NPASS Compound

Structure

NPC472515 OpenBabel07101719152D 22 23 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 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 1.7321 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 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 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 8 1 0 0 0 0 2 8 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 12 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 21 1 0 0 0 0 12 17 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 19 2 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.09
Volume:	302.465
LogP:	1.922
LogD:	2.077
LogS:	-4.252
# Rotatable Bonds:	5
TPSA:	82.81
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	2.632
Fsp3:	0.312
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.634
MDCK Permeability:	4.3546304368646815e-05
Pgp-inhibitor:	0.252
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	80.81385040283203%
Volume Distribution (VD):	0.741
Pgp-substrate:	8.261968612670898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.451
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.707
CYP2D6-inhibitor:	0.552
CYP2D6-substrate:	0.605
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	9.507
Half-life (T1/2):	0.542

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.578
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.445
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.092
Skin Sensitization:	0.16
Carcinogencity:	0.502
Eye Corrosion:	0.004
Eye Irritation:	0.066
Respiratory Toxicity:	0.736

Download Data

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

Natural Product: NPC472515

Natural Product ID:	NPC472515
*Common Name:**	CRYMFGQAFXDXLP-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CRYMFGQAFXDXLP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O6/c1-8(2)14(18)15(19)13-11(21-4)7-10(20-3)9-5-6-12(17)22-16(9)13/h5-8H,1-4H3
SMILES:	COc1cc(OC)c2c(c1C(=O)C(=O)C(C)C)oc(=O)cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426668
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[559514]

☑ 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 NPC472515 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	431
0.1-0.2	1908
0.2-0.3	5239
0.3-0.4	10830
0.4-0.5	6984
0.5-0.6	4734
0.6-0.7	5772
0.7-0.8	4773
0.8-0.85	1438
0.85-0.9	436
0.9-0.95	140
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9776	High Similarity	NPC36414
0.9701	High Similarity	NPC253616
0.9627	High Similarity	NPC268081
0.9627	High Similarity	NPC472516
0.9474	High Similarity	NPC54503
0.9416	High Similarity	NPC473209
0.9328	High Similarity	NPC55147
0.9275	High Similarity	NPC136095
0.927	High Similarity	NPC38153
0.927	High Similarity	NPC103001
0.9209	High Similarity	NPC470856
0.9185	High Similarity	NPC229646
0.9167	High Similarity	NPC191104
0.9155	High Similarity	NPC470322
0.9155	High Similarity	NPC154217
0.9143	High Similarity	NPC254010
0.9124	High Similarity	NPC46869
0.9097	High Similarity	NPC88445
0.9091	High Similarity	NPC74539
0.9091	High Similarity	NPC304443
0.9085	High Similarity	NPC171656
0.9085	High Similarity	NPC294365
0.9085	High Similarity	NPC1886
0.9085	High Similarity	NPC196137
0.9078	High Similarity	NPC313036
0.9065	High Similarity	NPC199458
0.9065	High Similarity	NPC183639
0.9058	High Similarity	NPC254741
0.9058	High Similarity	NPC161196
0.903	High Similarity	NPC473894
0.9021	High Similarity	NPC181388
0.9014	High Similarity	NPC112791
0.9014	High Similarity	NPC94794
0.9014	High Similarity	NPC470296
0.9014	High Similarity	NPC87609
0.9014	High Similarity	NPC188632
0.9014	High Similarity	NPC196459
0.9007	High Similarity	NPC24075
0.9007	High Similarity	NPC201820
0.9	High Similarity	NPC19476
0.9	High Similarity	NPC241975
0.9	High Similarity	NPC262635
0.8993	High Similarity	NPC332594
0.8993	High Similarity	NPC474624
0.8993	High Similarity	NPC138047
0.8993	High Similarity	NPC131782
0.8978	High Similarity	NPC292998
0.8958	High Similarity	NPC282335
0.8958	High Similarity	NPC218300
0.8955	High Similarity	NPC473907
0.8951	High Similarity	NPC469935
0.8951	High Similarity	NPC234629
0.8951	High Similarity	NPC178627
0.8951	High Similarity	NPC311741
0.8951	High Similarity	NPC179970
0.8951	High Similarity	NPC469953
0.8944	High Similarity	NPC36181
0.8944	High Similarity	NPC470556
0.8929	High Similarity	NPC131130
0.8929	High Similarity	NPC470669
0.8929	High Similarity	NPC470668
0.8929	High Similarity	NPC470083
0.8929	High Similarity	NPC219584
0.8929	High Similarity	NPC17848
0.8921	High Similarity	NPC174999
0.8913	High Similarity	NPC61499
0.8913	High Similarity	NPC66705
0.8913	High Similarity	NPC229128
0.8905	High Similarity	NPC473655
0.8905	High Similarity	NPC101294
0.8904	High Similarity	NPC474660
0.8904	High Similarity	NPC474735
0.8897	High Similarity	NPC208303
0.8897	High Similarity	NPC161864
0.8897	High Similarity	NPC266743
0.8897	High Similarity	NPC472517
0.8889	High Similarity	NPC473927
0.8881	High Similarity	NPC307895
0.8881	High Similarity	NPC470553
0.8881	High Similarity	NPC475496
0.8881	High Similarity	NPC96216
0.8881	High Similarity	NPC474939
0.8881	High Similarity	NPC470909
0.8881	High Similarity	NPC49852
0.8873	High Similarity	NPC110969
0.8873	High Similarity	NPC470555
0.8873	High Similarity	NPC103362
0.8873	High Similarity	NPC282300
0.8872	High Similarity	NPC471828
0.8872	High Similarity	NPC471827
0.8865	High Similarity	NPC11566
0.8865	High Similarity	NPC472343
0.8865	High Similarity	NPC23257
0.8865	High Similarity	NPC477956
0.8857	High Similarity	NPC259685
0.8857	High Similarity	NPC157855
0.8844	High Similarity	NPC290671
0.8844	High Similarity	NPC98028
0.8841	High Similarity	NPC247743
0.8841	High Similarity	NPC223354
0.8836	High Similarity	NPC469932
0.8836	High Similarity	NPC19238
0.8836	High Similarity	NPC164299
0.8832	High Similarity	NPC284424
0.8832	High Similarity	NPC278556
0.8832	High Similarity	NPC175159
0.8828	High Similarity	NPC249942
0.8828	High Similarity	NPC297886
0.8828	High Similarity	NPC474108
0.8828	High Similarity	NPC129650
0.8828	High Similarity	NPC177995
0.8828	High Similarity	NPC180477
0.8828	High Similarity	NPC140120
0.8819	High Similarity	NPC206212
0.8819	High Similarity	NPC288910
0.8819	High Similarity	NPC118059
0.8819	High Similarity	NPC246903
0.8819	High Similarity	NPC71184
0.8819	High Similarity	NPC470554
0.8819	High Similarity	NPC133060
0.8811	High Similarity	NPC294432
0.8811	High Similarity	NPC112829
0.8811	High Similarity	NPC51146
0.8811	High Similarity	NPC11561
0.8811	High Similarity	NPC166858
0.8811	High Similarity	NPC226636
0.8803	High Similarity	NPC474037
0.8803	High Similarity	NPC270883
0.8803	High Similarity	NPC241100
0.8803	High Similarity	NPC307990
0.8803	High Similarity	NPC16455
0.8803	High Similarity	NPC172986
0.8803	High Similarity	NPC159275
0.8803	High Similarity	NPC471587
0.8803	High Similarity	NPC261227
0.8803	High Similarity	NPC472409
0.8803	High Similarity	NPC221173
0.8803	High Similarity	NPC150522
0.88	High Similarity	NPC269495
0.8794	High Similarity	NPC474504
0.8794	High Similarity	NPC474487
0.8794	High Similarity	NPC470672
0.8794	High Similarity	NPC470671
0.8792	High Similarity	NPC295608
0.8792	High Similarity	NPC250769
0.8792	High Similarity	NPC278010
0.8786	High Similarity	NPC156910
0.8777	High Similarity	NPC125269
0.8777	High Similarity	NPC125920
0.8776	High Similarity	NPC158866
0.8776	High Similarity	NPC473466
0.8776	High Similarity	NPC180351
0.8768	High Similarity	NPC182428
0.8767	High Similarity	NPC469933
0.8767	High Similarity	NPC39195
0.8767	High Similarity	NPC266572
0.8767	High Similarity	NPC211811
0.8767	High Similarity	NPC183236
0.8759	High Similarity	NPC477955
0.8759	High Similarity	NPC57470
0.8759	High Similarity	NPC470910
0.8759	High Similarity	NPC25844
0.875	High Similarity	NPC17262
0.875	High Similarity	NPC18585
0.875	High Similarity	NPC33653
0.875	High Similarity	NPC184702
0.875	High Similarity	NPC211120
0.875	High Similarity	NPC166138
0.875	High Similarity	NPC184738
0.875	High Similarity	NPC106985
0.875	High Similarity	NPC59522
0.8741	High Similarity	NPC55832
0.8741	High Similarity	NPC147688
0.8741	High Similarity	NPC156590
0.8741	High Similarity	NPC118840
0.8741	High Similarity	NPC52789
0.8741	High Similarity	NPC205006
0.8741	High Similarity	NPC26051
0.8741	High Similarity	NPC37512
0.8741	High Similarity	NPC268204
0.8741	High Similarity	NPC229916
0.8741	High Similarity	NPC471640
0.8741	High Similarity	NPC64908
0.8741	High Similarity	NPC471644
0.8733	High Similarity	NPC470625
0.8732	High Similarity	NPC78913
0.8732	High Similarity	NPC301217
0.8732	High Similarity	NPC217186
0.8732	High Similarity	NPC55018
0.8732	High Similarity	NPC18260
0.8732	High Similarity	NPC96565
0.8732	High Similarity	NPC220062
0.8732	High Similarity	NPC303633
0.8732	High Similarity	NPC139554
0.8732	High Similarity	NPC473076
0.8732	High Similarity	NPC53181
0.8732	High Similarity	NPC216978
0.8731	High Similarity	NPC65041
0.8725	High Similarity	NPC186507
0.8725	High Similarity	NPC131725

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 NPC472515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	392
0.1-0.2	990
0.2-0.3	1845
0.3-0.4	2714
0.4-0.5	1814
0.5-0.6	946
0.6-0.7	301
0.7-0.8	101
0.8-0.85	32
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD920	Approved
0.9	High Similarity	NPD1243	Approved
0.8921	High Similarity	NPD2796	Approved
0.8819	High Similarity	NPD642	Clinical (unspecified phase)
0.8811	High Similarity	NPD643	Clinical (unspecified phase)
0.869	High Similarity	NPD4378	Clinical (unspecified phase)
0.8658	High Similarity	NPD6801	Discontinued
0.8621	High Similarity	NPD6799	Approved
0.86	High Similarity	NPD7819	Suspended
0.86	High Similarity	NPD7096	Clinical (unspecified phase)
0.8591	High Similarity	NPD7411	Suspended
0.8451	Intermediate Similarity	NPD2799	Discontinued
0.8451	Intermediate Similarity	NPD3748	Approved
0.8435	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD7075	Discontinued
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6599	Discontinued
0.8377	Intermediate Similarity	NPD919	Approved
0.8322	Intermediate Similarity	NPD1510	Phase 2
0.8298	Intermediate Similarity	NPD1240	Approved
0.8276	Intermediate Similarity	NPD1549	Phase 2
0.8273	Intermediate Similarity	NPD6832	Phase 2
0.8219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD2800	Approved
0.8207	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1607	Approved
0.8163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3750	Approved
0.8158	Intermediate Similarity	NPD4380	Phase 2
0.8156	Intermediate Similarity	NPD2313	Discontinued
0.8156	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7768	Phase 2
0.8117	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3749	Approved
0.8067	Intermediate Similarity	NPD2532	Approved
0.8067	Intermediate Similarity	NPD2534	Approved
0.8067	Intermediate Similarity	NPD2533	Approved
0.8056	Intermediate Similarity	NPD6651	Approved
0.8028	Intermediate Similarity	NPD1296	Phase 2
0.8014	Intermediate Similarity	NPD1551	Phase 2
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD2801	Approved
0.7975	Intermediate Similarity	NPD5953	Discontinued
0.7971	Intermediate Similarity	NPD9717	Approved
0.7963	Intermediate Similarity	NPD7286	Phase 2
0.7962	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5403	Approved
0.7947	Intermediate Similarity	NPD5401	Approved
0.7929	Intermediate Similarity	NPD3266	Approved
0.7929	Intermediate Similarity	NPD3267	Approved
0.7925	Intermediate Similarity	NPD1247	Approved
0.7898	Intermediate Similarity	NPD3882	Suspended
0.7881	Intermediate Similarity	NPD1511	Approved
0.7872	Intermediate Similarity	NPD1019	Discontinued
0.7862	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3226	Approved
0.784	Intermediate Similarity	NPD7473	Discontinued
0.7834	Intermediate Similarity	NPD5402	Approved
0.7821	Intermediate Similarity	NPD1934	Approved
0.7801	Intermediate Similarity	NPD1203	Approved
0.7793	Intermediate Similarity	NPD4307	Phase 2
0.7778	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD3268	Approved
0.777	Intermediate Similarity	NPD422	Phase 1
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD2798	Approved
0.7744	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5124	Phase 1
0.7733	Intermediate Similarity	NPD2654	Approved
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD2346	Discontinued
0.7716	Intermediate Similarity	NPD3926	Phase 2
0.7702	Intermediate Similarity	NPD6959	Discontinued
0.7683	Intermediate Similarity	NPD3818	Discontinued
0.7682	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7676	Intermediate Similarity	NPD2797	Approved
0.7673	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5844	Phase 1
0.7626	Intermediate Similarity	NPD17	Approved
0.7619	Intermediate Similarity	NPD447	Suspended
0.7619	Intermediate Similarity	NPD1933	Approved
0.76	Intermediate Similarity	NPD2344	Approved
0.7584	Intermediate Similarity	NPD4308	Phase 3
0.7576	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD2403	Approved
0.756	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD411	Approved
0.7532	Intermediate Similarity	NPD5889	Approved
0.7532	Intermediate Similarity	NPD5890	Approved
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6585	Discontinued
0.7467	Intermediate Similarity	NPD7033	Discontinued
0.7465	Intermediate Similarity	NPD1608	Approved
0.7465	Intermediate Similarity	NPD3972	Approved
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6166	Phase 2
0.7455	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5710	Approved
0.7439	Intermediate Similarity	NPD5711	Approved
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7425	Intermediate Similarity	NPD7054	Approved
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2309	Approved
0.7391	Intermediate Similarity	NPD4288	Approved
0.7383	Intermediate Similarity	NPD230	Phase 1
0.7381	Intermediate Similarity	NPD7074	Phase 3
0.7381	Intermediate Similarity	NPD7472	Approved
0.7368	Intermediate Similarity	NPD1471	Phase 3
0.7361	Intermediate Similarity	NPD3225	Approved
0.7357	Intermediate Similarity	NPD9545	Approved
0.7351	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD6797	Phase 2
0.7333	Intermediate Similarity	NPD6808	Phase 2
0.7333	Intermediate Similarity	NPD7229	Phase 3
0.7315	Intermediate Similarity	NPD943	Approved
0.7303	Intermediate Similarity	NPD6100	Approved
0.7303	Intermediate Similarity	NPD6099	Approved
0.7297	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD7251	Discontinued
0.729	Intermediate Similarity	NPD3887	Approved
0.7284	Intermediate Similarity	NPD5353	Approved
0.7255	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2353	Approved
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.7247	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1876	Approved
0.7235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7003	Approved
0.72	Intermediate Similarity	NPD3142	Approved
0.72	Intermediate Similarity	NPD3140	Approved
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7188	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5242	Approved
0.7183	Intermediate Similarity	NPD5691	Approved
0.7176	Intermediate Similarity	NPD1729	Discontinued
0.7174	Intermediate Similarity	NPD5535	Approved
0.7164	Intermediate Similarity	NPD9697	Approved
0.7162	Intermediate Similarity	NPD4908	Phase 1
0.7161	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD6279	Approved
0.716	Intermediate Similarity	NPD6280	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7111	Intermediate Similarity	NPD3134	Approved
0.7107	Intermediate Similarity	NPD2186	Approved
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7107	Intermediate Similarity	NPD6273	Approved
0.7102	Intermediate Similarity	NPD4287	Approved
0.7095	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4361	Phase 2
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7078	Intermediate Similarity	NPD4477	Approved
0.7078	Intermediate Similarity	NPD4476	Approved
0.7075	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD2354	Approved
0.7067	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3764	Approved
0.7067	Intermediate Similarity	NPD6798	Discontinued
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7034	Intermediate Similarity	NPD1610	Phase 2
0.7025	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD9261	Approved
0.7014	Intermediate Similarity	NPD1778	Approved
0.7014	Intermediate Similarity	NPD4626	Approved
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7007	Intermediate Similarity	NPD1283	Approved
0.6994	Remote Similarity	NPD6386	Approved
0.6994	Remote Similarity	NPD6385	Approved
0.6993	Remote Similarity	NPD1548	Phase 1
0.6989	Remote Similarity	NPD8434	Phase 2
0.6988	Remote Similarity	NPD6971	Discontinued
0.6987	Remote Similarity	NPD2424	Discontinued
0.6982	Remote Similarity	NPD7184	Clinical (unspecified phase)

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