NPASS Compound

Structure

NPC61499 OpenBabel07101718182D 22 23 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 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 2.0981 -2.3660 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 O 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 2.5981 -3.2321 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 20 1 0 0 0 0 4 21 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 13 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.11
Volume:	305.102
LogP:	2.383
LogD:	1.514
LogS:	-3.38
# Rotatable Bonds:	5
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.854
Synthetic Accessibility Score:	2.562
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.87
MDCK Permeability:	4.385992724564858e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.537

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	77.33814239501953%
Volume Distribution (VD):	0.85
Pgp-substrate:	23.422739028930664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.31
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	3.558
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.826
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.221
Carcinogencity:	0.39
Eye Corrosion:	0.004
Eye Irritation:	0.031
Respiratory Toxicity:	0.354

Download Data

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

Natural Product: NPC61499

Natural Product ID:	NPC61499
*Common Name:**	SAIWRXJZCXKHCP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SAIWRXJZCXKHCP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H18O6/c1-16(2,15(18)19)8-10-12(21-4)7-11(20-3)9-5-6-13(17)22-14(9)10/h5-7H,8H2,1-4H3,(H,18,19)
SMILES:	COc1cc(OC)c2c(c1CC(C(=O)O)(C)C)oc(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426661
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[479814]

☑ 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 NPC61499 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	354
0.1-0.2	1708
0.2-0.3	4302
0.3-0.4	10363
0.4-0.5	8246
0.5-0.6	4403
0.6-0.7	6075
0.7-0.8	4900
0.8-0.85	1468
0.85-0.9	720
0.9-0.95	154
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC229128
0.9191	High Similarity	NPC155552
0.9098	High Similarity	NPC54503
0.9065	High Similarity	NPC71739
0.9051	High Similarity	NPC183642
0.9051	High Similarity	NPC310370
0.9044	High Similarity	NPC253616
0.9008	High Similarity	NPC185066
0.8992	High Similarity	NPC73413
0.8992	High Similarity	NPC201667
0.8978	High Similarity	NPC71903
0.8971	High Similarity	NPC471069
0.8971	High Similarity	NPC268081
0.8971	High Similarity	NPC471068
0.8955	High Similarity	NPC55147
0.8947	High Similarity	NPC472517
0.8931	High Similarity	NPC243688
0.8923	High Similarity	NPC471827
0.8923	High Similarity	NPC471828
0.8915	High Similarity	NPC273772
0.8915	High Similarity	NPC109675
0.8915	High Similarity	NPC472518
0.8913	High Similarity	NPC170812
0.8913	High Similarity	NPC472515
0.8905	High Similarity	NPC307883
0.8905	High Similarity	NPC471070
0.8905	High Similarity	NPC471071
0.8905	High Similarity	NPC471072
0.8881	High Similarity	NPC175159
0.8864	High Similarity	NPC157212
0.8864	High Similarity	NPC472519
0.8846	High Similarity	NPC27671
0.8841	High Similarity	NPC36414
0.8837	High Similarity	NPC96286
0.8837	High Similarity	NPC248429
0.8815	High Similarity	NPC83535
0.8815	High Similarity	NPC31849
0.8797	High Similarity	NPC474289
0.8794	High Similarity	NPC295696
0.8786	High Similarity	NPC229916
0.8779	High Similarity	NPC244495
0.8779	High Similarity	NPC93219
0.8768	High Similarity	NPC221046
0.8768	High Similarity	NPC332594
0.876	High Similarity	NPC144418
0.8759	High Similarity	NPC283331
0.875	High Similarity	NPC213173
0.875	High Similarity	NPC224475
0.875	High Similarity	NPC180716
0.875	High Similarity	NPC146014
0.8741	High Similarity	NPC142863
0.8732	High Similarity	NPC206212
0.8732	High Similarity	NPC469953
0.8732	High Similarity	NPC71184
0.8731	High Similarity	NPC86774
0.8731	High Similarity	NPC327457
0.8731	High Similarity	NPC32463
0.8723	High Similarity	NPC36181
0.8723	High Similarity	NPC251372
0.8712	High Similarity	NPC471826
0.8696	High Similarity	NPC155963
0.8696	High Similarity	NPC174999
0.8686	High Similarity	NPC472525
0.8681	High Similarity	NPC146388
0.8671	High Similarity	NPC470322
0.8671	High Similarity	NPC154217
0.8667	High Similarity	NPC37009
0.8667	High Similarity	NPC66430
0.8662	High Similarity	NPC94794
0.8662	High Similarity	NPC196459
0.8662	High Similarity	NPC87609
0.8662	High Similarity	NPC188632
0.8662	High Similarity	NPC470296
0.8662	High Similarity	NPC112791
0.8657	High Similarity	NPC168710
0.8652	High Similarity	NPC103362
0.8652	High Similarity	NPC110969
0.8647	High Similarity	NPC121740
0.8647	High Similarity	NPC289316
0.8647	High Similarity	NPC258567
0.8647	High Similarity	NPC224774
0.8647	High Similarity	NPC37512
0.8643	High Similarity	NPC23257
0.8636	High Similarity	NPC232692
0.8636	High Similarity	NPC202594
0.8633	High Similarity	NPC319870
0.8633	High Similarity	NPC138047
0.8633	High Similarity	NPC131782
0.8633	High Similarity	NPC23870
0.8633	High Similarity	NPC73078
0.8633	High Similarity	NPC148738
0.8633	High Similarity	NPC474624
0.8633	High Similarity	NPC151946
0.8633	High Similarity	NPC38153
0.8633	High Similarity	NPC327612
0.8626	High Similarity	NPC154176
0.8626	High Similarity	NPC173350
0.8626	High Similarity	NPC290605
0.8623	High Similarity	NPC26954
0.8623	High Similarity	NPC38099
0.8623	High Similarity	NPC223616
0.8613	High Similarity	NPC326600
0.8613	High Similarity	NPC50896
0.8613	High Similarity	NPC27643
0.8613	High Similarity	NPC62366
0.8613	High Similarity	NPC204353
0.8611	High Similarity	NPC180477
0.8603	High Similarity	NPC194277
0.8601	High Similarity	NPC469935
0.8601	High Similarity	NPC1886
0.8601	High Similarity	NPC196137
0.8601	High Similarity	NPC178627
0.8593	High Similarity	NPC113098
0.8592	High Similarity	NPC11561
0.8592	High Similarity	NPC226636
0.8582	High Similarity	NPC2401
0.8582	High Similarity	NPC221173
0.8582	High Similarity	NPC159275
0.8582	High Similarity	NPC150522
0.8582	High Similarity	NPC471587
0.8582	High Similarity	NPC16455
0.8582	High Similarity	NPC241100
0.8582	High Similarity	NPC469453
0.8582	High Similarity	NPC172986
0.8582	High Similarity	NPC307990
0.8582	High Similarity	NPC261227
0.8582	High Similarity	NPC270883
0.8571	High Similarity	NPC131130
0.8571	High Similarity	NPC163248
0.8571	High Similarity	NPC183639
0.8571	High Similarity	NPC199458
0.8571	High Similarity	NPC219584
0.8571	High Similarity	NPC470668
0.8571	High Similarity	NPC470669
0.8571	High Similarity	NPC470083
0.8571	High Similarity	NPC312881
0.8561	High Similarity	NPC291899
0.8561	High Similarity	NPC131198
0.8561	High Similarity	NPC89630
0.8561	High Similarity	NPC472516
0.8552	High Similarity	NPC211811
0.8551	High Similarity	NPC125920
0.855	High Similarity	NPC150214
0.8542	High Similarity	NPC181388
0.8542	High Similarity	NPC286038
0.8542	High Similarity	NPC57470
0.854	High Similarity	NPC222036
0.854	High Similarity	NPC163557
0.854	High Similarity	NPC229646
0.854	High Similarity	NPC7526
0.8538	High Similarity	NPC180006
0.8538	High Similarity	NPC235190
0.8538	High Similarity	NPC163200
0.8531	High Similarity	NPC11700
0.8529	High Similarity	NPC29734
0.8529	High Similarity	NPC267336
0.8529	High Similarity	NPC272650
0.8527	High Similarity	NPC298796
0.8521	High Similarity	NPC282300
0.8521	High Similarity	NPC205006
0.8521	High Similarity	NPC470555
0.8521	High Similarity	NPC64908
0.8521	High Similarity	NPC156590
0.8521	High Similarity	NPC147688
0.8521	High Similarity	NPC118840
0.8511	High Similarity	NPC152771
0.8511	High Similarity	NPC287286
0.8511	High Similarity	NPC216978
0.8511	High Similarity	NPC53181
0.8511	High Similarity	NPC55018
0.8511	High Similarity	NPC18260
0.8511	High Similarity	NPC195357
0.8511	High Similarity	NPC301217
0.8511	High Similarity	NPC472343
0.8511	High Similarity	NPC241975
0.8511	High Similarity	NPC138149
0.8511	High Similarity	NPC78913
0.8511	High Similarity	NPC96565
0.8511	High Similarity	NPC473209
0.8511	High Similarity	NPC139554
0.8511	High Similarity	NPC473076
0.8511	High Similarity	NPC217186
0.8511	High Similarity	NPC220062
0.8511	High Similarity	NPC19476
0.8511	High Similarity	NPC303633
0.8511	High Similarity	NPC136095
0.8507	High Similarity	NPC121104
0.85	High Similarity	NPC103001
0.85	High Similarity	NPC279573
0.85	High Similarity	NPC211110
0.8496	Intermediate Similarity	NPC165556
0.8493	Intermediate Similarity	NPC103116
0.8493	Intermediate Similarity	NPC19238
0.8489	Intermediate Similarity	NPC101752
0.8489	Intermediate Similarity	NPC55615
0.8489	Intermediate Similarity	NPC317045
0.8489	Intermediate Similarity	NPC60667
0.8489	Intermediate Similarity	NPC246177
0.8489	Intermediate Similarity	NPC46869
0.8489	Intermediate Similarity	NPC151113

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 NPC61499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	981
0.2-0.3	1734
0.3-0.4	2656
0.4-0.5	1897
0.5-0.6	1062
0.6-0.7	341
0.7-0.8	110
0.8-0.85	35
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8872	High Similarity	NPD6859	Clinical (unspecified phase)
0.8473	Intermediate Similarity	NPD422	Phase 1
0.838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD7411	Suspended
0.8345	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6801	Discontinued
0.8322	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1296	Phase 2
0.8311	Intermediate Similarity	NPD6599	Discontinued
0.8276	Intermediate Similarity	NPD6799	Approved
0.8273	Intermediate Similarity	NPD5124	Phase 1
0.8273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD7819	Suspended
0.8252	Intermediate Similarity	NPD1243	Approved
0.8231	Intermediate Similarity	NPD920	Approved
0.8222	Intermediate Similarity	NPD2797	Approved
0.8219	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3750	Approved
0.8188	Intermediate Similarity	NPD3268	Approved
0.8169	Intermediate Similarity	NPD2796	Approved
0.8105	Intermediate Similarity	NPD7075	Discontinued
0.8099	Intermediate Similarity	NPD3748	Approved
0.8082	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1240	Approved
0.8069	Intermediate Similarity	NPD4628	Phase 3
0.8056	Intermediate Similarity	NPD1549	Phase 2
0.8056	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD3225	Approved
0.8	Intermediate Similarity	NPD2800	Approved
0.7986	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1510	Phase 2
0.7958	Intermediate Similarity	NPD6651	Approved
0.7958	Intermediate Similarity	NPD1607	Approved
0.7956	Intermediate Similarity	NPD3266	Approved
0.7956	Intermediate Similarity	NPD3267	Approved
0.7922	Intermediate Similarity	NPD7768	Phase 2
0.7914	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD9717	Approved
0.7847	Intermediate Similarity	NPD7033	Discontinued
0.7847	Intermediate Similarity	NPD2799	Discontinued
0.7829	Intermediate Similarity	NPD4380	Phase 2
0.7799	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD2935	Discontinued
0.7793	Intermediate Similarity	NPD6100	Approved
0.7793	Intermediate Similarity	NPD6099	Approved
0.7793	Intermediate Similarity	NPD1551	Phase 2
0.7792	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6832	Phase 2
0.7778	Intermediate Similarity	NPD1778	Approved
0.7778	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD1652	Phase 2
0.7742	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3817	Phase 2
0.7737	Intermediate Similarity	NPD1608	Approved
0.7733	Intermediate Similarity	NPD2533	Approved
0.7733	Intermediate Similarity	NPD2532	Approved
0.7733	Intermediate Similarity	NPD2534	Approved
0.7724	Intermediate Similarity	NPD4308	Phase 3
0.7707	Intermediate Similarity	NPD919	Approved
0.7703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1203	Approved
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6798	Discontinued
0.7676	Intermediate Similarity	NPD2313	Discontinued
0.7676	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7286	Phase 2
0.7643	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3749	Approved
0.7632	Intermediate Similarity	NPD5403	Approved
0.763	Intermediate Similarity	NPD1548	Phase 1
0.763	Intermediate Similarity	NPD9545	Approved
0.7616	Intermediate Similarity	NPD5401	Approved
0.7616	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4307	Phase 2
0.7564	Intermediate Similarity	NPD2801	Approved
0.7562	Intermediate Similarity	NPD7229	Phase 3
0.7561	Intermediate Similarity	NPD5953	Discontinued
0.755	Intermediate Similarity	NPD1511	Approved
0.7535	Intermediate Similarity	NPD4908	Phase 1
0.7519	Intermediate Similarity	NPD1241	Discontinued
0.7518	Intermediate Similarity	NPD17	Approved
0.7517	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD1894	Discontinued
0.75	Intermediate Similarity	NPD6005	Phase 3
0.75	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6002	Phase 3
0.75	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6004	Phase 3
0.75	Intermediate Similarity	NPD1934	Approved
0.7482	Intermediate Similarity	NPD3972	Approved
0.7468	Intermediate Similarity	NPD3882	Suspended
0.7467	Intermediate Similarity	NPD7003	Approved
0.7453	Intermediate Similarity	NPD6232	Discontinued
0.7452	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD1512	Approved
0.7444	Intermediate Similarity	NPD5535	Approved
0.7442	Intermediate Similarity	NPD9697	Approved
0.7439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4477	Approved
0.7432	Intermediate Similarity	NPD4476	Approved
0.7419	Intermediate Similarity	NPD7458	Discontinued
0.7419	Intermediate Similarity	NPD3226	Approved
0.741	Intermediate Similarity	NPD1610	Phase 2
0.7405	Intermediate Similarity	NPD4288	Approved
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD1019	Discontinued
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD6959	Discontinued
0.7391	Intermediate Similarity	NPD4626	Approved
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7338	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD3847	Discontinued
0.7338	Intermediate Similarity	NPD3496	Discontinued
0.7329	Intermediate Similarity	NPD5494	Approved
0.732	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5691	Approved
0.7317	Intermediate Similarity	NPD7473	Discontinued
0.7312	Intermediate Similarity	NPD6971	Discontinued
0.731	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD411	Approved
0.7301	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5402	Approved
0.7292	Intermediate Similarity	NPD2614	Approved
0.7286	Intermediate Similarity	NPD1535	Discovery
0.7279	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD447	Suspended
0.7273	Intermediate Similarity	NPD3818	Discontinued
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.726	Intermediate Similarity	NPD4062	Phase 3
0.726	Intermediate Similarity	NPD8032	Phase 2
0.7254	Intermediate Similarity	NPD1283	Approved
0.7254	Intermediate Similarity	NPD8651	Approved
0.7252	Intermediate Similarity	NPD3134	Approved
0.7244	Intermediate Similarity	NPD1653	Approved
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7241	Intermediate Similarity	NPD7095	Approved
0.7234	Intermediate Similarity	NPD1481	Phase 2
0.7226	Intermediate Similarity	NPD9493	Approved
0.7226	Intermediate Similarity	NPD5049	Phase 3
0.7219	Intermediate Similarity	NPD2424	Discontinued
0.7211	Intermediate Similarity	NPD4060	Phase 1
0.7202	Intermediate Similarity	NPD6559	Discontinued
0.7202	Intermediate Similarity	NPD6104	Discontinued
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1358	Approved
0.7197	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2354	Approved
0.7183	Intermediate Similarity	NPD4749	Approved
0.7178	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD8127	Discontinued
0.7171	Intermediate Similarity	NPD2654	Approved
0.7162	Intermediate Similarity	NPD1933	Approved
0.716	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2798	Approved
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6502	Phase 2
0.7152	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD5711	Approved
0.7126	Intermediate Similarity	NPD7054	Approved
0.7125	Intermediate Similarity	NPD8455	Phase 2
0.7124	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD4534	Discontinued
0.7095	Intermediate Similarity	NPD4140	Approved
0.7083	Intermediate Similarity	NPD7074	Phase 3
0.7083	Intermediate Similarity	NPD7472	Approved
0.7078	Intermediate Similarity	NPD3887	Approved
0.7075	Intermediate Similarity	NPD3764	Approved
0.7071	Intermediate Similarity	NPD5585	Approved
0.7071	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7097	Phase 1
0.7063	Intermediate Similarity	NPD37	Approved
0.7062	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4340	Discontinued
0.7042	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1281	Approved
0.7041	Intermediate Similarity	NPD6797	Phase 2
0.7039	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2353	Approved
0.7037	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD4965	Approved
0.7037	Intermediate Similarity	NPD4967	Phase 2
0.7029	Intermediate Similarity	NPD7157	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