NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.1
Volume:	255.566
LogP:	3.203
LogD:	2.87
LogS:	-3.489
# Rotatable Bonds:	3
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.838
Synthetic Accessibility Score:	2.291
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.727
MDCK Permeability:	2.5048833776963875e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	87.73674011230469%
Volume Distribution (VD):	1.154
Pgp-substrate:	9.411317825317383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.754
CYP2C9-substrate:	0.902
CYP2D6-inhibitor:	0.374
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.609

ADMET: Excretion

Clearance (CL):	4.932
Half-life (T1/2):	0.454

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.689
AMES Toxicity:	0.499
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.343
Carcinogencity:	0.06
Eye Corrosion:	0.071
Eye Irritation:	0.939
Respiratory Toxicity:	0.418

Download Data

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

Natural Product: NPC473894

Natural Product ID:	NPC473894
*Common Name:**	2-Isopropyl-5,7-Dimethoxychromone
IUPAC Name:	5,7-dimethoxy-2-propan-2-ylchromen-4-one
Synonyms:
Standard InCHIKey:	VVYHDHMKQMHFSH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16O4/c1-8(2)11-7-10(15)14-12(17-4)5-9(16-3)6-13(14)18-11/h5-8H,1-4H3
SMILES:	CC(C)C1=CC(=O)C2=C(O1)C=C(C=C2OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454539
PubChem CID:	10879462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	94.2	ug.mL-1	PMID[514038]

☑ 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 NPC473894 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	427
0.1-0.2	1833
0.2-0.3	5135
0.3-0.4	12429
0.4-0.5	5331
0.5-0.6	4897
0.6-0.7	6069
0.7-0.8	4254
0.8-0.85	1603
0.85-0.9	622
0.9-0.95	86
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC473907
0.9836	High Similarity	NPC475496
0.9836	High Similarity	NPC49852
0.9528	High Similarity	NPC101294
0.9528	High Similarity	NPC473655
0.9528	High Similarity	NPC25937
0.9449	High Similarity	NPC278556
0.9449	High Similarity	NPC31872
0.9449	High Similarity	NPC473584
0.9449	High Similarity	NPC475589
0.9375	High Similarity	NPC229646
0.9375	High Similarity	NPC10971
0.937	High Similarity	NPC270369
0.937	High Similarity	NPC5515
0.9355	High Similarity	NPC65041
0.9308	High Similarity	NPC46869
0.9302	High Similarity	NPC223457
0.9297	High Similarity	NPC284424
0.9242	High Similarity	NPC36414
0.9237	High Similarity	NPC268081
0.9237	High Similarity	NPC254741
0.9237	High Similarity	NPC174999
0.9237	High Similarity	NPC61546
0.9237	High Similarity	NPC72452
0.9237	High Similarity	NPC161196
0.9231	High Similarity	NPC236974
0.9231	High Similarity	NPC125269
0.9231	High Similarity	NPC144027
0.9231	High Similarity	NPC125920
0.9225	High Similarity	NPC203817
0.9213	High Similarity	NPC211120
0.9167	High Similarity	NPC253616
0.916	High Similarity	NPC99854
0.916	High Similarity	NPC60667
0.9154	High Similarity	NPC292998
0.9154	High Similarity	NPC108113
0.9154	High Similarity	NPC93756
0.9098	High Similarity	NPC17848
0.9098	High Similarity	NPC470668
0.9098	High Similarity	NPC470669
0.9098	High Similarity	NPC131130
0.9098	High Similarity	NPC276905
0.9091	High Similarity	NPC29353
0.9091	High Similarity	NPC127447
0.9091	High Similarity	NPC472883
0.9091	High Similarity	NPC470397
0.9091	High Similarity	NPC234133
0.9091	High Similarity	NPC13408
0.9091	High Similarity	NPC156910
0.9091	High Similarity	NPC470398
0.9091	High Similarity	NPC187826
0.9091	High Similarity	NPC194281
0.9091	High Similarity	NPC47815
0.9091	High Similarity	NPC231772
0.9091	High Similarity	NPC473887
0.9091	High Similarity	NPC124784
0.9062	High Similarity	NPC69235
0.9062	High Similarity	NPC212379
0.9055	High Similarity	NPC305518
0.9055	High Similarity	NPC41721
0.9055	High Similarity	NPC128428
0.9037	High Similarity	NPC282300
0.903	High Similarity	NPC472515
0.903	High Similarity	NPC23257
0.903	High Similarity	NPC139554
0.9023	High Similarity	NPC259685
0.9023	High Similarity	NPC266597
0.9023	High Similarity	NPC250266
0.9023	High Similarity	NPC188879
0.9008	High Similarity	NPC78540
0.9008	High Similarity	NPC223354
0.9008	High Similarity	NPC274121
0.9008	High Similarity	NPC247743
0.9008	High Similarity	NPC50898
0.9008	High Similarity	NPC213216
0.8984	High Similarity	NPC475017
0.8963	High Similarity	NPC284550
0.8963	High Similarity	NPC76445
0.8963	High Similarity	NPC241100
0.8963	High Similarity	NPC159275
0.8963	High Similarity	NPC150522
0.8963	High Similarity	NPC129853
0.8963	High Similarity	NPC471587
0.8955	High Similarity	NPC470399
0.8955	High Similarity	NPC474487
0.8955	High Similarity	NPC470671
0.8955	High Similarity	NPC470672
0.8955	High Similarity	NPC124269
0.8955	High Similarity	NPC474504
0.8947	High Similarity	NPC240147
0.8947	High Similarity	NPC121243
0.8947	High Similarity	NPC240593
0.8947	High Similarity	NPC472516
0.8939	High Similarity	NPC172262
0.8931	High Similarity	NPC182428
0.8923	High Similarity	NPC324482
0.8915	High Similarity	NPC187907
0.8897	High Similarity	NPC471640
0.8897	High Similarity	NPC90582
0.8897	High Similarity	NPC471644
0.8897	High Similarity	NPC110969
0.8897	High Similarity	NPC262094
0.8897	High Similarity	NPC103362
0.8897	High Similarity	NPC29536
0.8889	High Similarity	NPC143799
0.8889	High Similarity	NPC220062
0.8889	High Similarity	NPC11566
0.8889	High Similarity	NPC217186
0.8889	High Similarity	NPC301217
0.8889	High Similarity	NPC18260
0.8889	High Similarity	NPC473209
0.8889	High Similarity	NPC140890
0.8889	High Similarity	NPC78913
0.8889	High Similarity	NPC55018
0.8889	High Similarity	NPC136095
0.8889	High Similarity	NPC471697
0.8889	High Similarity	NPC241838
0.8889	High Similarity	NPC96565
0.8889	High Similarity	NPC152042
0.8889	High Similarity	NPC303633
0.8889	High Similarity	NPC53181
0.8889	High Similarity	NPC216978
0.8881	High Similarity	NPC103001
0.8881	High Similarity	NPC157855
0.8872	High Similarity	NPC101752
0.8872	High Similarity	NPC151113
0.8872	High Similarity	NPC242712
0.8864	High Similarity	NPC28753
0.8864	High Similarity	NPC337373
0.8864	High Similarity	NPC192304
0.8864	High Similarity	NPC56031
0.8864	High Similarity	NPC175098
0.8864	High Similarity	NPC204960
0.8864	High Similarity	NPC242294
0.8864	High Similarity	NPC20560
0.8864	High Similarity	NPC159623
0.8864	High Similarity	NPC263670
0.8864	High Similarity	NPC139813
0.8864	High Similarity	NPC472365
0.8864	High Similarity	NPC294593
0.8864	High Similarity	NPC18877
0.8864	High Similarity	NPC188646
0.8864	High Similarity	NPC144051
0.8864	High Similarity	NPC57601
0.8864	High Similarity	NPC312318
0.8864	High Similarity	NPC82225
0.8855	High Similarity	NPC113006
0.8855	High Similarity	NPC27490
0.8846	High Similarity	NPC185497
0.8846	High Similarity	NPC84772
0.8841	High Similarity	NPC294365
0.8837	High Similarity	NPC80694
0.8837	High Similarity	NPC186098
0.8832	High Similarity	NPC11561
0.8832	High Similarity	NPC226636
0.8832	High Similarity	NPC204469
0.8832	High Similarity	NPC9966
0.8832	High Similarity	NPC70853
0.8824	High Similarity	NPC230285
0.8824	High Similarity	NPC472409
0.8824	High Similarity	NPC59951
0.8824	High Similarity	NPC188243
0.8824	High Similarity	NPC6407
0.8824	High Similarity	NPC184536
0.8824	High Similarity	NPC270883
0.8824	High Similarity	NPC281207
0.8824	High Similarity	NPC269652
0.8824	High Similarity	NPC474037
0.8824	High Similarity	NPC172986
0.8824	High Similarity	NPC103342
0.8824	High Similarity	NPC261227
0.8824	High Similarity	NPC477272
0.8824	High Similarity	NPC110228
0.8824	High Similarity	NPC171094
0.8824	High Similarity	NPC103904
0.8824	High Similarity	NPC146679
0.8819	High Similarity	NPC255073
0.8815	High Similarity	NPC280284
0.8815	High Similarity	NPC57380
0.8815	High Similarity	NPC188947
0.8815	High Similarity	NPC99333
0.8815	High Similarity	NPC118813
0.8815	High Similarity	NPC201395
0.8806	High Similarity	NPC116775
0.8806	High Similarity	NPC256042
0.8806	High Similarity	NPC281917
0.8806	High Similarity	NPC216361
0.8806	High Similarity	NPC187432
0.8797	High Similarity	NPC286336
0.8797	High Similarity	NPC66705
0.8788	High Similarity	NPC257756
0.8788	High Similarity	NPC87231
0.8788	High Similarity	NPC129132
0.8788	High Similarity	NPC212631
0.8788	High Similarity	NPC205468
0.8777	High Similarity	NPC474161
0.8777	High Similarity	NPC476088
0.8769	High Similarity	NPC230818
0.8769	High Similarity	NPC60558
0.8768	High Similarity	NPC59522

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 NPC473894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	998
0.2-0.3	1638
0.3-0.4	2798
0.4-0.5	1774
0.5-0.6	1062
0.6-0.7	331
0.7-0.8	106
0.8-0.85	33
0.85-0.9	9
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9091	High Similarity	NPD2796	Approved
0.8741	High Similarity	NPD1550	Clinical (unspecified phase)
0.8741	High Similarity	NPD1552	Clinical (unspecified phase)
0.8712	High Similarity	NPD1240	Approved
0.8705	High Similarity	NPD4378	Clinical (unspecified phase)
0.8676	High Similarity	NPD970	Clinical (unspecified phase)
0.8676	High Similarity	NPD1549	Phase 2
0.8633	High Similarity	NPD6799	Approved
0.8613	High Similarity	NPD1243	Approved
0.8593	High Similarity	NPD1510	Phase 2
0.8582	High Similarity	NPD1607	Approved
0.844	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1511	Approved
0.8345	Intermediate Similarity	NPD2654	Approved
0.8322	Intermediate Similarity	NPD920	Approved
0.8298	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6599	Discontinued
0.8252	Intermediate Similarity	NPD1512	Approved
0.8231	Intermediate Similarity	NPD2801	Approved
0.8219	Intermediate Similarity	NPD7411	Suspended
0.8188	Intermediate Similarity	NPD3748	Approved
0.8182	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD6651	Approved
0.8163	Intermediate Similarity	NPD6801	Discontinued
0.8134	Intermediate Similarity	NPD6832	Phase 2
0.8108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7819	Suspended
0.8108	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD2800	Approved
0.8041	Intermediate Similarity	NPD1934	Approved
0.8027	Intermediate Similarity	NPD4380	Phase 2
0.8016	Intermediate Similarity	NPD1241	Discontinued
0.8015	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1296	Phase 2
0.8	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7961	Intermediate Similarity	NPD5494	Approved
0.7955	Intermediate Similarity	NPD9717	Approved
0.7947	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7075	Discontinued
0.7945	Intermediate Similarity	NPD5403	Approved
0.7931	Intermediate Similarity	NPD5401	Approved
0.7902	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD919	Approved
0.7879	Intermediate Similarity	NPD422	Phase 1
0.7852	Intermediate Similarity	NPD1019	Discontinued
0.7832	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD1247	Approved
0.7778	Intermediate Similarity	NPD1203	Approved
0.7778	Intermediate Similarity	NPD3267	Approved
0.7778	Intermediate Similarity	NPD3266	Approved
0.7737	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD2798	Approved
0.7692	Intermediate Similarity	NPD3926	Phase 2
0.7687	Intermediate Similarity	NPD2534	Approved
0.7687	Intermediate Similarity	NPD3972	Approved
0.7687	Intermediate Similarity	NPD2532	Approved
0.7687	Intermediate Similarity	NPD2533	Approved
0.7677	Intermediate Similarity	NPD6959	Discontinued
0.7647	Intermediate Similarity	NPD7768	Phase 2
0.7643	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2403	Approved
0.7643	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6166	Phase 2
0.7626	Intermediate Similarity	NPD3268	Approved
0.7622	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD6100	Approved
0.761	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7054	Approved
0.7597	Intermediate Similarity	NPD3749	Approved
0.7594	Intermediate Similarity	NPD17	Approved
0.7589	Intermediate Similarity	NPD1933	Approved
0.7589	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5402	Approved
0.7576	Intermediate Similarity	NPD1548	Phase 1
0.7569	Intermediate Similarity	NPD2344	Approved
0.7562	Intermediate Similarity	NPD7472	Approved
0.7547	Intermediate Similarity	NPD3818	Discontinued
0.7531	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3142	Approved
0.7518	Intermediate Similarity	NPD2797	Approved
0.7518	Intermediate Similarity	NPD3140	Approved
0.7516	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7467	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7444	Intermediate Similarity	NPD9545	Approved
0.7431	Intermediate Similarity	NPD7033	Discontinued
0.7426	Intermediate Similarity	NPD1608	Approved
0.7424	Intermediate Similarity	NPD9493	Approved
0.7423	Intermediate Similarity	NPD7808	Phase 3
0.7419	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5953	Discontinued
0.7394	Intermediate Similarity	NPD943	Approved
0.7394	Intermediate Similarity	NPD4307	Phase 2
0.7391	Intermediate Similarity	NPD7286	Phase 2
0.7376	Intermediate Similarity	NPD411	Approved
0.7375	Intermediate Similarity	NPD7473	Discontinued
0.7365	Intermediate Similarity	NPD2309	Approved
0.7357	Intermediate Similarity	NPD4908	Phase 1
0.7353	Intermediate Similarity	NPD1610	Phase 2
0.7343	Intermediate Similarity	NPD230	Phase 1
0.7343	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD447	Suspended
0.7343	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD1471	Phase 3
0.7319	Intermediate Similarity	NPD1876	Approved
0.7319	Intermediate Similarity	NPD3225	Approved
0.7317	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6232	Discontinued
0.7256	Intermediate Similarity	NPD6104	Discontinued
0.7254	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1652	Phase 2
0.7192	Intermediate Similarity	NPD4308	Phase 3
0.7161	Intermediate Similarity	NPD5889	Approved
0.7161	Intermediate Similarity	NPD5890	Approved
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD3226	Approved
0.7134	Intermediate Similarity	NPD1729	Discontinued
0.7134	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD5353	Approved
0.7133	Intermediate Similarity	NPD3887	Approved
0.7122	Intermediate Similarity	NPD4749	Approved
0.7115	Intermediate Similarity	NPD6280	Approved
0.7115	Intermediate Similarity	NPD6279	Approved
0.7109	Intermediate Similarity	NPD9697	Approved
0.7097	Intermediate Similarity	NPD6585	Discontinued
0.7095	Intermediate Similarity	NPD2353	Approved
0.7095	Intermediate Similarity	NPD2346	Discontinued
0.7095	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4363	Phase 3
0.7093	Intermediate Similarity	NPD4360	Phase 2
0.7087	Intermediate Similarity	NPD9261	Approved
0.7081	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD5710	Approved
0.708	Intermediate Similarity	NPD1778	Approved
0.7075	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5844	Phase 1
0.707	Intermediate Similarity	NPD1465	Phase 2
0.7054	Intermediate Similarity	NPD3134	Approved
0.7052	Intermediate Similarity	NPD4361	Phase 2
0.7052	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7390	Discontinued
0.7014	Intermediate Similarity	NPD6798	Discontinued
0.7012	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1651	Approved
0.7	Intermediate Similarity	NPD1358	Approved
0.6993	Remote Similarity	NPD4662	Approved
0.6993	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4661	Approved
0.6992	Remote Similarity	NPD5535	Approved
0.6988	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6355	Discontinued
0.6975	Remote Similarity	NPD6808	Phase 2
0.6974	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2186	Approved
0.6934	Remote Similarity	NPD1894	Discontinued
0.6929	Remote Similarity	NPD1481	Phase 2
0.6923	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7199	Phase 2
0.6908	Remote Similarity	NPD2354	Approved
0.6899	Remote Similarity	NPD6844	Discontinued
0.6897	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7229	Phase 3
0.687	Remote Similarity	NPD9264	Approved
0.687	Remote Similarity	NPD9263	Approved
0.687	Remote Similarity	NPD9267	Approved
0.6867	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5536	Phase 2
0.6857	Remote Similarity	NPD1281	Approved
0.6857	Remote Similarity	NPD1535	Discovery
0.6849	Remote Similarity	NPD6233	Phase 2
0.6832	Remote Similarity	NPD6971	Discontinued
0.6829	Remote Similarity	NPD5242	Approved
0.6829	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2424	Discontinued
0.6818	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2684	Approved
0.6818	Remote Similarity	NPD74	Approved
0.6818	Remote Similarity	NPD9266	Approved
0.6815	Remote Similarity	NPD7458	Discontinued
0.6813	Remote Similarity	NPD2296	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