NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.13
Volume:	255.332
LogP:	3.646
LogD:	2.424
LogS:	-3.472
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	2.678
Fsp3:	0.357
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:	-4.643
MDCK Permeability:	2.464789940859191e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	99.71089172363281%
Volume Distribution (VD):	0.31
Pgp-substrate:	1.0240516662597656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.749
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.318
CYP2C19-substrate:	0.34
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.55
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	8.67
Half-life (T1/2):	0.788

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.15
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.342
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.929
Carcinogencity:	0.265
Eye Corrosion:	0.033
Eye Irritation:	0.922
Respiratory Toxicity:	0.169

Download Data

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

Natural Product: NPC303737

Natural Product ID:	NPC303737
*Common Name:**	2',3'-Dihydrosorbicillin
IUPAC Name:	(E)-1-(2,4-dihydroxy-3,5-dimethylphenyl)hex-4-en-1-one
Synonyms:	2',3'-Dihydrosorbicillin
Standard InCHIKey:	QQBOFNUXGPKLIK-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C14H18O3/c1-4-5-6-7-12(15)11-8-9(2)13(16)10(3)14(11)17/h4-5,8,16-17H,6-7H2,1-3H3/b5-4+
SMILES:	C/C=C/CCC(=O)c1cc(C)c(c(c1O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460262
PubChem CID:	21676140
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO32492	penicillium notatum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[466488]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[466488]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[466488]

☑ 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 NPC303737 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	292
0.1-0.2	1571
0.2-0.3	4200
0.3-0.4	11825
0.4-0.5	7435
0.5-0.6	5794
0.6-0.7	6596
0.7-0.8	3992
0.8-0.85	730
0.85-0.9	177
0.9-0.95	62
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9913	High Similarity	NPC309765
0.9655	High Similarity	NPC215392
0.958	High Similarity	NPC62952
0.9573	High Similarity	NPC91105
0.9565	High Similarity	NPC161617
0.95	High Similarity	NPC103356
0.95	High Similarity	NPC72158
0.95	High Similarity	NPC162612
0.95	High Similarity	NPC30501
0.95	High Similarity	NPC266689
0.95	High Similarity	NPC190043
0.95	High Similarity	NPC100067
0.95	High Similarity	NPC98254
0.95	High Similarity	NPC23126
0.95	High Similarity	NPC169250
0.95	High Similarity	NPC105157
0.9492	High Similarity	NPC65761
0.9492	High Similarity	NPC472029
0.9421	High Similarity	NPC221777
0.9421	High Similarity	NPC473017
0.9421	High Similarity	NPC21305
0.9417	High Similarity	NPC267846
0.9402	High Similarity	NPC149246
0.9344	High Similarity	NPC474998
0.9339	High Similarity	NPC116513
0.9333	High Similarity	NPC475733
0.9322	High Similarity	NPC226275
0.9322	High Similarity	NPC156139
0.9316	High Similarity	NPC294037
0.931	High Similarity	NPC40649
0.931	High Similarity	NPC209486
0.9244	High Similarity	NPC133909
0.9244	High Similarity	NPC32032
0.9237	High Similarity	NPC146642
0.9237	High Similarity	NPC297186
0.9224	High Similarity	NPC121259
0.9194	High Similarity	NPC475042
0.9187	High Similarity	NPC476119
0.916	High Similarity	NPC242895
0.916	High Similarity	NPC143427
0.916	High Similarity	NPC115159
0.916	High Similarity	NPC224273
0.916	High Similarity	NPC45438
0.916	High Similarity	NPC73532
0.916	High Similarity	NPC19174
0.916	High Similarity	NPC267552
0.913	High Similarity	NPC276111
0.913	High Similarity	NPC118288
0.9048	High Similarity	NPC139074
0.9048	High Similarity	NPC213485
0.9048	High Similarity	NPC40524
0.9043	High Similarity	NPC242136
0.904	High Similarity	NPC275504
0.9016	High Similarity	NPC477454
0.9	High Similarity	NPC196976
0.8992	High Similarity	NPC159525
0.8976	High Similarity	NPC282780
0.8976	High Similarity	NPC166480
0.8943	High Similarity	NPC328983
0.8943	High Similarity	NPC473691
0.8943	High Similarity	NPC8745
0.8934	High Similarity	NPC13238
0.8917	High Similarity	NPC229649
0.8908	High Similarity	NPC195262
0.8908	High Similarity	NPC188814
0.8908	High Similarity	NPC158222
0.8906	High Similarity	NPC470210
0.8906	High Similarity	NPC164136
0.8906	High Similarity	NPC283590
0.8906	High Similarity	NPC70859
0.8906	High Similarity	NPC61153
0.8906	High Similarity	NPC130899
0.888	High Similarity	NPC92624
0.8871	High Similarity	NPC329205
0.8871	High Similarity	NPC316625
0.8862	High Similarity	NPC10926
0.8837	High Similarity	NPC65005
0.8837	High Similarity	NPC156092
0.8837	High Similarity	NPC131039
0.8837	High Similarity	NPC264112
0.8837	High Similarity	NPC194764
0.8828	High Similarity	NPC475088
0.8824	High Similarity	NPC161943
0.8824	High Similarity	NPC273282
0.8824	High Similarity	NPC241089
0.8824	High Similarity	NPC474890
0.8824	High Similarity	NPC283844
0.8819	High Similarity	NPC175738
0.8814	High Similarity	NPC83718
0.881	High Similarity	NPC84772
0.881	High Similarity	NPC259942
0.88	High Similarity	NPC470981
0.88	High Similarity	NPC186098
0.88	High Similarity	NPC80694
0.879	High Similarity	NPC473751
0.877	High Similarity	NPC232708
0.877	High Similarity	NPC66252
0.8769	High Similarity	NPC41461
0.8769	High Similarity	NPC25287
0.8769	High Similarity	NPC477243
0.8769	High Similarity	NPC66349
0.8769	High Similarity	NPC249606
0.8769	High Similarity	NPC274109
0.8769	High Similarity	NPC186838
0.8769	High Similarity	NPC12165
0.8769	High Similarity	NPC477244
0.8769	High Similarity	NPC98115
0.8769	High Similarity	NPC168105
0.8769	High Similarity	NPC150399
0.8769	High Similarity	NPC1486
0.8769	High Similarity	NPC477242
0.876	High Similarity	NPC103842
0.874	High Similarity	NPC324482
0.873	High Similarity	NPC230818
0.873	High Similarity	NPC102829
0.873	High Similarity	NPC109123
0.873	High Similarity	NPC120488
0.8718	High Similarity	NPC211421
0.8702	High Similarity	NPC153979
0.8702	High Similarity	NPC317119
0.8702	High Similarity	NPC472419
0.8699	High Similarity	NPC306288
0.8696	High Similarity	NPC95172
0.8692	High Similarity	NPC151113
0.8692	High Similarity	NPC13575
0.8672	High Similarity	NPC313618
0.8672	High Similarity	NPC27490
0.8661	High Similarity	NPC17840
0.8661	High Similarity	NPC247477
0.8661	High Similarity	NPC21378
0.8661	High Similarity	NPC470987
0.8661	High Similarity	NPC62219
0.864	High Similarity	NPC95309
0.8636	High Similarity	NPC242994
0.8636	High Similarity	NPC19622
0.8636	High Similarity	NPC471620
0.8636	High Similarity	NPC112789
0.8636	High Similarity	NPC138099
0.8636	High Similarity	NPC162939
0.8636	High Similarity	NPC21350
0.8626	High Similarity	NPC44960
0.8626	High Similarity	NPC53414
0.8626	High Similarity	NPC474110
0.8626	High Similarity	NPC222633
0.8626	High Similarity	NPC53206
0.8618	High Similarity	NPC218333
0.8615	High Similarity	NPC286336
0.8609	High Similarity	NPC224584
0.8607	High Similarity	NPC248363
0.8605	High Similarity	NPC48036
0.8605	High Similarity	NPC37299
0.8605	High Similarity	NPC267205
0.8605	High Similarity	NPC180261
0.8595	High Similarity	NPC473767
0.8594	High Similarity	NPC250057
0.8594	High Similarity	NPC198249
0.8583	High Similarity	NPC230349
0.8583	High Similarity	NPC212379
0.8583	High Similarity	NPC69235
0.8571	High Similarity	NPC477956
0.8571	High Similarity	NPC472366
0.8571	High Similarity	NPC305518
0.8571	High Similarity	NPC181560
0.8571	High Similarity	NPC470211
0.8571	High Similarity	NPC169452
0.8571	High Similarity	NPC275903
0.8571	High Similarity	NPC128428
0.8571	High Similarity	NPC283429
0.8561	High Similarity	NPC473622
0.856	High Similarity	NPC290466
0.856	High Similarity	NPC201728
0.856	High Similarity	NPC262671
0.855	High Similarity	NPC191976
0.855	High Similarity	NPC475955
0.855	High Similarity	NPC84699
0.855	High Similarity	NPC474726
0.855	High Similarity	NPC118919
0.855	High Similarity	NPC254847
0.8538	High Similarity	NPC144051
0.8538	High Similarity	NPC82225
0.8538	High Similarity	NPC108113
0.8538	High Similarity	NPC188646
0.8538	High Similarity	NPC294593
0.8538	High Similarity	NPC204960
0.8538	High Similarity	NPC27643
0.8538	High Similarity	NPC139813
0.8538	High Similarity	NPC312318
0.8538	High Similarity	NPC159623
0.8538	High Similarity	NPC263670
0.8538	High Similarity	NPC56031
0.8538	High Similarity	NPC44437
0.8538	High Similarity	NPC474519
0.8538	High Similarity	NPC93756
0.8538	High Similarity	NPC192304
0.8538	High Similarity	NPC175098
0.8538	High Similarity	NPC18877
0.8538	High Similarity	NPC28753
0.8538	High Similarity	NPC472365
0.8538	High Similarity	NPC242294
0.8538	High Similarity	NPC20560

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 NPC303737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	979
0.2-0.3	1529
0.3-0.4	2879
0.4-0.5	1985
0.5-0.6	1034
0.6-0.7	328
0.7-0.8	91
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8672	High Similarity	NPD1240	Approved
0.855	High Similarity	NPD1509	Clinical (unspecified phase)
0.8538	High Similarity	NPD1607	Approved
0.8527	High Similarity	NPD943	Approved
0.8443	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1510	Phase 2
0.8261	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD9266	Approved
0.8136	Intermediate Similarity	NPD74	Approved
0.8134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1164	Approved
0.8088	Intermediate Similarity	NPD1549	Phase 2
0.8087	Intermediate Similarity	NPD846	Approved
0.8087	Intermediate Similarity	NPD940	Approved
0.8058	Intermediate Similarity	NPD7390	Discontinued
0.8051	Intermediate Similarity	NPD9263	Approved
0.8051	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8051	Intermediate Similarity	NPD9264	Approved
0.8051	Intermediate Similarity	NPD9267	Approved
0.8049	Intermediate Similarity	NPD9493	Approved
0.8015	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD6651	Approved
0.7953	Intermediate Similarity	NPD1201	Approved
0.7847	Intermediate Similarity	NPD4380	Phase 2
0.7846	Intermediate Similarity	NPD1470	Approved
0.781	Intermediate Similarity	NPD5406	Approved
0.781	Intermediate Similarity	NPD5408	Approved
0.781	Intermediate Similarity	NPD5405	Approved
0.781	Intermediate Similarity	NPD5404	Approved
0.781	Intermediate Similarity	NPD2796	Approved
0.7793	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD9545	Approved
0.777	Intermediate Similarity	NPD2800	Approved
0.776	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD9261	Approved
0.7698	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD2935	Discontinued
0.7651	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD1243	Approved
0.7635	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2533	Approved
0.7622	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD2532	Approved
0.7615	Intermediate Similarity	NPD9269	Phase 2
0.76	Intermediate Similarity	NPD9281	Approved
0.7578	Intermediate Similarity	NPD9268	Approved
0.7568	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD7819	Suspended
0.7552	Intermediate Similarity	NPD6799	Approved
0.7552	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7481	Intermediate Similarity	NPD9717	Approved
0.7465	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1512	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD230	Phase 1
0.7383	Intermediate Similarity	NPD1934	Approved
0.7376	Intermediate Similarity	NPD2344	Approved
0.7365	Intermediate Similarity	NPD6599	Discontinued
0.7361	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD2799	Discontinued
0.7355	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3882	Suspended
0.7351	Intermediate Similarity	NPD7768	Phase 2
0.735	Intermediate Similarity	NPD1809	Phase 2
0.7343	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD2801	Approved
0.7328	Intermediate Similarity	NPD845	Approved
0.7313	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD1551	Phase 2
0.7303	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD920	Approved
0.7273	Intermediate Similarity	NPD2654	Approved
0.726	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD2798	Approved
0.7226	Intermediate Similarity	NPD6232	Discontinued
0.72	Intermediate Similarity	NPD4750	Phase 3
0.7197	Intermediate Similarity	NPD7473	Discontinued
0.719	Intermediate Similarity	NPD3749	Approved
0.7174	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2313	Discontinued
0.7172	Intermediate Similarity	NPD2309	Approved
0.7161	Intermediate Similarity	NPD6959	Discontinued
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7125	Intermediate Similarity	NPD5953	Discontinued
0.712	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7286	Phase 2
0.7107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1242	Phase 1
0.7107	Intermediate Similarity	NPD6020	Phase 2
0.709	Intermediate Similarity	NPD3972	Approved
0.7073	Intermediate Similarity	NPD1237	Approved
0.7063	Intermediate Similarity	NPD1729	Discontinued
0.7059	Intermediate Similarity	NPD2859	Approved
0.7059	Intermediate Similarity	NPD2860	Approved
0.7027	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6166	Phase 2
0.7015	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD520	Approved
0.6993	Remote Similarity	NPD3748	Approved
0.6992	Remote Similarity	NPD3019	Approved
0.6992	Remote Similarity	NPD2932	Approved
0.6987	Remote Similarity	NPD5494	Approved
0.6975	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2934	Approved
0.6975	Remote Similarity	NPD2933	Approved
0.6948	Remote Similarity	NPD3817	Phase 2
0.6944	Remote Similarity	NPD6099	Approved
0.6944	Remote Similarity	NPD6100	Approved
0.6937	Remote Similarity	NPD3818	Discontinued
0.6933	Remote Similarity	NPD5403	Approved
0.6933	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3764	Approved
0.6929	Remote Similarity	NPD411	Approved
0.6923	Remote Similarity	NPD9258	Approved
0.6923	Remote Similarity	NPD919	Approved
0.6923	Remote Similarity	NPD9256	Approved
0.6917	Remote Similarity	NPD844	Approved
0.6906	Remote Similarity	NPD6832	Phase 2
0.6901	Remote Similarity	NPD447	Suspended
0.6899	Remote Similarity	NPD5711	Approved
0.6899	Remote Similarity	NPD5710	Approved
0.6897	Remote Similarity	NPD2346	Discontinued
0.6892	Remote Similarity	NPD3300	Phase 2
0.6885	Remote Similarity	NPD3020	Approved
0.6871	Remote Similarity	NPD6559	Discontinued
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.687	Remote Similarity	NPD255	Approved
0.687	Remote Similarity	NPD256	Approved
0.6855	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1929	Approved
0.6855	Remote Similarity	NPD1930	Approved
0.6852	Remote Similarity	NPD7074	Phase 3
0.6846	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD3226	Approved
0.6842	Remote Similarity	NPD1759	Phase 1
0.6835	Remote Similarity	NPD9494	Approved
0.6835	Remote Similarity	NPD1247	Approved
0.6812	Remote Similarity	NPD2797	Approved
0.6809	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD5401	Approved
0.6795	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5951	Approved
0.679	Remote Similarity	NPD7054	Approved
0.6788	Remote Similarity	NPD1755	Approved
0.6783	Remote Similarity	NPD111	Approved
0.6767	Remote Similarity	NPD1758	Phase 1
0.6763	Remote Similarity	NPD1019	Discontinued
0.6757	Remote Similarity	NPD4628	Phase 3
0.6757	Remote Similarity	NPD7003	Approved
0.6748	Remote Similarity	NPD7472	Approved
0.6732	Remote Similarity	NPD7458	Discontinued
0.6731	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD288	Approved
0.6716	Remote Similarity	NPD1548	Phase 1
0.6714	Remote Similarity	NPD4208	Discontinued
0.6711	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6797	Phase 2
0.6694	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.669	Remote Similarity	NPD1296	Phase 2
0.669	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD4207	Discontinued
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD5124	Phase 1
0.6646	Remote Similarity	NPD3926	Phase 2
0.6644	Remote Similarity	NPD4308	Phase 3
0.6644	Remote Similarity	NPD3400	Discontinued
0.6644	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1610	Phase 2
0.6627	Remote Similarity	NPD7808	Phase 3
0.6624	Remote Similarity	NPD5402	Approved
0.6624	Remote Similarity	NPD2296	Approved
0.6619	Remote Similarity	NPD1876	Approved
0.6618	Remote Similarity	NPD4626	Approved
0.6613	Remote Similarity	NPD2066	Phase 3
0.6594	Remote Similarity	NPD1608	Approved
0.6591	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD9257	Approved
0.6581	Remote Similarity	NPD9259	Approved
0.6575	Remote Similarity	NPD9279	Approved
0.6571	Remote Similarity	NPD1131	Approved
0.6571	Remote Similarity	NPD1133	Approved
0.6571	Remote Similarity	NPD1134	Approved
0.6571	Remote Similarity	NPD1135	Approved
0.6571	Remote Similarity	NPD1129	Approved
0.6567	Remote Similarity	NPD9568	Approved
0.6566	Remote Similarity	NPD6104	Discontinued
0.6561	Remote Similarity	NPD1465	Phase 2
0.6554	Remote Similarity	NPD1471	Phase 3
0.6554	Remote Similarity	NPD2343	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