NPASS Compound

Structure

NPC83375 OpenBabel07101719122D 27 29 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 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 4.3301 0.5000 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 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 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 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 24 1 0 0 0 0 2 25 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 21 2 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 22 1 0 0 0 0 14 15 2 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 25 1 0 0 0 0 18 11 1 6 0 0 0 18 20 1 0 0 0 0 18 26 1 0 0 0 0 19 23 1 0 0 0 0 20 13 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	369.247
LogP:	1.871
LogD:	2.158
LogS:	-4.324
# Rotatable Bonds:	6
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	3.405
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	2.49604581767926e-05
Pgp-inhibitor:	0.639
Pgp-substrate:	0.133
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.542
Plasma Protein Binding (PPB):	82.55804443359375%
Volume Distribution (VD):	0.588
Pgp-substrate:	12.994933128356934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.484
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.645
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.618

ADMET: Excretion

Clearance (CL):	8.31
Half-life (T1/2):	0.636

ADMET: Toxicity

hERG Blockers:	0.224
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.277
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.892
Carcinogencity:	0.825
Eye Corrosion:	0.004
Eye Irritation:	0.173
Respiratory Toxicity:	0.359

Download Data

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

Natural Product: NPC83375

Natural Product ID:	NPC83375
*Common Name:**	(7's,8's)-5-Demethoxybilagrewin
IUPAC Name:	(E)-3-[(2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal
Synonyms:	(7'S,8'S)-5-Demethoxybilagrewin
Standard InCHIKey:	FDMXJKZGHCAZAI-XCJDPYLSSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-24-16-9-13(10-17(25-2)19(16)23)20-18(11-22)26-14-6-5-12(4-3-7-21)8-15(14)27-20/h3-10,18,20,22-23H,11H2,1-2H3/b4-3+/t18-,20-/m0/s1
SMILES:	O=C/C=C/c1ccc2c(c1)O[C@H]([C@@H](O2)CO)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL255298
PubChem CID:	24799853
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]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	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	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	>	50000.0	nM	PMID[469086]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	26880.0	nM	PMID[469086]

☑ 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 NPC83375 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	346
0.1-0.2	1491
0.2-0.3	4512
0.3-0.4	11269
0.4-0.5	6814
0.5-0.6	3682
0.6-0.7	6237
0.7-0.8	6609
0.8-0.85	1262
0.85-0.9	377
0.9-0.95	88
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224876
0.9925	High Similarity	NPC278469
0.9925	High Similarity	NPC193722
0.9776	High Similarity	NPC267291
0.9624	High Similarity	NPC214729
0.9549	High Similarity	NPC237594
0.9549	High Similarity	NPC119060
0.9549	High Similarity	NPC476387
0.9549	High Similarity	NPC249791
0.9474	High Similarity	NPC36490
0.9403	High Similarity	NPC170694
0.9338	High Similarity	NPC126206
0.9323	High Similarity	NPC472597
0.9291	High Similarity	NPC476347
0.9265	High Similarity	NPC306441
0.9265	High Similarity	NPC16435
0.9265	High Similarity	NPC471665
0.9265	High Similarity	NPC471664
0.9254	High Similarity	NPC35932
0.9254	High Similarity	NPC253105
0.9254	High Similarity	NPC201587
0.9254	High Similarity	NPC160991
0.9254	High Similarity	NPC16208
0.9254	High Similarity	NPC7903
0.9254	High Similarity	NPC184447
0.9248	High Similarity	NPC472338
0.9225	High Similarity	NPC187398
0.9225	High Similarity	NPC476348
0.9225	High Similarity	NPC473408
0.9191	High Similarity	NPC47398
0.9191	High Similarity	NPC260898
0.9191	High Similarity	NPC234333
0.9191	High Similarity	NPC112939
0.9191	High Similarity	NPC112246
0.9191	High Similarity	NPC470356
0.9191	High Similarity	NPC474206
0.9191	High Similarity	NPC61946
0.9191	High Similarity	NPC94750
0.9191	High Similarity	NPC121812
0.9173	High Similarity	NPC202582
0.9173	High Similarity	NPC470258
0.9173	High Similarity	NPC5851
0.9173	High Similarity	NPC190629
0.9173	High Similarity	NPC86030
0.9173	High Similarity	NPC3439
0.9173	High Similarity	NPC218856
0.9173	High Similarity	NPC222004
0.9173	High Similarity	NPC226788
0.9173	High Similarity	NPC210623
0.9173	High Similarity	NPC285339
0.9173	High Similarity	NPC273295
0.9161	High Similarity	NPC106138
0.9124	High Similarity	NPC269091
0.9124	High Similarity	NPC227503
0.9124	High Similarity	NPC302701
0.9124	High Similarity	NPC230734
0.9124	High Similarity	NPC474639
0.9118	High Similarity	NPC310854
0.9111	High Similarity	NPC470752
0.9098	High Similarity	NPC72529
0.9097	High Similarity	NPC205727
0.9097	High Similarity	NPC21184
0.9097	High Similarity	NPC294522
0.9097	High Similarity	NPC120426
0.9058	High Similarity	NPC107551
0.9058	High Similarity	NPC211549
0.9058	High Similarity	NPC326797
0.9058	High Similarity	NPC474282
0.9058	High Similarity	NPC103976
0.9058	High Similarity	NPC102904
0.9058	High Similarity	NPC176051
0.9051	High Similarity	NPC472337
0.9051	High Similarity	NPC164787
0.9051	High Similarity	NPC151224
0.9044	High Similarity	NPC168059
0.9044	High Similarity	NPC475840
0.9044	High Similarity	NPC229442
0.9044	High Similarity	NPC263064
0.9044	High Similarity	NPC11060
0.9041	High Similarity	NPC470769
0.9037	High Similarity	NPC30043
0.9037	High Similarity	NPC470096
0.9037	High Similarity	NPC470095
0.9037	High Similarity	NPC469613
0.9037	High Similarity	NPC469625
0.9037	High Similarity	NPC309787
0.903	High Similarity	NPC170844
0.903	High Similarity	NPC476968
0.9028	High Similarity	NPC475250
0.9028	High Similarity	NPC30688
0.9028	High Similarity	NPC176903
0.9023	High Similarity	NPC147821
0.9023	High Similarity	NPC41706
0.9023	High Similarity	NPC319625
0.9023	High Similarity	NPC292056
0.9023	High Similarity	NPC118787
0.9023	High Similarity	NPC111247
0.9023	High Similarity	NPC210355
0.9023	High Similarity	NPC163332
0.9023	High Similarity	NPC183181
0.9023	High Similarity	NPC474119
0.9	High Similarity	NPC471389
0.8993	High Similarity	NPC22517
0.8986	High Similarity	NPC472334
0.8986	High Similarity	NPC270456
0.8986	High Similarity	NPC248727
0.8986	High Similarity	NPC472336
0.8986	High Similarity	NPC471719
0.8986	High Similarity	NPC470802
0.8986	High Similarity	NPC162659
0.8986	High Similarity	NPC265433
0.8978	High Similarity	NPC317380
0.8978	High Similarity	NPC135127
0.8978	High Similarity	NPC111635
0.8971	High Similarity	NPC261619
0.8971	High Similarity	NPC219876
0.8971	High Similarity	NPC127624
0.8971	High Similarity	NPC61477
0.8971	High Similarity	NPC202762
0.8971	High Similarity	NPC15658
0.8971	High Similarity	NPC78770
0.8971	High Similarity	NPC185604
0.8971	High Similarity	NPC86655
0.8971	High Similarity	NPC126029
0.8963	High Similarity	NPC469612
0.8963	High Similarity	NPC469614
0.8958	High Similarity	NPC478237
0.8955	High Similarity	NPC252307
0.8955	High Similarity	NPC206615
0.8955	High Similarity	NPC474178
0.8955	High Similarity	NPC98631
0.8955	High Similarity	NPC186843
0.8955	High Similarity	NPC245826
0.8955	High Similarity	NPC470213
0.8951	High Similarity	NPC40222
0.8951	High Similarity	NPC268515
0.8947	High Similarity	NPC191037
0.8947	High Similarity	NPC178284
0.8947	High Similarity	NPC58607
0.8944	High Similarity	NPC284881
0.8944	High Similarity	NPC474444
0.8944	High Similarity	NPC264706
0.8944	High Similarity	NPC93433
0.8936	High Similarity	NPC189115
0.8936	High Similarity	NPC469559
0.8929	High Similarity	NPC210478
0.8929	High Similarity	NPC291101
0.8929	High Similarity	NPC184797
0.8929	High Similarity	NPC309124
0.8929	High Similarity	NPC266197
0.8921	High Similarity	NPC276490
0.8921	High Similarity	NPC474390
0.8913	High Similarity	NPC473413
0.8897	High Similarity	NPC474017
0.8897	High Similarity	NPC268266
0.8897	High Similarity	NPC268342
0.8897	High Similarity	NPC42760
0.8897	High Similarity	NPC220825
0.8889	High Similarity	NPC15577
0.8873	High Similarity	NPC478239
0.8872	High Similarity	NPC87113
0.8872	High Similarity	NPC271985
0.8872	High Similarity	NPC194519
0.8865	High Similarity	NPC469661
0.8857	High Similarity	NPC98777
0.8857	High Similarity	NPC25966
0.8857	High Similarity	NPC319647
0.8857	High Similarity	NPC471388
0.8857	High Similarity	NPC245207
0.8857	High Similarity	NPC212770
0.8857	High Similarity	NPC236306
0.8857	High Similarity	NPC260741
0.8857	High Similarity	NPC473739
0.8857	High Similarity	NPC70682
0.8857	High Similarity	NPC232164
0.8857	High Similarity	NPC127218
0.8849	High Similarity	NPC234952
0.8844	High Similarity	NPC163598
0.8844	High Similarity	NPC264875
0.8844	High Similarity	NPC120774
0.8841	High Similarity	NPC309744
0.8841	High Similarity	NPC478085
0.8841	High Similarity	NPC287745
0.8832	High Similarity	NPC5423
0.8832	High Similarity	NPC245120
0.8828	High Similarity	NPC93924
0.8824	High Similarity	NPC91291
0.8819	High Similarity	NPC287495
0.8819	High Similarity	NPC199928
0.8819	High Similarity	NPC9370
0.8811	High Similarity	NPC473045
0.8811	High Similarity	NPC25292
0.8803	High Similarity	NPC140502
0.8803	High Similarity	NPC475084
0.8803	High Similarity	NPC107161
0.8803	High Similarity	NPC157816
0.88	High Similarity	NPC470827
0.8797	High Similarity	NPC109822
0.8797	High Similarity	NPC293701
0.8797	High Similarity	NPC114901

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 NPC83375 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	892
0.2-0.3	1815
0.3-0.4	2745
0.4-0.5	1692
0.5-0.6	921
0.6-0.7	625
0.7-0.8	136
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
0.903	High Similarity	NPD3027	Phase 3
0.8971	High Similarity	NPD1612	Clinical (unspecified phase)
0.8971	High Similarity	NPD1613	Approved
0.8676	High Similarity	NPD1529	Clinical (unspecified phase)
0.8603	High Similarity	NPD1530	Clinical (unspecified phase)
0.8533	High Similarity	NPD1934	Approved
0.8514	High Similarity	NPD1653	Approved
0.8355	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2801	Approved
0.8228	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6166	Phase 2
0.8207	Intermediate Similarity	NPD7266	Discontinued
0.8175	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3882	Suspended
0.8075	Intermediate Similarity	NPD7054	Approved
0.8025	Intermediate Similarity	NPD7074	Phase 3
0.8025	Intermediate Similarity	NPD7472	Approved
0.8014	Intermediate Similarity	NPD4908	Phase 1
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD1511	Approved
0.7902	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD1610	Phase 2
0.7895	Intermediate Similarity	NPD1512	Approved
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7866	Intermediate Similarity	NPD6797	Phase 2
0.7853	Intermediate Similarity	NPD5844	Phase 1
0.7852	Intermediate Similarity	NPD1652	Phase 2
0.7834	Intermediate Similarity	NPD3817	Phase 2
0.7818	Intermediate Similarity	NPD7251	Discontinued
0.7806	Intermediate Similarity	NPD4380	Phase 2
0.7786	Intermediate Similarity	NPD2982	Phase 2
0.7786	Intermediate Similarity	NPD2983	Phase 2
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6190	Approved
0.7744	Intermediate Similarity	NPD228	Approved
0.7736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2981	Phase 2
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD2861	Phase 2
0.7692	Intermediate Similarity	NPD3018	Phase 2
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7667	Intermediate Similarity	NPD1549	Phase 2
0.7664	Intermediate Similarity	NPD5536	Phase 2
0.7658	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD4357	Discontinued
0.7643	Intermediate Similarity	NPD422	Phase 1
0.764	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD5124	Phase 1
0.7619	Intermediate Similarity	NPD230	Phase 1
0.7619	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD4625	Phase 3
0.7576	Intermediate Similarity	NPD7228	Approved
0.7569	Intermediate Similarity	NPD9494	Approved
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD4965	Approved
0.7562	Intermediate Similarity	NPD4966	Approved
0.7562	Intermediate Similarity	NPD4967	Phase 2
0.7551	Intermediate Similarity	NPD1558	Phase 1
0.7547	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4749	Approved
0.7534	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1091	Approved
0.7517	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4538	Approved
0.7517	Intermediate Similarity	NPD4536	Approved
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD5283	Phase 1
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4675	Approved
0.7468	Intermediate Similarity	NPD4678	Approved
0.7456	Intermediate Similarity	NPD7549	Discontinued
0.7432	Intermediate Similarity	NPD3620	Phase 2
0.7432	Intermediate Similarity	NPD4060	Phase 1
0.7432	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6799	Approved
0.7419	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2796	Approved
0.7417	Intermediate Similarity	NPD1551	Phase 2
0.7389	Intermediate Similarity	NPD5403	Approved
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2684	Approved
0.7386	Intermediate Similarity	NPD6674	Discontinued
0.7383	Intermediate Similarity	NPD4340	Discontinued
0.7375	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD6233	Phase 2
0.7351	Intermediate Similarity	NPD5588	Approved
0.7351	Intermediate Similarity	NPD5960	Phase 3
0.7351	Intermediate Similarity	NPD1510	Phase 2
0.7338	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD6232	Discontinued
0.7329	Intermediate Similarity	NPD7819	Suspended
0.7321	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2424	Discontinued
0.7299	Intermediate Similarity	NPD7843	Approved
0.7294	Intermediate Similarity	NPD7685	Pre-registration
0.729	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3060	Approved
0.7273	Intermediate Similarity	NPD3705	Approved
0.7266	Intermediate Similarity	NPD7157	Approved
0.7262	Intermediate Similarity	NPD3751	Discontinued
0.7261	Intermediate Similarity	NPD5401	Approved
0.7244	Intermediate Similarity	NPD5058	Phase 3
0.7233	Intermediate Similarity	NPD3686	Approved
0.7233	Intermediate Similarity	NPD3687	Approved
0.723	Intermediate Similarity	NPD7095	Approved
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3022	Approved
0.7206	Intermediate Similarity	NPD3021	Approved
0.7205	Intermediate Similarity	NPD7411	Suspended
0.7203	Intermediate Similarity	NPD3496	Discontinued
0.7202	Intermediate Similarity	NPD7473	Discontinued
0.72	Intermediate Similarity	NPD1240	Approved
0.7197	Intermediate Similarity	NPD7213	Phase 3
0.7197	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD6099	Approved
0.719	Intermediate Similarity	NPD6100	Approved
0.7188	Intermediate Similarity	NPD4005	Discontinued
0.7188	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD290	Approved
0.7183	Intermediate Similarity	NPD1357	Approved
0.7181	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD2219	Phase 1
0.7169	Intermediate Similarity	NPD1247	Approved
0.7169	Intermediate Similarity	NPD6959	Discontinued
0.7169	Intermediate Similarity	NPD8127	Discontinued
0.7161	Intermediate Similarity	NPD4162	Approved
0.7161	Intermediate Similarity	NPD4237	Approved
0.7161	Intermediate Similarity	NPD5177	Phase 3
0.7161	Intermediate Similarity	NPD4236	Phase 3
0.7152	Intermediate Similarity	NPD4123	Phase 3
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD919	Approved
0.7152	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD3540	Phase 1
0.7134	Intermediate Similarity	NPD7768	Phase 2
0.7133	Intermediate Similarity	NPD6516	Phase 2
0.7133	Intermediate Similarity	NPD5846	Approved
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7123	Intermediate Similarity	NPD8651	Approved
0.7115	Intermediate Similarity	NPD4110	Phase 3
0.7115	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD968	Approved
0.7107	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1607	Approved
0.7105	Intermediate Similarity	NPD6653	Approved
0.7099	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7240	Approved
0.7093	Intermediate Similarity	NPD7038	Approved
0.7093	Intermediate Similarity	NPD7039	Approved
0.7091	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5297	Approved
0.7086	Intermediate Similarity	NPD943	Approved
0.7081	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3539	Phase 1
0.7078	Intermediate Similarity	NPD2935	Discontinued
0.7073	Intermediate Similarity	NPD5353	Approved
0.707	Intermediate Similarity	NPD2677	Approved
0.7068	Intermediate Similarity	NPD291	Approved
0.7059	Intermediate Similarity	NPD1358	Approved
0.7051	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5535	Approved
0.7047	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6843	Phase 3
0.7045	Intermediate Similarity	NPD6841	Approved
0.7045	Intermediate Similarity	NPD6842	Approved
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6355	Discontinued
0.7039	Intermediate Similarity	NPD1933	Approved
0.7039	Intermediate Similarity	NPD5735	Approved
0.7032	Intermediate Similarity	NPD5762	Approved
0.7032	Intermediate Similarity	NPD5763	Approved
0.7027	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4062	Phase 3
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7013	Intermediate Similarity	NPD3748	Approved
0.7012	Intermediate Similarity	NPD5773	Approved
0.7012	Intermediate Similarity	NPD2978	Approved
0.7012	Intermediate Similarity	NPD5772	Approved
0.7012	Intermediate Similarity	NPD2977	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