NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.09
Volume:	247.009
LogP:	2.42
LogD:	2.563
LogS:	-3.201
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.839
Synthetic Accessibility Score:	3.385
Fsp3:	0.357
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:	-4.744
MDCK Permeability:	1.4108189134276472e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.349
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.901

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	92.25605010986328%
Volume Distribution (VD):	0.588
Pgp-substrate:	8.965853691101074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.85
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.705
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	2.329
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.315
Rat Oral Acute Toxicity:	0.718
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.744
Carcinogencity:	0.712
Eye Corrosion:	0.068
Eye Irritation:	0.152
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC149533

Natural Product ID:	NPC149533
*Common Name:**	BRXZPQCUSKJYDB-JTQLQIEISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BRXZPQCUSKJYDB-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C14H14O4/c1-7-5-8-12(9(15)6-7)14(16)18-11-4-3-10(17-2)13(8)11/h5-6,10,15H,3-4H2,1-2H3/t10-/m0/s1
SMILES:	CO[C@H]1CCc2c1c1cc(C)cc(c1c(=O)o2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3422274
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins 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
NPO32511	Penicillium chrysogenum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25611519]

☑ 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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	10800.0	nM	PMID[493170]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	31400.0	nM	PMID[493170]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	12600.0	nM	PMID[493170]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	22500.0	nM	PMID[493170]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	40500.0	nM	PMID[493170]

☑ 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 NPC149533 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	362
0.1-0.2	1692
0.2-0.3	3773
0.3-0.4	9023
0.4-0.5	9937
0.5-0.6	4084
0.6-0.7	6181
0.7-0.8	6244
0.8-0.85	1228
0.85-0.9	164
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9058	High Similarity	NPC291454
0.9014	High Similarity	NPC159721
0.8986	High Similarity	NPC142027
0.8986	High Similarity	NPC27407
0.8971	High Similarity	NPC470831
0.8971	High Similarity	NPC214702
0.8951	High Similarity	NPC151607
0.8951	High Similarity	NPC42540
0.8929	High Similarity	NPC221104
0.8921	High Similarity	NPC158481
0.8921	High Similarity	NPC50455
0.8897	High Similarity	NPC53362
0.8897	High Similarity	NPC166583
0.8881	High Similarity	NPC471731
0.8873	High Similarity	NPC37530
0.8873	High Similarity	NPC470842
0.8865	High Similarity	NPC268052
0.8865	High Similarity	NPC275356
0.8865	High Similarity	NPC88269
0.8865	High Similarity	NPC32360
0.8851	High Similarity	NPC271681
0.8844	High Similarity	NPC119929
0.8811	High Similarity	NPC314271
0.8811	High Similarity	NPC82913
0.8811	High Similarity	NPC471733
0.8803	High Similarity	NPC165172
0.8803	High Similarity	NPC168471
0.8803	High Similarity	NPC99441
0.8803	High Similarity	NPC472601
0.8803	High Similarity	NPC472600
0.8794	High Similarity	NPC126739
0.8794	High Similarity	NPC197666
0.8786	High Similarity	NPC235115
0.8777	High Similarity	NPC175943
0.8741	High Similarity	NPC158634
0.8741	High Similarity	NPC472603
0.8741	High Similarity	NPC472605
0.8741	High Similarity	NPC472604
0.8723	High Similarity	NPC261292
0.8723	High Similarity	NPC301915
0.8723	High Similarity	NPC70380
0.8705	High Similarity	NPC153783
0.8662	High Similarity	NPC61590
0.8662	High Similarity	NPC212693
0.8662	High Similarity	NPC472602
0.8662	High Similarity	NPC191835
0.8662	High Similarity	NPC94248
0.8639	High Similarity	NPC8817
0.8639	High Similarity	NPC471734
0.8633	High Similarity	NPC477406
0.863	High Similarity	NPC474630
0.863	High Similarity	NPC75694
0.8621	High Similarity	NPC469542
0.8621	High Similarity	NPC51106
0.8621	High Similarity	NPC472610
0.8621	High Similarity	NPC478202
0.8611	High Similarity	NPC90411
0.8611	High Similarity	NPC1704
0.8611	High Similarity	NPC53649
0.8611	High Similarity	NPC67650
0.8601	High Similarity	NPC92655
0.8601	High Similarity	NPC139634
0.8601	High Similarity	NPC295339
0.8601	High Similarity	NPC105456
0.8601	High Similarity	NPC247409
0.86	High Similarity	NPC175978
0.86	High Similarity	NPC273483
0.8593	High Similarity	NPC265910
0.8593	High Similarity	NPC91475
0.8592	High Similarity	NPC245058
0.8592	High Similarity	NPC194579
0.8592	High Similarity	NPC135837
0.8582	High Similarity	NPC470844
0.8581	High Similarity	NPC37139
0.8571	High Similarity	NPC225173
0.8571	High Similarity	NPC473023
0.8571	High Similarity	NPC470357
0.8571	High Similarity	NPC163846
0.8571	High Similarity	NPC471735
0.8561	High Similarity	NPC219892
0.8561	High Similarity	NPC189823
0.8561	High Similarity	NPC7012
0.8552	High Similarity	NPC322112
0.8542	High Similarity	NPC155205
0.8531	High Similarity	NPC478200
0.8531	High Similarity	NPC33144
0.8523	High Similarity	NPC233267
0.8523	High Similarity	NPC291049
0.8521	High Similarity	NPC156967
0.8521	High Similarity	NPC472599
0.8514	High Similarity	NPC125801
0.8514	High Similarity	NPC137296
0.8503	High Similarity	NPC473692
0.8493	Intermediate Similarity	NPC472006
0.8493	Intermediate Similarity	NPC21873
0.8489	Intermediate Similarity	NPC473271
0.8489	Intermediate Similarity	NPC296158
0.8487	Intermediate Similarity	NPC471456
0.8483	Intermediate Similarity	NPC478217
0.8483	Intermediate Similarity	NPC257003
0.8483	Intermediate Similarity	NPC283292
0.8483	Intermediate Similarity	NPC313123
0.8483	Intermediate Similarity	NPC244923
0.8477	Intermediate Similarity	NPC115249
0.8472	Intermediate Similarity	NPC216312
0.8472	Intermediate Similarity	NPC256463
0.8472	Intermediate Similarity	NPC29771
0.8472	Intermediate Similarity	NPC471602
0.8472	Intermediate Similarity	NPC111422
0.8472	Intermediate Similarity	NPC299405
0.8472	Intermediate Similarity	NPC306835
0.8472	Intermediate Similarity	NPC476477
0.8467	Intermediate Similarity	NPC179178
0.8467	Intermediate Similarity	NPC158866
0.8462	Intermediate Similarity	NPC71256
0.8456	Intermediate Similarity	NPC153417
0.8456	Intermediate Similarity	NPC105415
0.8451	Intermediate Similarity	NPC278375
0.8451	Intermediate Similarity	NPC180905
0.8451	Intermediate Similarity	NPC182496
0.8446	Intermediate Similarity	NPC107625
0.8446	Intermediate Similarity	NPC260946
0.844	Intermediate Similarity	NPC43627
0.844	Intermediate Similarity	NPC263817
0.8435	Intermediate Similarity	NPC89664
0.8435	Intermediate Similarity	NPC274085
0.8435	Intermediate Similarity	NPC103910
0.8431	Intermediate Similarity	NPC478027
0.8425	Intermediate Similarity	NPC469579
0.8425	Intermediate Similarity	NPC94076
0.8425	Intermediate Similarity	NPC182255
0.8425	Intermediate Similarity	NPC474385
0.8421	Intermediate Similarity	NPC137301
0.8421	Intermediate Similarity	NPC472799
0.8414	Intermediate Similarity	NPC220496
0.8414	Intermediate Similarity	NPC147542
0.8414	Intermediate Similarity	NPC156872
0.8414	Intermediate Similarity	NPC158472
0.8414	Intermediate Similarity	NPC37992
0.8414	Intermediate Similarity	NPC241349
0.8414	Intermediate Similarity	NPC327916
0.8414	Intermediate Similarity	NPC42262
0.8414	Intermediate Similarity	NPC32749
0.8411	Intermediate Similarity	NPC133856
0.8406	Intermediate Similarity	NPC181715
0.84	Intermediate Similarity	NPC237440
0.84	Intermediate Similarity	NPC270160
0.8389	Intermediate Similarity	NPC7943
0.8389	Intermediate Similarity	NPC22005
0.8389	Intermediate Similarity	NPC119767
0.8389	Intermediate Similarity	NPC123202
0.8389	Intermediate Similarity	NPC14098
0.838	Intermediate Similarity	NPC474394
0.838	Intermediate Similarity	NPC474097
0.838	Intermediate Similarity	NPC475645
0.8378	Intermediate Similarity	NPC83272
0.8377	Intermediate Similarity	NPC263483
0.8367	Intermediate Similarity	NPC84266
0.8367	Intermediate Similarity	NPC476473
0.8366	Intermediate Similarity	NPC89625
0.8366	Intermediate Similarity	NPC149618
0.8356	Intermediate Similarity	NPC478201
0.8356	Intermediate Similarity	NPC471444
0.8356	Intermediate Similarity	NPC130485
0.8356	Intermediate Similarity	NPC472035
0.8356	Intermediate Similarity	NPC475730
0.8355	Intermediate Similarity	NPC217447
0.8355	Intermediate Similarity	NPC76041
0.8355	Intermediate Similarity	NPC184284
0.8345	Intermediate Similarity	NPC52358
0.8344	Intermediate Similarity	NPC150928
0.8344	Intermediate Similarity	NPC472891
0.8344	Intermediate Similarity	NPC202595
0.8333	Intermediate Similarity	NPC178467
0.8333	Intermediate Similarity	NPC2569
0.8333	Intermediate Similarity	NPC65837
0.8333	Intermediate Similarity	NPC256672
0.8333	Intermediate Similarity	NPC471642
0.8333	Intermediate Similarity	NPC117985
0.8333	Intermediate Similarity	NPC24761
0.8333	Intermediate Similarity	NPC7025
0.8333	Intermediate Similarity	NPC27221
0.8333	Intermediate Similarity	NPC474849
0.8333	Intermediate Similarity	NPC471641
0.8333	Intermediate Similarity	NPC172329
0.8333	Intermediate Similarity	NPC474771
0.8333	Intermediate Similarity	NPC240622
0.8333	Intermediate Similarity	NPC149372
0.8333	Intermediate Similarity	NPC240253
0.8322	Intermediate Similarity	NPC120536
0.8322	Intermediate Similarity	NPC290803
0.8322	Intermediate Similarity	NPC471346
0.8322	Intermediate Similarity	NPC470570
0.8312	Intermediate Similarity	NPC146211
0.8311	Intermediate Similarity	NPC280404
0.8311	Intermediate Similarity	NPC471451
0.8311	Intermediate Similarity	NPC277426
0.8311	Intermediate Similarity	NPC210425
0.8311	Intermediate Similarity	NPC469385
0.8311	Intermediate Similarity	NPC478203

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 NPC149533 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	980
0.2-0.3	1718
0.3-0.4	2622
0.4-0.5	1940
0.5-0.6	1040
0.6-0.7	346
0.7-0.8	136
0.8-0.85	21
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.863	High Similarity	NPD2532	Approved
0.863	High Similarity	NPD2534	Approved
0.863	High Similarity	NPD2533	Approved
0.8601	High Similarity	NPD970	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD3226	Approved
0.7959	Intermediate Similarity	NPD2935	Discontinued
0.7949	Intermediate Similarity	NPD7819	Suspended
0.7937	Intermediate Similarity	NPD5711	Approved
0.7937	Intermediate Similarity	NPD5710	Approved
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7905	Intermediate Similarity	NPD2346	Discontinued
0.7891	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6959	Discontinued
0.7847	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1551	Phase 2
0.7794	Intermediate Similarity	NPD9493	Approved
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1510	Phase 2
0.7755	Intermediate Similarity	NPD1607	Approved
0.7722	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5406	Approved
0.7718	Intermediate Similarity	NPD5404	Approved
0.7718	Intermediate Similarity	NPD5408	Approved
0.7718	Intermediate Similarity	NPD5405	Approved
0.7714	Intermediate Similarity	NPD1201	Approved
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7681	Intermediate Similarity	NPD9545	Approved
0.7667	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4380	Phase 2
0.7632	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1470	Approved
0.7619	Intermediate Similarity	NPD1240	Approved
0.7616	Intermediate Similarity	NPD1549	Phase 2
0.7603	Intermediate Similarity	NPD411	Approved
0.7597	Intermediate Similarity	NPD7390	Discontinued
0.759	Intermediate Similarity	NPD5844	Phase 1
0.758	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7075	Discontinued
0.7566	Intermediate Similarity	NPD1243	Approved
0.7566	Intermediate Similarity	NPD2800	Approved
0.7564	Intermediate Similarity	NPD920	Approved
0.7548	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1934	Approved
0.7544	Intermediate Similarity	NPD8150	Discontinued
0.7535	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD3750	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.7484	Intermediate Similarity	NPD1511	Approved
0.7484	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD3764	Approved
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7471	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD447	Suspended
0.7438	Intermediate Similarity	NPD6801	Discontinued
0.7436	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1283	Approved
0.7421	Intermediate Similarity	NPD6599	Discontinued
0.7419	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7033	Discontinued
0.7413	Intermediate Similarity	NPD1608	Approved
0.7407	Intermediate Similarity	NPD7768	Phase 2
0.7389	Intermediate Similarity	NPD1512	Approved
0.7379	Intermediate Similarity	NPD1164	Approved
0.7368	Intermediate Similarity	NPD2796	Approved
0.7368	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD8313	Approved
0.7362	Intermediate Similarity	NPD3749	Approved
0.7353	Intermediate Similarity	NPD6559	Discontinued
0.7346	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4626	Approved
0.732	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6005	Phase 3
0.732	Intermediate Similarity	NPD6004	Phase 3
0.732	Intermediate Similarity	NPD6002	Phase 3
0.732	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD919	Approved
0.7305	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4308	Phase 3
0.7303	Intermediate Similarity	NPD2799	Discontinued
0.7301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2801	Approved
0.7261	Intermediate Similarity	NPD6799	Approved
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6100	Approved
0.7255	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD5691	Approved
0.7239	Intermediate Similarity	NPD5402	Approved
0.723	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD1281	Approved
0.7219	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1019	Discontinued
0.7211	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD9266	Approved
0.7206	Intermediate Similarity	NPD74	Approved
0.7203	Intermediate Similarity	NPD1778	Approved
0.7203	Intermediate Similarity	NPD17	Approved
0.7195	Intermediate Similarity	NPD3882	Suspended
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3748	Approved
0.7179	Intermediate Similarity	NPD7003	Approved
0.7178	Intermediate Similarity	NPD1465	Phase 2
0.7176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6651	Approved
0.717	Intermediate Similarity	NPD6273	Approved
0.7169	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD943	Approved
0.7152	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD2797	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7133	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.7132	Intermediate Similarity	NPD9263	Approved
0.7125	Intermediate Similarity	NPD5403	Approved
0.7117	Intermediate Similarity	NPD37	Approved
0.7108	Intermediate Similarity	NPD6234	Discontinued
0.7107	Intermediate Similarity	NPD5401	Approved
0.7101	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6166	Phase 2
0.7097	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2344	Approved
0.7095	Intermediate Similarity	NPD2798	Approved
0.7091	Intermediate Similarity	NPD4966	Approved
0.7091	Intermediate Similarity	NPD4967	Phase 2
0.7091	Intermediate Similarity	NPD4965	Approved
0.7086	Intermediate Similarity	NPD6663	Approved
0.7076	Intermediate Similarity	NPD7054	Approved
0.7067	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7435	Discontinued
0.7047	Intermediate Similarity	NPD5736	Approved
0.7039	Intermediate Similarity	NPD4307	Phase 2
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7035	Intermediate Similarity	NPD7472	Approved
0.7035	Intermediate Similarity	NPD7074	Phase 3
0.7032	Intermediate Similarity	NPD2438	Suspended
0.7024	Intermediate Similarity	NPD1247	Approved
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6535	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6994	Remote Similarity	NPD5953	Discontinued
0.6994	Remote Similarity	NPD6797	Phase 2
0.6987	Remote Similarity	NPD1471	Phase 3
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD5763	Approved
0.6986	Remote Similarity	NPD422	Phase 1
0.6986	Remote Similarity	NPD1611	Approved
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7229	Phase 3
0.6977	Remote Similarity	NPD7286	Phase 2
0.6974	Remote Similarity	NPD520	Approved
0.697	Remote Similarity	NPD5760	Phase 2
0.697	Remote Similarity	NPD5761	Phase 2
0.6959	Remote Similarity	NPD6696	Suspended
0.6959	Remote Similarity	NPD3225	Approved
0.6954	Remote Similarity	NPD7251	Discontinued
0.6954	Remote Similarity	NPD4625	Phase 3
0.6944	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6212	Phase 3
0.6944	Remote Similarity	NPD6213	Phase 3
0.6939	Remote Similarity	NPD9269	Phase 2
0.6937	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8319	Approved
0.6935	Remote Similarity	NPD8320	Phase 1
0.6928	Remote Similarity	NPD4060	Phase 1
0.6919	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2309	Approved
0.6914	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7808	Phase 3
0.6913	Remote Similarity	NPD3266	Approved
0.6913	Remote Similarity	NPD3267	Approved
0.6901	Remote Similarity	NPD9281	Approved
0.6897	Remote Similarity	NPD9268	Approved
0.6897	Remote Similarity	NPD1651	Approved
0.6894	Remote Similarity	NPD1578	Phase 2
0.6893	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7699	Phase 2
0.6885	Remote Similarity	NPD7700	Phase 2
0.6884	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7697	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