NPASS Compound

Structure

NPC469700 OpenBabel07101719152D 30 32 0 0 1 0 0 0 0 0999 V2000 -4.3005 3.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 2.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8005 1.5827 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3005 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3005 2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 29 1 0 0 0 0 12 28 1 0 0 0 0 13 8 1 6 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 29 1 6 0 0 0 19 30 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.17
Volume:	406.163
LogP:	-0.138
LogD:	-0.216
LogS:	-1.977
# Rotatable Bonds:	7
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	4.213
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.123
MDCK Permeability:	0.00013549966388382018
Pgp-inhibitor:	0.003
Pgp-substrate:	0.8
Human Intestinal Absorption (HIA):	0.247
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	72.6419448852539%
Volume Distribution (VD):	0.312
Pgp-substrate:	14.239278793334961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.026
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.404
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	1.593
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.223
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.038
Carcinogencity:	0.106
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.004

Download Data

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

Natural Product: NPC469700

Natural Product ID:	NPC469700
*Common Name:**	3-[2-(1-Hydroxy-1-Methyl-Ethyl)-6-(3,4,5-Trihydroxy-6-Hydroxymethyl-Tetrahydro-Pyran-2-Yloxy)-2,3-Dihydro-Benzofuran-5-Yl]-Propionic Acid
IUPAC Name:	3-[2-(2-hydroxypropan-2-yl)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydro-1-benzofuran-5-yl]propanoic acid
Synonyms:
Standard InCHIKey:	KSRAFVSVWQIUDE-IMGWSGCXSA-N
Standard InCHI:	InChI=1S/C20H28O10/c1-20(2,27)14-6-10-5-9(3-4-15(22)23)11(7-12(10)28-14)29-19-18(26)17(25)16(24)13(8-21)30-19/h5,7,13-14,16-19,21,24-27H,3-4,6,8H2,1-2H3,(H,22,23)/t13-,14?,16-,17+,18-,19-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc3OC(Cc3cc2CCC(=O)O)C(O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159436
PubChem CID:	44715456
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	roots	Miyazaki prefecture, Japan	n.a.	PMID[9873511]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3509	Angelica furcijuga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3509	Angelica furcijuga	Species	Apiaceae	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
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	100000.0	nM	PMID[541692]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	0.6	%	PMID[541692]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[541692]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	32.0	%	PMID[541692]

☑ 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 NPC469700 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	310
0.1-0.2	1298
0.2-0.3	3109
0.3-0.4	6895
0.4-0.5	10519
0.5-0.6	5878
0.6-0.7	6202
0.7-0.8	7880
0.8-0.85	568
0.85-0.9	36
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC107197
0.9133	High Similarity	NPC17521
0.9041	High Similarity	NPC296377
0.9013	High Similarity	NPC470607
0.9	High Similarity	NPC34456
0.8986	High Similarity	NPC104172
0.8986	High Similarity	NPC88886
0.898	High Similarity	NPC169510
0.8947	High Similarity	NPC470606
0.8904	High Similarity	NPC85624
0.8867	High Similarity	NPC23253
0.8857	High Similarity	NPC269421
0.8844	High Similarity	NPC474044
0.8816	High Similarity	NPC470603
0.8816	High Similarity	NPC470604
0.8816	High Similarity	NPC470605
0.8784	High Similarity	NPC87950
0.8784	High Similarity	NPC471764
0.8766	High Similarity	NPC279732
0.875	High Similarity	NPC87304
0.875	High Similarity	NPC268950
0.875	High Similarity	NPC108706
0.875	High Similarity	NPC78021
0.875	High Similarity	NPC211158
0.8742	High Similarity	NPC190217
0.8699	High Similarity	NPC307287
0.8675	High Similarity	NPC477240
0.8675	High Similarity	NPC106025
0.8675	High Similarity	NPC214454
0.8667	High Similarity	NPC199335
0.8645	High Similarity	NPC43761
0.8636	High Similarity	NPC127406
0.863	High Similarity	NPC476442
0.863	High Similarity	NPC215512
0.8618	High Similarity	NPC470264
0.8618	High Similarity	NPC302610
0.8601	High Similarity	NPC471029
0.86	High Similarity	NPC218685
0.86	High Similarity	NPC23084
0.8599	High Similarity	NPC93215
0.8591	High Similarity	NPC74320
0.8591	High Similarity	NPC107120
0.8582	High Similarity	NPC474491
0.8581	High Similarity	NPC43638
0.8581	High Similarity	NPC23817
0.8571	High Similarity	NPC184053
0.8562	High Similarity	NPC312881
0.8562	High Similarity	NPC256141
0.8562	High Similarity	NPC473202
0.8553	High Similarity	NPC191154
0.8553	High Similarity	NPC213723
0.8553	High Similarity	NPC38775
0.8552	High Similarity	NPC155963
0.8544	High Similarity	NPC91288
0.8544	High Similarity	NPC183672
0.8544	High Similarity	NPC471286
0.8533	High Similarity	NPC474302
0.8528	High Similarity	NPC325176
0.8526	High Similarity	NPC50430
0.8526	High Similarity	NPC241600
0.8526	High Similarity	NPC173726
0.8516	High Similarity	NPC149368
0.8516	High Similarity	NPC265480
0.8516	High Similarity	NPC45165
0.8506	High Similarity	NPC106625
0.8503	High Similarity	NPC108674
0.8503	High Similarity	NPC152771
0.8503	High Similarity	NPC287286
0.8503	High Similarity	NPC195357
0.8497	Intermediate Similarity	NPC134819
0.8493	Intermediate Similarity	NPC151946
0.8491	Intermediate Similarity	NPC294722
0.8491	Intermediate Similarity	NPC222531
0.8491	Intermediate Similarity	NPC475979
0.8491	Intermediate Similarity	NPC72016
0.8487	Intermediate Similarity	NPC100818
0.8481	Intermediate Similarity	NPC131745
0.8481	Intermediate Similarity	NPC259834
0.8481	Intermediate Similarity	NPC44947
0.8477	Intermediate Similarity	NPC47388
0.8477	Intermediate Similarity	NPC91902
0.8477	Intermediate Similarity	NPC202494
0.8477	Intermediate Similarity	NPC470670
0.8477	Intermediate Similarity	NPC14875
0.8477	Intermediate Similarity	NPC473133
0.8471	Intermediate Similarity	NPC470358
0.8471	Intermediate Similarity	NPC200708
0.8471	Intermediate Similarity	NPC472320
0.8467	Intermediate Similarity	NPC212697
0.8462	Intermediate Similarity	NPC122809
0.8457	Intermediate Similarity	NPC271755
0.8457	Intermediate Similarity	NPC254071
0.8457	Intermediate Similarity	NPC149502
0.8457	Intermediate Similarity	NPC222665
0.8452	Intermediate Similarity	NPC99233
0.8446	Intermediate Similarity	NPC472353
0.8446	Intermediate Similarity	NPC164599
0.8442	Intermediate Similarity	NPC259182
0.8442	Intermediate Similarity	NPC121001
0.8431	Intermediate Similarity	NPC180351
0.8431	Intermediate Similarity	NPC321387
0.8431	Intermediate Similarity	NPC327059
0.8431	Intermediate Similarity	NPC470908
0.8428	Intermediate Similarity	NPC66087
0.8428	Intermediate Similarity	NPC179198
0.8428	Intermediate Similarity	NPC257566
0.8428	Intermediate Similarity	NPC278419
0.8428	Intermediate Similarity	NPC124155
0.8425	Intermediate Similarity	NPC471069
0.8425	Intermediate Similarity	NPC471068
0.8425	Intermediate Similarity	NPC153818
0.8425	Intermediate Similarity	NPC232246
0.8421	Intermediate Similarity	NPC287294
0.8421	Intermediate Similarity	NPC10097
0.8418	Intermediate Similarity	NPC115624
0.8418	Intermediate Similarity	NPC47923
0.8414	Intermediate Similarity	NPC33986
0.8414	Intermediate Similarity	NPC472525
0.8408	Intermediate Similarity	NPC73511
0.84	Intermediate Similarity	NPC226722
0.8397	Intermediate Similarity	NPC165483
0.8397	Intermediate Similarity	NPC206378
0.8395	Intermediate Similarity	NPC298778
0.8395	Intermediate Similarity	NPC76047
0.8389	Intermediate Similarity	NPC242756
0.8378	Intermediate Similarity	NPC80098
0.8377	Intermediate Similarity	NPC474772
0.8377	Intermediate Similarity	NPC250488
0.8377	Intermediate Similarity	NPC318424
0.8377	Intermediate Similarity	NPC474744
0.8377	Intermediate Similarity	NPC472423
0.8377	Intermediate Similarity	NPC472636
0.8375	Intermediate Similarity	NPC7752
0.8367	Intermediate Similarity	NPC471070
0.8367	Intermediate Similarity	NPC471072
0.8367	Intermediate Similarity	NPC211110
0.8367	Intermediate Similarity	NPC279573
0.8367	Intermediate Similarity	NPC471071
0.8366	Intermediate Similarity	NPC307052
0.8366	Intermediate Similarity	NPC139966
0.8366	Intermediate Similarity	NPC158635
0.8366	Intermediate Similarity	NPC229882
0.8366	Intermediate Similarity	NPC103116
0.8365	Intermediate Similarity	NPC190450
0.8365	Intermediate Similarity	NPC125991
0.8365	Intermediate Similarity	NPC150164
0.8356	Intermediate Similarity	NPC78746
0.8356	Intermediate Similarity	NPC38099
0.8356	Intermediate Similarity	NPC188380
0.8356	Intermediate Similarity	NPC103409
0.8356	Intermediate Similarity	NPC224543
0.8356	Intermediate Similarity	NPC26954
0.8355	Intermediate Similarity	NPC85773
0.8355	Intermediate Similarity	NPC472339
0.8355	Intermediate Similarity	NPC270751
0.8354	Intermediate Similarity	NPC19554
0.8354	Intermediate Similarity	NPC43971
0.8354	Intermediate Similarity	NPC74749
0.8354	Intermediate Similarity	NPC306978
0.8345	Intermediate Similarity	NPC213173
0.8345	Intermediate Similarity	NPC307412
0.8345	Intermediate Similarity	NPC62366
0.8345	Intermediate Similarity	NPC55149
0.8345	Intermediate Similarity	NPC224475
0.8345	Intermediate Similarity	NPC180716
0.8345	Intermediate Similarity	NPC98179
0.8345	Intermediate Similarity	NPC253574
0.8344	Intermediate Similarity	NPC171656
0.8344	Intermediate Similarity	NPC197896
0.8344	Intermediate Similarity	NPC6985
0.8344	Intermediate Similarity	NPC294365
0.8344	Intermediate Similarity	NPC297788
0.8344	Intermediate Similarity	NPC316535
0.8344	Intermediate Similarity	NPC156457
0.8344	Intermediate Similarity	NPC313163
0.8344	Intermediate Similarity	NPC258035
0.8344	Intermediate Similarity	NPC161749
0.8333	Intermediate Similarity	NPC95090
0.8333	Intermediate Similarity	NPC191653
0.8333	Intermediate Similarity	NPC39351
0.8333	Intermediate Similarity	NPC26195
0.8333	Intermediate Similarity	NPC169248
0.8333	Intermediate Similarity	NPC72649
0.8333	Intermediate Similarity	NPC27408
0.8333	Intermediate Similarity	NPC97052
0.8333	Intermediate Similarity	NPC108937
0.8333	Intermediate Similarity	NPC279218
0.8323	Intermediate Similarity	NPC473996
0.8323	Intermediate Similarity	NPC310661
0.8323	Intermediate Similarity	NPC105827
0.8323	Intermediate Similarity	NPC178851
0.8323	Intermediate Similarity	NPC88484
0.8323	Intermediate Similarity	NPC259767
0.8322	Intermediate Similarity	NPC84207
0.8322	Intermediate Similarity	NPC49542
0.8322	Intermediate Similarity	NPC5253
0.8322	Intermediate Similarity	NPC139976
0.8322	Intermediate Similarity	NPC128337
0.8322	Intermediate Similarity	NPC230718
0.8313	Intermediate Similarity	NPC121703

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 NPC469700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	838
0.2-0.3	1755
0.3-0.4	2621
0.4-0.5	1958
0.5-0.6	1078
0.6-0.7	486
0.7-0.8	153
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8344	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7199	Phase 2
0.8269	Intermediate Similarity	NPD8455	Phase 2
0.8221	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD37	Approved
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8165	Intermediate Similarity	NPD4965	Approved
0.8165	Intermediate Similarity	NPD4966	Approved
0.8165	Intermediate Similarity	NPD4967	Phase 2
0.8153	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7075	Discontinued
0.8086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6234	Discontinued
0.8049	Intermediate Similarity	NPD7228	Approved
0.8049	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD6801	Discontinued
0.7962	Intermediate Similarity	NPD4380	Phase 2
0.7952	Intermediate Similarity	NPD7074	Phase 3
0.7943	Intermediate Similarity	NPD1091	Approved
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7054	Approved
0.7857	Intermediate Similarity	NPD7240	Approved
0.7844	Intermediate Similarity	NPD7472	Approved
0.7834	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7819	Suspended
0.7811	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6799	Approved
0.7799	Intermediate Similarity	NPD7411	Suspended
0.7798	Intermediate Similarity	NPD6797	Phase 2
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6355	Discontinued
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7763	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6004	Phase 3
0.7763	Intermediate Similarity	NPD6002	Phase 3
0.7763	Intermediate Similarity	NPD6005	Phase 3
0.7763	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7251	Discontinued
0.7748	Intermediate Similarity	NPD7033	Discontinued
0.7727	Intermediate Similarity	NPD4628	Phase 3
0.7712	Intermediate Similarity	NPD2424	Discontinued
0.7706	Intermediate Similarity	NPD7808	Phase 3
0.7703	Intermediate Similarity	NPD6798	Discontinued
0.7688	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7097	Phase 1
0.7679	Intermediate Similarity	NPD5844	Phase 1
0.7662	Intermediate Similarity	NPD1652	Phase 2
0.7658	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3817	Phase 2
0.7643	Intermediate Similarity	NPD2534	Approved
0.7643	Intermediate Similarity	NPD2533	Approved
0.7643	Intermediate Similarity	NPD2532	Approved
0.7643	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1934	Approved
0.7628	Intermediate Similarity	NPD5058	Phase 3
0.7625	Intermediate Similarity	NPD6599	Discontinued
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3787	Discontinued
0.759	Intermediate Similarity	NPD7229	Phase 3
0.758	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1243	Approved
0.7548	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD920	Approved
0.7546	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6233	Phase 2
0.7532	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1549	Phase 2
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD2796	Approved
0.7467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5403	Approved
0.7436	Intermediate Similarity	NPD6674	Discontinued
0.7436	Intermediate Similarity	NPD2800	Approved
0.7421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5401	Approved
0.7421	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7583	Approved
0.7405	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3882	Suspended
0.7389	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7585	Approved
0.7351	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5402	Approved
0.7333	Intermediate Similarity	NPD4908	Phase 1
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7321	Intermediate Similarity	NPD6959	Discontinued
0.731	Intermediate Similarity	NPD3751	Discontinued
0.7305	Intermediate Similarity	NPD919	Approved
0.7303	Intermediate Similarity	NPD4062	Phase 3
0.7289	Intermediate Similarity	NPD7768	Phase 2
0.7285	Intermediate Similarity	NPD3027	Phase 3
0.7279	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD3750	Approved
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD2801	Approved
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8312	Approved
0.7257	Intermediate Similarity	NPD8313	Approved
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7246	Intermediate Similarity	NPD3749	Approved
0.7241	Intermediate Similarity	NPD7685	Pre-registration
0.7239	Intermediate Similarity	NPD7458	Discontinued
0.7237	Intermediate Similarity	NPD1296	Phase 2
0.7237	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1610	Phase 2
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7197	Intermediate Similarity	NPD5763	Approved
0.7192	Intermediate Similarity	NPD1778	Approved
0.7181	Intermediate Similarity	NPD8651	Approved
0.7179	Intermediate Similarity	NPD5588	Approved
0.7179	Intermediate Similarity	NPD1510	Phase 2
0.7179	Intermediate Similarity	NPD3748	Approved
0.7176	Intermediate Similarity	NPD5710	Approved
0.7176	Intermediate Similarity	NPD5711	Approved
0.7161	Intermediate Similarity	NPD6653	Approved
0.7151	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD1240	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7134	Intermediate Similarity	NPD4476	Approved
0.7134	Intermediate Similarity	NPD4477	Approved
0.7134	Intermediate Similarity	NPD1551	Phase 2
0.7134	Intermediate Similarity	NPD2935	Discontinued
0.7133	Intermediate Similarity	NPD2797	Approved
0.7125	Intermediate Similarity	NPD6190	Approved
0.7124	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD4538	Approved
0.7115	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4536	Approved
0.7114	Intermediate Similarity	NPD4749	Approved
0.7113	Intermediate Similarity	NPD7843	Approved
0.7107	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3705	Approved
0.7086	Intermediate Similarity	NPD5647	Approved
0.7086	Intermediate Similarity	NPD5953	Discontinued
0.7083	Intermediate Similarity	NPD7157	Approved
0.7075	Intermediate Similarity	NPD17	Approved
0.7071	Intermediate Similarity	NPD2684	Approved
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7068	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7783	Phase 2
0.7063	Intermediate Similarity	NPD4110	Phase 3
0.7063	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD7680	Approved
0.7059	Intermediate Similarity	NPD7435	Discontinued
0.7059	Intermediate Similarity	NPD4625	Phase 3
0.7055	Intermediate Similarity	NPD1512	Approved
0.7055	Intermediate Similarity	NPD1548	Phase 1
0.7055	Intermediate Similarity	NPD1894	Discontinued
0.7053	Intermediate Similarity	NPD8151	Discontinued
0.7051	Intermediate Similarity	NPD1607	Approved
0.7051	Intermediate Similarity	NPD6651	Approved
0.7044	Intermediate Similarity	NPD5958	Discontinued
0.7044	Intermediate Similarity	NPD4534	Discontinued
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7032	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2438	Suspended
0.7022	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8127	Discontinued
0.7018	Intermediate Similarity	NPD1247	Approved
0.7013	Intermediate Similarity	NPD7985	Registered
0.7006	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD290	Approved
0.6994	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6832	Phase 2
0.6989	Remote Similarity	NPD6781	Approved
0.6989	Remote Similarity	NPD6776	Approved
0.6989	Remote Similarity	NPD6780	Approved
0.6989	Remote Similarity	NPD6777	Approved
0.6989	Remote Similarity	NPD6782	Approved
0.6989	Remote Similarity	NPD6779	Approved
0.6989	Remote Similarity	NPD6778	Approved
0.6987	Remote Similarity	NPD1933	Approved
0.6981	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7286	Phase 2
0.6962	Remote Similarity	NPD5960	Phase 3
0.6959	Remote Similarity	NPD5126	Approved
0.6959	Remote Similarity	NPD5125	Phase 3

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