NPASS Compound

Structure

NPC50696 OpenBabel07101719242D 27 30 0 0 1 0 0 0 0 0999 V2000 7.3250 -2.6395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2569 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0219 -1.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9811 -0.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9182 -1.7260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9237 -1.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3830 0.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3830 -1.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5659 -1.0169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2490 0.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2490 -0.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5170 0.2921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9781 -0.2079 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5170 -0.7079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1151 0.7921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -1.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1151 -1.2079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 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 4.5659 0.6011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 17 2 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 11 26 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 6 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 27 1 0 0 0 0 19 13 1 6 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 21 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.14
Volume:	371.832
LogP:	3.059
LogD:	2.947
LogS:	-4.526
# Rotatable Bonds:	5
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	4.347
Fsp3:	0.381
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:	-4.658
MDCK Permeability:	1.6834865164128132e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	87.7139663696289%
Volume Distribution (VD):	1.18
Pgp-substrate:	7.085323333740234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.81
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.788
CYP2C9-substrate:	0.616
CYP2D6-inhibitor:	0.956
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	10.083
Half-life (T1/2):	0.313

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.815
Drug-inuced Liver Injury (DILI):	0.069
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.412
Maximum Recommended Daily Dose:	0.765
Skin Sensitization:	0.8
Carcinogencity:	0.871
Eye Corrosion:	0.007
Eye Irritation:	0.028
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC50696

Natural Product ID:	NPC50696
*Common Name:**	(2R,3S,3As)-5-Methoxy-2-(7-Methoxy-1,3-Benzodioxol-5-Yl)-3-Methyl-3A-Prop-2-Enyl-2,3-Dihydro-1-Benzofuran-6-One
IUPAC Name:	(2R,3S,3aS)-5-methoxy-2-(7-methoxy-1,3-benzodioxol-5-yl)-3-methyl-3a-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
Synonyms:
Standard InCHIKey:	URBCBHTUEUNACZ-PCFDJQJPSA-N
Standard InCHI:	InChI=1S/C21H22O6/c1-5-6-21-10-17(24-4)14(22)9-18(21)27-19(12(21)2)13-7-15(23-3)20-16(8-13)25-11-26-20/h5,7-10,12,19H,1,6,11H2,2-4H3/t12-,19-,21-/m1/s1
SMILES:	C=CC[C@@]12C=C(C(=O)C=C2O[C@H]([C@H]1C)c1cc(c2c(c1)OCO2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524122
PubChem CID:	44576119
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO14069	Endlicheria dysodantha	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1665173]
NPO14069	Endlicheria dysodantha	Species	Lauraceae	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
ED50	3
Others	1

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	100.0	ug ml-1	PMID[491163]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	79.0	ug ml-1	PMID[491163]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	96.5	ug ml-1	PMID[491163]
NPT140	Organism	Artemia	Artemia	LC50	=	162.1	ppm	PMID[491163]

☑ 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 NPC50696 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	458
0.1-0.2	1489
0.2-0.3	3560
0.3-0.4	8976
0.4-0.5	10187
0.5-0.6	4841
0.6-0.7	10488
0.7-0.8	2446
0.8-0.85	203
0.85-0.9	41
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC278076
0.9441	High Similarity	NPC475170
0.9231	High Similarity	NPC25496
0.9137	High Similarity	NPC166184
0.9122	High Similarity	NPC117154
0.9071	High Similarity	NPC178290
0.8986	High Similarity	NPC136750
0.8986	High Similarity	NPC266848
0.8951	High Similarity	NPC474966
0.8921	High Similarity	NPC145769
0.8913	High Similarity	NPC72046
0.8913	High Similarity	NPC65183
0.8913	High Similarity	NPC261812
0.8857	High Similarity	NPC189474
0.8841	High Similarity	NPC192255
0.8828	High Similarity	NPC476841
0.8828	High Similarity	NPC476843
0.8794	High Similarity	NPC11453
0.8786	High Similarity	NPC31530
0.8759	High Similarity	NPC15743
0.8723	High Similarity	NPC49235
0.8723	High Similarity	NPC25333
0.8723	High Similarity	NPC148893
0.8662	High Similarity	NPC143895
0.8662	High Similarity	NPC121651
0.8643	High Similarity	NPC7744
0.8633	High Similarity	NPC339621
0.8633	High Similarity	NPC280399
0.8633	High Similarity	NPC233961
0.8623	High Similarity	NPC165128
0.8623	High Similarity	NPC82862
0.8623	High Similarity	NPC158471
0.8623	High Similarity	NPC222127
0.8623	High Similarity	NPC226862
0.8623	High Similarity	NPC57119
0.8621	High Similarity	NPC46180
0.8621	High Similarity	NPC476840
0.8621	High Similarity	NPC476842
0.8621	High Similarity	NPC287124
0.8601	High Similarity	NPC185908
0.8591	High Similarity	NPC85141
0.8571	High Similarity	NPC227160
0.8571	High Similarity	NPC82111
0.8552	High Similarity	NPC51681
0.8552	High Similarity	NPC312199
0.8551	High Similarity	NPC473092
0.8551	High Similarity	NPC8050
0.8551	High Similarity	NPC473093
0.8544	High Similarity	NPC474948
0.8544	High Similarity	NPC42230
0.8542	High Similarity	NPC113550
0.8533	High Similarity	NPC177830
0.8514	High Similarity	NPC472560
0.8503	High Similarity	NPC141569
0.8503	High Similarity	NPC475000
0.8503	High Similarity	NPC166884
0.8503	High Similarity	NPC477701
0.85	High Similarity	NPC233224
0.85	High Similarity	NPC271208
0.8497	Intermediate Similarity	NPC476363
0.8493	Intermediate Similarity	NPC80326
0.8493	Intermediate Similarity	NPC210354
0.8493	Intermediate Similarity	NPC176586
0.8493	Intermediate Similarity	NPC472562
0.8489	Intermediate Similarity	NPC54321
0.8489	Intermediate Similarity	NPC328682
0.8489	Intermediate Similarity	NPC281864
0.8483	Intermediate Similarity	NPC216434
0.8483	Intermediate Similarity	NPC46591
0.8483	Intermediate Similarity	NPC103448
0.8483	Intermediate Similarity	NPC177868
0.8478	Intermediate Similarity	NPC50683
0.8478	Intermediate Similarity	NPC285725
0.8478	Intermediate Similarity	NPC112571
0.8477	Intermediate Similarity	NPC163002
0.8472	Intermediate Similarity	NPC283949
0.8467	Intermediate Similarity	NPC472567
0.8462	Intermediate Similarity	NPC150534
0.8462	Intermediate Similarity	NPC174191
0.8451	Intermediate Similarity	NPC196937
0.8451	Intermediate Similarity	NPC1474
0.8447	Intermediate Similarity	NPC474568
0.8446	Intermediate Similarity	NPC477702
0.8446	Intermediate Similarity	NPC474158
0.8435	Intermediate Similarity	NPC255566
0.8435	Intermediate Similarity	NPC298317
0.8425	Intermediate Similarity	NPC58137
0.8425	Intermediate Similarity	NPC300798
0.8418	Intermediate Similarity	NPC475953
0.8417	Intermediate Similarity	NPC64948
0.84	Intermediate Similarity	NPC198129
0.84	Intermediate Similarity	NPC327352
0.84	Intermediate Similarity	NPC477375
0.84	Intermediate Similarity	NPC252281
0.8389	Intermediate Similarity	NPC212890
0.8389	Intermediate Similarity	NPC193779
0.838	Intermediate Similarity	NPC171928
0.838	Intermediate Similarity	NPC129687
0.838	Intermediate Similarity	NPC33611
0.838	Intermediate Similarity	NPC158526
0.838	Intermediate Similarity	NPC100223
0.838	Intermediate Similarity	NPC16830
0.8378	Intermediate Similarity	NPC191158
0.8378	Intermediate Similarity	NPC177644
0.8367	Intermediate Similarity	NPC151423
0.8367	Intermediate Similarity	NPC474295
0.8367	Intermediate Similarity	NPC174522
0.8367	Intermediate Similarity	NPC40237
0.8367	Intermediate Similarity	NPC311057
0.8356	Intermediate Similarity	NPC226547
0.8356	Intermediate Similarity	NPC56091
0.8345	Intermediate Similarity	NPC88297
0.8345	Intermediate Similarity	NPC186845
0.8345	Intermediate Similarity	NPC9891
0.8344	Intermediate Similarity	NPC322426
0.8344	Intermediate Similarity	NPC477376
0.8344	Intermediate Similarity	NPC477374
0.8333	Intermediate Similarity	NPC121783
0.8333	Intermediate Similarity	NPC474139
0.8333	Intermediate Similarity	NPC18449
0.8333	Intermediate Similarity	NPC34902
0.8322	Intermediate Similarity	NPC180953
0.8312	Intermediate Similarity	NPC178195
0.8312	Intermediate Similarity	NPC348849
0.8312	Intermediate Similarity	NPC198461
0.8312	Intermediate Similarity	NPC312763
0.8311	Intermediate Similarity	NPC185071
0.8311	Intermediate Similarity	NPC474808
0.8311	Intermediate Similarity	NPC12728
0.8311	Intermediate Similarity	NPC76415
0.8311	Intermediate Similarity	NPC218510
0.8311	Intermediate Similarity	NPC474288
0.8302	Intermediate Similarity	NPC474647
0.8301	Intermediate Similarity	NPC475229
0.8301	Intermediate Similarity	NPC477378
0.8298	Intermediate Similarity	NPC476748
0.8289	Intermediate Similarity	NPC316989
0.8278	Intermediate Similarity	NPC262804
0.8278	Intermediate Similarity	NPC40654
0.8276	Intermediate Similarity	NPC32189
0.8273	Intermediate Similarity	NPC85830
0.8264	Intermediate Similarity	NPC170779
0.8264	Intermediate Similarity	NPC37065
0.8264	Intermediate Similarity	NPC47181
0.8264	Intermediate Similarity	NPC90083
0.8255	Intermediate Similarity	NPC218841
0.8255	Intermediate Similarity	NPC326144
0.8255	Intermediate Similarity	NPC92693
0.8252	Intermediate Similarity	NPC147616
0.8252	Intermediate Similarity	NPC259742
0.8252	Intermediate Similarity	NPC219671
0.8252	Intermediate Similarity	NPC104077
0.825	Intermediate Similarity	NPC476277
0.8247	Intermediate Similarity	NPC477377
0.8219	Intermediate Similarity	NPC474039
0.8219	Intermediate Similarity	NPC20796
0.8219	Intermediate Similarity	NPC196420
0.8207	Intermediate Similarity	NPC18576
0.8207	Intermediate Similarity	NPC236522
0.8207	Intermediate Similarity	NPC135777
0.8207	Intermediate Similarity	NPC99572
0.8207	Intermediate Similarity	NPC126409
0.8207	Intermediate Similarity	NPC142547
0.82	Intermediate Similarity	NPC205316
0.82	Intermediate Similarity	NPC327651
0.82	Intermediate Similarity	NPC318286
0.8188	Intermediate Similarity	NPC288238
0.8182	Intermediate Similarity	NPC56184
0.817	Intermediate Similarity	NPC12854
0.817	Intermediate Similarity	NPC473989
0.8163	Intermediate Similarity	NPC88640
0.8163	Intermediate Similarity	NPC123526
0.8163	Intermediate Similarity	NPC9068
0.8163	Intermediate Similarity	NPC193666
0.8162	Intermediate Similarity	NPC119949
0.8156	Intermediate Similarity	NPC158737
0.8151	Intermediate Similarity	NPC209229
0.8151	Intermediate Similarity	NPC78047
0.8151	Intermediate Similarity	NPC25695
0.8151	Intermediate Similarity	NPC172818
0.8146	Intermediate Similarity	NPC321696
0.8146	Intermediate Similarity	NPC321958
0.8141	Intermediate Similarity	NPC188962
0.8141	Intermediate Similarity	NPC202249
0.8141	Intermediate Similarity	NPC42871
0.8138	Intermediate Similarity	NPC145722
0.8138	Intermediate Similarity	NPC185680
0.8138	Intermediate Similarity	NPC256776
0.8133	Intermediate Similarity	NPC239254
0.8133	Intermediate Similarity	NPC297342
0.8133	Intermediate Similarity	NPC172171
0.8129	Intermediate Similarity	NPC297271
0.8129	Intermediate Similarity	NPC53669
0.8129	Intermediate Similarity	NPC77237
0.8129	Intermediate Similarity	NPC16791
0.8129	Intermediate Similarity	NPC126405
0.8129	Intermediate Similarity	NPC24562
0.8129	Intermediate Similarity	NPC308555
0.8129	Intermediate Similarity	NPC308739
0.8129	Intermediate Similarity	NPC217708

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 NPC50696 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	878
0.2-0.3	1899
0.3-0.4	2807
0.4-0.5	1788
0.5-0.6	978
0.6-0.7	406
0.7-0.8	37
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD3705	Approved
0.7922	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4966	Approved
0.7862	Intermediate Similarity	NPD4965	Approved
0.7862	Intermediate Similarity	NPD4967	Phase 2
0.7764	Intermediate Similarity	NPD6234	Discontinued
0.7683	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD37	Approved
0.7671	Intermediate Similarity	NPD3027	Phase 3
0.7532	Intermediate Similarity	NPD1653	Approved
0.7518	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5494	Approved
0.7464	Intermediate Similarity	NPD5283	Phase 1
0.7455	Intermediate Similarity	NPD7199	Phase 2
0.744	Intermediate Similarity	NPD3818	Discontinued
0.744	Intermediate Similarity	NPD7228	Approved
0.7438	Intermediate Similarity	NPD7028	Phase 2
0.7423	Intermediate Similarity	NPD3882	Suspended
0.7376	Intermediate Similarity	NPD5536	Phase 2
0.7362	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD919	Approved
0.731	Intermediate Similarity	NPD2981	Phase 2
0.7299	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7240	Approved
0.726	Intermediate Similarity	NPD2983	Phase 2
0.726	Intermediate Similarity	NPD2982	Phase 2
0.7246	Intermediate Similarity	NPD1247	Approved
0.7226	Intermediate Similarity	NPD7266	Discontinued
0.7225	Intermediate Similarity	NPD7808	Phase 3
0.7222	Intermediate Similarity	NPD6599	Discontinued
0.7209	Intermediate Similarity	NPD6797	Phase 2
0.7181	Intermediate Similarity	NPD3018	Phase 2
0.7178	Intermediate Similarity	NPD5089	Approved
0.7178	Intermediate Similarity	NPD5090	Approved
0.7171	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1613	Approved
0.7168	Intermediate Similarity	NPD7251	Discontinued
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7074	Phase 3
0.7143	Intermediate Similarity	NPD6111	Discontinued
0.7134	Intermediate Similarity	NPD1934	Approved
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7124	Phase 2
0.7093	Intermediate Similarity	NPD7054	Approved
0.7091	Intermediate Similarity	NPD4585	Approved
0.7089	Intermediate Similarity	NPD4110	Phase 3
0.7089	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5297	Approved
0.7063	Intermediate Similarity	NPD6799	Approved
0.7052	Intermediate Similarity	NPD7472	Approved
0.7048	Intermediate Similarity	NPD5353	Approved
0.7029	Intermediate Similarity	NPD1358	Approved
0.7027	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6674	Discontinued
0.702	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7095	Approved
0.6971	Remote Similarity	NPD6559	Discontinued
0.6968	Remote Similarity	NPD2492	Phase 1
0.6964	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5242	Approved
0.6957	Remote Similarity	NPD4357	Discontinued
0.6957	Remote Similarity	NPD3134	Approved
0.6954	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4060	Phase 1
0.6943	Remote Similarity	NPD2796	Approved
0.6941	Remote Similarity	NPD8127	Discontinued
0.6936	Remote Similarity	NPD3751	Discontinued
0.6928	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6841	Approved
0.6927	Remote Similarity	NPD6843	Phase 3
0.6927	Remote Similarity	NPD6842	Approved
0.6918	Remote Similarity	NPD5691	Approved
0.6908	Remote Similarity	NPD4908	Phase 1
0.6905	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3657	Discovery
0.6903	Remote Similarity	NPD6355	Discontinued
0.6899	Remote Similarity	NPD5763	Approved
0.6899	Remote Similarity	NPD5762	Approved
0.6897	Remote Similarity	NPD5844	Phase 1
0.6897	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1091	Approved
0.689	Remote Similarity	NPD4210	Discontinued
0.6886	Remote Similarity	NPD2801	Approved
0.6879	Remote Similarity	NPD3748	Approved
0.6875	Remote Similarity	NPD7157	Approved
0.6875	Remote Similarity	NPD4628	Phase 3
0.6871	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7075	Discontinued
0.6864	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5402	Approved
0.6839	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3620	Phase 2
0.6832	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6190	Approved
0.6826	Remote Similarity	NPD3382	Approved
0.6826	Remote Similarity	NPD3383	Approved
0.6826	Remote Similarity	NPD3384	Approved
0.6826	Remote Similarity	NPD6801	Discontinued
0.6821	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1652	Phase 2
0.6803	Remote Similarity	NPD5585	Approved
0.6802	Remote Similarity	NPD3787	Discontinued
0.68	Remote Similarity	NPD4749	Approved
0.68	Remote Similarity	NPD5327	Phase 3
0.6795	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD230	Phase 1
0.6795	Remote Similarity	NPD5124	Phase 1
0.6782	Remote Similarity	NPD7473	Discontinued
0.678	Remote Similarity	NPD7685	Pre-registration
0.6779	Remote Similarity	NPD1610	Phase 2
0.6779	Remote Similarity	NPD422	Phase 1
0.6768	Remote Similarity	NPD1512	Approved
0.6755	Remote Similarity	NPD8651	Approved
0.6755	Remote Similarity	NPD5005	Approved
0.6755	Remote Similarity	NPD5006	Approved
0.6746	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7549	Discontinued
0.6736	Remote Similarity	NPD1241	Discontinued
0.6732	Remote Similarity	NPD2861	Phase 2
0.6731	Remote Similarity	NPD4140	Approved
0.673	Remote Similarity	NPD3539	Phase 1
0.6727	Remote Similarity	NPD5403	Approved
0.6724	Remote Similarity	NPD4481	Phase 3
0.6724	Remote Similarity	NPD2403	Approved
0.6723	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD228	Approved
0.6711	Remote Similarity	NPD3496	Discontinued
0.671	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4236	Phase 3
0.6708	Remote Similarity	NPD4237	Approved
0.6707	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5401	Approved
0.6707	Remote Similarity	NPD3146	Approved
0.6707	Remote Similarity	NPD4380	Phase 2
0.6707	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6232	Discontinued
0.6688	Remote Similarity	NPD1933	Approved
0.6688	Remote Similarity	NPD5735	Approved
0.6688	Remote Similarity	NPD4340	Discontinued
0.6687	Remote Similarity	NPD5058	Phase 3
0.6687	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3540	Phase 1
0.6686	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7819	Suspended
0.6684	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD6386	Approved
0.6647	Remote Similarity	NPD2560	Approved
0.6647	Remote Similarity	NPD2563	Approved
0.6647	Remote Similarity	NPD7458	Discontinued
0.6646	Remote Similarity	NPD1511	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2424	Discontinued
0.6644	Remote Similarity	NPD4626	Approved
0.6632	Remote Similarity	NPD7680	Approved
0.6631	Remote Similarity	NPD4420	Approved
0.663	Remote Similarity	NPD7296	Approved
0.6628	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD920	Approved
0.6626	Remote Similarity	NPD2219	Phase 1
0.6625	Remote Similarity	NPD6100	Approved
0.6625	Remote Similarity	NPD6099	Approved
0.6625	Remote Similarity	NPD2438	Suspended
0.6625	Remote Similarity	NPD2161	Phase 2
0.6623	Remote Similarity	NPD3972	Approved
0.662	Remote Similarity	NPD2684	Approved
0.6608	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2532	Approved
0.6606	Remote Similarity	NPD2533	Approved
0.6606	Remote Similarity	NPD2534	Approved
0.6605	Remote Similarity	NPD2800	Approved
0.6604	Remote Similarity	NPD6896	Approved
0.6604	Remote Similarity	NPD6895	Approved
0.6603	Remote Similarity	NPD5111	Phase 2
0.6603	Remote Similarity	NPD6798	Discontinued
0.6603	Remote Similarity	NPD5109	Approved
0.6603	Remote Similarity	NPD5110	Phase 2
0.6597	Remote Similarity	NPD969	Suspended
0.6593	Remote Similarity	NPD8434	Phase 2
0.6588	Remote Similarity	NPD2977	Approved
0.6588	Remote Similarity	NPD2978	Approved
0.6587	Remote Similarity	NPD3686	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