NPASS Compound

Structure

CID45846 OpenBabel06191715382D 22 23 0 0 0 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 6.0622 -0.5000 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 3.4641 1.0000 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 3.4641 -0.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 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 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 9 2 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.09
Volume:	296.596
LogP:	2.899
LogD:	3.34
LogS:	-3.964
# Rotatable Bonds:	5
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.835
Synthetic Accessibility Score:	2.358
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	2.006224895012565e-05
Pgp-inhibitor:	0.11
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	84.79402160644531%
Volume Distribution (VD):	0.702
Pgp-substrate:	20.439144134521484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.676
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.762
CYP2D6-inhibitor:	0.133
CYP2D6-substrate:	0.576
CYP3A4-inhibitor:	0.301
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	10.93
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.44
AMES Toxicity:	0.305
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.531
Carcinogencity:	0.023
Eye Corrosion:	0.005
Eye Irritation:	0.68
Respiratory Toxicity:	0.313

Download Data

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

Natural Product: NPC45846

Natural Product ID:	NPC45846
*Common Name:**	Busseihydroquinone A
IUPAC Name:	methyl 1,8-dihydroxy-4,6,7-trimethoxynaphthalene-2-carboxylate
Synonyms:	Busseihydroquinone A
Standard InCHIKey:	WHXSAEDTQLTZPH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O7/c1-19-9-6-8(15(18)22-4)12(16)11-7(9)5-10(20-2)14(21-3)13(11)17/h5-6,16-17H,1-4H3
SMILES:	COC(=O)c1cc(OC)c2c(c1O)c(O)c(c(c2)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071293
PubChem CID:	60201020
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0001871] Naphthalenecarboxylic acids and derivatives [CHEMONTID:0002421] Naphthalenecarboxylic acids

*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
NPO7587	Mallotus resinosus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387675]
NPO15231	Axinella damicornis	Species	Axinellidae	Eukaryota	n.a.	Mediterranean	n.a.	PMID[17582775]
NPO33631	Pentas bussei	Species	Rubiaceae	Eukaryota	Roots	Mombasa, coastal region of Kenya	2010-JUL	PMID[22709138]
NPO6195	Rhodopentas bussei	Species	Rubiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[27518587]
NPO21314	Trametes sanguinea	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1433	Hepialus californicus	Species	Hepialidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11743	Phryxe caudata	Species	Tachinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4718	Daphne sericea	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15231	Axinella damicornis	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12699	Cronartium fusiforme	Species	Cronartiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4641	Baccharis nitida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10390	Orbexilum onobrychis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12803	Leuzea longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21314	Trametes sanguinea	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6195	Rhodopentas bussei	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2973	Euphorbia bungei	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8158	Euchresta horsfieldii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3514.1	Klebsiella pneumoniae subsp. ozaenae	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4906	Streptomyces flavoviridis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7587	Mallotus resinosus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2522	Fannia femoralis	Species	Fanniidae	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
LD50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	LD50	=	304.13	uM	PMID[539108]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	36030.0	nM	PMID[539108]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	144430.0	nM	PMID[539108]
NPT2	Others	Unspecified		Selectivity Index	=	8.44	n.a.	PMID[539108]
NPT2	Others	Unspecified		Selectivity Index	=	2.11	n.a.	PMID[539108]

☑ 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 NPC45846 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	388
0.1-0.2	1941
0.2-0.3	4582
0.3-0.4	10391
0.4-0.5	7447
0.5-0.6	3575
0.6-0.7	5224
0.7-0.8	6435
0.8-0.85	1933
0.85-0.9	728
0.9-0.95	52
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9313	High Similarity	NPC109827
0.9313	High Similarity	NPC124470
0.9295	High Similarity	NPC84571
0.9255	High Similarity	NPC158226
0.925	High Similarity	NPC163130
0.925	High Similarity	NPC165979
0.9241	High Similarity	NPC270837
0.9236	High Similarity	NPC311740
0.9177	High Similarity	NPC294965
0.9167	High Similarity	NPC199463
0.9167	High Similarity	NPC37543
0.9161	High Similarity	NPC472048
0.9139	High Similarity	NPC138978
0.913	High Similarity	NPC49487
0.913	High Similarity	NPC99613
0.9125	High Similarity	NPC29160
0.9119	High Similarity	NPC156082
0.9119	High Similarity	NPC236132
0.9119	High Similarity	NPC477689
0.9114	High Similarity	NPC66288
0.9103	High Similarity	NPC14561
0.9103	High Similarity	NPC5379
0.9103	High Similarity	NPC77807
0.9068	High Similarity	NPC234331
0.9062	High Similarity	NPC26386
0.9062	High Similarity	NPC112981
0.9057	High Similarity	NPC144843
0.9051	High Similarity	NPC14353
0.9051	High Similarity	NPC228785
0.9051	High Similarity	NPC56085
0.9045	High Similarity	NPC179732
0.9045	High Similarity	NPC178976
0.9038	High Similarity	NPC38898
0.9038	High Similarity	NPC134287
0.9038	High Similarity	NPC130589
0.9032	High Similarity	NPC175978
0.9024	High Similarity	NPC139350
0.902	High Similarity	NPC287395
0.902	High Similarity	NPC183655
0.9006	High Similarity	NPC20216
0.9006	High Similarity	NPC472452
0.9	High Similarity	NPC474350
0.9	High Similarity	NPC197168
0.8994	High Similarity	NPC40491
0.8994	High Similarity	NPC278052
0.8994	High Similarity	NPC61010
0.8987	High Similarity	NPC315157
0.8987	High Similarity	NPC83763
0.8987	High Similarity	NPC168616
0.8987	High Similarity	NPC100123
0.8987	High Similarity	NPC238381
0.8981	High Similarity	NPC54928
0.8974	High Similarity	NPC93552
0.8974	High Similarity	NPC281477
0.8974	High Similarity	NPC107109
0.8968	High Similarity	NPC204350
0.8963	High Similarity	NPC181523
0.8961	High Similarity	NPC102003
0.8961	High Similarity	NPC92722
0.8957	High Similarity	NPC239440
0.8957	High Similarity	NPC20543
0.8957	High Similarity	NPC246716
0.8957	High Similarity	NPC10576
0.8957	High Similarity	NPC17219
0.8951	High Similarity	NPC272485
0.8951	High Similarity	NPC292788
0.8944	High Similarity	NPC25361
0.8938	High Similarity	NPC215612
0.8938	High Similarity	NPC470694
0.8931	High Similarity	NPC119224
0.8931	High Similarity	NPC161947
0.8931	High Similarity	NPC47623
0.8931	High Similarity	NPC155302
0.8931	High Similarity	NPC320359
0.8924	High Similarity	NPC165977
0.8924	High Similarity	NPC262286
0.8924	High Similarity	NPC36852
0.8924	High Similarity	NPC217677
0.8924	High Similarity	NPC300727
0.8924	High Similarity	NPC78103
0.8924	High Similarity	NPC241904
0.8917	High Similarity	NPC39184
0.8917	High Similarity	NPC20541
0.8917	High Similarity	NPC16082
0.8917	High Similarity	NPC82592
0.8917	High Similarity	NPC199926
0.891	High Similarity	NPC149889
0.891	High Similarity	NPC289968
0.891	High Similarity	NPC312338
0.8903	High Similarity	NPC119929
0.8903	High Similarity	NPC472279
0.8896	High Similarity	NPC26568
0.8896	High Similarity	NPC55327
0.8896	High Similarity	NPC172329
0.8896	High Similarity	NPC131451
0.8896	High Similarity	NPC2569
0.8896	High Similarity	NPC15329
0.8889	High Similarity	NPC260946
0.8889	High Similarity	NPC163846
0.8889	High Similarity	NPC225173
0.8889	High Similarity	NPC37870
0.8882	High Similarity	NPC133065
0.8882	High Similarity	NPC152659
0.8882	High Similarity	NPC248638
0.8882	High Similarity	NPC300984
0.8882	High Similarity	NPC220313
0.8882	High Similarity	NPC7483
0.8882	High Similarity	NPC236521
0.8875	High Similarity	NPC303565
0.8875	High Similarity	NPC87431
0.8868	High Similarity	NPC476242
0.8862	High Similarity	NPC113446
0.8861	High Similarity	NPC227062
0.8861	High Similarity	NPC150227
0.8861	High Similarity	NPC138243
0.8861	High Similarity	NPC274730
0.8861	High Similarity	NPC474167
0.8861	High Similarity	NPC142339
0.8861	High Similarity	NPC470762
0.8854	High Similarity	NPC250557
0.8854	High Similarity	NPC273248
0.8854	High Similarity	NPC124714
0.8846	High Similarity	NPC171010
0.8846	High Similarity	NPC78505
0.8846	High Similarity	NPC75377
0.8846	High Similarity	NPC272566
0.8846	High Similarity	NPC19980
0.8846	High Similarity	NPC45291
0.8841	High Similarity	NPC1827
0.8839	High Similarity	NPC134293
0.8831	High Similarity	NPC125801
0.8831	High Similarity	NPC93034
0.8831	High Similarity	NPC119660
0.8827	High Similarity	NPC39306
0.8827	High Similarity	NPC239752
0.8827	High Similarity	NPC472450
0.8827	High Similarity	NPC8070
0.8827	High Similarity	NPC326520
0.8827	High Similarity	NPC275780
0.882	High Similarity	NPC108767
0.882	High Similarity	NPC25152
0.8816	High Similarity	NPC84266
0.8812	High Similarity	NPC475886
0.8812	High Similarity	NPC474287
0.8812	High Similarity	NPC476980
0.8805	High Similarity	NPC247713
0.8805	High Similarity	NPC84935
0.8805	High Similarity	NPC190020
0.8805	High Similarity	NPC77679
0.8805	High Similarity	NPC78225
0.8805	High Similarity	NPC236796
0.8802	High Similarity	NPC207467
0.8797	High Similarity	NPC79998
0.8797	High Similarity	NPC234485
0.8797	High Similarity	NPC113906
0.8797	High Similarity	NPC471800
0.8795	High Similarity	NPC289147
0.879	High Similarity	NPC291802
0.879	High Similarity	NPC101996
0.879	High Similarity	NPC161778
0.879	High Similarity	NPC35763
0.879	High Similarity	NPC39007
0.879	High Similarity	NPC121522
0.879	High Similarity	NPC131266
0.879	High Similarity	NPC100263
0.879	High Similarity	NPC216769
0.879	High Similarity	NPC100971
0.879	High Similarity	NPC269451
0.879	High Similarity	NPC245382
0.879	High Similarity	NPC199773
0.879	High Similarity	NPC161277
0.879	High Similarity	NPC181209
0.879	High Similarity	NPC209487
0.8788	High Similarity	NPC260263
0.8788	High Similarity	NPC471181
0.8782	High Similarity	NPC96501
0.8782	High Similarity	NPC294646
0.8782	High Similarity	NPC103509
0.8782	High Similarity	NPC239363
0.8773	High Similarity	NPC170245
0.8773	High Similarity	NPC39091
0.8766	High Similarity	NPC226987
0.8766	High Similarity	NPC143903
0.8766	High Similarity	NPC165389
0.8765	High Similarity	NPC189473
0.8765	High Similarity	NPC234004
0.8765	High Similarity	NPC207690
0.8765	High Similarity	NPC23298
0.8765	High Similarity	NPC146134
0.8765	High Similarity	NPC101769
0.8758	High Similarity	NPC474351
0.8758	High Similarity	NPC474186
0.8758	High Similarity	NPC475883
0.8758	High Similarity	NPC32694
0.8758	High Similarity	NPC474187
0.8758	High Similarity	NPC258331
0.875	High Similarity	NPC85121
0.875	High Similarity	NPC94076
0.875	High Similarity	NPC182255
0.875	High Similarity	NPC40702

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 NPC45846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	1046
0.2-0.3	1970
0.3-0.4	2659
0.4-0.5	1677
0.5-0.6	927
0.6-0.7	326
0.7-0.8	146
0.8-0.85	29
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9177	High Similarity	NPD6232	Discontinued
0.9006	High Similarity	NPD7473	Discontinued
0.8667	High Similarity	NPD5844	Phase 1
0.8616	High Similarity	NPD1465	Phase 2
0.8616	High Similarity	NPD2801	Approved
0.8462	Intermediate Similarity	NPD2534	Approved
0.8462	Intermediate Similarity	NPD2533	Approved
0.8462	Intermediate Similarity	NPD2532	Approved
0.8385	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1934	Approved
0.8312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2935	Discontinued
0.8282	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD3882	Suspended
0.8276	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD1511	Approved
0.816	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD5494	Approved
0.811	Intermediate Similarity	NPD3817	Phase 2
0.8105	Intermediate Similarity	NPD1607	Approved
0.8084	Intermediate Similarity	NPD6959	Discontinued
0.8063	Intermediate Similarity	NPD1512	Approved
0.8059	Intermediate Similarity	NPD3818	Discontinued
0.8039	Intermediate Similarity	NPD230	Phase 1
0.8035	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4380	Phase 2
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7974	Intermediate Similarity	NPD1240	Approved
0.7974	Intermediate Similarity	NPD943	Approved
0.7964	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1510	Phase 2
0.7879	Intermediate Similarity	NPD37	Approved
0.7879	Intermediate Similarity	NPD6801	Discontinued
0.7877	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD1247	Approved
0.7861	Intermediate Similarity	NPD7074	Phase 3
0.7857	Intermediate Similarity	NPD919	Approved
0.7826	Intermediate Similarity	NPD6799	Approved
0.7824	Intermediate Similarity	NPD5711	Approved
0.7824	Intermediate Similarity	NPD5710	Approved
0.7805	Intermediate Similarity	NPD3226	Approved
0.7803	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6559	Discontinued
0.7759	Intermediate Similarity	NPD7472	Approved
0.7738	Intermediate Similarity	NPD4966	Approved
0.7738	Intermediate Similarity	NPD4965	Approved
0.7738	Intermediate Similarity	NPD4967	Phase 2
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7716	Intermediate Similarity	NPD7390	Discontinued
0.7714	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7411	Suspended
0.7692	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD3749	Approved
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD920	Approved
0.7679	Intermediate Similarity	NPD5402	Approved
0.7673	Intermediate Similarity	NPD2346	Discontinued
0.7669	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7228	Approved
0.764	Intermediate Similarity	NPD4628	Phase 3
0.764	Intermediate Similarity	NPD3750	Approved
0.763	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1549	Phase 2
0.7614	Intermediate Similarity	NPD6797	Phase 2
0.761	Intermediate Similarity	NPD5408	Approved
0.761	Intermediate Similarity	NPD5405	Approved
0.761	Intermediate Similarity	NPD5404	Approved
0.761	Intermediate Similarity	NPD5406	Approved
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1243	Approved
0.7578	Intermediate Similarity	NPD2800	Approved
0.7572	Intermediate Similarity	NPD3926	Phase 2
0.7571	Intermediate Similarity	NPD7251	Discontinued
0.7562	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD9269	Phase 2
0.7539	Intermediate Similarity	NPD8151	Discontinued
0.7528	Intermediate Similarity	NPD7808	Phase 3
0.7471	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7457	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1283	Approved
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7436	Intermediate Similarity	NPD3027	Phase 3
0.7423	Intermediate Similarity	NPD7003	Approved
0.7423	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6651	Approved
0.7419	Intermediate Similarity	NPD9494	Approved
0.7401	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7394	Intermediate Similarity	NPD6776	Approved
0.7394	Intermediate Similarity	NPD6779	Approved
0.7394	Intermediate Similarity	NPD6780	Approved
0.7394	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6777	Approved
0.7394	Intermediate Similarity	NPD6781	Approved
0.7394	Intermediate Similarity	NPD6778	Approved
0.7394	Intermediate Similarity	NPD6782	Approved
0.7391	Intermediate Similarity	NPD2796	Approved
0.7389	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8312	Approved
0.7378	Intermediate Similarity	NPD6190	Approved
0.7371	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5242	Approved
0.7362	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3748	Approved
0.7321	Intermediate Similarity	NPD1653	Approved
0.7318	Intermediate Similarity	NPD5953	Discontinued
0.7308	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9268	Approved
0.7282	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7783	Phase 2
0.7278	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5403	Approved
0.7261	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1281	Approved
0.7247	Intermediate Similarity	NPD3751	Discontinued
0.7231	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7229	Phase 3
0.7188	Intermediate Similarity	NPD1613	Approved
0.7188	Intermediate Similarity	NPD7697	Approved
0.7188	Intermediate Similarity	NPD7698	Approved
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7188	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7685	Pre-registration
0.7182	Intermediate Similarity	NPD7240	Approved
0.7179	Intermediate Similarity	NPD1203	Approved
0.7179	Intermediate Similarity	NPD1470	Approved
0.7179	Intermediate Similarity	NPD1164	Approved
0.7178	Intermediate Similarity	NPD6099	Approved
0.7178	Intermediate Similarity	NPD6100	Approved
0.7174	Intermediate Similarity	NPD8434	Phase 2
0.717	Intermediate Similarity	NPD2313	Discontinued
0.7168	Intermediate Similarity	NPD5353	Approved
0.7161	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD1933	Approved
0.7135	Intermediate Similarity	NPD6823	Phase 2
0.7134	Intermediate Similarity	NPD2344	Approved
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD7701	Phase 2
0.7128	Intermediate Similarity	NPD6534	Approved
0.7124	Intermediate Similarity	NPD4626	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7107	Intermediate Similarity	NPD4625	Phase 3
0.7093	Intermediate Similarity	NPD6385	Approved
0.7093	Intermediate Similarity	NPD6386	Approved
0.7081	Intermediate Similarity	NPD2979	Phase 3
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7073	Intermediate Similarity	NPD2438	Suspended
0.7063	Intermediate Similarity	NPD411	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD1651	Approved
0.7056	Intermediate Similarity	NPD7177	Discontinued
0.7041	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1201	Approved
0.702	Intermediate Similarity	NPD7801	Approved
0.7016	Intermediate Similarity	NPD7700	Phase 2
0.7016	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1608	Approved
0.6987	Remote Similarity	NPD9717	Approved
0.6974	Remote Similarity	NPD9493	Approved
0.6964	Remote Similarity	NPD2309	Approved
0.6937	Remote Similarity	NPD6832	Phase 2
0.6933	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1611	Approved
0.6918	Remote Similarity	NPD2798	Approved
0.6909	Remote Similarity	NPD4308	Phase 3
0.6905	Remote Similarity	NPD8166	Discontinued
0.6895	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6212	Phase 3
0.6895	Remote Similarity	NPD6213	Phase 3
0.6891	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD8319	Approved
0.6888	Remote Similarity	NPD8320	Phase 1
0.6883	Remote Similarity	NPD9545	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