NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.07
Volume:	244.373
LogP:	3.019
LogD:	3.003
LogS:	-3.269
# Rotatable Bonds:	0
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	2.906
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.704
MDCK Permeability:	2.0426188712008297e-05
Pgp-inhibitor:	0.189
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.577

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	96.32157135009766%
Volume Distribution (VD):	0.548
Pgp-substrate:	6.773091793060303%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.803
CYP2C19-inhibitor:	0.337
CYP2C19-substrate:	0.168
CYP2C9-inhibitor:	0.35
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.855
CYP2D6-substrate:	0.59
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	7.741
Half-life (T1/2):	0.477

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.826
Drug-inuced Liver Injury (DILI):	0.857
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.632
Maximum Recommended Daily Dose:	0.7
Skin Sensitization:	0.64
Carcinogencity:	0.854
Eye Corrosion:	0.007
Eye Irritation:	0.536
Respiratory Toxicity:	0.527

Download Data

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

Natural Product: NPC230157

Natural Product ID:	NPC230157
*Common Name:**	Cedrecoumarin A
IUPAC Name:	5-hydroxy-3,3-dimethylpyrano[3,2-f]chromen-8-one
Synonyms:
Standard InCHIKey:	OGTYTYOKQRCQEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O4/c1-14(2)6-5-9-8-3-4-12(16)17-11(8)7-10(15)13(9)18-14/h3-7,15H,1-2H3
SMILES:	CC1(C)C=Cc2c3ccc(=O)oc3cc(c2O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491519
PubChem CID:	10263845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO32494	cedrelopsis microfoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350164]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19319	Cedrelopsis grevei	Species	Rutaceae	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
IC50	2
Others	2

Activity Type	# Activity
Individual Protein	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	20.0	%	PMID[497108]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	20.0	%	PMID[497108]
NPT2	Others	Unspecified		IC50	=	13.0	ug.mL-1	PMID[497108]
NPT2	Others	Unspecified		IC50	=	0.2	ug.mL-1	PMID[497108]

☑ 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 NPC230157 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	408
0.1-0.2	2143
0.2-0.3	5486
0.3-0.4	11543
0.4-0.5	5570
0.5-0.6	4171
0.6-0.7	5479
0.7-0.8	5386
0.8-0.85	1785
0.85-0.9	686
0.9-0.95	38
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9424	High Similarity	NPC236419
0.9412	High Similarity	NPC82271
0.9412	High Similarity	NPC126682
0.9343	High Similarity	NPC148835
0.9343	High Similarity	NPC95162
0.9343	High Similarity	NPC76336
0.9343	High Similarity	NPC20511
0.9343	High Similarity	NPC52086
0.9343	High Similarity	NPC139548
0.9275	High Similarity	NPC13067
0.9191	High Similarity	NPC26673
0.9191	High Similarity	NPC277021
0.9149	High Similarity	NPC34245
0.9149	High Similarity	NPC6568
0.9149	High Similarity	NPC91492
0.9149	High Similarity	NPC256555
0.9149	High Similarity	NPC7439
0.9149	High Similarity	NPC110067
0.9124	High Similarity	NPC92830
0.9118	High Similarity	NPC137949
0.9065	High Similarity	NPC38874
0.9044	High Similarity	NPC73738
0.9028	High Similarity	NPC178129
0.9028	High Similarity	NPC231149
0.8966	High Similarity	NPC139839
0.8951	High Similarity	NPC185127
0.8929	High Similarity	NPC105493
0.8904	High Similarity	NPC30688
0.8904	High Similarity	NPC176903
0.8897	High Similarity	NPC27239
0.8897	High Similarity	NPC123127
0.8873	High Similarity	NPC300611
0.8865	High Similarity	NPC164148
0.8865	High Similarity	NPC43500
0.8857	High Similarity	NPC167517
0.8844	High Similarity	NPC294522
0.8844	High Similarity	NPC205727
0.8844	High Similarity	NPC120426
0.8844	High Similarity	NPC21184
0.8836	High Similarity	NPC48366
0.8832	High Similarity	NPC240722
0.8832	High Similarity	NPC244799
0.8819	High Similarity	NPC471763
0.8794	High Similarity	NPC474886
0.8777	High Similarity	NPC474810
0.8767	High Similarity	NPC476347
0.8732	High Similarity	NPC270256
0.8725	High Similarity	NPC163598
0.8725	High Similarity	NPC264875
0.8725	High Similarity	NPC120774
0.8714	High Similarity	NPC309953
0.8707	High Similarity	NPC187398
0.8707	High Similarity	NPC476348
0.8705	High Similarity	NPC137669
0.8699	High Similarity	NPC205361
0.8662	High Similarity	NPC476171
0.8658	High Similarity	NPC213197
0.8652	High Similarity	NPC472521
0.8652	High Similarity	NPC234865
0.8649	High Similarity	NPC313334
0.8649	High Similarity	NPC206264
0.8649	High Similarity	NPC212670
0.8643	High Similarity	NPC241341
0.8643	High Similarity	NPC233018
0.8643	High Similarity	NPC36437
0.8639	High Similarity	NPC275125
0.8639	High Similarity	NPC15577
0.8639	High Similarity	NPC97937
0.8639	High Similarity	NPC170239
0.8633	High Similarity	NPC142530
0.8633	High Similarity	NPC147317
0.863	High Similarity	NPC476450
0.8621	High Similarity	NPC138212
0.8611	High Similarity	NPC279851
0.8611	High Similarity	NPC472520
0.8592	High Similarity	NPC286843
0.8592	High Similarity	NPC309031
0.8582	High Similarity	NPC147030
0.8582	High Similarity	NPC111635
0.8571	High Similarity	NPC319969
0.8571	High Similarity	NPC123954
0.8571	High Similarity	NPC474635
0.8571	High Similarity	NPC475896
0.8552	High Similarity	NPC469564
0.8531	High Similarity	NPC276328
0.8523	High Similarity	NPC113790
0.8521	High Similarity	NPC240915
0.8521	High Similarity	NPC252095
0.8514	High Similarity	NPC41844
0.8503	High Similarity	NPC125617
0.8503	High Similarity	NPC292256
0.8467	Intermediate Similarity	NPC300326
0.8467	Intermediate Similarity	NPC58279
0.8456	Intermediate Similarity	NPC248786
0.8456	Intermediate Similarity	NPC96294
0.8451	Intermediate Similarity	NPC106215
0.8451	Intermediate Similarity	NPC474600
0.844	Intermediate Similarity	NPC245120
0.8429	Intermediate Similarity	NPC19242
0.8421	Intermediate Similarity	NPC149735
0.8417	Intermediate Similarity	NPC474616
0.8417	Intermediate Similarity	NPC109275
0.8414	Intermediate Similarity	NPC144284
0.8403	Intermediate Similarity	NPC225106
0.8403	Intermediate Similarity	NPC294456
0.8403	Intermediate Similarity	NPC20796
0.8403	Intermediate Similarity	NPC212124
0.8403	Intermediate Similarity	NPC281014
0.8403	Intermediate Similarity	NPC184861
0.8392	Intermediate Similarity	NPC73071
0.8389	Intermediate Similarity	NPC137352
0.8389	Intermediate Similarity	NPC183083
0.838	Intermediate Similarity	NPC105554
0.838	Intermediate Similarity	NPC168059
0.838	Intermediate Similarity	NPC229442
0.838	Intermediate Similarity	NPC472522
0.8369	Intermediate Similarity	NPC469907
0.8366	Intermediate Similarity	NPC473736
0.8357	Intermediate Similarity	NPC48315
0.8357	Intermediate Similarity	NPC45824
0.8345	Intermediate Similarity	NPC127218
0.8345	Intermediate Similarity	NPC245207
0.8345	Intermediate Similarity	NPC319647
0.8345	Intermediate Similarity	NPC25966
0.8344	Intermediate Similarity	NPC470916
0.8344	Intermediate Similarity	NPC114740
0.8333	Intermediate Similarity	NPC78746
0.8333	Intermediate Similarity	NPC188380
0.8333	Intermediate Similarity	NPC301089
0.8333	Intermediate Similarity	NPC224543
0.8333	Intermediate Similarity	NPC155101
0.8323	Intermediate Similarity	NPC247713
0.8322	Intermediate Similarity	NPC268515
0.8322	Intermediate Similarity	NPC7163
0.8322	Intermediate Similarity	NPC40222
0.8322	Intermediate Similarity	NPC287275
0.8311	Intermediate Similarity	NPC50250
0.831	Intermediate Similarity	NPC86655
0.831	Intermediate Similarity	NPC202762
0.8309	Intermediate Similarity	NPC52247
0.8309	Intermediate Similarity	NPC187868
0.8301	Intermediate Similarity	NPC475141
0.8301	Intermediate Similarity	NPC150442
0.8298	Intermediate Similarity	NPC214860
0.8298	Intermediate Similarity	NPC474617
0.8298	Intermediate Similarity	NPC91291
0.8291	Intermediate Similarity	NPC67959
0.8288	Intermediate Similarity	NPC234568
0.8286	Intermediate Similarity	NPC46274
0.8286	Intermediate Similarity	NPC226331
0.8278	Intermediate Similarity	NPC474393
0.8278	Intermediate Similarity	NPC474347
0.8278	Intermediate Similarity	NPC10010
0.8276	Intermediate Similarity	NPC153818
0.8276	Intermediate Similarity	NPC102904
0.8276	Intermediate Similarity	NPC232246
0.8276	Intermediate Similarity	NPC35550
0.8276	Intermediate Similarity	NPC276490
0.8276	Intermediate Similarity	NPC126206
0.8276	Intermediate Similarity	NPC326797
0.8276	Intermediate Similarity	NPC176051
0.8276	Intermediate Similarity	NPC103976
0.8276	Intermediate Similarity	NPC474282
0.8276	Intermediate Similarity	NPC107551
0.8273	Intermediate Similarity	NPC476006
0.8269	Intermediate Similarity	NPC37502
0.8269	Intermediate Similarity	NPC474290
0.8269	Intermediate Similarity	NPC267627
0.8269	Intermediate Similarity	NPC238381
0.8269	Intermediate Similarity	NPC40702
0.8264	Intermediate Similarity	NPC472337
0.8264	Intermediate Similarity	NPC472525
0.8264	Intermediate Similarity	NPC327382
0.8264	Intermediate Similarity	NPC33986
0.8261	Intermediate Similarity	NPC183446
0.8255	Intermediate Similarity	NPC86069
0.8252	Intermediate Similarity	NPC36661
0.8247	Intermediate Similarity	NPC8712
0.8247	Intermediate Similarity	NPC62903
0.8247	Intermediate Similarity	NPC268484
0.8247	Intermediate Similarity	NPC178134
0.8247	Intermediate Similarity	NPC7178
0.8239	Intermediate Similarity	NPC82503
0.8239	Intermediate Similarity	NPC66430
0.8239	Intermediate Similarity	NPC85057
0.8239	Intermediate Similarity	NPC37009
0.8239	Intermediate Similarity	NPC130920
0.8235	Intermediate Similarity	NPC169404
0.8235	Intermediate Similarity	NPC302107
0.8235	Intermediate Similarity	NPC53587
0.8235	Intermediate Similarity	NPC307253
0.8235	Intermediate Similarity	NPC176186
0.8231	Intermediate Similarity	NPC195357
0.8231	Intermediate Similarity	NPC83375
0.8231	Intermediate Similarity	NPC152771
0.8231	Intermediate Similarity	NPC224876
0.8231	Intermediate Similarity	NPC471389
0.8228	Intermediate Similarity	NPC8300
0.8227	Intermediate Similarity	NPC58164
0.8227	Intermediate Similarity	NPC10225

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 NPC230157 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1077
0.2-0.3	2051
0.3-0.4	2707
0.4-0.5	1619
0.5-0.6	867
0.6-0.7	294
0.7-0.8	112
0.8-0.85	20
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD1653	Approved
0.8309	Intermediate Similarity	NPD422	Phase 1
0.8286	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1465	Phase 2
0.8214	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1613	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.7895	Intermediate Similarity	NPD1511	Approved
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1512	Approved
0.7748	Intermediate Similarity	NPD1652	Phase 2
0.7724	Intermediate Similarity	NPD3027	Phase 3
0.7722	Intermediate Similarity	NPD1934	Approved
0.7688	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7549	Discontinued
0.7635	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD5124	Phase 1
0.7635	Intermediate Similarity	NPD447	Suspended
0.7625	Intermediate Similarity	NPD3817	Phase 2
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1548	Phase 1
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7483	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3882	Suspended
0.7455	Intermediate Similarity	NPD6232	Discontinued
0.7453	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4060	Phase 1
0.7431	Intermediate Similarity	NPD4749	Approved
0.7415	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1610	Phase 2
0.7407	Intermediate Similarity	NPD5402	Approved
0.7394	Intermediate Similarity	NPD7199	Phase 2
0.7381	Intermediate Similarity	NPD3818	Discontinued
0.7379	Intermediate Similarity	NPD3225	Approved
0.7372	Intermediate Similarity	NPD228	Approved
0.7343	Intermediate Similarity	NPD3496	Discontinued
0.7337	Intermediate Similarity	NPD7054	Approved
0.7321	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4908	Phase 1
0.7294	Intermediate Similarity	NPD7472	Approved
0.7292	Intermediate Similarity	NPD1611	Approved
0.7284	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7262	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6166	Phase 2
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD4965	Approved
0.7239	Intermediate Similarity	NPD7819	Suspended
0.7212	Intermediate Similarity	NPD3749	Approved
0.7211	Intermediate Similarity	NPD2797	Approved
0.72	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6190	Approved
0.7193	Intermediate Similarity	NPD7074	Phase 3
0.7176	Intermediate Similarity	NPD7228	Approved
0.7169	Intermediate Similarity	NPD919	Approved
0.7163	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD6696	Suspended
0.7133	Intermediate Similarity	NPD7095	Approved
0.7126	Intermediate Similarity	NPD5494	Approved
0.7125	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3018	Phase 2
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.711	Intermediate Similarity	NPD7251	Discontinued
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7107	Intermediate Similarity	NPD6799	Approved
0.7105	Intermediate Similarity	NPD1558	Phase 1
0.7097	Intermediate Similarity	NPD2935	Discontinued
0.7097	Intermediate Similarity	NPD6100	Approved
0.7097	Intermediate Similarity	NPD1551	Phase 2
0.7097	Intermediate Similarity	NPD6099	Approved
0.7086	Intermediate Similarity	NPD3268	Approved
0.7086	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5403	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.7073	Intermediate Similarity	NPD6801	Discontinued
0.7069	Intermediate Similarity	NPD7808	Phase 3
0.7063	Intermediate Similarity	NPD5401	Approved
0.7063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9697	Approved
0.7055	Intermediate Similarity	NPD3705	Approved
0.7045	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1510	Phase 2
0.7032	Intermediate Similarity	NPD4308	Phase 3
0.703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD9269	Phase 2
0.7007	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD1549	Phase 2
0.7006	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3226	Approved
0.6988	Remote Similarity	NPD4288	Approved
0.6982	Remote Similarity	NPD8127	Discontinued
0.6982	Remote Similarity	NPD1247	Approved
0.698	Remote Similarity	NPD1203	Approved
0.6975	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5691	Approved
0.6962	Remote Similarity	NPD6674	Discontinued
0.6959	Remote Similarity	NPD2982	Phase 2
0.6959	Remote Similarity	NPD2983	Phase 2
0.6957	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2534	Approved
0.6951	Remote Similarity	NPD6599	Discontinued
0.6951	Remote Similarity	NPD4380	Phase 2
0.6948	Remote Similarity	NPD4340	Discontinued
0.6946	Remote Similarity	NPD7768	Phase 2
0.6943	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5762	Approved
0.6943	Remote Similarity	NPD5763	Approved
0.6939	Remote Similarity	NPD1535	Discovery
0.6939	Remote Similarity	NPD1091	Approved
0.6928	Remote Similarity	NPD6233	Phase 2
0.6918	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4628	Phase 3
0.6909	Remote Similarity	NPD5090	Approved
0.6909	Remote Similarity	NPD5089	Approved
0.6901	Remote Similarity	NPD1398	Phase 1
0.6894	Remote Similarity	NPD4357	Discontinued
0.6892	Remote Similarity	NPD1608	Approved
0.6892	Remote Similarity	NPD1481	Phase 2
0.6892	Remote Similarity	NPD2981	Phase 2
0.6887	Remote Similarity	NPD9494	Approved
0.6883	Remote Similarity	NPD1240	Approved
0.6883	Remote Similarity	NPD943	Approved
0.6871	Remote Similarity	NPD920	Approved
0.6867	Remote Similarity	NPD3266	Approved
0.6867	Remote Similarity	NPD3267	Approved
0.6863	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD411	Approved
0.6863	Remote Similarity	NPD7985	Registered
0.6863	Remote Similarity	NPD3764	Approved
0.6855	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1243	Approved
0.6842	Remote Similarity	NPD3787	Discontinued
0.6839	Remote Similarity	NPD1933	Approved
0.6835	Remote Similarity	NPD1358	Approved
0.6835	Remote Similarity	NPD2346	Discontinued
0.6831	Remote Similarity	NPD5535	Approved
0.6829	Remote Similarity	NPD3686	Approved
0.6829	Remote Similarity	NPD3687	Approved
0.6828	Remote Similarity	NPD5536	Phase 2
0.6828	Remote Similarity	NPD7644	Approved
0.6818	Remote Similarity	NPD6559	Discontinued
0.6818	Remote Similarity	NPD7685	Pre-registration
0.6807	Remote Similarity	NPD7411	Suspended
0.6803	Remote Similarity	NPD1778	Approved
0.6795	Remote Similarity	NPD1607	Approved
0.6784	Remote Similarity	NPD6959	Discontinued
0.6783	Remote Similarity	NPD5283	Phase 1
0.6778	Remote Similarity	NPD6841	Approved
0.6778	Remote Similarity	NPD6843	Phase 3
0.6778	Remote Similarity	NPD6842	Approved
0.6774	Remote Similarity	NPD3620	Phase 2
0.6774	Remote Similarity	NPD4307	Phase 2
0.6774	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4140	Approved
0.6772	Remote Similarity	NPD2796	Approved
0.6759	Remote Similarity	NPD7340	Approved
0.6755	Remote Similarity	NPD987	Approved
0.6753	Remote Similarity	NPD6798	Discontinued
0.675	Remote Similarity	NPD2800	Approved
0.675	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7229	Phase 3
0.6735	Remote Similarity	NPD9268	Approved
0.6731	Remote Similarity	NPD6355	Discontinued
0.673	Remote Similarity	NPD1375	Discontinued
0.6725	Remote Similarity	NPD5677	Discontinued
0.6723	Remote Similarity	NPD7240	Approved
0.6714	Remote Similarity	NPD290	Approved
0.6711	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7033	Discontinued
0.6708	Remote Similarity	NPD4110	Phase 3
0.6708	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD8166	Discontinued
0.6707	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD8053	Approved
0.6704	Remote Similarity	NPD8054	Approved
0.6689	Remote Similarity	NPD8651	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