NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.06
Volume:	189.018
LogP:	0.155
LogD:	0.674
LogS:	-2.096
# Rotatable Bonds:	0
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	3.302
Fsp3:	0.3
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:	-4.995
MDCK Permeability:	7.547702352894703e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.573
20% Bioavailability (F20%):	0.486
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.74
Plasma Protein Binding (PPB):	45.511070251464844%
Volume Distribution (VD):	1.207
Pgp-substrate:	59.33875274658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.115
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.204
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.749
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.319
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	8.188
Half-life (T1/2):	0.54

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.508
AMES Toxicity:	0.43
Rat Oral Acute Toxicity:	0.682
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.239
Carcinogencity:	0.327
Eye Corrosion:	0.003
Eye Irritation:	0.586
Respiratory Toxicity:	0.333

Download Data

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

Natural Product: NPC767

Natural Product ID:	NPC767
*Common Name:**	Cis-3,4-Dihydro-3,4,8-Trihydroxynaphthalen-1(2H)-One
IUPAC Name:	(3R,4S)-3,4,8-trihydroxy-3,4-dihydro-2H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	HPIFRXWPEZBFHJ-SCZZXKLOSA-N
Standard InCHI:	InChI=1S/C10H10O4/c11-6-3-1-2-5-9(6)7(12)4-8(13)10(5)14/h1-3,8,10-11,13-14H,4H2/t8-,10+/m1/s1
SMILES:	O[C@@H]1CC(=O)c2c([C@@H]1O)cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229113
PubChem CID:	42612830
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14519932]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26258762]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3748	Astragalus eremophilus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3641	Polyporus tuberaster	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16391	Protea neriifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO318	Glycosmis trichanthera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12318	Ayapana amygdalina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4567	Senecio chrysocoma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6773	Bryoria implexa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19908	Fejervarya limnocharis	Species	Dicroglossidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[485107]

☑ 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 NPC767 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	335
0.1-0.2	1320
0.2-0.3	3446
0.3-0.4	8989
0.4-0.5	10268
0.5-0.6	4613
0.6-0.7	8585
0.7-0.8	4706
0.8-0.85	377
0.85-0.9	48
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC247250
0.968	High Similarity	NPC17843
0.9256	High Similarity	NPC216297
0.9256	High Similarity	NPC473662
0.9256	High Similarity	NPC7151
0.9213	High Similarity	NPC147757
0.907	High Similarity	NPC478190
0.8889	High Similarity	NPC74507
0.8889	High Similarity	NPC234890
0.8797	High Similarity	NPC315275
0.8779	High Similarity	NPC70622
0.874	High Similarity	NPC68756
0.874	High Similarity	NPC152525
0.8712	High Similarity	NPC314048
0.8712	High Similarity	NPC52407
0.8682	High Similarity	NPC473787
0.8667	High Similarity	NPC126739
0.8667	High Similarity	NPC175552
0.8667	High Similarity	NPC197666
0.8636	High Similarity	NPC246693
0.8636	High Similarity	NPC242358
0.8636	High Similarity	NPC110609
0.8626	High Similarity	NPC199253
0.8626	High Similarity	NPC117609
0.8626	High Similarity	NPC136588
0.8603	High Similarity	NPC103337
0.8603	High Similarity	NPC114620
0.8593	High Similarity	NPC147418
0.8593	High Similarity	NPC170742
0.8571	High Similarity	NPC294226
0.8561	High Similarity	NPC469526
0.8561	High Similarity	NPC244691
0.8561	High Similarity	NPC34070
0.8551	High Similarity	NPC137649
0.8538	High Similarity	NPC470841
0.8529	High Similarity	NPC416
0.8529	High Similarity	NPC61398
0.8527	High Similarity	NPC103540
0.8521	High Similarity	NPC478219
0.8496	Intermediate Similarity	NPC135801
0.8496	Intermediate Similarity	NPC477406
0.8485	Intermediate Similarity	NPC26697
0.8485	Intermediate Similarity	NPC233056
0.8478	Intermediate Similarity	NPC130485
0.8473	Intermediate Similarity	NPC165257
0.8468	Intermediate Similarity	NPC108288
0.8467	Intermediate Similarity	NPC190457
0.8462	Intermediate Similarity	NPC51037
0.8462	Intermediate Similarity	NPC1991
0.8462	Intermediate Similarity	NPC3224
0.8462	Intermediate Similarity	NPC8745
0.8462	Intermediate Similarity	NPC231774
0.8456	Intermediate Similarity	NPC290030
0.8456	Intermediate Similarity	NPC305060
0.845	Intermediate Similarity	NPC310540
0.845	Intermediate Similarity	NPC13238
0.8444	Intermediate Similarity	NPC72918
0.844	Intermediate Similarity	NPC285122
0.844	Intermediate Similarity	NPC136878
0.8429	Intermediate Similarity	NPC48130
0.8429	Intermediate Similarity	NPC79627
0.8429	Intermediate Similarity	NPC218866
0.8429	Intermediate Similarity	NPC29932
0.8429	Intermediate Similarity	NPC84568
0.8429	Intermediate Similarity	NPC300684
0.8417	Intermediate Similarity	NPC474961
0.8417	Intermediate Similarity	NPC469520
0.8417	Intermediate Similarity	NPC85310
0.8413	Intermediate Similarity	NPC232178
0.8409	Intermediate Similarity	NPC120488
0.8409	Intermediate Similarity	NPC99731
0.8409	Intermediate Similarity	NPC474546
0.8409	Intermediate Similarity	NPC92624
0.8409	Intermediate Similarity	NPC102829
0.8406	Intermediate Similarity	NPC203063
0.8403	Intermediate Similarity	NPC205918
0.8394	Intermediate Similarity	NPC141368
0.8392	Intermediate Similarity	NPC280753
0.8392	Intermediate Similarity	NPC44378
0.8385	Intermediate Similarity	NPC10926
0.8372	Intermediate Similarity	NPC375356
0.837	Intermediate Similarity	NPC166480
0.837	Intermediate Similarity	NPC282780
0.837	Intermediate Similarity	NPC44437
0.8369	Intermediate Similarity	NPC170055
0.8359	Intermediate Similarity	NPC198336
0.8357	Intermediate Similarity	NPC238629
0.8346	Intermediate Similarity	NPC475741
0.8346	Intermediate Similarity	NPC31799
0.8346	Intermediate Similarity	NPC259942
0.8346	Intermediate Similarity	NPC285829
0.8346	Intermediate Similarity	NPC206778
0.8345	Intermediate Similarity	NPC305845
0.8345	Intermediate Similarity	NPC204045
0.8345	Intermediate Similarity	NPC472904
0.8333	Intermediate Similarity	NPC41567
0.8333	Intermediate Similarity	NPC472903
0.8333	Intermediate Similarity	NPC179898
0.8333	Intermediate Similarity	NPC282923
0.8333	Intermediate Similarity	NPC237225
0.8333	Intermediate Similarity	NPC95537
0.8322	Intermediate Similarity	NPC94781
0.8321	Intermediate Similarity	NPC96915
0.8321	Intermediate Similarity	NPC261292
0.8321	Intermediate Similarity	NPC301915
0.832	Intermediate Similarity	NPC477453
0.8309	Intermediate Similarity	NPC129752
0.8309	Intermediate Similarity	NPC142027
0.8309	Intermediate Similarity	NPC27407
0.8309	Intermediate Similarity	NPC258502
0.8308	Intermediate Similarity	NPC173978
0.8298	Intermediate Similarity	NPC471906
0.8296	Intermediate Similarity	NPC139074
0.8296	Intermediate Similarity	NPC213485
0.8296	Intermediate Similarity	NPC40524
0.8295	Intermediate Similarity	NPC283514
0.8295	Intermediate Similarity	NPC217756
0.8295	Intermediate Similarity	NPC300274
0.8286	Intermediate Similarity	NPC135524
0.8284	Intermediate Similarity	NPC93015
0.8284	Intermediate Similarity	NPC41847
0.8284	Intermediate Similarity	NPC205992
0.8284	Intermediate Similarity	NPC214702
0.8284	Intermediate Similarity	NPC470831
0.8273	Intermediate Similarity	NPC158472
0.8273	Intermediate Similarity	NPC471853
0.8271	Intermediate Similarity	NPC278928
0.8261	Intermediate Similarity	NPC206207
0.8261	Intermediate Similarity	NPC173980
0.8252	Intermediate Similarity	NPC476821
0.8252	Intermediate Similarity	NPC476463
0.8248	Intermediate Similarity	NPC223836
0.8248	Intermediate Similarity	NPC86524
0.8244	Intermediate Similarity	NPC167055
0.8244	Intermediate Similarity	NPC201728
0.8244	Intermediate Similarity	NPC262671
0.8244	Intermediate Similarity	NPC127975
0.8244	Intermediate Similarity	NPC240744
0.8244	Intermediate Similarity	NPC477454
0.824	Intermediate Similarity	NPC240163
0.8239	Intermediate Similarity	NPC83272
0.8235	Intermediate Similarity	NPC288089
0.8219	Intermediate Similarity	NPC268992
0.8219	Intermediate Similarity	NPC51824
0.8219	Intermediate Similarity	NPC113608
0.8219	Intermediate Similarity	NPC470337
0.8219	Intermediate Similarity	NPC470338
0.8217	Intermediate Similarity	NPC242895
0.8217	Intermediate Similarity	NPC115159
0.8217	Intermediate Similarity	NPC143427
0.8217	Intermediate Similarity	NPC45438
0.8217	Intermediate Similarity	NPC267552
0.8217	Intermediate Similarity	NPC224273
0.8217	Intermediate Similarity	NPC19174
0.8217	Intermediate Similarity	NPC73532
0.8211	Intermediate Similarity	NPC114682
0.8209	Intermediate Similarity	NPC244441
0.8201	Intermediate Similarity	NPC247409
0.8201	Intermediate Similarity	NPC268052
0.8201	Intermediate Similarity	NPC471819
0.8195	Intermediate Similarity	NPC41263
0.8195	Intermediate Similarity	NPC234175
0.8189	Intermediate Similarity	NPC249435
0.8188	Intermediate Similarity	NPC53414
0.8188	Intermediate Similarity	NPC53206
0.8182	Intermediate Similarity	NPC472047
0.8182	Intermediate Similarity	NPC306765
0.8182	Intermediate Similarity	NPC160499
0.8182	Intermediate Similarity	NPC473691
0.8176	Intermediate Similarity	NPC478223
0.8175	Intermediate Similarity	NPC283590
0.8175	Intermediate Similarity	NPC130899
0.8175	Intermediate Similarity	NPC61153
0.8175	Intermediate Similarity	NPC70859
0.8169	Intermediate Similarity	NPC103910
0.8162	Intermediate Similarity	NPC267205
0.8156	Intermediate Similarity	NPC73061
0.8156	Intermediate Similarity	NPC248068
0.8154	Intermediate Similarity	NPC91478
0.8154	Intermediate Similarity	NPC32032
0.8154	Intermediate Similarity	NPC133909
0.8154	Intermediate Similarity	NPC307174
0.8154	Intermediate Similarity	NPC86900
0.8148	Intermediate Similarity	NPC85342
0.8148	Intermediate Similarity	NPC475042
0.8145	Intermediate Similarity	NPC231717
0.8143	Intermediate Similarity	NPC183345
0.8143	Intermediate Similarity	NPC155205
0.814	Intermediate Similarity	NPC297186
0.814	Intermediate Similarity	NPC190971
0.8138	Intermediate Similarity	NPC120171
0.8129	Intermediate Similarity	NPC9121
0.8129	Intermediate Similarity	NPC478200
0.8129	Intermediate Similarity	NPC33144
0.8129	Intermediate Similarity	NPC177307
0.8129	Intermediate Similarity	NPC13715
0.8129	Intermediate Similarity	NPC475974
0.8125	Intermediate Similarity	NPC473767
0.812	Intermediate Similarity	NPC324209
0.812	Intermediate Similarity	NPC107672

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 NPC767 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	864
0.2-0.3	1611
0.3-0.4	2809
0.4-0.5	1988
0.5-0.6	1085
0.6-0.7	417
0.7-0.8	73
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8527	High Similarity	NPD1470	Approved
0.8519	High Similarity	NPD651	Clinical (unspecified phase)
0.8504	High Similarity	NPD1201	Approved
0.8496	Intermediate Similarity	NPD943	Approved
0.8468	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD3300	Phase 2
0.7793	Intermediate Similarity	NPD1511	Approved
0.7733	Intermediate Similarity	NPD1934	Approved
0.773	Intermediate Similarity	NPD1510	Phase 2
0.7692	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1512	Approved
0.7682	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7390	Discontinued
0.7622	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD9269	Phase 2
0.76	Intermediate Similarity	NPD4380	Phase 2
0.7571	Intermediate Similarity	NPD1240	Approved
0.7569	Intermediate Similarity	NPD1549	Phase 2
0.7566	Intermediate Similarity	NPD2801	Approved
0.7552	Intermediate Similarity	NPD5406	Approved
0.7552	Intermediate Similarity	NPD5404	Approved
0.7552	Intermediate Similarity	NPD5405	Approved
0.7552	Intermediate Similarity	NPD5408	Approved
0.7518	Intermediate Similarity	NPD230	Phase 1
0.7468	Intermediate Similarity	NPD3882	Suspended
0.7465	Intermediate Similarity	NPD1607	Approved
0.746	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1164	Approved
0.7444	Intermediate Similarity	NPD9268	Approved
0.7402	Intermediate Similarity	NPD74	Approved
0.7402	Intermediate Similarity	NPD9266	Approved
0.7375	Intermediate Similarity	NPD3818	Discontinued
0.7368	Intermediate Similarity	NPD9545	Approved
0.7358	Intermediate Similarity	NPD6166	Phase 2
0.7358	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9493	Approved
0.7342	Intermediate Similarity	NPD6232	Discontinued
0.7338	Intermediate Similarity	NPD9494	Approved
0.7323	Intermediate Similarity	NPD9263	Approved
0.7323	Intermediate Similarity	NPD9267	Approved
0.7323	Intermediate Similarity	NPD9264	Approved
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD3226	Approved
0.7297	Intermediate Similarity	NPD6190	Approved
0.7267	Intermediate Similarity	NPD2534	Approved
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2532	Approved
0.7267	Intermediate Similarity	NPD2533	Approved
0.726	Intermediate Similarity	NPD2344	Approved
0.726	Intermediate Similarity	NPD2346	Discontinued
0.723	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4628	Phase 3
0.7226	Intermediate Similarity	NPD7819	Suspended
0.7222	Intermediate Similarity	NPD1237	Approved
0.7222	Intermediate Similarity	NPD7054	Approved
0.7186	Intermediate Similarity	NPD8150	Discontinued
0.7185	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3817	Phase 2
0.7179	Intermediate Similarity	NPD5402	Approved
0.7178	Intermediate Similarity	NPD7472	Approved
0.7178	Intermediate Similarity	NPD7074	Phase 3
0.717	Intermediate Similarity	NPD6959	Discontinued
0.716	Intermediate Similarity	NPD3751	Discontinued
0.7153	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD447	Suspended
0.7152	Intermediate Similarity	NPD36	Approved
0.7152	Intermediate Similarity	NPD5026	Approved
0.7152	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5034	Approved
0.7152	Intermediate Similarity	NPD5028	Approved
0.7152	Intermediate Similarity	NPD4955	Approved
0.7152	Intermediate Similarity	NPD4954	Approved
0.7134	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2932	Approved
0.7132	Intermediate Similarity	NPD3019	Approved
0.7091	Intermediate Similarity	NPD7251	Discontinued
0.7091	Intermediate Similarity	NPD5030	Phase 2
0.7089	Intermediate Similarity	NPD7075	Discontinued
0.7086	Intermediate Similarity	NPD6799	Approved
0.7083	Intermediate Similarity	NPD5038	Approved
0.7083	Intermediate Similarity	NPD5037	Approved
0.7075	Intermediate Similarity	NPD1551	Phase 2
0.7075	Intermediate Similarity	NPD2796	Approved
0.7075	Intermediate Similarity	NPD9570	Approved
0.7071	Intermediate Similarity	NPD1203	Approved
0.707	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9281	Approved
0.7067	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD7808	Phase 3
0.7024	Intermediate Similarity	NPD5036	Approved
0.7021	Intermediate Similarity	NPD2798	Approved
0.7019	Intermediate Similarity	NPD3787	Discontinued
0.7018	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD9261	Approved
0.7007	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD8312	Approved
0.7006	Intermediate Similarity	NPD8313	Approved
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD5494	Approved
0.6981	Remote Similarity	NPD3749	Approved
0.695	Remote Similarity	NPD3094	Phase 2
0.6948	Remote Similarity	NPD5403	Approved
0.6947	Remote Similarity	NPD3022	Approved
0.6947	Remote Similarity	NPD3021	Approved
0.6943	Remote Similarity	NPD6801	Discontinued
0.6933	Remote Similarity	NPD2800	Approved
0.6933	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD6599	Discontinued
0.6913	Remote Similarity	NPD1471	Phase 3
0.6909	Remote Similarity	NPD5844	Phase 1
0.6909	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3092	Approved
0.6905	Remote Similarity	NPD5035	Approved
0.6897	Remote Similarity	NPD520	Approved
0.6887	Remote Similarity	NPD3400	Discontinued
0.6887	Remote Similarity	NPD8166	Discontinued
0.6886	Remote Similarity	NPD5029	Approved
0.6886	Remote Similarity	NPD5031	Approved
0.6886	Remote Similarity	NPD5027	Approved
0.6859	Remote Similarity	NPD2649	Approved
0.6859	Remote Similarity	NPD2651	Approved
0.6857	Remote Similarity	NPD9717	Approved
0.6857	Remote Similarity	NPD1608	Approved
0.685	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6535	Approved
0.6839	Remote Similarity	NPD6534	Approved
0.6835	Remote Similarity	NPD6844	Discontinued
0.6826	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD9495	Approved
0.6818	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1755	Approved
0.6809	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6559	Discontinued
0.6781	Remote Similarity	NPD6663	Approved
0.6772	Remote Similarity	NPD7411	Suspended
0.6767	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD9381	Approved
0.6763	Remote Similarity	NPD9384	Approved
0.6761	Remote Similarity	NPD1283	Approved
0.6761	Remote Similarity	NPD1876	Approved
0.6752	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD288	Approved
0.6742	Remote Similarity	NPD6777	Approved
0.6742	Remote Similarity	NPD6779	Approved
0.6742	Remote Similarity	NPD6780	Approved
0.6742	Remote Similarity	NPD6778	Approved
0.6742	Remote Similarity	NPD6776	Approved
0.6742	Remote Similarity	NPD6782	Approved
0.6742	Remote Similarity	NPD6781	Approved
0.6739	Remote Similarity	NPD3091	Approved
0.6738	Remote Similarity	NPD3972	Approved
0.6736	Remote Similarity	NPD5736	Approved
0.6735	Remote Similarity	NPD1613	Approved
0.6735	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7700	Phase 2
0.6723	Remote Similarity	NPD7699	Phase 2
0.6719	Remote Similarity	NPD1242	Phase 1
0.6714	Remote Similarity	NPD3026	Approved
0.6714	Remote Similarity	NPD3023	Approved
0.6712	Remote Similarity	NPD411	Approved
0.671	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5710	Approved
0.6707	Remote Similarity	NPD5711	Approved
0.6691	Remote Similarity	NPD1651	Approved
0.6691	Remote Similarity	NPD3025	Approved
0.6691	Remote Similarity	NPD3024	Approved
0.669	Remote Similarity	NPD6832	Phase 2
0.6689	Remote Similarity	NPD7266	Discontinued
0.6686	Remote Similarity	NPD8434	Phase 2
0.6686	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6213	Phase 3
0.6686	Remote Similarity	NPD6212	Phase 3
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD844	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD2342	Discontinued
0.6646	Remote Similarity	NPD3455	Phase 2
0.6646	Remote Similarity	NPD7458	Discontinued
0.6646	Remote Similarity	NPD1247	Approved
0.6645	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6651	Approved
0.6644	Remote Similarity	NPD3027	Phase 3
0.6643	Remote Similarity	NPD17	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