity	NPD291	Approved
0.7013	Intermediate Similarity	NPD7097	Phase 1
0.7007	Intermediate Similarity	NPD1358	Approved
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5535	Approved
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5735	Approved
0.6993	Remote Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD1933	Approved
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD5763	Approved
0.698	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4062	Phase 3
0.697	Remote Similarity	NPD2978	Approved
0.697	Remote Similarity	NPD5773	Approved
0.697	Remote Similarity	NPD8455	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