NPASS Compound

Structure

NPC102260 OpenBabel07101718222D 26 30 0 0 1 0 0 0 0 0999 V2000 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7248 2.9074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9328 3.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4345 5.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2851 5.0035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8838 4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6270 3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 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 2.8412 4.7080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2905 5.1081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4400 5.5170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4930 4.0254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 12 1 0 0 0 0 2 4 2 0 0 0 0 2 13 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 6 15 2 0 0 0 0 7 12 2 0 0 0 0 7 18 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 10 25 1 0 0 0 0 11 24 1 0 0 0 0 11 26 1 0 0 0 0 14 5 1 6 0 0 0 14 15 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 19 2 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.09
Volume:	343.344
LogP:	3.809
LogD:	4.027
LogS:	-5.781
# Rotatable Bonds:	3
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	3.098
Fsp3:	0.25
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:	-4.927
MDCK Permeability:	2.9357919629546814e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	99.07682800292969%
Volume Distribution (VD):	0.727
Pgp-substrate:	2.200848340988159%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.983
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.925
CYP2C9-substrate:	0.84
CYP2D6-inhibitor:	0.985
CYP2D6-substrate:	0.824
CYP3A4-inhibitor:	0.98
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	17.177
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.616
AMES Toxicity:	0.252
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.641
Carcinogencity:	0.883
Eye Corrosion:	0.004
Eye Irritation:	0.426
Respiratory Toxicity:	0.73

Download Data

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

Natural Product: NPC102260

Natural Product ID:	NPC102260
*Common Name:**	Isogadian
IUPAC Name:	(3E,4S)-4-(1,3-benzodioxol-5-ylmethyl)-3-(1,3-benzodioxol-5-ylmethylidene)oxolan-2-one
Synonyms:	Isogadian
Standard InCHIKey:	CMJGAYUQSLJSCR-SMCAMXITSA-N
Standard InCHI:	InChI=1S/C20H16O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,6-8,14H,5,9-11H2/b15-6+/t14-/m1/s1
SMILES:	O=C1OC[C@H](/C/1=Cc1ccc2c(c1)OCO2)Cc1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459851
PubChem CID:	44560359
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO33358	phyllanthus acutissima	Species	n.a.	Eukaryota	aerial parts	n.a.	n.a.	PMID[18271551]

☑ 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
EC50	1
ED50	6
IC50	1
Others	2

Activity Type	# Activity
Cell Line	5
Individual Protein	1
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	39.7	%	PMID[570009]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570009]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570009]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570009]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[570009]
NPT168	Cell Line	P388	Mus musculus	ED50	>	5.0	ug ml-1	PMID[570009]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	34.6	ug.mL-1	PMID[570009]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	>	125.0	ug.mL-1	PMID[570009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	5.0	ug ml-1	PMID[570009]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Ratio IC50/EC50	>	3.6	n.a.	PMID[570009]

☑ 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 NPC102260 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	353
0.1-0.2	1432
0.2-0.3	3315
0.3-0.4	8841
0.4-0.5	10221
0.5-0.6	4901
0.6-0.7	11202
0.7-0.8	2192
0.8-0.85	182
0.85-0.9	44
0.9-0.95	10
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC230968
0.9692	High Similarity	NPC110958
0.9692	High Similarity	NPC19890
0.9466	High Similarity	NPC205915
0.9265	High Similarity	NPC218092
0.9265	High Similarity	NPC246474
0.9265	High Similarity	NPC162851
0.9071	High Similarity	NPC193779
0.9065	High Similarity	NPC177644
0.9065	High Similarity	NPC191158
0.9008	High Similarity	NPC223807
0.8986	High Similarity	NPC166137
0.8986	High Similarity	NPC282291
0.8936	High Similarity	NPC3982
0.8929	High Similarity	NPC475000
0.8929	High Similarity	NPC92693
0.8929	High Similarity	NPC218841
0.8921	High Similarity	NPC176586
0.8921	High Similarity	NPC210354
0.8881	High Similarity	NPC24193
0.8872	High Similarity	NPC476748
0.8865	High Similarity	NPC474158
0.8832	High Similarity	NPC90431
0.8811	High Similarity	NPC181464
0.8786	High Similarity	NPC151423
0.8786	High Similarity	NPC40237
0.8776	High Similarity	NPC254163
0.8768	High Similarity	NPC14022
0.875	High Similarity	NPC127827
0.8741	High Similarity	NPC153620
0.8741	High Similarity	NPC24257
0.8732	High Similarity	NPC327052
0.8722	High Similarity	NPC158737
0.8692	High Similarity	NPC114845
0.8662	High Similarity	NPC15743
0.8639	High Similarity	NPC308555
0.863	High Similarity	NPC32079
0.8621	High Similarity	NPC177476
0.8621	High Similarity	NPC262455
0.8592	High Similarity	NPC474288
0.8582	High Similarity	NPC64948
0.8581	High Similarity	NPC54179
0.8571	High Similarity	NPC85830
0.8562	High Similarity	NPC475722
0.8551	High Similarity	NPC5310
0.8551	High Similarity	NPC4982
0.8551	High Similarity	NPC300776
0.8551	High Similarity	NPC176814
0.8551	High Similarity	NPC68779
0.855	High Similarity	NPC301641
0.855	High Similarity	NPC80241
0.8543	High Similarity	NPC239818
0.8543	High Similarity	NPC218471
0.8529	High Similarity	NPC477705
0.8529	High Similarity	NPC477694
0.8529	High Similarity	NPC271208
0.8529	High Similarity	NPC233224
0.8529	High Similarity	NPC134764
0.8529	High Similarity	NPC171550
0.8521	High Similarity	NPC52664
0.8503	High Similarity	NPC164082
0.8503	High Similarity	NPC477700
0.85	High Similarity	NPC166184
0.8493	Intermediate Similarity	NPC145569
0.8493	Intermediate Similarity	NPC216223
0.8489	Intermediate Similarity	NPC211386
0.8483	Intermediate Similarity	NPC80230
0.8483	Intermediate Similarity	NPC104024
0.8483	Intermediate Similarity	NPC304687
0.8483	Intermediate Similarity	NPC101755
0.8483	Intermediate Similarity	NPC65574
0.8467	Intermediate Similarity	NPC82111
0.8467	Intermediate Similarity	NPC261484
0.8467	Intermediate Similarity	NPC477706
0.8467	Intermediate Similarity	NPC227160
0.8462	Intermediate Similarity	NPC137920
0.8462	Intermediate Similarity	NPC86455
0.8462	Intermediate Similarity	NPC125134
0.8462	Intermediate Similarity	NPC69670
0.8462	Intermediate Similarity	NPC472564
0.8456	Intermediate Similarity	NPC348849
0.8456	Intermediate Similarity	NPC178195
0.8451	Intermediate Similarity	NPC51681
0.8451	Intermediate Similarity	NPC28398
0.8425	Intermediate Similarity	NPC40654
0.8425	Intermediate Similarity	NPC262804
0.8406	Intermediate Similarity	NPC100223
0.8406	Intermediate Similarity	NPC158526
0.8406	Intermediate Similarity	NPC16830
0.8406	Intermediate Similarity	NPC129687
0.8406	Intermediate Similarity	NPC171928
0.8406	Intermediate Similarity	NPC33611
0.8403	Intermediate Similarity	NPC46880
0.84	Intermediate Similarity	NPC186316
0.8397	Intermediate Similarity	NPC344161
0.8385	Intermediate Similarity	NPC277460
0.8382	Intermediate Similarity	NPC165128
0.8382	Intermediate Similarity	NPC57119
0.8382	Intermediate Similarity	NPC158471
0.8382	Intermediate Similarity	NPC226862
0.837	Intermediate Similarity	NPC40352
0.837	Intermediate Similarity	NPC213711
0.8369	Intermediate Similarity	NPC231719
0.8369	Intermediate Similarity	NPC52968
0.8367	Intermediate Similarity	NPC293757
0.8367	Intermediate Similarity	NPC668
0.8367	Intermediate Similarity	NPC174512
0.8367	Intermediate Similarity	NPC477695
0.8367	Intermediate Similarity	NPC477698
0.8367	Intermediate Similarity	NPC474965
0.8357	Intermediate Similarity	NPC72796
0.8357	Intermediate Similarity	NPC44245
0.8346	Intermediate Similarity	NPC256167
0.8333	Intermediate Similarity	NPC471877
0.8322	Intermediate Similarity	NPC56184
0.8311	Intermediate Similarity	NPC149505
0.831	Intermediate Similarity	NPC178290
0.8309	Intermediate Similarity	NPC286683
0.8308	Intermediate Similarity	NPC199209
0.8308	Intermediate Similarity	NPC212643
0.8301	Intermediate Similarity	NPC139876
0.8298	Intermediate Similarity	NPC11453
0.8289	Intermediate Similarity	NPC19600
0.8289	Intermediate Similarity	NPC82733
0.8289	Intermediate Similarity	NPC76458
0.8288	Intermediate Similarity	NPC189054
0.8286	Intermediate Similarity	NPC47181
0.8286	Intermediate Similarity	NPC37065
0.8276	Intermediate Similarity	NPC474036
0.8271	Intermediate Similarity	NPC193484
0.8255	Intermediate Similarity	NPC210642
0.8255	Intermediate Similarity	NPC303519
0.8255	Intermediate Similarity	NPC13985
0.8252	Intermediate Similarity	NPC470855
0.8235	Intermediate Similarity	NPC76211
0.8235	Intermediate Similarity	NPC15764
0.8231	Intermediate Similarity	NPC25496
0.8227	Intermediate Similarity	NPC18576
0.8227	Intermediate Similarity	NPC189474
0.8227	Intermediate Similarity	NPC474139
0.8224	Intermediate Similarity	NPC115123
0.8224	Intermediate Similarity	NPC239113
0.8224	Intermediate Similarity	NPC473900
0.8219	Intermediate Similarity	NPC223185
0.8201	Intermediate Similarity	NPC192255
0.82	Intermediate Similarity	NPC477699
0.8194	Intermediate Similarity	NPC29599
0.8194	Intermediate Similarity	NPC323601
0.8194	Intermediate Similarity	NPC100675
0.8188	Intermediate Similarity	NPC241354
0.8188	Intermediate Similarity	NPC158635
0.8188	Intermediate Similarity	NPC229882
0.8182	Intermediate Similarity	NPC96593
0.8182	Intermediate Similarity	NPC470637
0.8182	Intermediate Similarity	NPC57501
0.8175	Intermediate Similarity	NPC177167
0.8169	Intermediate Similarity	NPC143895
0.8162	Intermediate Similarity	NPC120066
0.8158	Intermediate Similarity	NPC234730
0.8156	Intermediate Similarity	NPC31530
0.8151	Intermediate Similarity	NPC141569
0.8151	Intermediate Similarity	NPC477701
0.8151	Intermediate Similarity	NPC166884
0.8143	Intermediate Similarity	NPC7744
0.8138	Intermediate Similarity	NPC253481
0.8138	Intermediate Similarity	NPC253722
0.8138	Intermediate Similarity	NPC31751
0.8138	Intermediate Similarity	NPC104956
0.8133	Intermediate Similarity	NPC474975
0.8129	Intermediate Similarity	NPC288149
0.8129	Intermediate Similarity	NPC309335
0.8129	Intermediate Similarity	NPC191352
0.8129	Intermediate Similarity	NPC296540
0.8129	Intermediate Similarity	NPC239890
0.8129	Intermediate Similarity	NPC209411
0.8129	Intermediate Similarity	NPC258322
0.8129	Intermediate Similarity	NPC15212
0.8125	Intermediate Similarity	NPC278076
0.8121	Intermediate Similarity	NPC85141
0.8112	Intermediate Similarity	NPC101807
0.8112	Intermediate Similarity	NPC469981
0.8108	Intermediate Similarity	NPC476336
0.8105	Intermediate Similarity	NPC261090
0.8105	Intermediate Similarity	NPC478055
0.8102	Intermediate Similarity	NPC120225
0.8102	Intermediate Similarity	NPC213552
0.8099	Intermediate Similarity	NPC113295
0.8099	Intermediate Similarity	NPC148893
0.8099	Intermediate Similarity	NPC49235
0.8099	Intermediate Similarity	NPC477301
0.8099	Intermediate Similarity	NPC25333
0.8092	Intermediate Similarity	NPC273578
0.8092	Intermediate Similarity	NPC30009
0.8092	Intermediate Similarity	NPC103197
0.8092	Intermediate Similarity	NPC111225
0.8092	Intermediate Similarity	NPC136757
0.8085	Intermediate Similarity	NPC136750
0.8085	Intermediate Similarity	NPC169973
0.8085	Intermediate Similarity	NPC266848
0.8082	Intermediate Similarity	NPC106920

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 NPC102260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	873
0.2-0.3	1469
0.3-0.4	2628
0.4-0.5	2071
0.5-0.6	1214
0.6-0.7	528
0.7-0.8	74
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD5536	Phase 2
0.7987	Intermediate Similarity	NPD4967	Phase 2
0.7987	Intermediate Similarity	NPD4966	Approved
0.7987	Intermediate Similarity	NPD4965	Approved
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7863	Intermediate Similarity	NPD5283	Phase 1
0.7792	Intermediate Similarity	NPD37	Approved
0.7778	Intermediate Similarity	NPD7028	Phase 2
0.777	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4110	Phase 3
0.7737	Intermediate Similarity	NPD3705	Approved
0.7708	Intermediate Similarity	NPD1933	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7626	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6355	Discontinued
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7228	Approved
0.7538	Intermediate Similarity	NPD1358	Approved
0.7517	Intermediate Similarity	NPD2979	Phase 3
0.75	Intermediate Similarity	NPD6385	Approved
0.75	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD6386	Approved
0.7482	Intermediate Similarity	NPD1281	Approved
0.7462	Intermediate Similarity	NPD3134	Approved
0.7439	Intermediate Similarity	NPD3818	Discontinued
0.7405	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5585	Approved
0.7391	Intermediate Similarity	NPD1357	Approved
0.7389	Intermediate Similarity	NPD6873	Phase 2
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD7458	Discontinued
0.7365	Intermediate Similarity	NPD7240	Approved
0.7338	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD1241	Discontinued
0.7324	Intermediate Similarity	NPD1283	Approved
0.7324	Intermediate Similarity	NPD1876	Approved
0.7319	Intermediate Similarity	NPD1894	Discontinued
0.7315	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.7297	Intermediate Similarity	NPD2492	Phase 1
0.7292	Intermediate Similarity	NPD9494	Approved
0.7284	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD2531	Phase 2
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7266	Intermediate Similarity	NPD1651	Approved
0.7266	Intermediate Similarity	NPD5691	Approved
0.7262	Intermediate Similarity	NPD7685	Pre-registration
0.7259	Intermediate Similarity	NPD5535	Approved
0.7255	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6832	Phase 2
0.7239	Intermediate Similarity	NPD8127	Discontinued
0.7235	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD447	Suspended
0.7222	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD7266	Discontinued
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7211	Intermediate Similarity	NPD4062	Phase 3
0.7211	Intermediate Similarity	NPD8032	Phase 2
0.7205	Intermediate Similarity	NPD3882	Suspended
0.7205	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7095	Approved
0.719	Intermediate Similarity	NPD8166	Discontinued
0.7183	Intermediate Similarity	NPD1608	Approved
0.7183	Intermediate Similarity	NPD3972	Approved
0.7179	Intermediate Similarity	NPD6273	Approved
0.7171	Intermediate Similarity	NPD5958	Discontinued
0.7163	Intermediate Similarity	NPD3847	Discontinued
0.7162	Intermediate Similarity	NPD4060	Phase 1
0.7153	Intermediate Similarity	NPD2797	Approved
0.7153	Intermediate Similarity	NPD3266	Approved
0.7153	Intermediate Similarity	NPD3267	Approved
0.7152	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD4359	Approved
0.7117	Intermediate Similarity	NPD919	Approved
0.7114	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7281	Phase 3
0.7076	Intermediate Similarity	NPD7280	Phase 3
0.7037	Intermediate Similarity	NPD5978	Approved
0.7037	Intermediate Similarity	NPD5977	Approved
0.7037	Intermediate Similarity	NPD5353	Approved
0.7027	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD3268	Approved
0.7018	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2614	Approved
0.7006	Intermediate Similarity	NPD3146	Approved
0.7006	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1535	Discovery
0.6993	Remote Similarity	NPD2353	Approved
0.6993	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD4420	Approved
0.6981	Remote Similarity	NPD1653	Approved
0.6975	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3748	Approved
0.6972	Remote Similarity	NPD4626	Approved
0.6959	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3027	Phase 3
0.6954	Remote Similarity	NPD2653	Approved
0.6948	Remote Similarity	NPD4534	Discontinued
0.6946	Remote Similarity	NPD3926	Phase 2
0.6944	Remote Similarity	NPD1481	Phase 2
0.6943	Remote Similarity	NPD6799	Approved
0.6941	Remote Similarity	NPD7074	Phase 3
0.6937	Remote Similarity	NPD3455	Phase 2
0.6934	Remote Similarity	NPD228	Approved
0.6933	Remote Similarity	NPD4307	Phase 2
0.6928	Remote Similarity	NPD6032	Approved
0.6923	Remote Similarity	NPD3496	Discontinued
0.6914	Remote Similarity	NPD1934	Approved
0.6913	Remote Similarity	NPD5111	Phase 2
0.6913	Remote Similarity	NPD5110	Phase 2
0.6913	Remote Similarity	NPD5109	Approved
0.6912	Remote Similarity	NPD2067	Discontinued
0.6892	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD230	Phase 1
0.6887	Remote Similarity	NPD4622	Approved
0.6887	Remote Similarity	NPD4618	Approved
0.6886	Remote Similarity	NPD6232	Discontinued
0.6885	Remote Similarity	NPD7680	Approved
0.6883	Remote Similarity	NPD2346	Discontinued
0.6882	Remote Similarity	NPD7054	Approved
0.6882	Remote Similarity	NPD5844	Phase 1
0.6875	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2801	Approved
0.6871	Remote Similarity	NPD8455	Phase 2
0.6871	Remote Similarity	NPD5647	Approved
0.6867	Remote Similarity	NPD4870	Approved
0.6864	Remote Similarity	NPD7473	Discontinued
0.6861	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6559	Discontinued
0.6859	Remote Similarity	NPD7003	Approved
0.6848	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6653	Approved
0.6842	Remote Similarity	NPD7472	Approved
0.6838	Remote Similarity	NPD2684	Approved
0.6835	Remote Similarity	NPD4357	Discontinued
0.6832	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5005	Approved
0.6831	Remote Similarity	NPD5006	Approved
0.6828	Remote Similarity	NPD2981	Phase 2
0.6826	Remote Similarity	NPD1247	Approved
0.6821	Remote Similarity	NPD4140	Approved
0.6818	Remote Similarity	NPD4477	Approved
0.6818	Remote Similarity	NPD4476	Approved
0.6818	Remote Similarity	NPD2796	Approved
0.6815	Remote Similarity	NPD2354	Approved
0.6803	Remote Similarity	NPD1203	Approved
0.6798	Remote Similarity	NPD7296	Approved
0.6797	Remote Similarity	NPD5688	Approved
0.6797	Remote Similarity	NPD5689	Approved
0.6792	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6599	Discontinued
0.6781	Remote Similarity	NPD2983	Phase 2
0.6781	Remote Similarity	NPD2982	Phase 2
0.6776	Remote Similarity	NPD4340	Discontinued
0.6776	Remote Similarity	NPD3657	Discovery
0.6774	Remote Similarity	NPD2344	Approved
0.6772	Remote Similarity	NPD7440	Discontinued
0.6768	Remote Similarity	NPD1465	Phase 2
0.6768	Remote Similarity	NPD7819	Suspended
0.6768	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7843	Approved
0.6758	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6663	Approved
0.6755	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4108	Discontinued
0.6753	Remote Similarity	NPD4308	Phase 3
0.6753	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3750	Approved
0.6752	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1238	Approved
0.6741	Remote Similarity	NPD9697	Approved
0.6738	Remote Similarity	NPD7157	Approved
0.6736	Remote Similarity	NPD1778	Approved
0.6731	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2897	Discontinued
0.6727	Remote Similarity	NPD5402	Approved
0.6726	Remote Similarity	NPD2821	Approved
0.6724	Remote Similarity	NPD7808	Phase 3
0.6713	Remote Similarity	NPD9545	Approved
0.6711	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3620	Phase 2
0.6711	Remote Similarity	NPD3018	Phase 2
0.671	Remote Similarity	NPD1501	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data