NPASS Compound

Structure

NPC229128 OpenBabel07101718292D 21 22 0 0 0 0 0 0 0 0999 V2000 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 2.5981 1.5000 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 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 -0.8660 0.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0981 -2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 3.4641 -0.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 16 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.12
Volume:	296.312
LogP:	2.173
LogD:	2.384
LogS:	-3.77
# Rotatable Bonds:	5
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	2.781
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.64
MDCK Permeability:	2.1706548068323173e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.195

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	74.8018569946289%
Volume Distribution (VD):	1.128
Pgp-substrate:	25.161344528198242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.792
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.762
CYP2D6-substrate:	0.744
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.474

ADMET: Excretion

Clearance (CL):	9.918
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.886
AMES Toxicity:	0.347
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.656
Carcinogencity:	0.39
Eye Corrosion:	0.012
Eye Irritation:	0.074
Respiratory Toxicity:	0.459

Download Data

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

Natural Product: NPC229128

Natural Product ID:	NPC229128
*Common Name:**	LSRWIDNPKXLEGE-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LSRWIDNPKXLEGE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O5/c1-16(2,9-17)8-11-13(20-4)7-12(19-3)10-5-6-14(18)21-15(10)11/h5-7,9H,8H2,1-4H3
SMILES:	O=CC(Cc1c(OC)cc(c2c1oc(=O)cc2)OC)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426660
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO33003	murraya alata	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25621853]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	12400.0	nM	PMID[518204]

☑ 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 NPC229128 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	406
0.1-0.2	1859
0.2-0.3	5006
0.3-0.4	11105
0.4-0.5	7099
0.5-0.6	4815
0.6-0.7	5920
0.7-0.8	4873
0.8-0.85	1119
0.85-0.9	404
0.9-0.95	84
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC61499
0.9385	High Similarity	NPC472517
0.9313	High Similarity	NPC175159
0.9302	High Similarity	NPC472519
0.9098	High Similarity	NPC54503
0.9044	High Similarity	NPC307883
0.9044	High Similarity	NPC253616
0.8992	High Similarity	NPC73413
0.8992	High Similarity	NPC201667
0.8971	High Similarity	NPC268081
0.8955	High Similarity	NPC55147
0.8923	High Similarity	NPC471827
0.8923	High Similarity	NPC471828
0.8915	High Similarity	NPC472518
0.8915	High Similarity	NPC109675
0.8915	High Similarity	NPC273772
0.8913	High Similarity	NPC155552
0.8913	High Similarity	NPC472515
0.8897	High Similarity	NPC283331
0.8864	High Similarity	NPC157212
0.8857	High Similarity	NPC251372
0.8846	High Similarity	NPC27671
0.8841	High Similarity	NPC36414
0.8837	High Similarity	NPC96286
0.8837	High Similarity	NPC248429
0.8811	High Similarity	NPC266743
0.876	High Similarity	NPC144418
0.8732	High Similarity	NPC208584
0.8712	High Similarity	NPC471826
0.8696	High Similarity	NPC471069
0.8696	High Similarity	NPC471068
0.869	High Similarity	NPC191104
0.8682	High Similarity	NPC163200
0.8682	High Similarity	NPC180006
0.8682	High Similarity	NPC235190
0.8676	High Similarity	NPC222036
0.8676	High Similarity	NPC7526
0.8662	High Similarity	NPC71739
0.8657	High Similarity	NPC168710
0.8647	High Similarity	NPC289316
0.8647	High Similarity	NPC37512
0.8643	High Similarity	NPC310370
0.8643	High Similarity	NPC136095
0.8643	High Similarity	NPC183642
0.8633	High Similarity	NPC471070
0.8633	High Similarity	NPC471072
0.8633	High Similarity	NPC471071
0.8633	High Similarity	NPC38153
0.8626	High Similarity	NPC154176
0.8626	High Similarity	NPC173350
0.8626	High Similarity	NPC290605
0.8623	High Similarity	NPC55615
0.8623	High Similarity	NPC283019
0.8623	High Similarity	NPC149320
0.8623	High Similarity	NPC177281
0.8623	High Similarity	NPC128529
0.8623	High Similarity	NPC471630
0.8623	High Similarity	NPC476455
0.8623	High Similarity	NPC160727
0.8621	High Similarity	NPC88445
0.8613	High Similarity	NPC164269
0.8613	High Similarity	NPC74655
0.8613	High Similarity	NPC307412
0.8613	High Similarity	NPC84894
0.8613	High Similarity	NPC100986
0.8613	High Similarity	NPC198381
0.8613	High Similarity	NPC166672
0.8613	High Similarity	NPC287182
0.8613	High Similarity	NPC127888
0.8613	High Similarity	NPC47163
0.8613	High Similarity	NPC195343
0.8613	High Similarity	NPC319859
0.8613	High Similarity	NPC55149
0.8613	High Similarity	NPC267412
0.8613	High Similarity	NPC18804
0.8613	High Similarity	NPC260265
0.8611	High Similarity	NPC304443
0.8611	High Similarity	NPC74539
0.8603	High Similarity	NPC14248
0.8593	High Similarity	NPC80170
0.8582	High Similarity	NPC470856
0.8582	High Similarity	NPC199204
0.8582	High Similarity	NPC185066
0.8571	High Similarity	NPC163248
0.8571	High Similarity	NPC234109
0.8571	High Similarity	NPC188327
0.8571	High Similarity	NPC71903
0.8561	High Similarity	NPC291899
0.8561	High Similarity	NPC472516
0.8551	High Similarity	NPC281241
0.8551	High Similarity	NPC471909
0.8551	High Similarity	NPC86892
0.8551	High Similarity	NPC472424
0.8551	High Similarity	NPC471625
0.855	High Similarity	NPC150214
0.854	High Similarity	NPC471910
0.854	High Similarity	NPC31849
0.854	High Similarity	NPC296624
0.854	High Similarity	NPC229646
0.854	High Similarity	NPC318400
0.854	High Similarity	NPC207002
0.854	High Similarity	NPC167111
0.854	High Similarity	NPC133956
0.8527	High Similarity	NPC298796
0.8527	High Similarity	NPC281356
0.8521	High Similarity	NPC229916
0.8511	High Similarity	NPC170812
0.8511	High Similarity	NPC473209
0.8507	High Similarity	NPC243688
0.85	High Similarity	NPC103001
0.8496	Intermediate Similarity	NPC165556
0.8493	Intermediate Similarity	NPC146014
0.8489	Intermediate Similarity	NPC46869
0.8489	Intermediate Similarity	NPC104796
0.8485	Intermediate Similarity	NPC50720
0.8485	Intermediate Similarity	NPC315807
0.8478	Intermediate Similarity	NPC224475
0.8478	Intermediate Similarity	NPC213173
0.8478	Intermediate Similarity	NPC180716
0.8472	Intermediate Similarity	NPC171656
0.8467	Intermediate Similarity	NPC270044
0.8462	Intermediate Similarity	NPC51146
0.8462	Intermediate Similarity	NPC166858
0.845	Intermediate Similarity	NPC265547
0.845	Intermediate Similarity	NPC152306
0.845	Intermediate Similarity	NPC96705
0.8429	Intermediate Similarity	NPC306365
0.8429	Intermediate Similarity	NPC14697
0.8429	Intermediate Similarity	NPC161196
0.8429	Intermediate Similarity	NPC254741
0.8429	Intermediate Similarity	NPC155963
0.8425	Intermediate Similarity	NPC146388
0.8421	Intermediate Similarity	NPC111347
0.8417	Intermediate Similarity	NPC469675
0.8417	Intermediate Similarity	NPC472525
0.8417	Intermediate Similarity	NPC66705
0.8409	Intermediate Similarity	NPC13007
0.8409	Intermediate Similarity	NPC257188
0.8406	Intermediate Similarity	NPC83535
0.8403	Intermediate Similarity	NPC295696
0.8392	Intermediate Similarity	NPC22467
0.8392	Intermediate Similarity	NPC201820
0.8389	Intermediate Similarity	NPC131725
0.8382	Intermediate Similarity	NPC474289
0.838	Intermediate Similarity	NPC11566
0.838	Intermediate Similarity	NPC23257
0.838	Intermediate Similarity	NPC472523
0.837	Intermediate Similarity	NPC224774
0.837	Intermediate Similarity	NPC258567
0.837	Intermediate Similarity	NPC121740
0.8369	Intermediate Similarity	NPC151946
0.8369	Intermediate Similarity	NPC221046
0.8369	Intermediate Similarity	NPC211110
0.8369	Intermediate Similarity	NPC259685
0.8369	Intermediate Similarity	NPC332594
0.8358	Intermediate Similarity	NPC232692
0.8358	Intermediate Similarity	NPC202594
0.8358	Intermediate Similarity	NPC93219
0.8358	Intermediate Similarity	NPC244495
0.8357	Intermediate Similarity	NPC38099
0.8357	Intermediate Similarity	NPC26954
0.8356	Intermediate Similarity	NPC218300
0.8356	Intermediate Similarity	NPC282335
0.8356	Intermediate Similarity	NPC142863
0.8346	Intermediate Similarity	NPC143725
0.8345	Intermediate Similarity	NPC294365
0.8345	Intermediate Similarity	NPC206212
0.8345	Intermediate Similarity	NPC246903
0.8345	Intermediate Similarity	NPC204353
0.8345	Intermediate Similarity	NPC71184
0.8345	Intermediate Similarity	NPC62366
0.8345	Intermediate Similarity	NPC50896
0.8345	Intermediate Similarity	NPC469953
0.8345	Intermediate Similarity	NPC326600
0.8344	Intermediate Similarity	NPC269495
0.8333	Intermediate Similarity	NPC295608
0.8333	Intermediate Similarity	NPC280476
0.8333	Intermediate Similarity	NPC194277
0.8333	Intermediate Similarity	NPC19157
0.8333	Intermediate Similarity	NPC36181
0.8333	Intermediate Similarity	NPC278010
0.8333	Intermediate Similarity	NPC250769
0.8333	Intermediate Similarity	NPC469956
0.8333	Intermediate Similarity	NPC119985
0.8322	Intermediate Similarity	NPC472409
0.8322	Intermediate Similarity	NPC307990
0.8322	Intermediate Similarity	NPC471587
0.8322	Intermediate Similarity	NPC16455
0.8321	Intermediate Similarity	NPC183348
0.8321	Intermediate Similarity	NPC327457
0.8321	Intermediate Similarity	NPC113098
0.8321	Intermediate Similarity	NPC32463
0.8321	Intermediate Similarity	NPC86774
0.8321	Intermediate Similarity	NPC282230
0.831	Intermediate Similarity	NPC312881
0.831	Intermediate Similarity	NPC17848
0.8309	Intermediate Similarity	NPC293642
0.8309	Intermediate Similarity	NPC469453
0.8309	Intermediate Similarity	NPC473907
0.8309	Intermediate Similarity	NPC60704

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 NPC229128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	1003
0.2-0.3	1866
0.3-0.4	2709
0.4-0.5	1819
0.5-0.6	948
0.6-0.7	305
0.7-0.8	88
0.8-0.85	28
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8611	High Similarity	NPD920	Approved
0.8593	High Similarity	NPD6859	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1296	Phase 2
0.8298	Intermediate Similarity	NPD2796	Approved
0.8252	Intermediate Similarity	NPD1243	Approved
0.82	Intermediate Similarity	NPD6801	Discontinued
0.8188	Intermediate Similarity	NPD6599	Discontinued
0.8151	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD7411	Suspended
0.8125	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD3748	Approved
0.806	Intermediate Similarity	NPD422	Phase 1
0.8052	Intermediate Similarity	NPD919	Approved
0.8026	Intermediate Similarity	NPD7819	Suspended
0.8026	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD5124	Phase 1
0.7973	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD3267	Approved
0.7956	Intermediate Similarity	NPD3266	Approved
0.7945	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6832	Phase 2
0.7914	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD7075	Discontinued
0.7852	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD2797	Approved
0.7823	Intermediate Similarity	NPD4628	Phase 3
0.7823	Intermediate Similarity	NPD3750	Approved
0.7808	Intermediate Similarity	NPD1549	Phase 2
0.7801	Intermediate Similarity	NPD3268	Approved
0.7793	Intermediate Similarity	NPD1551	Phase 2
0.774	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1510	Phase 2
0.7692	Intermediate Similarity	NPD1240	Approved
0.7692	Intermediate Similarity	NPD7768	Phase 2
0.7687	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1241	Discontinued
0.7635	Intermediate Similarity	NPD2800	Approved
0.7628	Intermediate Similarity	NPD3817	Phase 2
0.7626	Intermediate Similarity	NPD3225	Approved
0.7603	Intermediate Similarity	NPD7033	Discontinued
0.7597	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD6651	Approved
0.7586	Intermediate Similarity	NPD1607	Approved
0.7578	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4307	Phase 2
0.7564	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD1019	Discontinued
0.7518	Intermediate Similarity	NPD17	Approved
0.7518	Intermediate Similarity	NPD1778	Approved
0.7517	Intermediate Similarity	NPD1652	Phase 2
0.7516	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.7482	Intermediate Similarity	NPD9717	Approved
0.7482	Intermediate Similarity	NPD3972	Approved
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5691	Approved
0.7444	Intermediate Similarity	NPD5535	Approved
0.7442	Intermediate Similarity	NPD9697	Approved
0.7439	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD5494	Approved
0.7432	Intermediate Similarity	NPD6100	Approved
0.7432	Intermediate Similarity	NPD2935	Discontinued
0.7432	Intermediate Similarity	NPD6099	Approved
0.7431	Intermediate Similarity	NPD6798	Discontinued
0.7431	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD3134	Approved
0.7372	Intermediate Similarity	NPD1548	Phase 1
0.7372	Intermediate Similarity	NPD9545	Approved
0.7365	Intermediate Similarity	NPD4308	Phase 3
0.7357	Intermediate Similarity	NPD1608	Approved
0.7349	Intermediate Similarity	NPD5953	Discontinued
0.7346	Intermediate Similarity	NPD7229	Phase 3
0.7328	Intermediate Similarity	NPD1358	Approved
0.7324	Intermediate Similarity	NPD1203	Approved
0.7312	Intermediate Similarity	NPD3749	Approved
0.731	Intermediate Similarity	NPD2313	Discontinued
0.7308	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4908	Phase 1
0.7279	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD1934	Approved
0.7267	Intermediate Similarity	NPD6002	Phase 3
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6005	Phase 3
0.7267	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6004	Phase 3
0.726	Intermediate Similarity	NPD8032	Phase 2
0.7255	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3882	Suspended
0.7246	Intermediate Similarity	NPD1894	Discontinued
0.7233	Intermediate Similarity	NPD2801	Approved
0.7229	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3496	Discontinued
0.7208	Intermediate Similarity	NPD1511	Approved
0.7202	Intermediate Similarity	NPD6559	Discontinued
0.72	Intermediate Similarity	NPD4476	Approved
0.72	Intermediate Similarity	NPD4477	Approved
0.7197	Intermediate Similarity	NPD7458	Discontinued
0.7194	Intermediate Similarity	NPD5585	Approved
0.719	Intermediate Similarity	NPD3887	Approved
0.7188	Intermediate Similarity	NPD5402	Approved
0.7188	Intermediate Similarity	NPD4288	Approved
0.7178	Intermediate Similarity	NPD6959	Discontinued
0.7178	Intermediate Similarity	NPD7199	Phase 2
0.7171	Intermediate Similarity	NPD2654	Approved
0.7163	Intermediate Similarity	NPD1610	Phase 2
0.7163	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD230	Phase 1
0.7162	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD4626	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7133	Intermediate Similarity	NPD8651	Approved
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7124	Intermediate Similarity	NPD7003	Approved
0.7115	Intermediate Similarity	NPD1512	Approved
0.7115	Intermediate Similarity	NPD6273	Approved
0.7115	Intermediate Similarity	NPD2186	Approved
0.7107	Intermediate Similarity	NPD5889	Approved
0.7107	Intermediate Similarity	NPD5890	Approved
0.7095	Intermediate Similarity	NPD3142	Approved
0.7095	Intermediate Similarity	NPD2979	Phase 3
0.7095	Intermediate Similarity	NPD3140	Approved
0.7091	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3226	Approved
0.7075	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3818	Discontinued
0.7042	Intermediate Similarity	NPD1281	Approved
0.7039	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2353	Approved
0.7027	Intermediate Similarity	NPD4062	Phase 3
0.7025	Intermediate Similarity	NPD1653	Approved
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD6104	Discontinued
0.6994	Remote Similarity	NPD6971	Discontinued
0.6993	Remote Similarity	NPD2424	Discontinued
0.6988	Remote Similarity	NPD3926	Phase 2
0.6988	Remote Similarity	NPD5242	Approved
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4060	Phase 1
0.6975	Remote Similarity	NPD5353	Approved
0.6974	Remote Similarity	NPD2438	Suspended
0.6972	Remote Similarity	NPD3847	Discontinued
0.697	Remote Similarity	NPD8127	Discontinued
0.6964	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD411	Approved
0.695	Remote Similarity	NPD1651	Approved
0.6946	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6166	Phase 2
0.6944	Remote Similarity	NPD4359	Approved
0.6941	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2614	Approved
0.6937	Remote Similarity	NPD6585	Discontinued
0.6933	Remote Similarity	NPD4622	Approved
0.6933	Remote Similarity	NPD4618	Approved
0.6933	Remote Similarity	NPD4340	Discontinued
0.6933	Remote Similarity	NPD447	Suspended
0.6928	Remote Similarity	NPD5711	Approved
0.6928	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD5710	Approved
0.6923	Remote Similarity	NPD1535	Discovery
0.6923	Remote Similarity	NPD6666	Approved
0.6923	Remote Similarity	NPD7054	Approved
0.6923	Remote Similarity	NPD6667	Approved
0.6923	Remote Similarity	NPD1611	Approved
0.6918	Remote Similarity	NPD2798	Approved
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8455	Phase 2
0.6906	Remote Similarity	NPD7157	Approved
0.6903	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4110	Phase 3
0.6899	Remote Similarity	NPD5049	Phase 3
0.6899	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1283	Approved
0.6892	Remote Similarity	NPD7095	Approved
0.6892	Remote Similarity	NPD4625	Phase 3
0.6889	Remote Similarity	NPD2684	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