NPASS Compound

Structure

NPC69043 OpenBabel07101719132D 29 31 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 2.5981 -1.5000 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 -4.3301 -1.5000 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 -2.5981 -2.5000 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 -4.3301 -2.5000 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 0.8660 -1.5000 0.0000 C 0 0 2 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 0.8660 0.5000 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 0.0000 -1.0000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 1 11 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 14 1 0 0 0 0 5 22 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 28 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 10 1 1 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 6 0 0 0 19 29 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 2 1 1 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	395.333
LogP:	1.782
LogD:	1.985
LogS:	-2.809
# Rotatable Bonds:	5
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	4.471
Fsp3:	0.333
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:	-5.142
MDCK Permeability:	1.3583161489805207e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.145
30% Bioavailability (F30%):	0.363

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	80.88668060302734%
Volume Distribution (VD):	0.676
Pgp-substrate:	14.236675262451172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.862
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.278
CYP2D6-inhibitor:	0.247
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.81
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	8.215
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.641
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.503
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.952
Carcinogencity:	0.696
Eye Corrosion:	0.136
Eye Irritation:	0.938
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC69043

Natural Product ID:	NPC69043
*Common Name:**	Pinophilin B
IUPAC Name:	[(7S,8S,8aS)-7-hydroxy-3-[(E)-3-hydroxyprop-1-enyl]-7-methyl-6-oxo-8,8a-dihydro-1H-isochromen-8-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:	Pinophilin B
Standard InCHIKey:	KKSKNERURMTALE-XWEVTOJWSA-N
Standard InCHI:	InChI=1S/C21H22O8/c1-11-6-13(23)9-16(24)18(11)20(26)29-19-15-10-28-14(4-3-5-22)7-12(15)8-17(25)21(19,2)27/h3-4,6-9,15,19,22-24,27H,5,10H2,1-2H3/b4-3+/t15-,19+,21-/m1/s1
SMILES:	Cc1cc(cc(c1C(=O)O[C@H]1[C@@H]2COC(=CC2=CC(=O)[C@@]1(C)O)/C=C/CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011647
PubChem CID:	57333718
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264170]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26291474]
NPO33693	Talaromyces aculeatus DS-62013	Species	Trichocomaceae	Eukaryota	n.a.	saline-alkali soil, Shandong Province, China	2013-APR	PMID[28749670]
NPO40294	Pleosporales sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[32243144]

☑ 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
GI50	7
IC50	28
MIC	1

Activity Type	# Activity
Cell Line	11
Individual Protein	13
Organism	1
Others	10
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4232	Individual Protein	DNA polymerase delta subunit 1	Homo sapiens	IC50	=	96400.0	nM	PMID[529833]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	200000.0	nM	PMID[529833]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	>	200000.0	nM	PMID[529833]
NPT6396	Individual Protein	DNA-directed DNA/RNA polymerase mu	Homo sapiens	IC50	>	200000.0	nM	PMID[529833]
NPT4538	Individual Protein	DNA nucleotidylexotransferase	Bos taurus	IC50	>	200000.0	nM	PMID[529833]
NPT6251	Individual Protein	DNA polymerase nu	Homo sapiens	IC50	=	92100.0	nM	PMID[529833]
NPT6281	Individual Protein	DNA polymerase iota	Mus musculus	IC50	=	91000.0	nM	PMID[529833]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	IC50	=	88900.0	nM	PMID[529833]
NPT6333	Individual Protein	DNA polymerase	Enterobacteria phage T4	IC50	>	200000.0	nM	PMID[529833]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200000.0	nM	PMID[529833]
NPT6383	Individual Protein	Inosine-5'-monophosphate dehydrogenase 2	Mus musculus	IC50	>	200000.0	nM	PMID[529833]
NPT6223	Individual Protein	Polynucleotide kinase	Enterobacteria phage T4	IC50	>	200000.0	nM	PMID[529833]
NPT4478	Individual Protein	Deoxyribonuclease-1	Bos taurus	IC50	>	200000.0	nM	PMID[529833]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	93100.0	nM	PMID[529833]
NPT2298	Cell Line	BALL-1	Homo sapiens	GI50	=	90400.0	nM	PMID[529833]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	=	92500.0	nM	PMID[529833]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	99000.0	nM	PMID[529833]
NPT2477	Cell Line	NUGC-3	Homo sapiens	GI50	=	96800.0	nM	PMID[529833]
NPT737	Cell Line	HUVEC	Homo sapiens	GI50	>	200000.0	nM	PMID[529833]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	97000.0	nM	PMID[529836]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	78000.0	nM	PMID[529836]
NPT3140	Cell Line	MGC-803	Homo sapiens	IC50	=	84000.0	nM	PMID[529836]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	95000.0	nM	PMID[529836]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	89000.0	nM	PMID[529836]
NPT2	Others	Unspecified		IC50	=	93700.0	nM	PMID[529833]
NPT2	Others	Unspecified		IC50	=	89500.0	nM	PMID[529833]
NPT2	Others	Unspecified		IC50	=	93900.0	nM	PMID[529833]
NPT2	Others	Unspecified		IC50	>	200000.0	nM	PMID[529833]
NPT27	Others	Unspecified		GI50	>	200000.0	nM	PMID[529833]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	>	8.28	ug.mL-1	PMID[529835]
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	>	200000.0	nM	PMID[529835]

☑ 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 NPC69043 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	345
0.1-0.2	1347
0.2-0.3	3260
0.3-0.4	7183
0.4-0.5	10371
0.5-0.6	5136
0.6-0.7	6098
0.7-0.8	7598
0.8-0.85	1138
0.85-0.9	180
0.9-0.95	24
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478230
0.9865	High Similarity	NPC170189
0.9865	High Similarity	NPC208173
0.9865	High Similarity	NPC472890
0.9864	High Similarity	NPC76041
0.9864	High Similarity	NPC184284
0.9864	High Similarity	NPC478224
0.9797	High Similarity	NPC137301
0.9797	High Similarity	NPC478231
0.9733	High Similarity	NPC472889
0.9733	High Similarity	NPC478225
0.9732	High Similarity	NPC478221
0.973	High Similarity	NPC115249
0.9728	High Similarity	NPC472891
0.9603	High Similarity	NPC478226
0.96	High Similarity	NPC317585
0.9474	High Similarity	NPC246466
0.9416	High Similarity	NPC317544
0.94	High Similarity	NPC91809
0.9333	High Similarity	NPC164762
0.9267	High Similarity	NPC84142
0.9241	High Similarity	NPC283041
0.9236	High Similarity	NPC191930
0.9177	High Similarity	NPC20237
0.9172	High Similarity	NPC249181
0.915	High Similarity	NPC471695
0.9133	High Similarity	NPC210320
0.9116	High Similarity	NPC158634
0.9103	High Similarity	NPC472055
0.9079	High Similarity	NPC56204
0.9073	High Similarity	NPC215711
0.9073	High Similarity	NPC73411
0.9062	High Similarity	NPC328321
0.9048	High Similarity	NPC158472
0.9038	High Similarity	NPC470339
0.902	High Similarity	NPC70016
0.902	High Similarity	NPC215921
0.9013	High Similarity	NPC270160
0.9013	High Similarity	NPC237440
0.8986	High Similarity	NPC244923
0.898	High Similarity	NPC32360
0.898	High Similarity	NPC268052
0.898	High Similarity	NPC247409
0.8968	High Similarity	NPC99381
0.8933	High Similarity	NPC210425
0.8933	High Similarity	NPC277426
0.8933	High Similarity	NPC86373
0.8933	High Similarity	NPC280404
0.8924	High Similarity	NPC117985
0.8912	High Similarity	NPC478200
0.8912	High Similarity	NPC33144
0.891	High Similarity	NPC472050
0.8896	High Similarity	NPC200773
0.8896	High Similarity	NPC240768
0.8889	High Similarity	NPC4423
0.8889	High Similarity	NPC77325
0.8874	High Similarity	NPC83272
0.8867	High Similarity	NPC478202
0.8839	High Similarity	NPC470340
0.8839	High Similarity	NPC167903
0.8831	High Similarity	NPC469670
0.8831	High Similarity	NPC469619
0.8816	High Similarity	NPC473023
0.88	High Similarity	NPC82913
0.88	High Similarity	NPC474385
0.8784	High Similarity	NPC212693
0.8784	High Similarity	NPC191835
0.8784	High Similarity	NPC94248
0.8782	High Similarity	NPC155686
0.8765	High Similarity	NPC473094
0.8758	High Similarity	NPC81835
0.8758	High Similarity	NPC472036
0.875	High Similarity	NPC257558
0.8742	High Similarity	NPC51106
0.8733	High Similarity	NPC313123
0.8733	High Similarity	NPC130485
0.8733	High Similarity	NPC478217
0.8733	High Similarity	NPC478201
0.8733	High Similarity	NPC53649
0.8733	High Similarity	NPC472035
0.8726	High Similarity	NPC471456
0.8726	High Similarity	NPC68727
0.8726	High Similarity	NPC473241
0.8725	High Similarity	NPC52358
0.8718	High Similarity	NPC113608
0.8718	High Similarity	NPC470338
0.8718	High Similarity	NPC51824
0.8718	High Similarity	NPC470337
0.8718	High Similarity	NPC268992
0.8716	High Similarity	NPC70380
0.8712	High Similarity	NPC473095
0.8712	High Similarity	NPC473096
0.8701	High Similarity	NPC94781
0.8701	High Similarity	NPC240622
0.8701	High Similarity	NPC240253
0.8701	High Similarity	NPC471642
0.8701	High Similarity	NPC471641
0.8684	High Similarity	NPC126882
0.8684	High Similarity	NPC151607
0.8684	High Similarity	NPC210966
0.8684	High Similarity	NPC103910
0.8684	High Similarity	NPC42540
0.8684	High Similarity	NPC478203
0.8671	High Similarity	NPC478027
0.8658	High Similarity	NPC197666
0.8658	High Similarity	NPC126739
0.8658	High Similarity	NPC472602
0.8654	High Similarity	NPC205918
0.8654	High Similarity	NPC46882
0.8654	High Similarity	NPC132990
0.8649	High Similarity	NPC235115
0.8645	High Similarity	NPC280753
0.8645	High Similarity	NPC44378
0.8645	High Similarity	NPC476684
0.8642	High Similarity	NPC472049
0.8642	High Similarity	NPC294722
0.8639	High Similarity	NPC175943
0.8636	High Similarity	NPC53362
0.8636	High Similarity	NPC166583
0.8627	High Similarity	NPC472034
0.8618	High Similarity	NPC471731
0.8618	High Similarity	NPC159721
0.8618	High Similarity	NPC469542
0.8618	High Similarity	NPC472006
0.8616	High Similarity	NPC473395
0.8616	High Similarity	NPC257309
0.8614	High Similarity	NPC294149
0.8609	High Similarity	NPC67650
0.8609	High Similarity	NPC472605
0.8609	High Similarity	NPC472603
0.8609	High Similarity	NPC472604
0.8609	High Similarity	NPC1704
0.8609	High Similarity	NPC475730
0.8608	High Similarity	NPC16082
0.8608	High Similarity	NPC82592
0.8606	High Similarity	NPC472620
0.86	High Similarity	NPC105456
0.86	High Similarity	NPC92655
0.86	High Similarity	NPC139634
0.8599	High Similarity	NPC180944
0.8599	High Similarity	NPC256141
0.8598	High Similarity	NPC472619
0.8591	High Similarity	NPC71256
0.859	High Similarity	NPC158866
0.859	High Similarity	NPC179178
0.8581	High Similarity	NPC221352
0.8571	High Similarity	NPC112418
0.8571	High Similarity	NPC202112
0.8571	High Similarity	NPC107625
0.8571	High Similarity	NPC153783
0.8571	High Similarity	NPC51513
0.8571	High Similarity	NPC472033
0.8563	High Similarity	NPC324220
0.8563	High Similarity	NPC312630
0.8562	High Similarity	NPC257025
0.8553	High Similarity	NPC164427
0.8553	High Similarity	NPC227062
0.8553	High Similarity	NPC20530
0.8553	High Similarity	NPC215917
0.8553	High Similarity	NPC469579
0.8553	High Similarity	NPC471733
0.8553	High Similarity	NPC272550
0.8553	High Similarity	NPC10754
0.8553	High Similarity	NPC322112
0.8544	High Similarity	NPC192189
0.8544	High Similarity	NPC281703
0.8544	High Similarity	NPC281477
0.8544	High Similarity	NPC125487
0.8544	High Similarity	NPC472799
0.8544	High Similarity	NPC301233
0.8543	High Similarity	NPC472601
0.8543	High Similarity	NPC64664
0.8543	High Similarity	NPC472600
0.8543	High Similarity	NPC155205
0.8543	High Similarity	NPC156872
0.8535	High Similarity	NPC295650
0.8533	High Similarity	NPC475974
0.8533	High Similarity	NPC177307
0.8533	High Similarity	NPC9121
0.8533	High Similarity	NPC472403
0.8528	High Similarity	NPC475979
0.8528	High Similarity	NPC211592
0.8526	High Similarity	NPC307052
0.8526	High Similarity	NPC139966
0.8519	High Similarity	NPC471745
0.8519	High Similarity	NPC315772
0.8516	High Similarity	NPC259632
0.8516	High Similarity	NPC476463
0.8509	High Similarity	NPC243701
0.8509	High Similarity	NPC471744
0.8509	High Similarity	NPC470183
0.8506	High Similarity	NPC312789
0.85	High Similarity	NPC84935
0.85	High Similarity	NPC77679
0.85	High Similarity	NPC190020
0.8497	Intermediate Similarity	NPC354984
0.8491	Intermediate Similarity	NPC237560
0.8491	Intermediate Similarity	NPC175192
0.8491	Intermediate Similarity	NPC80534
0.8491	Intermediate Similarity	NPC304207

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 NPC69043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	857
0.2-0.3	1832
0.3-0.4	2632
0.4-0.5	1924
0.5-0.6	1049
0.6-0.7	406
0.7-0.8	136
0.8-0.85	19
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.86	High Similarity	NPD970	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD3817	Phase 2
0.8385	Intermediate Similarity	NPD7075	Discontinued
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD4380	Phase 2
0.8261	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8205	Intermediate Similarity	NPD6799	Approved
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8199	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD6166	Phase 2
0.8182	Intermediate Similarity	NPD6232	Discontinued
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6797	Phase 2
0.8165	Intermediate Similarity	NPD5403	Approved
0.816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2532	Approved
0.8153	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2533	Approved
0.8153	Intermediate Similarity	NPD2534	Approved
0.8137	Intermediate Similarity	NPD1934	Approved
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8118	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD1512	Approved
0.8092	Intermediate Similarity	NPD8150	Discontinued
0.8086	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD2801	Approved
0.807	Intermediate Similarity	NPD7808	Phase 3
0.8047	Intermediate Similarity	NPD7054	Approved
0.8047	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5401	Approved
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7472	Approved
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD1510	Phase 2
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD3750	Approved
0.7895	Intermediate Similarity	NPD7074	Phase 3
0.7879	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD6190	Approved
0.7843	Intermediate Similarity	NPD230	Phase 1
0.7836	Intermediate Similarity	NPD5844	Phase 1
0.7821	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6559	Discontinued
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1549	Phase 2
0.7756	Intermediate Similarity	NPD2796	Approved
0.7746	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7677	Intermediate Similarity	NPD1607	Approved
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7673	Intermediate Similarity	NPD4628	Phase 3
0.7662	Intermediate Similarity	NPD1240	Approved
0.764	Intermediate Similarity	NPD7390	Discontinued
0.7619	Intermediate Similarity	NPD3749	Approved
0.759	Intermediate Similarity	NPD37	Approved
0.7581	Intermediate Similarity	NPD7435	Discontinued
0.758	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3748	Approved
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.7558	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1465	Phase 2
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.754	Intermediate Similarity	NPD8319	Approved
0.754	Intermediate Similarity	NPD8320	Phase 1
0.7532	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD5494	Approved
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.7515	Intermediate Similarity	NPD3226	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7471	Intermediate Similarity	NPD919	Approved
0.7456	Intermediate Similarity	NPD7768	Phase 2
0.7452	Intermediate Similarity	NPD6651	Approved
0.7436	Intermediate Similarity	NPD943	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7700	Phase 2
0.7405	Intermediate Similarity	NPD7699	Phase 2
0.7391	Intermediate Similarity	NPD2800	Approved
0.7371	Intermediate Similarity	NPD7228	Approved
0.7365	Intermediate Similarity	NPD9545	Approved
0.7362	Intermediate Similarity	NPD3300	Phase 2
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7874	Approved
0.7344	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5408	Approved
0.7312	Intermediate Similarity	NPD5404	Approved
0.7312	Intermediate Similarity	NPD5406	Approved
0.7312	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7303	Intermediate Similarity	NPD7685	Pre-registration
0.7302	Intermediate Similarity	NPD7698	Approved
0.7302	Intermediate Similarity	NPD7697	Approved
0.7302	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.7289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD920	Approved
0.7284	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.7263	Intermediate Similarity	NPD7870	Phase 2
0.7263	Intermediate Similarity	NPD7871	Phase 2
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7246	Intermediate Similarity	NPD1653	Approved
0.724	Intermediate Similarity	NPD7701	Phase 2
0.723	Intermediate Similarity	NPD9493	Approved
0.7216	Intermediate Similarity	NPD7801	Approved
0.7215	Intermediate Similarity	NPD4060	Phase 1
0.7202	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3926	Phase 2
0.7184	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD1243	Approved
0.7178	Intermediate Similarity	NPD1652	Phase 2
0.7171	Intermediate Similarity	NPD1201	Approved
0.717	Intermediate Similarity	NPD447	Suspended
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6355	Discontinued
0.717	Intermediate Similarity	NPD5124	Phase 1
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7236	Approved
0.7151	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD8166	Discontinued
0.7128	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7783	Phase 2
0.7124	Intermediate Similarity	NPD9269	Phase 2
0.7111	Intermediate Similarity	NPD8368	Discontinued
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7097	Intermediate Similarity	NPD1470	Approved
0.7089	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD6798	Discontinued
0.7079	Intermediate Similarity	NPD7799	Discontinued
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7069	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD7266	Discontinued
0.7055	Intermediate Similarity	NPD5763	Approved
0.7055	Intermediate Similarity	NPD5762	Approved
0.7051	Intermediate Similarity	NPD2798	Approved
0.7045	Intermediate Similarity	NPD7229	Phase 3
0.7044	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7239	Suspended
0.7039	Intermediate Similarity	NPD7286	Phase 2
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD6273	Approved
0.7017	Intermediate Similarity	NPD7240	Approved
0.7013	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6213	Phase 3
0.7005	Intermediate Similarity	NPD6212	Phase 3
0.7	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1613	Approved
0.6995	Remote Similarity	NPD8407	Phase 2
0.6994	Remote Similarity	NPD2438	Suspended
0.6994	Remote Similarity	NPD4288	Approved
0.6994	Remote Similarity	NPD5353	Approved
0.6987	Remote Similarity	NPD2797	Approved
0.6987	Remote Similarity	NPD1203	Approved
0.6981	Remote Similarity	NPD411	Approved
0.6981	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2313	Discontinued
0.698	Remote Similarity	NPD8155	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