NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	134.07
Volume:	147.988
LogP:	2.617
LogD:	2.467
LogS:	-2.006
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	1.794
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.497
MDCK Permeability:	2.3834149033064023e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.938
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.879
Plasma Protein Binding (PPB):	77.17647552490234%
Volume Distribution (VD):	1.98
Pgp-substrate:	19.52077293395996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.689
CYP2C19-substrate:	0.244
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	13.653
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.07
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.923
Carcinogencity:	0.429
Eye Corrosion:	0.905
Eye Irritation:	0.992
Respiratory Toxicity:	0.167

Download Data

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

Natural Product: NPC202986

Natural Product ID:	NPC202986
*Common Name:**	5-Indanol
IUPAC Name:	2,3-dihydro-1H-inden-5-ol
Synonyms:
Standard InCHIKey:	PEHSSTUGJUBZBI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O/c10-9-5-4-7-2-1-3-8(7)6-9/h4-6,10H,1-3H2
SMILES:	Oc1ccc2c(c1)CCC2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3218378
PubChem CID:	15118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000027] Indanes

*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
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	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
Potency	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	10870.7	nM	PubChem BioAssay data set

☑ 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 NPC202986 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	2266
0.2-0.3	7312
0.3-0.4	12133
0.4-0.5	6617
0.5-0.6	9319
0.6-0.7	3591
0.7-0.8	850
0.8-0.85	149
0.85-0.9	46
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC254965
0.9375	High Similarity	NPC327811
0.9255	High Similarity	NPC32674
0.914	High Similarity	NPC245187
0.9011	High Similarity	NPC27974
0.8925	High Similarity	NPC304541
0.8901	High Similarity	NPC23167
0.8889	High Similarity	NPC175313
0.8866	High Similarity	NPC211885
0.8854	High Similarity	NPC156313
0.8842	High Similarity	NPC274678
0.883	High Similarity	NPC55903
0.8817	High Similarity	NPC192
0.8804	High Similarity	NPC25493
0.8804	High Similarity	NPC113460
0.8791	High Similarity	NPC197783
0.8778	High Similarity	NPC265146
0.8738	High Similarity	NPC322753
0.8737	High Similarity	NPC316301
0.8737	High Similarity	NPC27323
0.8723	High Similarity	NPC155908
0.871	High Similarity	NPC280347
0.871	High Similarity	NPC242240
0.871	High Similarity	NPC318325
0.871	High Similarity	NPC123273
0.871	High Similarity	NPC258219
0.871	High Similarity	NPC177420
0.8681	High Similarity	NPC248817
0.8681	High Similarity	NPC150837
0.866	High Similarity	NPC109955
0.8632	High Similarity	NPC3358
0.8632	High Similarity	NPC210497
0.8632	High Similarity	NPC94139
0.8632	High Similarity	NPC306884
0.8632	High Similarity	NPC147284
0.8632	High Similarity	NPC162314
0.8617	High Similarity	NPC300017
0.8617	High Similarity	NPC55561
0.8587	High Similarity	NPC155393
0.8571	High Similarity	NPC124436
0.8557	High Similarity	NPC312132
0.8557	High Similarity	NPC259512
0.8542	High Similarity	NPC76938
0.8526	High Similarity	NPC45040
0.8526	High Similarity	NPC231150
0.85	High Similarity	NPC168393
0.85	High Similarity	NPC233827
0.8495	Intermediate Similarity	NPC407
0.8495	Intermediate Similarity	NPC184169
0.8495	Intermediate Similarity	NPC307235
0.8469	Intermediate Similarity	NPC79241
0.8469	Intermediate Similarity	NPC6597
0.8469	Intermediate Similarity	NPC77492
0.8469	Intermediate Similarity	NPC225464
0.8454	Intermediate Similarity	NPC32714
0.8454	Intermediate Similarity	NPC222146
0.8454	Intermediate Similarity	NPC8392
0.8447	Intermediate Similarity	NPC11554
0.8447	Intermediate Similarity	NPC233835
0.8447	Intermediate Similarity	NPC64586
0.8438	Intermediate Similarity	NPC325292
0.8438	Intermediate Similarity	NPC138117
0.8431	Intermediate Similarity	NPC21594
0.8421	Intermediate Similarity	NPC312304
0.8416	Intermediate Similarity	NPC475580
0.8416	Intermediate Similarity	NPC120719
0.8404	Intermediate Similarity	NPC104216
0.8404	Intermediate Similarity	NPC19680
0.84	Intermediate Similarity	NPC110764
0.8384	Intermediate Similarity	NPC299762
0.8384	Intermediate Similarity	NPC92730
0.8384	Intermediate Similarity	NPC33675
0.8384	Intermediate Similarity	NPC122005
0.8384	Intermediate Similarity	NPC252821
0.8367	Intermediate Similarity	NPC82664
0.8367	Intermediate Similarity	NPC132271
0.8367	Intermediate Similarity	NPC292730
0.8367	Intermediate Similarity	NPC216520
0.8365	Intermediate Similarity	NPC314187
0.8365	Intermediate Similarity	NPC58865
0.8365	Intermediate Similarity	NPC202647
0.8351	Intermediate Similarity	NPC128062
0.8351	Intermediate Similarity	NPC152415
0.8351	Intermediate Similarity	NPC151715
0.835	Intermediate Similarity	NPC151477
0.8333	Intermediate Similarity	NPC257540
0.8333	Intermediate Similarity	NPC471350
0.8333	Intermediate Similarity	NPC474358
0.8333	Intermediate Similarity	NPC306074
0.8333	Intermediate Similarity	NPC247858
0.8333	Intermediate Similarity	NPC137496
0.8333	Intermediate Similarity	NPC204210
0.8333	Intermediate Similarity	NPC154511
0.8333	Intermediate Similarity	NPC474387
0.8333	Intermediate Similarity	NPC239291
0.8317	Intermediate Similarity	NPC196479
0.8316	Intermediate Similarity	NPC98772
0.83	Intermediate Similarity	NPC72729
0.83	Intermediate Similarity	NPC225506
0.8286	Intermediate Similarity	NPC13482
0.8283	Intermediate Similarity	NPC152097
0.8283	Intermediate Similarity	NPC474073
0.828	Intermediate Similarity	NPC286904
0.8265	Intermediate Similarity	NPC26244
0.8265	Intermediate Similarity	NPC313650
0.8265	Intermediate Similarity	NPC107522
0.8252	Intermediate Similarity	NPC54765
0.8252	Intermediate Similarity	NPC477814
0.8252	Intermediate Similarity	NPC310456
0.8252	Intermediate Similarity	NPC67250
0.8247	Intermediate Similarity	NPC29373
0.8247	Intermediate Similarity	NPC271440
0.8235	Intermediate Similarity	NPC30506
0.8235	Intermediate Similarity	NPC238696
0.8235	Intermediate Similarity	NPC272029
0.8235	Intermediate Similarity	NPC12278
0.8235	Intermediate Similarity	NPC471511
0.8229	Intermediate Similarity	NPC300478
0.8218	Intermediate Similarity	NPC12221
0.8218	Intermediate Similarity	NPC252105
0.8208	Intermediate Similarity	NPC95716
0.82	Intermediate Similarity	NPC131587
0.82	Intermediate Similarity	NPC260775
0.8182	Intermediate Similarity	NPC473388
0.8182	Intermediate Similarity	NPC48342
0.8182	Intermediate Similarity	NPC164649
0.8155	Intermediate Similarity	NPC117115
0.8144	Intermediate Similarity	NPC270547
0.8137	Intermediate Similarity	NPC168829
0.8131	Intermediate Similarity	NPC250323
0.8131	Intermediate Similarity	NPC46940
0.8125	Intermediate Similarity	NPC70436
0.8119	Intermediate Similarity	NPC275053
0.8119	Intermediate Similarity	NPC248396
0.8119	Intermediate Similarity	NPC48730
0.8119	Intermediate Similarity	NPC248573
0.8119	Intermediate Similarity	NPC70677
0.8119	Intermediate Similarity	NPC161571
0.8119	Intermediate Similarity	NPC223393
0.8119	Intermediate Similarity	NPC10588
0.8119	Intermediate Similarity	NPC12931
0.8119	Intermediate Similarity	NPC129373
0.8119	Intermediate Similarity	NPC294741
0.8119	Intermediate Similarity	NPC130756
0.8119	Intermediate Similarity	NPC166761
0.8119	Intermediate Similarity	NPC130103
0.8119	Intermediate Similarity	NPC174911
0.8113	Intermediate Similarity	NPC141782
0.8113	Intermediate Similarity	NPC224870
0.8108	Intermediate Similarity	NPC258366
0.8108	Intermediate Similarity	NPC31296
0.8108	Intermediate Similarity	NPC473974
0.8108	Intermediate Similarity	NPC79933
0.81	Intermediate Similarity	NPC475078
0.81	Intermediate Similarity	NPC260000
0.81	Intermediate Similarity	NPC107619
0.8095	Intermediate Similarity	NPC95344
0.8095	Intermediate Similarity	NPC306295
0.8081	Intermediate Similarity	NPC144682
0.8081	Intermediate Similarity	NPC257182
0.8061	Intermediate Similarity	NPC181709
0.8058	Intermediate Similarity	NPC475225
0.8058	Intermediate Similarity	NPC323810
0.8058	Intermediate Similarity	NPC288411
0.8056	Intermediate Similarity	NPC322239
0.8056	Intermediate Similarity	NPC321589
0.8056	Intermediate Similarity	NPC715
0.8056	Intermediate Similarity	NPC471485
0.8039	Intermediate Similarity	NPC284011
0.8039	Intermediate Similarity	NPC100340
0.8039	Intermediate Similarity	NPC143659
0.8039	Intermediate Similarity	NPC72947
0.8037	Intermediate Similarity	NPC151537
0.8037	Intermediate Similarity	NPC260323
0.8037	Intermediate Similarity	NPC176279
0.8036	Intermediate Similarity	NPC318552
0.8036	Intermediate Similarity	NPC68339
0.8036	Intermediate Similarity	NPC190501
0.8036	Intermediate Similarity	NPC99734
0.802	Intermediate Similarity	NPC132078
0.802	Intermediate Similarity	NPC280869
0.802	Intermediate Similarity	NPC78119
0.802	Intermediate Similarity	NPC216468
0.802	Intermediate Similarity	NPC80027
0.802	Intermediate Similarity	NPC245561
0.802	Intermediate Similarity	NPC51333
0.802	Intermediate Similarity	NPC128723
0.8019	Intermediate Similarity	NPC254833
0.8019	Intermediate Similarity	NPC228343
0.8	Intermediate Similarity	NPC320439
0.7982	Intermediate Similarity	NPC107240
0.7982	Intermediate Similarity	NPC195922
0.7981	Intermediate Similarity	NPC47284
0.7981	Intermediate Similarity	NPC292452
0.7981	Intermediate Similarity	NPC138942
0.798	Intermediate Similarity	NPC289769
0.798	Intermediate Similarity	NPC81010
0.798	Intermediate Similarity	NPC32977
0.7965	Intermediate Similarity	NPC190971
0.7965	Intermediate Similarity	NPC328504

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 NPC202986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	1063
0.2-0.3	1482
0.3-0.4	3001
0.4-0.5	1777
0.5-0.6	1007
0.6-0.7	336
0.7-0.8	50
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD1432	Clinical (unspecified phase)
0.8571	High Similarity	NPD111	Approved
0.8557	High Similarity	NPD288	Approved
0.8454	Intermediate Similarity	NPD844	Approved
0.8384	Intermediate Similarity	NPD3020	Approved
0.8351	Intermediate Similarity	NPD2934	Approved
0.8351	Intermediate Similarity	NPD2933	Approved
0.83	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8265	Intermediate Similarity	NPD2859	Approved
0.8265	Intermediate Similarity	NPD2860	Approved
0.8182	Intermediate Similarity	NPD3091	Approved
0.8119	Intermediate Similarity	NPD1242	Phase 1
0.8081	Intermediate Similarity	NPD1809	Phase 2
0.8061	Intermediate Similarity	NPD845	Approved
0.8036	Intermediate Similarity	NPD4059	Approved
0.8036	Intermediate Similarity	NPD3019	Approved
0.8036	Intermediate Similarity	NPD2932	Approved
0.8019	Intermediate Similarity	NPD3021	Approved
0.8019	Intermediate Similarity	NPD3022	Approved
0.8	Intermediate Similarity	NPD2342	Discontinued
0.7905	Intermediate Similarity	NPD1444	Approved
0.7905	Intermediate Similarity	NPD1445	Approved
0.7895	Intermediate Similarity	NPD3092	Approved
0.7864	Intermediate Similarity	NPD846	Approved
0.7864	Intermediate Similarity	NPD940	Approved
0.785	Intermediate Similarity	NPD1792	Phase 2
0.7719	Intermediate Similarity	NPD3095	Discontinued
0.7714	Intermediate Similarity	NPD9610	Approved
0.7714	Intermediate Similarity	NPD9608	Approved
0.7706	Intermediate Similarity	NPD228	Approved
0.7636	Intermediate Similarity	NPD7635	Approved
0.7636	Intermediate Similarity	NPD9379	Approved
0.7636	Intermediate Similarity	NPD9377	Approved
0.7632	Intermediate Similarity	NPD4093	Discontinued
0.7627	Intermediate Similarity	NPD3094	Phase 2
0.7565	Intermediate Similarity	NPD2286	Discontinued
0.7565	Intermediate Similarity	NPD1751	Approved
0.7556	Intermediate Similarity	NPD9087	Approved
0.7523	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD5736	Approved
0.7453	Intermediate Similarity	NPD9500	Approved
0.7411	Intermediate Similarity	NPD2228	Approved
0.7411	Intermediate Similarity	NPD2229	Approved
0.7411	Intermediate Similarity	NPD2234	Approved
0.7391	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD3023	Approved
0.735	Intermediate Similarity	NPD3026	Approved
0.7345	Intermediate Similarity	NPD1793	Approved
0.7345	Intermediate Similarity	NPD1791	Approved
0.7333	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3024	Approved
0.7328	Intermediate Similarity	NPD3025	Approved
0.7312	Intermediate Similarity	NPD9294	Approved
0.7311	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4624	Approved
0.7265	Intermediate Similarity	NPD4626	Approved
0.7264	Intermediate Similarity	NPD3028	Approved
0.7258	Intermediate Similarity	NPD6663	Approved
0.7238	Intermediate Similarity	NPD9273	Approved
0.7234	Intermediate Similarity	NPD9088	Approved
0.7213	Intermediate Similarity	NPD2861	Phase 2
0.7193	Intermediate Similarity	NPD9614	Approved
0.7193	Intermediate Similarity	NPD9618	Approved
0.7143	Intermediate Similarity	NPD1201	Approved
0.7131	Intermediate Similarity	NPD2195	Approved
0.7131	Intermediate Similarity	NPD2194	Approved
0.713	Intermediate Similarity	NPD6671	Approved
0.713	Intermediate Similarity	NPD709	Approved
0.7119	Intermediate Similarity	NPD9384	Approved
0.7119	Intermediate Similarity	NPD9381	Approved
0.7091	Intermediate Similarity	NPD968	Approved
0.708	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3636	Approved
0.7073	Intermediate Similarity	NPD3637	Approved
0.7073	Intermediate Similarity	NPD3635	Approved
0.7063	Intermediate Similarity	NPD3620	Phase 2
0.7063	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD475	Phase 2
0.7043	Intermediate Similarity	NPD497	Approved
0.7027	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5327	Phase 3
0.7016	Intermediate Similarity	NPD2606	Approved
0.7016	Intermediate Similarity	NPD3595	Approved
0.7016	Intermediate Similarity	NPD2605	Approved
0.7016	Intermediate Similarity	NPD3594	Approved
0.7009	Intermediate Similarity	NPD9613	Approved
0.7009	Intermediate Similarity	NPD9615	Approved
0.7009	Intermediate Similarity	NPD9616	Approved
0.6983	Remote Similarity	NPD256	Approved
0.6983	Remote Similarity	NPD255	Approved
0.6977	Remote Similarity	NPD7742	Approved
0.6977	Remote Similarity	NPD7743	Approved
0.6975	Remote Similarity	NPD4589	Approved
0.6967	Remote Similarity	NPD1283	Approved
0.6964	Remote Similarity	NPD2684	Approved
0.696	Remote Similarity	NPD5155	Approved
0.696	Remote Similarity	NPD5156	Approved
0.6957	Remote Similarity	NPD498	Approved
0.6957	Remote Similarity	NPD5283	Phase 1
0.6957	Remote Similarity	NPD495	Approved
0.6957	Remote Similarity	NPD496	Approved
0.6957	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD316	Approved
0.6949	Remote Similarity	NPD5303	Approved
0.6949	Remote Similarity	NPD5304	Approved
0.6942	Remote Similarity	NPD1840	Phase 2
0.6939	Remote Similarity	NPD9089	Approved
0.6929	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD9568	Approved
0.6911	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1357	Approved
0.6891	Remote Similarity	NPD1651	Approved
0.6891	Remote Similarity	NPD5691	Approved
0.6885	Remote Similarity	NPD9622	Approved
0.6885	Remote Similarity	NPD1669	Approved
0.6875	Remote Similarity	NPD5735	Approved
0.687	Remote Similarity	NPD821	Approved
0.6864	Remote Similarity	NPD317	Approved
0.6864	Remote Similarity	NPD856	Approved
0.6864	Remote Similarity	NPD16	Approved
0.6864	Remote Similarity	NPD318	Approved
0.686	Remote Similarity	NPD1610	Phase 2
0.686	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7157	Approved
0.6837	Remote Similarity	NPD9093	Approved
0.6829	Remote Similarity	NPD5310	Approved
0.6829	Remote Similarity	NPD5311	Approved
0.6829	Remote Similarity	NPD6696	Suspended
0.6829	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6353	Approved
0.6822	Remote Similarity	NPD2157	Approved
0.6818	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1548	Phase 1
0.6803	Remote Similarity	NPD2233	Approved
0.6803	Remote Similarity	NPD2232	Approved
0.6803	Remote Similarity	NPD2230	Approved
0.6797	Remote Similarity	NPD4060	Phase 1
0.678	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3055	Approved
0.6774	Remote Similarity	NPD3053	Approved
0.6772	Remote Similarity	NPD3764	Approved
0.6767	Remote Similarity	NPD3638	Discontinued
0.6757	Remote Similarity	NPD9244	Approved
0.675	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1755	Approved
0.6733	Remote Similarity	NPD9073	Approved
0.6726	Remote Similarity	NPD290	Approved
0.6724	Remote Similarity	NPD7843	Approved
0.6721	Remote Similarity	NPD1281	Approved
0.6721	Remote Similarity	NPD3705	Approved
0.672	Remote Similarity	NPD257	Approved
0.672	Remote Similarity	NPD258	Approved
0.672	Remote Similarity	NPD9621	Approved
0.672	Remote Similarity	NPD6584	Phase 3
0.672	Remote Similarity	NPD9619	Approved
0.672	Remote Similarity	NPD9620	Approved
0.6694	Remote Similarity	NPD1876	Approved
0.6694	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2667	Approved
0.6694	Remote Similarity	NPD2668	Approved
0.6693	Remote Similarity	NPD4625	Phase 3
0.6692	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD9569	Approved
0.6667	Remote Similarity	NPD1712	Approved
0.6667	Remote Similarity	NPD74	Approved
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1398	Phase 1
0.6667	Remote Similarity	NPD3683	Approved
0.6667	Remote Similarity	NPD4720	Approved
0.6667	Remote Similarity	NPD9266	Approved
0.6667	Remote Similarity	NPD1182	Approved
0.6667	Remote Similarity	NPD4718	Approved
0.6667	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4717	Approved
0.6667	Remote Similarity	NPD9545	Approved
0.6667	Remote Similarity	NPD3681	Approved
0.664	Remote Similarity	NPD1164	Approved
0.6639	Remote Similarity	NPD1983	Approved
0.6639	Remote Similarity	NPD1981	Approved
0.6639	Remote Similarity	NPD1980	Approved
0.6639	Remote Similarity	NPD3143	Discontinued
0.6636	Remote Similarity	NPD1616	Discontinued
0.6635	Remote Similarity	NPD9295	Approved
0.6614	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD4749	Approved
0.6613	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5451	Approved
0.6591	Remote Similarity	NPD1753	Discontinued
0.6591	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8032	Phase 2
0.6585	Remote Similarity	NPD1535	Discovery
0.6585	Remote Similarity	NPD422	Phase 1
0.6579	Remote Similarity	NPD9263	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